View source for Drospirenone

{{Short description|Medication drug}}
{{Use dmy dates|date=March 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
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{{Infobox drug
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 443713428
| image = Drospirenone.svg
| width = 225
| alt =
| image2 = Drospirenone molecule ball.png
| width2 = 225
| alt2 =

<!-- Clinical data -->
| pronounce = Droe-SPY-re-nown
| tradename = Alone: Slynd<br />With [[estradiol (medication)|estradiol]]: Angeliq<br />With [[ethinylestradiol]]: Yasmin, Yasminelle, Yaz, others<br />With [[estetrol (medication)|estetrol]]: Nextstellis
| Drugs.com = {{drugs.com|ppa|drospirenone}}
| MedlinePlus = 
| DailyMedID = Drospirenone
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU_comment = 
| pregnancy_category= 
| routes_of_administration= [[Oral administration|By mouth]]<ref name="Kuhl2005" />
| class = [[Progestogen (medication)|Progestogen]]; [[Progestin]]; [[Antimineralocorticoid]]; [[Steroidal antiandrogen]]
| ATC_prefix = G03
| ATC_suffix = AC10
| ATC_supplemental = <br />{{ATC|G03|AA12}} {{ATC|G03|FA17}} (combinations with [[estrogen (medication)|estrogen]]s)

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment = <ref>{{cite web | title=Lucinda (Lupin Australia Pty Limited) | website=Therapeutic Goods Administration (TGA) | date=14 January 2025 | url=https://www.tga.gov.au/resources/prescription-medicines-registrations/lucinda-lupin-australia-pty-limited | access-date=20 January 2025}}</ref>
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment = 
| legal_CA = Rx-only
| legal_CA_comment = <ref>{{cite web | title=Health product highlights 2021: Annexes of products approved in 2021 | website=[[Health Canada]] | date=3 August 2022 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/health-product-highlights-2021/appendices.html | access-date=25 March 2024}}</ref>
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment = 
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment = 
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment = 
| legal_US = Rx-only
| legal_US_comment = <ref name="Slynd-Label" />
| legal_EU = 
| legal_EU_comment = 
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment = 
| legal_status = Rx-only

<!-- Pharmacokinetic data -->
| bioavailability = 66–85%<ref name="Kuhl2005" /><ref name="Krattenmacher2000">{{cite journal | vauthors = Krattenmacher R | title = Drospirenone: pharmacology and pharmacokinetics of a unique progestogen | journal = Contraception | volume = 62 | issue = 1 | pages = 29–38 | date = July 2000 | pmid = 11024226 | doi = 10.1016/S0010-7824(00)00133-5 }}</ref><ref name="pmid23238854">{{cite journal | vauthors = Stanczyk FZ, Hapgood JP, Winer S, Mishell DR | title = Progestogens used in postmenopausal hormone therapy: differences in their pharmacological properties, intracellular actions, and clinical effects | journal = Endocrine Reviews | volume = 34 | issue = 2 | pages = 171–208 | date = April 2013 | pmid = 23238854 | pmc = 3610676 | doi = 10.1210/er.2012-1008 }}</ref>
| protein_bound = 95–97% (to [[human serum albumin|albumin]])<ref name="Slynd-Label" /><ref name="Kuhl2005" /><ref name="Krattenmacher2000" />
| metabolism = [[Liver]] (mostly [[cytochrome P450|CYP450]]-independent ([[redox|reduction]], [[sulfation]], and [[bond cleavage|cleavage]] of [[lactone]] [[ring (chemistry)|ring]]), some [[CYP3A4]] contribution)<ref name="Krattenmacher2000" /><ref>{{cite journal | vauthors = Gaspard U, Endrikat J, Desager JP, Buicu C, Gerlinger C, Heithecker R | title = A randomized study on the influence of oral contraceptives containing ethinylestradiol combined with drospirenone or desogestrel on lipid and lipoprotein metabolism over a period of 13 cycles | journal = Contraception | volume = 69 | issue = 4 | pages = 271–278 | date = April 2004 | pmid = 15033400 | doi = 10.1016/j.contraception.2003.11.003 }}</ref><ref name="Bachmann2009">{{cite journal | vauthors = Bachmann G, Kopacz S | title = Drospirenone/ethinyl estradiol 3 mg/20 mug (24/4 day regimen): hormonal contraceptive choices - use of a fourth-generation progestin | journal = Patient Preference and Adherence | volume = 3 | pages = 259–264 | date = November 2009 | pmid = 19936169 | pmc = 2778416 | doi = 10.2147/PPA.S3901 | doi-access = free }}</ref><ref name="WiesingerBerse2015">{{cite journal | vauthors = Wiesinger H, Berse M, Klein S, Gschwend S, Höchel J, Zollmann FS, Schütt B | title = Pharmacokinetic interaction between the CYP3A4 inhibitor ketoconazole and the hormone drospirenone in combination with ethinylestradiol or estradiol | journal = British Journal of Clinical Pharmacology | volume = 80 | issue = 6 | pages = 1399–1410 | date = December 2015 | pmid = 26271371 | pmc = 4693482 | doi = 10.1111/bcp.12745 }}</ref>
| metabolites = • Drospirenone acid<ref name="Slynd-Label" /><br />• 4,5-Dihydrodrospirenone 3-sulfate<ref name="Slynd-Label" />
| onset = 
| elimination_half-life= 25–33 hours<ref name="Slynd-Label" /><ref name="Krattenmacher2000" /><ref name="Kuhl2005" />
| duration_of_action = 
| excretion = [[Urine]], [[feces]]<ref name="Slynd-Label" />

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 67392-87-4
| CAS_supplemental = 
| PubChem = 68873
| IUPHAR_ligand = 
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01395
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 62105
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = N295J34A25
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D03917
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 50838
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1509
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = Dihydrospirenone; Dihydrospirorenone; 1,2-Dihydrospirorenone; MSp; SH-470; ZK-30595; LF-111; 17β-Hydroxy-6β,7β:15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21-carboxylic acid, γ-lactone

<!-- Chemical and physical data -->
| IUPAC_name = (6''R'',7''R'',8''R'',9''S'',10''R'',13''S'',14''S'',15''S'',16''S'',17''S'')-1,3',4',6,6a,7,8,9,10,11,12,13,14,15,15a,16-Hexadecahydro-10,13-dimethylspiro-[17''H''-dicyclopropa[6,7:15,16]cyclopenta[''a'']phenantrene-17,2'(5<nowiki>'</nowiki>''H'')-furan]-3,5'(2''H'')-dione
| C=24 | H=30 | O=3
| SMILES = O=C7O[C@@]6([C@@]3([C@H]([C@@H]2[C@@H]4[C@H](/C1=C/C(=O)CC[C@]1(C)[C@H]2CC3)C4)[C@@H]5C[C@@H]56)C)CC7
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C24H30O3/c1-22-6-3-12(25)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(26)27-24/h9,13-16,18,20-21H,3-8,10-11H2,1-2H3/t13-,14+,15-,16+,18+,20-,21+,22-,23+,24+/m1/s1
| StdInChI_comment = 
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = METQSPRSQINEEU-HXCATZOESA-N
| density = 
| density_notes = 
| melting_point = 
| melting_high = 
| melting_notes = 
| boiling_point = 
| boiling_notes = 
| solubility = 
| sol_units = 
| specific_rotation = 
}}

<!-- Definition and medical uses -->
'''Drospirenone''' is a [[progestin]] and [[antiandrogen]] medication which is used in [[birth control pill]]s to prevent [[pregnancy]] and in [[menopausal hormone therapy]], among other uses.<ref name="Kuhl2005">{{cite journal |vauthors=[[Herbert Kuhl|Kuhl H]] |date=August 2005 |title=Pharmacology of estrogens and progestogens: influence of different routes of administration |journal=[[Climacteric (journal)|Climacteric]] |volume=8 Suppl 1 |issue=sup1 |pages=3–63 |doi=10.1080/13697130500148875 |pmid=16112947 |s2cid=24616324}}</ref><ref name="Drugs.com" /> It is available both alone under the brand name '''Slynd''' and in combination with an [[estrogen (medication)|estrogen]] under the brand name '''Yasmin''' among others.<ref name="Drugs.com" /><ref name="Slynd-Label">{{DailyMed|db32bc55-f295-4d87-9dbb-0a2f45573dcf|Slynd-drospirenone tablet, film coated}}</ref> The medication is an [[structural analog|analog]] of the drug [[spironolactone]].<ref>{{cite journal |vauthors=Krattenmacher R |date=July 2000 |title=Drospirenone: pharmacology and pharmacokinetics of a unique progestogen |journal=[[Contraception (journal)|Contraception]] |language=English |volume=62 |issue=1 |pages=29–38 |doi=10.1016/S0010-7824(00)00133-5 |pmid=11024226}}</ref> Drospirenone is taken [[oral administration|by mouth]].<ref name="Kuhl2005" /><ref name="Slynd-Label" />

<!-- Side effects and mechanism -->
Common [[side effect]]s include [[acne]], [[headache]], [[breast tenderness]], [[weight gain|weight increase]], and [[menstrual abnormalities|menstrual changes]].<ref name="Slynd-Label" /> Rare side effects may include [[hyperkalemia|high potassium levels]] and [[blood clot]]s (when taken as a combined oestrogen-progestogen pill), among others.<ref name="Slynd-Label" /><ref name="pmid26598309" /> Drospirenone is a progestin, or a [[synthetic compound|synthetic]] [[progestogen (medication)|progestogen]], and hence is an [[agonist]] of the [[progesterone receptor]], the [[biological target]] of progestogens like [[progesterone]].<ref name="Kuhl2005" /> It has additional [[antimineralocorticoid]] and [[antiandrogen]]ic activity and no other important [[hormonal agent|hormonal]] activity.<ref name="Kuhl2005" /> Because of its antimineralocorticoid activity and lack of undesirable [[off-target activity]], drospirenone is said to more closely resemble [[bioidentical hormone therapy|bioidentical]] [[progesterone (medication)|progesterone]] than other progestins.<ref name="pmid11246598">{{cite journal |vauthors=Oelkers W |date=December 2000 |title=Drospirenone--a new progestogen with antimineralocorticoid activity, resembling natural progesterone |journal=[[The European Journal of Contraception & Reproductive Health Care]] |type=Review |volume=5 |issue=Suppl 3 |pages=17–24 |doi=10.1080/14730782.2000.12288986 |pmid=11246598 |s2cid=35051390}}</ref><ref name="pmid12659403">{{cite journal |vauthors=Oelkers W |date=December 2002 |title=Antimineralocorticoid activity of a novel oral contraceptive containing drospirenone, a unique progestogen resembling natural progesterone |journal=[[The European Journal of Contraception & Reproductive Health Care]] |type=Review |volume=7 |issue=Suppl 3 |pages=19–26; discussion 42–3 |doi=10.1080/14730782.2000.12288986 |pmid=12659403}}</ref>

<!-- History, society, and culture -->
Drospirenone was patented in 1976 and introduced for medical use in 2000.<ref name="Ravina2011" /><ref name="Fis2006">{{cite book |chapter-url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA459 |title=Analogue-based Drug Discovery |vauthors=Alapi EM, Fischer J |date=2006 |publisher=John Wiley & Sons |isbn=978-3-527-60749-5 |veditors=Fischer J, [[C. Robin Ganellin|Ganellin CR]] |page=459 |language=en |chapter=Part III: Table of Selected Analogue Classes}}</ref> It is available widely throughout the world.<ref name="Drugs.com" /> The medication is sometimes referred to as a "fourth-generation" progestin.<ref name="HatcherM.D.2007" /><ref name="RossoZeichner2016" /> It is available as a [[generic drug|generic medication]].<ref name="Drugs.com-Generic">[https://www.drugs.com/availability/generic-yasmin.html Generic Yasmin Availability] via {{Drugs.com|parent|yasmin}}at Drugs.com</ref> In 2020, a formulation of drospirenone with [[ethinylestradiol]] was the 145th most commonly prescribed medication in the United States, with more than 4{{nbsp}}million prescriptions.<ref>{{cite web | title = The Top 300 of 2020 | url = https://clincalc.com/DrugStats/Top300Drugs.aspx | website = ClinCalc | access-date = 7 October 2022}}</ref><ref>{{cite web | title = Drospirenone; Ethinyl Estradiol - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/DrospirenoneEthinylEstradiol | access-date = 7 October 2022}}</ref>
{{TOC limit}}

==Medical uses==
Drospirenone (DRSP) is used by itself as a [[progestogen-only birth control pill]], in combination with the estrogens [[ethinylestradiol]] (EE) or [[estetrol (medication)|estetrol]] (E4), with or without supplemental [[folic acid]] ([[vitamin B9|vitamin B<sub>9</sub>]]), as a [[combined birth control pill]], and in combination with the estrogen [[estradiol (medication)|estradiol]] (E2) for use in [[menopausal hormone therapy]].<ref name="Slynd-Label" /> A birth control pill with low-dose ethinylestradiol is also indicated for the treatment of moderate [[acne]], [[premenstrual syndrome]] (PMS), [[premenstrual dysphoric disorder]] (PMDD), and [[dysmenorrhea]] (painful menstruation).<ref name="Yaz-Label" /><ref name="Drugs.com-EE/DRSP">{{cite web|author=Cerner Multum, Inc.|date=11 June 2012|title=drospirenone and ethinyl estradiol|location=Auckland, New Zealand|publisher=Drugs.com|url=https://www.drugs.com/mtm/drospirenone-and-ethinyl-estradiol.html|access-date=24 October 2011}}</ref> For use in menopausal hormone therapy, E2/DRSP is specifically approved to treat moderate to severe [[vasomotor symptoms]] (hot flashes), [[vaginal atrophy]], and [[postmenopausal osteoporosis]].<ref name="Angeliq-Label">{{cite web | title=Angeliq- drospirenone and estradiol tablet, film coated | work = DailyMed | publisher = U.S. National Library of Medicine| url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=761834c2-6b61-4583-84c2-f1ca4a97c4f2 | access-date=17 April 2021}}</ref><ref name="pmid15495039">{{cite journal | vauthors = Maclennan AH, Broadbent JL, Lester S, Moore V | title = Oral oestrogen and combined oestrogen/progestogen therapy versus placebo for hot flushes | journal = The Cochrane Database of Systematic Reviews | volume = 2004 | issue = 4 | pages = CD002978 | date = October 2004 | pmid = 15495039 | pmc = 7004247 | doi = 10.1002/14651858.CD002978.pub2 | author-link1 = Alastair MacLennan (medicine) }}</ref><ref name="pmid11401611">{{cite journal | vauthors = Torgerson DJ, Bell-Syer SE | title = Hormone replacement therapy and prevention of nonvertebral fractures: a meta-analysis of randomized trials | journal = JAMA | volume = 285 | issue = 22 | pages = 2891–2897 | date = June 2001 | pmid = 11401611 | doi = 10.1001/jama.285.22.2891 | s2cid = 25078579 }}</ref> The drospirenone component in this formulation is included specifically to prevent estrogen-induced [[endometrial hyperplasia]].<ref name="pmid16513012" /> Drospirenone has also been used in combination with an estrogen as a component of [[transgender hormone therapy (male-to-female)|hormone therapy for transgender women]].<ref name="pmid28217493">{{cite journal | vauthors = Majumder A, Sanyal D | title = Outcome and preferences in male-to-female subjects with gender dysphoria: Experience from Eastern India | journal = Indian Journal of Endocrinology and Metabolism | volume = 21 | issue = 1 | pages = 21–25 | date = 2017 | pmid = 28217493 | pmc = 5240066 | doi = 10.4103/2230-8210.196000 | doi-access = free }}</ref><ref name="MajumderChatterjee2020">{{cite journal | vauthors = Majumder A, Chatterjee S, Maji D, Roychaudhuri S, Ghosh S, Selvan C, George B, Kalra P, Maisnam I, Sanyal D | title = IDEA Group Consensus Statement on Medical Management of Adult Gender Incongruent Individuals Seeking Gender Reaffirmation as Female | journal = Indian Journal of Endocrinology and Metabolism | volume = 24 | issue = 2 | pages = 128–135 | year = 2020 | pmid = 32699777 | pmc = 7333765 | doi = 10.4103/ijem.IJEM_593_19 | doi-access = free }}</ref>

Studies have found that EE/DRSP is superior to [[placebo]] in reducing premenstrual emotional and physical symptoms while also improving [[quality of life]].<ref name="pmid28477648">{{cite journal | vauthors = Lanza di Scalea T, Pearlstein T | title = Premenstrual Dysphoric Disorder | journal = The Psychiatric Clinics of North America | volume = 40 | issue = 2 | pages = 201–216 | date = June 2017 | pmid = 28477648 | doi = 10.1016/j.psc.2017.01.002 }}</ref><ref name = "Ma_2023">{{cite journal | vauthors = Ma S, Song SJ | title = Oral contraceptives containing drospirenone for premenstrual syndrome | journal = The Cochrane Database of Systematic Reviews | volume = 2023 | issue = 6 | pages = CD006586 | date = June 2023 | pmid = 37365881 | pmc = 10289136 | doi = 10.1002/14651858.CD006586.pub5 }}</ref> E2/DRSP has been found to increase [[bone mineral density]] and to reduce the occurrence of [[bone fracture]]s in [[postmenopausal]] women.<ref name="pmid16203654">{{cite journal | vauthors = Christiansen C | title = Effects of drospirenone/estrogen combinations on bone metabolism | journal = Climacteric | volume = 8 | issue = Suppl 3 | pages = 35–41 | date = October 2005 | pmid = 16203654 | doi = 10.1080/13697130500330283 | s2cid = 42803561 }}</ref><ref name="pmid16513012">{{cite journal | vauthors = Whitehead M | title = Hormone replacement therapy with estradiol and drospirenone: an overview of the clinical data | journal = The Journal of the British Menopause Society | volume = 12 | issue = Suppl 1 | pages = 4–7 | date = March 2006 | pmid = 16513012 | doi = 10.1258/136218006775992185 | s2cid = 38095916 }}</ref><ref name="pmid17364592">{{cite journal | vauthors = Archer DF | title = Drospirenone and estradiol: a new option for the postmenopausal woman | journal = Climacteric | volume = 10 | issue = Suppl 1 | pages = 3–10 | date = February 2007 | pmid = 17364592 | doi = 10.1080/13697130601114859 | s2cid = 9221524 }}</ref><ref name="pmid19357298">{{cite journal | vauthors =  | title = Drospirenone in HRT? | journal = Drug and Therapeutics Bulletin | volume = 47 | issue = 4 | pages = 41–44 | date = April 2009 | pmid = 19357298 | doi = 10.1136/dtb.2009.03.0011 | s2cid = 1909717 }}</ref> In addition, E2/DRSP has a favorable influence on [[cholesterol]] and [[triglyceride]] levels and decreases [[blood pressure]] in women with [[hypertension|high blood pressure]].<ref name="pmid17364592" /><ref name="pmid19357298" /> Due to its [[antimineralocorticoid]] activity, drospirenone opposes estrogen-induced [[salt retention|salt]] and [[fluid retention (medicine)|water retention]] and maintains or slightly reduces [[body weight]].<ref name="pmid18075844">{{cite journal | vauthors = Foidart JM, Faustmann T | title = Advances in hormone replacement therapy: weight benefits of drospirenone, a 17alpha-spirolactone-derived progestogen | journal = Gynecological Endocrinology | volume = 23 | issue = 12 | pages = 692–699 | date = December 2007 | pmid = 18075844 | doi = 10.1080/09513590701582323 | s2cid = 12572825 }}</ref>

===Available forms===
Drospirenone is available in the following formulations, brand names, and indications:<ref name="Drugs@FDA">{{cite web | title = Drugs@FDA: FDA Approved Drug Products | publisher = United States Food and Drug Administration | access-date = 23 December 2019 | url = https://www.accessdata.fda.gov/scripts/cder/daf/}}</ref><ref name="FDADrugSafety">{{Cite web|url=https://www.fda.gov/Drugs/DrugSafety/ucm299305.htm#table|archive-url=https://web.archive.org/web/20120412192800/http://www.fda.gov/Drugs/DrugSafety/ucm299305.htm#table|url-status=dead|archive-date=12 April 2012|title=Drug Safety and Availability - FDA Drug Safety Communication: Updated information about the risk of blood clots in women taking birth control pills containing drospirenone | author = Center for Drug Evaluation and Research |website=www.fda.gov|language=en|access-date=7 November 2017}}</ref>

* Drospirenone 4&nbsp;mg (''Slynd'') – progestogen-only birth control pill<ref name="Slynd-Label" />
* [[Drospirenone/estetrol|Drospirenone 3&nbsp;mg and estetrol 14.2&nbsp;mg]] (''Nextstellis'' (US)) – combined birth control pill<ref>{{cite web | title = NEXTSTELLIS (drospirenone and estetrol tablets) | work = Mayne Pharma | publisher = U.S. Food and Drug Administration | date = April 2021 | url = https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/214154s000lbl.pdf| archive-url = https://web.archive.org/web/20210415185247/https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/214154s000lbl.pdf| url-status = dead| archive-date = 15 April 2021}}</ref><ref>{{cite web | title = U.S. FDA Approved NEXTSTELLIS®, New Oral Contraceptive | work = Mayne Pharma  | url = https://www.maynepharma.com/media/2507/mayne_pharma_drsp-e4_news_release_041421.pdf | archive-url = https://web.archive.org/web/20210417214927/https://www.maynepharma.com/media/2507/mayne_pharma_drsp-e4_news_release_041421.pdf | archive-date = 17 April 2021 }}</ref><ref>{{cite web | title = Mayne Pharma and Mithra Announce FDA Approval of New Oral Contraceptive Nextstellis® | url = https://www.maynepharma.com/media/2506/fda-approval-of-novel-oral-contraceptive-nextstellis.pdf}}</ref>
* [[Ethinylestradiol/drospirenone|Ethinylestradiol 30&nbsp;μg and drospirenone 3&nbsp;mg]] (''Ocella'', ''Syeda'', ''Yasmin'', ''Zarah'', ''Zumandimine'') – combined birth control pill<ref>{{cite web | title=Ocella- drospirenone and ethinyl estradiol kit | work = DailyMed | publisher = U.S. National Library of Medicine| url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0d729f4d-2fa3-47f6-8a1f-d8cfea4cff37 | access-date=17 April 2021}}</ref><ref>{{cite web | title=Syeda- drospirenone and ethinyl estradiol kit | work = DailyMed | publisher = U.S. National Library of Medicine| url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e1586633-1973-c396-6f4a-4c55cce4b59e | access-date=17 April 2021}}</ref><ref name="Yasmin-Label">{{cite web | title=Yasmin- drospirenone and ethinyl estradiol kit | work = DailyMed | publisher = U.S. National Library of Medicine| url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d7ea6a60-5a56-4f81-b206-9b27b7e58875 | access-date=17 April 2021}}</ref><ref>{{cite web | title=Zarah- drospirenone and ethinyl estradiol kit | work = DailyMed | publisher = U.S. National Library of Medicine| url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=71b20915-97a0-4cc7-a8d0-a966126d53b5 | access-date=17 April 2021}}</ref>
* [[Ethinylestradiol/drospirenone|Ethinylestradiol 20&nbsp;μg and drospirenone 3&nbsp;mg]] (''Gianvi'',  ''Jasmiel'', ''Loryna'', ''Lo-Zumandimine'', ''Nikki'', ''Vestura'', ''Yaz'') – combined birth control pill, acne, PMS, PMDD, dysmenorrhea<ref name="Yaz-Label">{{cite web | title=Yaz- drospirenone and ethinyl estradiol kit | work = DailyMed | publisher = U.S. National Library of Medicine| url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=065f33e4-b587-4e66-b896-ca9ab7b7c876 | access-date=17 April 2021}}</ref>
* [[Ethinylestradiol/drospirenone/levomefolic acid|Ethinylestradiol 30&nbsp;μg, drospirenone 3&nbsp;mg, and levomefolate calcium 0.451&nbsp;mg]] (''Beyaz'', ''Tydemy'') – combined birth control pill with [[vitamin B9|vitamin B<sub>9</sub>]] supplementation, acne, PMS<ref name="Beyaz-Label">{{cite web | title=Beyaz- drospirenone/ethinyl estradiol/levomefolate calcium and levomefolate calcium kit | work = DailyMed | publisher = U.S. National Library of Medicine| url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8132454a-6135-4bac-b206-83a55eb8dbc6 | access-date=17 April 2021}}</ref><ref>{{cite web | title=Tydemy- drospirenone, ethinyl estradiol and levomefolate calcium and levomefolate calcium kit | work = DailyMed | publisher = U.S. National Library of Medicine| url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9b1a133d-2ab0-44a7-8c3c-5ac0f8551813 | access-date=17 April 2021}}</ref>
* [[Estetrol/drospirenone|Estetrol 15&nbsp;mg and drospirenone 3&nbsp;mg]] (''Nextstellis'' (CA)) – combined birth control pill<ref name="Nextstellis-Label-Canada">{{cite web |url=https://pdf.hres.ca/dpd_pm/00060352.PDF |title=Estetrol monohydrate and Drospirenone Tablets | work = Searchlight Pharma Inc. |access-date=15 January 2022 |archive-url=https://web.archive.org/web/20210413054728/https://pdf.hres.ca/dpd_pm/00060352.PDF |archive-date=13 April 2021 |url-status=dead}}</ref><ref>{{cite press release | title=Mithra and Searchlight Pharma Announce Nextstellis Approval in Canada | website=Searchlight Pharma | date=8 March 2021 | url=http://searchlightpharma.com/mithra-and-searchlight-pharma-announce-nextstellis-approval-in-canada | access-date=17 April 2021 | archive-date=19 April 2021 | archive-url=https://web.archive.org/web/20210419020628/http://searchlightpharma.com/mithra-and-searchlight-pharma-announce-nextstellis-approval-in-canada/ | url-status=dead }}</ref>
* [[Estradiol/drospirenone|Estradiol 0.5 or 1&nbsp;mg and drospirenone 0.25 or 0.5&nbsp;mg]] (''Angeliq'') – menopausal hormone therapy (menopausal syndrome, postmenopausal osteoporosis)<ref name="Angeliq-Label" />

==Contraindications==
[[Contraindication]]s of drospirenone include [[renal impairment]] or [[chronic kidney disease]], [[adrenal insufficiency]], presence or history of [[cervical cancer]] or other [[hormone-sensitive cancer|progestogen-sensitive cancer]]s, [[benign liver tumor|benign]] or [[malignant liver tumor]]s or [[hepatic impairment]], undiagnosed [[abnormal uterine bleeding]], and [[hyperkalemia]] (high potassium levels).<ref name="Slynd-Label" /><ref name="Yasmin SPC 2013"/><ref name="Yasmin PI 2012">{{cite web|author=Bayer|date=10 April 2012|title=Yasmin full prescribing information|location=Silver Spring, Md.|publisher=Food and Drug Administration (FDA)|url=http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s022lbl.pdf|archive-url=https://web.archive.org/web/20120425002550/http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021098s022lbl.pdf|url-status=dead|archive-date=25 April 2012|access-date=14 April 2012|quote=4. Contraindications: • Renal impairment. • Adrenal insufficiency. • Liver disease.}}</ref> Renal impairment, hepatic impairment, and adrenal insufficiency are contraindicated because they increase exposure to drospirenone and/or increase the risk of hyperkalemia with drospirenone.<ref name="Slynd-Label" />

==Side effects==
[[Adverse effect]]s of drospirenone alone occurring in more than 1% of women may include unscheduled [[menstrual bleeding]] ([[breakthrough bleeding|breakthrough]] or [[intracyclic bleeding|intracyclic]]) (40.3–64.4%), [[acne]] (3.8%), [[metrorrhagia]] (2.8%), [[headache]] (2.7%), [[breast pain]] (2.2%), [[weight gain]] (1.9%), [[dysmenorrhea]] (1.9%), [[nausea]] (1.8%), [[vaginal hemorrhage]] (1.7%), [[decreased libido]] (1.3%), [[breast tenderness]] (1.2%), and [[irregular menstruation]] (1.2%).<ref name="Slynd-Label" />

===High potassium levels===
Drospirenone is an [[antimineralocorticoid]] with [[potassium]]-sparing properties, though in most cases no increase of potassium levels is to be expected.<ref name="Yasmin SPC 2013">{{cite web|author=Bayer|date=25 March 2013|title=Summary of Product Characteristics (SPC): Yasmin|location=London|publisher=electronic Medicines Compendium (eMC), Datapharm|url=http://www.medicines.org.uk/emc/medicine/8777/SPC/Yasmin+film-coated+tablets+0.03mg+3mg/|access-date=24 April 2014|quote=4.3. Contraindications: • Severe chronic kidney disease or acute kidney failure. • Presence or history of severe hepatic disease as long as liver function values have not returned to normal.}}</ref> In women with mild or moderate chronic kidney disease, or in combination with chronic daily use of other potassium-sparing medications ([[ACE inhibitor]]s, [[angiotensin II receptor antagonist]]s, [[potassium-sparing diuretic]]s, [[heparin]], antimineralocorticoids, or [[nonsteroidal anti-inflammatory drug]]s), a potassium level should be checked after two weeks of use to test for [[hyperkalemia]].<ref name="Yasmin SPC 2013"/><ref name="Nelson 2011">{{cite book| vauthors = Nelson AL, Cwiak C |year=2011|chapter=Combined oral contraceptives (COCs)| veditors = Hatcher RA, Trussell J, Nelson AL, Cates Jr W, Kowal D, Policar MS |title=Contraceptive Technology|edition=20th revised|location=New York|publisher=Ardent Media|pages=249–341|isbn=978-1-59708-004-0|issn=0091-9721|oclc=781956734}}</ref> Persistent hyperkalemia that required discontinuation occurred in 2 out of around 1,000 women (0.2%) with 4&nbsp;mg/day drospirenone alone in clinical trials.<ref name="Slynd-Label" />

===Blood clots===
Birth control pills containing [[ethinylestradiol]] and a progestin are associated with an increased risk of [[venous thromboembolism]] (VTE), including [[deep vein thrombosis]] (DVT) and [[pulmonary embolism]] (PE).<ref name="pmid26780736">{{cite journal | vauthors = Heit JA, Spencer FA, White RH | title = The epidemiology of venous thromboembolism | journal = Journal of Thrombosis and Thrombolysis | volume = 41 | issue = 1 | pages = 3–14 | date = January 2016 | pmid = 26780736 | pmc = 4715842 | doi = 10.1007/s11239-015-1311-6 }}</ref> The incidence is about 4-fold higher on average than in women not taking a birth control pill.<ref name="pmid26780736" /> The [[absolute risk]] of VTE with ethinylestradiol-containing birth control pills is small, in the area of 3 to 10 out of 10,000 women per year, relative to 1 to 5 out of 10,000 women per year not taking a birth control pill.<ref name="pmid27051991" /><ref name="FDA2018">{{Cite web|url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-updated-information-about-risk-blood-clots-women-taking-birth-control|title=FDA Drug Safety Communication: Updated information about the risk of blood clots in women taking birth control pills containing drospirenone|website=[[Food and Drug Administration]]|date=27 April 2019|archive-url=https://web.archive.org/web/20190427143241/https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-updated-information-about-risk-blood-clots-women-taking-birth-control|archive-date=27 April 2019}}</ref> The risk of VTE during [[pregnancy]] is 5 to 20 in 10,000 women per year and during the [[postpartum period]] is 40 to 65 per 10,000 women per year.<ref name="FDA2018" /> The higher risk of VTE with combined birth control pills is thought to be due to the ethinylestradiol component, as ethinylestradiol has estrogenic effects on [[liver protein synthesis|liver synthesis]] of [[coagulation factor]]s which result in a [[procoagulation|procoagulatory]] state.<ref name="pmid26598309" /> In contrast to ethinylestradiol-containing birth control pills, neither [[progestogen-only birth control]] nor the combination of [[transdermal administration|transdermal]] [[estradiol (medication)|estradiol]] and an oral progestin in [[menopausal hormone therapy]] is associated with an increased risk of VTE.<ref name="pmid26598309" /><ref name="pmid30626577">{{cite journal | vauthors = Vinogradova Y, Coupland C, Hippisley-Cox J | title = Use of hormone replacement therapy and risk of venous thromboembolism: nested case-control studies using the QResearch and CPRD databases | journal = BMJ | volume = 364 | pages = k4810 | date = January 2019 | pmid = 30626577 | pmc = 6326068 | doi = 10.1136/bmj.k4810 }}</ref>

Different progestins in ethinylestradiol-containing birth control pills have been associated with different risks of VTE.<ref name="pmid26598309">{{cite journal |vauthors=Han L, Jensen JT |date=December 2015 |title=Does the Progestogen Used in Combined Hormonal Contraception Affect Venous Thrombosis Risk? |journal=Obstetrics and Gynecology Clinics of North America |publisher=Elsevier |volume=42 |issue=4 |pages=683–698 |doi=10.1016/j.ogc.2015.07.007 |eissn=1558-0474 |pmid=26598309 |doi-access=free}}</ref> Birth control pills containing progestins such as [[desogestrel]], [[gestodene]], drospirenone, and [[cyproterone acetate]] have been found to have 2- to 3-fold the risk of VTE of birth control pills containing [[levonorgestrel]] in [[retrospective cohort study|retrospective cohort]] and [[nested case control study|nested case–control]] [[observational study|observational studies]].<ref name="pmid26598309" /><ref name="pmid27051991" /> However, this area of research is controversial, and [[confounding factor]]s may have been present in these studies.<ref name="pmid26598309" /><ref name="pmid27051991">{{cite journal | vauthors = Bateson D, Butcher BE, Donovan C, Farrell L, Kovacs G, Mezzini T, Raynes-Greenow C, Pecoraro G, Read C, Baber R | title = Risk of venous thromboembolism in women taking the combined oral contraceptive: A systematic review and meta-analysis | journal = Australian Family Physician | volume = 45 | issue = 1 | pages = 59–64 | date = 2016 | pmid = 27051991 | url = https://www.racgp.org.au/afp/2016/januaryfebruary/risk-of-venous-thromboembolism-in-women-taking-the-combined-oral-contraceptive-a-systematic-review-and-meta-analysis/ }}</ref><ref name="pmid27854556">{{cite journal | vauthors = Batur P, Casey PM | title = Drospirenone Litigation: Does the Punishment Fit the Crime? | journal = Journal of Women's Health | volume = 26 | issue = 2 | pages = 99–102 | date = February 2017 | pmid = 27854556 | doi = 10.1089/jwh.2016.6092 | doi-access = free }}</ref> Other observational studies, specifically [[prospective cohort study|prospective cohort]] and [[case–control study|case control studies]], have found no differences in risk between different progestins, including between birth control pills containing drospirenone and birth control pills containing levonorgestrel.<ref name="pmid26598309" /><ref name="pmid27051991" /><ref name="pmid27854556" /><ref name="pmid27678035" /> These kinds of observational studies have certain advantages over the aforementioned types of studies, like better ability to control for confounding factors.<ref name="pmid27678035">{{cite journal | vauthors = Sitruk-Ware R | title = Hormonal contraception and thrombosis | journal = Fertility and Sterility | volume = 106 | issue = 6 | pages = 1289–1294 | date = November 2016 | pmid = 27678035 | doi = 10.1016/j.fertnstert.2016.08.039 | doi-access = free }}</ref> [[Systematic review]]s and [[meta-analysis|meta-analyses]] of all of the data in the mid-to-late 2010s found that birth control pills containing cyproterone acetate, desogestrel, drospirenone, or gestodene overall were associated with a risk of VTE of about 1.3- to 2.0-fold compared to that of levonorgestrel-containing birth control pills.<ref name="pmid29573722">{{cite journal | vauthors = Oedingen C, Scholz S, Razum O | title = Systematic review and meta-analysis of the association of combined oral contraceptives on the risk of venous thromboembolism: The role of the progestogen type and estrogen dose | journal = Thrombosis Research | volume = 165 | pages = 68–78 | date = May 2018 | pmid = 29573722 | doi = 10.1016/j.thromres.2018.03.005 }}</ref><ref name="pmid29388678">{{cite journal | vauthors = Dragoman MV, Tepper NK, Fu R, Curtis KM, Chou R, Gaffield ME | title = A systematic review and meta-analysis of venous thrombosis risk among users of combined oral contraception | journal = International Journal of Gynaecology and Obstetrics | volume = 141 | issue = 3 | pages = 287–294 | date = June 2018 | pmid = 29388678 | pmc = 5969307 | doi = 10.1002/ijgo.12455 }}</ref><ref name="pmid27051991" />

[[Androgen]]ic progestins have been found to antagonize to some degree the effects of ethinylestradiol on coagulation.<ref name="pmid17056444">{{cite journal | vauthors = Wiegratz I, Kuhl H | title = Metabolic and clinical effects of progestogens | journal = The European Journal of Contraception & Reproductive Health Care | volume = 11 | issue = 3 | pages = 153–161 | date = September 2006 | pmid = 17056444 | doi = 10.1080/13625180600772741 | s2cid = 27088428 }}</ref><ref name="pmid8794429">{{cite journal | vauthors = Kuhl H | title = Effects of progestogens on haemostasis | journal = Maturitas | volume = 24 | issue = 1–2 | pages = 1–19 | date = May 1996 | pmid = 8794429 | doi = 10.1016/0378-5122(96)00994-2 }}</ref><ref name="pmid23384742">{{cite journal | vauthors = Sitruk-Ware R, Nath A | title = Characteristics and metabolic effects of estrogen and progestins contained in oral contraceptive pills | journal = Best Practice & Research. Clinical Endocrinology & Metabolism | volume = 27 | issue = 1 | pages = 13–24 | date = February 2013 | pmid = 23384742 | doi = 10.1016/j.beem.2012.09.004 }}</ref><ref name="pmid26512437">{{cite journal | vauthors = Nelson AL | title = An update on new orally administered contraceptives for women | journal = Expert Opinion on Pharmacotherapy | volume = 16 | issue = 18 | pages = 2759–2772 | date = 2015 | pmid = 26512437 | doi = 10.1517/14656566.2015.1100173 | s2cid = 207481206 }}</ref> As a result, more androgenic progestins, like levonorgestrel and [[norethisterone]], may oppose the procoagulatory effects of ethinylestradiol and result in a lower increase in risk of VTE.<ref name="pmid26598309" /><ref name="pmid28712325" /> Conversely, this would be the case less or not at all with progestins that are less androgenic, like desogestrel and gestodene, as well as with progestins that are [[antiandrogen]]ic, like drospirenone and cyproterone acetate.<ref name="pmid26598309" /><ref name="pmid28712325">{{cite journal | vauthors = Farris M, Bastianelli C, Rosato E, Brosens I, Benagiano G | title = Pharmacodynamics of combined estrogen-progestin oral contraceptives: 2. effects on hemostasis | journal = Expert Review of Clinical Pharmacology | volume = 10 | issue = 10 | pages = 1129–1144 | date = October 2017 | pmid = 28712325 | doi = 10.1080/17512433.2017.1356718 | s2cid = 205931204 }}</ref>

In the early 2010s, the FDA updated the label for birth control pills containing drospirenone and other progestins to include warnings for stopping use prior to and after surgery, and to warn that such birth control pills may have a higher risk of blood clots.<ref name="Yasmin PI 2012"/>

{{Risk of venous thromboembolism with hormone therapy and birth control pills (QResearch/CPRD)}}

===Breast cancer===
Drospirenone has been found to stimulate the [[cell proliferation|proliferation]] and [[cell migration|migration]] of [[breast cancer]] [[cell (biology)|cell]]s in [[preclinical research]], similarly to certain other progestins.<ref name="pmid19938948">{{cite journal | vauthors = Simoncini T, Genazzani AR | title = A review of the cardiovascular and breast actions of drospirenone in preclinical studies | journal = Climacteric | volume = 13 | issue = 1 | pages = 22–33 | date = February 2010 | pmid = 19938948 | doi = 10.3109/13697130903437375 | s2cid = 4306359 }}</ref><ref name="pmid21414337" /> However, some evidence suggests that drospirenone may do this more weakly than certain other progestins, like [[medroxyprogesterone acetate]].<ref name="pmid19938948" /><ref name="pmid21414337" /> The combination of estradiol and drospirenone has been found to increase [[breast density]], an established risk factor for breast cancer, in postmenopausal women.<ref name="pmid27548404">{{cite journal | vauthors = Palacios S, Mejía A | title = Progestogen safety and tolerance in hormonal replacement therapy | journal = Expert Opinion on Drug Safety | volume = 15 | issue = 11 | pages = 1515–1525 | date = November 2016 | pmid = 27548404 | doi = 10.1080/14740338.2016.1223041 | s2cid = 31497860 }}</ref><ref name="pmid26357645">{{cite journal | vauthors = Caglayan EK, Caglayan K, Alkis I, Arslan E, Okur A, Banli O, Engin-Ustün Y | title = Factors Associated with Mammographic Density in Postmenopausal Women | journal = Journal of Menopausal Medicine | volume = 21 | issue = 2 | pages = 82–88 | date = August 2015 | pmid = 26357645 | pmc = 4561745 | doi = 10.6118/jmm.2015.21.2.82 }}</ref><ref name="pmid31239112">{{cite journal | vauthors = Hirschberg AL, Tani E, Brismar K, Lundström E | title = Effects of drospirenone and norethisterone acetate combined with estradiol on mammographic density and proliferation of breast epithelial cells-A prospective randomized trial | journal = Maturitas | volume = 126 | pages = 18–24 | date = August 2019 | pmid = 31239112 | doi = 10.1016/j.maturitas.2019.04.205 | doi-access = free }}</ref>

Data on risk of [[breast cancer]] in women with newer progestins like drospirenone are lacking at present.<ref name="pmid31512725" /> Progestogen-only birth control is not generally associated with a higher risk of breast cancer.<ref name="pmid31512725">{{cite journal | vauthors = Trabert B, Sherman ME, Kannan N, Stanczyk FZ | title = Progesterone and Breast Cancer | journal = Endocrine Reviews | volume = 41 | issue = 2 | pages = 320–344 | date = April 2020 | pmid = 31512725 | pmc = 7156851 | doi = 10.1210/endrev/bnz001 }}</ref> Conversely, combined birth control and menopausal hormone therapy with an estrogen and a progestogen are associated with higher risks of breast cancer.<ref name="pmid31474332">{{cite journal | title = Type and timing of menopausal hormone therapy and breast cancer risk: individual participant meta-analysis of the worldwide epidemiological evidence | journal = Lancet | volume = 394 | issue = 10204 | pages = 1159–1168 | date = September 2019 | pmid = 31474332 | pmc = 6891893 | doi = 10.1016/S0140-6736(19)31709-X | collaboration = Collaborative Group on Hormonal Factors in Breast Cancer | author1 = Collaborative Group on Hormonal Factors in Breast Cancer }}</ref><ref name="pmid31512725" /><ref name="pmid23651281">{{cite journal | vauthors = Sturdee DW | title = Are progestins really necessary as part of a combined HRT regimen? | journal = Climacteric | volume = 16 | issue = Suppl 1 | pages = 79–84 | date = August 2013 | pmid = 23651281 | doi = 10.3109/13697137.2013.803311 | s2cid = 21894200 }}</ref>

==Overdose==
These have been no reports of serious [[adverse effect]]s with [[overdose]] of drospirenone.<ref name="Slynd-Label" /> Symptoms that may occur in the event of an overdose may include [[nausea]], [[vomiting]], and [[vaginal bleeding]].<ref name="Slynd-Label" /> There is no [[antidote]] for overdose of drospirenone and treatment of overdose should be based on [[symptom]]s.<ref name="Slynd-Label" /> Since drospirenone has antimineralocorticoid activity, levels of [[potassium]] and [[sodium]] should be measured and signs of [[metabolic acidosis]] should be monitored.<ref name="Slynd-Label" />

== Interactions ==

[[Enzyme inhibitor|Inhibitor]]s and [[enzyme inducer|inducer]]s of the [[cytochrome P450]] [[enzyme]] [[CYP3A4]] may influence the levels and efficacy of drospirenone.<ref name="Slynd-Label" /> Treatment for 10&nbsp;days with 200&nbsp;mg twice daily [[ketoconazole]], a strong CYP3A4 inhibitor among other actions, has been found to result in a moderate 2.0- to 2.7-fold increase in exposure to drospirenone.<ref name="Slynd-Label" /> Drospirenone does not appear to influence the [[metabolism]] of [[omeprazole]] (metabolized via [[CYP2C19]]), [[simvastatin]] (metabolized via CYP3A4), or [[midazolam]] (metabolized via CYP3A4), and likely does not influence the metabolism of other medications that are metabolized via these [[metabolic pathway|pathway]]s.<ref name="Slynd-Label" /> Drospirenone may interact with [[potassium]]-sparing medications such as [[ACE inhibitor]]s, [[angiotensin II receptor antagonist]]s, [[potassium-sparing diuretic]]s, [[potassium supplement]]s, [[heparin]], [[antimineralocorticoid]]s, and [[nonsteroidal anti-inflammatory drug]]s to further increase potassium levels.<ref name="Slynd-Label" /> This may increase the risk of [[hyperkalemia]] (high potassium levels).<ref name="Slynd-Label" />

==Pharmacology==

===Pharmacodynamics===
Drospirenone binds with high [[affinity (pharmacology)|affinity]] to the [[progesterone receptor]] (PR) and [[mineralocorticoid receptor]] (MR), with lower affinity to the [[androgen receptor]] (AR), and with very low affinity to the [[glucocorticoid receptor]] (GR).<ref name="Kuhl2005" /><ref name="pmid7625729" /><ref name="FuhrmannKrattenmacher1996">{{cite journal | vauthors = Fuhrmann U, Krattenmacher R, Slater EP, Fritzemeier KH | title = The novel progestin drospirenone and its natural counterpart progesterone: biochemical profile and antiandrogenic potential | journal = Contraception | volume = 54 | issue = 4 | pages = 243–251 | date = October 1996 | pmid = 8922878 | doi = 10.1016/S0010-7824(96)00195-3 }}</ref><ref name="pmid23238854" /> It is an [[agonist]] of the PR and an [[receptor antagonist|antagonist]] of the MR and AR, and hence is a [[progestogen (medication)|progestogen]], [[antimineralocorticoid]], and [[antiandrogen]].<ref name="Kuhl2005" /><ref name="pmid7625729" /><ref name="pmid23238854" /><ref name="pmid21414337" /> Drospirenone has no [[estrogen (medication)|estrogen]]ic activity and no appreciable [[glucocorticoid]] or [[antiglucocorticoid]] activity.<ref name="Kuhl2005" /><ref name="pmid7625729" /><ref name="pmid23238854" /><ref name="pmid21414337" />

{| class="wikitable sortable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"
|+ class="nowrap" | Relative affinities (%) of drospirenone and related steroids
|-
! Progestogen !! {{abbrlink|PR|Progesterone receptor}} !! {{abbrlink|AR|Androgen receptor}} !! {{abbrlink|ER|Estrogen receptor}} !! {{abbrlink|GR|Glucocorticoid receptor}} !! {{abbrlink|MR|Mineralocorticoid receptor}} !! {{abbrlink|SHBG|Sex hormone-binding globulin}} !! {{abbrlink|CBG|Corticosteroid-binding globulin}}
|-
| Drospirenone || 19–70 || 1–65 || 0–1 || 1–6 || 100–500 || 0 || 0
|-
| [[Progesterone (medication)|Progesterone]] || 100 || 0–80 || 0–1 || 6–35 || 100–1000 || 0 || 0
|- class="sortbottom"
| colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' Values are percentages (%). Reference [[ligand (biochemistry)|ligand]]s (100%) were [[progesterone (medication)|progesterone]] for the {{abbrlink|PR|progesterone receptor}}, [[metribolone]] for the {{abbrlink|AR|androgen receptor}}, [[estradiol (medication)|estradiol]] for the {{abbrlink|ER|estrogen receptor}}, [[dexamethasone]] for the {{abbrlink|GR|glucocorticoid receptor}}, and [[aldosterone]] for the {{abbrlink|MR|mineralocorticoid receptor}}. '''Sources:'''<ref name="Krattenmacher2000" /><ref name="Kuhl2005" /><ref name="pmid23238854" /><ref name="pmid23954501">{{cite journal | vauthors = Hapgood JP, Africander D, Louw R, Ray RM, Rohwer JM | title = Potency of progestogens used in hormonal therapy: toward understanding differential actions | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 142 | pages = 39–47 | date = July 2014 | pmid = 23954501 | doi = 10.1016/j.jsbmb.2013.08.001 | s2cid = 12142015 }}</ref><ref name="pmid21414337">{{cite journal | vauthors = Africander D, Verhoog N, Hapgood JP | title = Molecular mechanisms of steroid receptor-mediated actions by synthetic progestins used in HRT and contraception | journal = Steroids | volume = 76 | issue = 7 | pages = 636–652 | date = June 2011 | pmid = 21414337 | doi = 10.1016/j.steroids.2011.03.001 | s2cid = 23630452 }}</ref>
|}

====Progestogenic activity====
Drospirenone is an [[agonist]] of the PR, the [[biological target]] of [[progestogen (medication)|progestogen]]s like [[progesterone (medication)|progesterone]].<ref name="Kuhl2005" /><ref name="pmid7625729" /> It has about 35% of the affinity of [[promegestone]] for the PR and about 19 to 70% of the affinity of progesterone for the PR.<ref name="Kuhl2005" /><ref name="Krattenmacher2000" /><ref name="pmid21414337" /> Drospirenone has [[antigonadotropic]] and functional [[antiestrogen]]ic effects as a result of PR activation.<ref name="Kuhl2005" /><ref name="pmid7625729" /> The [[ovulation]]-inhibiting dosage of drospirenone is 2 to 3&nbsp;mg/day.<ref name="pmid30325245">{{cite journal | vauthors = Bastianelli C, Farris M, Rosato E, Brosens I, Benagiano G | title = Pharmacodynamics of combined estrogen-progestin oral contraceptives 3. Inhibition of ovulation | journal = Expert Review of Clinical Pharmacology | volume = 11 | issue = 11 | pages = 1085–1098 | date = November 2018 | pmid = 30325245 | doi = 10.1080/17512433.2018.1536544 | s2cid = 53246678 }}</ref><ref name="pmid22078182">{{cite journal | vauthors = Endrikat J, Gerlinger C, Richard S, Rosenbaum P, Düsterberg B | title = Ovulation inhibition doses of progestins: a systematic review of the available literature and of marketed preparations worldwide | journal = Contraception | volume = 84 | issue = 6 | pages = 549–557 | date = December 2011 | pmid = 22078182 | doi = 10.1016/j.contraception.2011.04.009 }}</ref><ref name="Kuhl2005" /><ref name="Kuhl2011" /> Inhibition of ovulation occurred in about 90% of women at a dose of 0.5 to 2&nbsp;mg/day and in 100% of women at a dose of 3&nbsp;mg/day.<ref name="pmid14667981" /> The total [[endometrial transformation]] dose of drospirenone is about 50&nbsp;mg per cycle, whereas its daily dose is 2&nbsp;mg for partial transformation and 4 to 6&nbsp;mg for full transformation.<ref name="Kuhl2005" /><ref name="pmid14670641">{{cite journal | vauthors = Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH | title = Classification and pharmacology of progestins | journal = Maturitas | volume = 46 | issue = Suppl 1 | pages = S7–S16 | date = December 2003 | pmid = 14670641 | doi = 10.1016/j.maturitas.2003.09.014 }}</ref><ref name="pmid14667981">{{cite journal | vauthors = Elger W, Beier S, Pollow K, Garfield R, Shi SQ, Hillisch A | title = Conception and pharmacodynamic profile of drospirenone | journal = Steroids | volume = 68 | issue = 10–13 | pages = 891–905 | date = November 2003 | pmid = 14667981 | doi = 10.1016/j.steroids.2003.08.008 | s2cid = 41756726 }}</ref> The medication acts as a contraceptive by activating the PR, which suppresses the [[secretion]] of [[luteinizing hormone]], inhibits ovulation, and alters the [[cervix|cervical membrane]] and [[endometrium]].<ref name="Drospirenone">{{cite web|title=Drospirenone|url=https://pubchem.ncbi.nlm.nih.gov/compound/Drospirenone#section=InChI-Key|website=pubchem.ncbi.nlm.nih.gov|language=en}}</ref><ref name="Slynd-Label" />

Due to its antigonadotropic effects, drospirenone inhibits the secretion of the [[gonadotropin]]s, [[luteinizing hormone]] (LH) and [[follicle-stimulating hormone]] (FSH), and suppresses [[gonad]]al [[sex hormone]] [[biosynthesis|production]], including of [[estradiol]], [[progesterone]], and [[testosterone]].<ref name="Kuhl2005" /><ref name="pmid31446440">{{cite journal | vauthors = Hadji P, Colli E, Regidor PA | title = Bone health in estrogen-free contraception | journal = Osteoporosis International | volume = 30 | issue = 12 | pages = 2391–2400 | date = December 2019 | pmid = 31446440 | pmc = 7203087 | doi = 10.1007/s00198-019-05103-6 }}</ref><ref name="Krattenmacher2000" /> Drospirenone alone at 4&nbsp;mg/day has been found to suppress estradiol levels in [[premenopausal]] women to about 40 to 80&nbsp;pg/mL depending on the time of the cycle.<ref name="pmid31446440" /> No studies of the antigonadotropic effects of drospirenone or its influence on hormone levels appear to have been conducted in men.<ref name="CorniaAnawalt2005" /><ref name="pmid20933120">{{cite journal | vauthors = Nieschlag E | title = Clinical trials in male hormonal contraception | journal = Contraception | volume = 82 | issue = 5 | pages = 457–470 | date = November 2010 | pmid = 20933120 | doi = 10.1016/j.contraception.2010.03.020 | url = http://www.kup.at/kup/pdf/10172.pdf }}</ref><ref name="NieschlagBehre2012">{{cite book| vauthors = Nieschlag E, Behre HM |chapter=The essential role of testosterone in hormonal male contraception | veditors = Nieschlag E, Behre HM, Nieschlag S |title=Testosterone  |year=2012|pages=470–493|publisher=Cambridge University Press |doi=10.1017/CBO9781139003353.023|isbn=978-1-139-00335-3 }}</ref> In male [[cynomolgus monkey]]s however, 4&nbsp;mg/kg/day oral drospirenone strongly suppressed [[testosterone]] levels.<ref name="pmid7625729"/>

====Antimineralocorticoid activity====
Drospirenone is an [[receptor antagonist|antagonist]] of the MR, the [[biological target]] of [[mineralocorticoid]]s like [[aldosterone]], and hence is an antimineralocorticoid.<ref name="pmid7625729" /> It has about 100 to 500% of the affinity of aldosterone for the MR and about 50 to 230% of the affinity of progesterone for the MR.<ref name="Kuhl2005" /><ref name="Krattenmacher2000" /><ref name="pmid23954501" /><ref name="pmid21414337" /> Drospirenone is about 5.5 to 11&nbsp;times more potent as an antimineralocorticoid than [[spironolactone]] in animals.<ref name="pmid7625729" /><ref name="pmid14667981"/><ref name="Stanczyk2007" /> Accordingly, 3 to 4&nbsp;mg drospirenone is said to be equivalent to about 20 to 25&nbsp;mg spironolactone in terms of antimineralocorticoid activity.<ref name="SchneiderNaftolin2004">{{cite book| vauthors = Schneider HP, Naftolin F |title=Climacteric Medicine - Where Do We Go?: Proceedings of the 4th Workshop of the International Menopause Society|url=https://books.google.com/books?id=jaOebeNbAkUC&pg=PA133|date=22 September 2004|publisher=CRC Press|isbn=978-0-203-02496-6|pages=133–}}</ref><ref name="Slynd-Label" /> It has been said that the [[pharmacology|pharmacological]] profile of drospirenone more closely resembles that of progesterone than other progestins due to its antimineralocorticoid activity.<ref name="pmid7625729">{{cite journal | vauthors = Muhn P, Fuhrmann U, Fritzemeier KH, Krattenmacher R, Schillinger E | title = Drospirenone: a novel progestogen with antimineralocorticoid and antiandrogenic activity | journal = Annals of the New York Academy of Sciences | volume = 761 | issue = 3 | pages = 311–335 | date = June 1995 | pmid = 7625729 | doi = 10.1111/j.1749-6632.1995.tb31386.x | s2cid = 36861309 | bibcode = 1995NYASA.761..311M }}</ref> Drospirenone is the only clinically used progestogen with prominent antimineralocorticoid activity besides progesterone.<ref name="Kuhl2005" /> For comparison to progesterone, a 200&nbsp;mg dose of oral progesterone is considered to be approximately equivalent in antimineralocorticoid effect to a 25 to 50&nbsp;mg dose of spironolactone.<ref name="pmid8616985">{{cite journal | vauthors = Simon JA | title = Micronized progesterone: vaginal and oral uses | journal = Clinical Obstetrics and Gynecology | volume = 38 | issue = 4 | pages = 902–914 | date = December 1995 | pmid = 8616985 | doi = 10.1097/00003081-199538040-00024 }}</ref> Both drospirenone and progesterone are actually weak [[partial agonist]]s of the MR in the absence of [[mineralocorticoid]]s.<ref name="pmid23238854" /><ref name="Krattenmacher2000" /><ref name="pmid21414337" />

Due to its antimineralocorticoid activity, drospirenone increases [[natriuresis]], decreases [[water retention (medicine)|water retention]] and [[blood pressure]], and produces compensatory increases in [[plasma renin activity]] as well as circulating levels and [[urine|urinary]] [[excretion]] of [[aldosterone]].<ref name="Krattenmacher2000" /><ref name="Genazzani 2007">{{cite journal | vauthors = Genazzani AR, Mannella P, Simoncini T | title = Drospirenone and its antialdosterone properties | journal = Climacteric | volume = 10 Suppl 1 | issue = Supplement 1 | pages = 11–18 | date = February 2007 | pmid = 17364593 | doi = 10.1080/13697130601114891 | s2cid = 24872884 }}</ref><ref name="Kuhl2005" /> This has been shown to occur at doses of 2 to 4&nbsp;mg/day.<ref name="Krattenmacher2000" /> Similar effects occur during the [[luteal phase]] of the [[menstrual cycle]] due to increased progesterone levels and the resulting antagonism of the MR.<ref name="Krattenmacher2000" /> Estrogens, particularly [[ethinylestradiol]], activate [[liver protein synthesis|liver production]] of [[angiotensinogen]] and increase levels of angiotensinogen and [[angiotensin II]], thereby activating the [[renin–angiotensin–aldosterone system]].<ref name="Krattenmacher2000" /><ref name="Kuhl2005" /> As a result, they can produce undesirable side effects including increased [[sodium]] excretion, water retention, [[weight gain]], and increased blood pressure.<ref name="Krattenmacher2000" /> Progesterone and drospirenone counteract these undesirable effects via their antimineralocorticoid activity.<ref name="Krattenmacher2000" /> Accumulating research indicates that antimineralocorticoids like drospirenone and spironolactone may also have positive effects on [[adipose tissue]] and [[metabolism|metabolic]] health.<ref name="InfanteArmani2019">{{cite journal | vauthors = Infante M, Armani A, Marzolla V, Fabbri A, Caprio M | title = Adipocyte Mineralocorticoid Receptor | journal = Vitamins and Hormones | volume = 109 | pages = 189–209 | year = 2019 | pmid = 30678856 | doi = 10.1016/bs.vh.2018.10.005 | publisher = Elsevier | isbn = 978-0-12-817782-2 | s2cid = 59251387 }}</ref><ref name="pmid26965204">{{cite journal | vauthors = Giordano A, Frontini A, Cinti S | title = Convertible visceral fat as a therapeutic target to curb obesity | journal = Nature Reviews. Drug Discovery | volume = 15 | issue = 6 | pages = 405–424 | date = June 2016 | pmid = 26965204 | doi = 10.1038/nrd.2016.31 | hdl-access = free | s2cid = 2632187 | hdl = 11566/235770 }}</ref>

====Antiandrogenic activity====
Drospirenone is an antagonist of the AR, the biological target of [[androgen]]s like [[testosterone]] and [[dihydrotestosterone]] (DHT).<ref name="Kuhl2005" /><ref name="Krattenmacher2000" /> It has about 1 to 65% of the affinity of the synthetic [[anabolic steroid]] [[metribolone]] for the AR.<ref name="Kuhl2005" /><ref name="Krattenmacher2000" /><ref name="pmid23238854" /><ref name="pmid21414337" /> The medication is more potent as an antiandrogen than [[spironolactone]], but is less potent than [[cyproterone acetate]], with about 30% of its antiandrogenic activity in animals.<ref name="Kuhl2005" /><ref name="pmid15669548">{{cite journal | vauthors = Sitruk-Ware R, Husmann F, Thijssen JH, Skouby SO, Fruzzetti F, Hanker J, Huber J, Druckmann R | title = Role of progestins with partial antiandrogenic effects | journal = Climacteric | volume = 7 | issue = 3 | pages = 238–254 | date = September 2004 | pmid = 15669548 | doi = 10.1080/13697130400001307 | s2cid = 23112620 }}</ref><ref name="pmid7625729" /><ref name="pmid14667981" /> Progesterone displays antiandrogenic activity in some assays similarly to drospirenone,<ref name="Krattenmacher2000" /> although this issue is controversial and many researchers regard progesterone as having no significant antiandrogenic activity.<ref name="pmid23484104">{{cite journal | vauthors = Yeh YT, Chang CW, Wei RJ, Wang SN | title = Progesterone and related compounds in hepatocellular carcinoma: basic and clinical aspects | journal = BioMed Research International | volume = 2013 | pages = 290575 | date = 2013 | pmid = 23484104 | pmc = 3581253 | doi = 10.1155/2013/290575 | doi-access = free }}</ref><ref name="Kuhl2005" /><ref name="pmid23238854" />

Drospirenone shows antiandrogenic effects on the [[serum lipids|serum]] [[lipid profile]], including higher [[high-density lipoprotein|HDL]] [[cholesterol]] and [[triglyceride]] levels and lower [[low-density lipoprotein|LDL]] cholesterol levels, at a dose of 3&nbsp;mg/day in women.<ref name="Krattenmacher2000" /> The medication does not inhibit the effects of [[ethinylestradiol]] on [[sex hormone-binding globulin]] (SHBG) and serum lipids, in contrast to androgenic progestins like [[levonorgestrel]] but similarly to other antiandrogenic progestins like cyproterone acetate.<ref name="Krattenmacher2000" /><ref name="Kuhl2005" /><ref name="Kuhl2011">{{cite journal | vauthors = Kuhl H | title = Pharmacology of Progestogens | journal = J Reproduktionsmed Endokrinol | year = 2011 | volume = 8 | issue = 1 | pages = 157–177 | url = http://www.kup.at/kup/pdf/10168.pdf}}</ref> SHBG levels are significantly higher with [[ethinylestradiol/cyproterone acetate|ethinylestradiol and cyproterone acetate]] than with ethinylestradiol and drospirenone, owing to the more potent antiandrogenic activity of cyproterone acetate relative to drospirenone.<ref name="Schindler2015">{{cite book| vauthors = Schindler AE |title=Frontiers in Gynecological Endocrinology|chapter=Hormonal Contraceptives: Progestogen and Thrombotic Risk|year=2015|pages=69–75|issn=2197-8735|doi=10.1007/978-3-319-09662-9_8|series=ISGE Series|publisher=Springer |isbn=978-3-319-09661-2}}</ref> [[Androgen]]ic progestins like levonorgestrel have been found to inhibit the [[procoagulation|procoagulatory]] effects of estrogens like ethinylestradiol on hepatic synthesis of [[coagulation factor]]s, whereas this may occur less or not at all with weakly androgenic progestins like [[desogestrel]] and antiandrogenic progestins like drospirenone.<ref name="pmid26598309" /><ref name="pmid28712325" /><ref name="pmid17056444" /><ref name="pmid8794429" /><ref name="pmid23384742" /><ref name="pmid26512437" />

====Other activity====
Drospirenone stimulates the [[cell proliferation|proliferation]] of [[MCF-7]] [[breast cancer]] [[cell (biology)|cell]]s ''[[in vitro]]'', an action that is independent of the classical PRs and is instead mediated via the [[progesterone receptor membrane component-1]] (PGRMC1).<ref name="pmid23758160">{{cite journal | vauthors = Neubauer H, Ma Q, Zhou J, Yu Q, Ruan X, Seeger H, Fehm T, Mueck AO | title = Possible role of PGRMC1 in breast cancer development | journal = Climacteric | volume = 16 | issue = 5 | pages = 509–513 | date = October 2013 | pmid = 23758160 | doi = 10.3109/13697137.2013.800038 | s2cid = 29808177 }}</ref> Certain other progestins act similarly in this assay, whereas [[progesterone (medication)|progesterone]] acts neutrally.<ref name="pmid23758160" /> It is unclear if these findings may explain the different risks of breast cancer observed with progesterone and progestins in [[clinical trial|clinical studies]].<ref name="pmid31512725"/>

===Pharmacokinetics===

====Absorption====
The [[oral administration|oral]] [[bioavailability]] of drospirenone is between 66 and 85%.<ref name="Kuhl2005" /><ref name="Krattenmacher2000" /><ref name="pmid23238854" /> [[Cmax (pharmacology)|Peak]] levels occur 1 to 6&nbsp;hours after an oral dose.<ref name="Kuhl2005" /><ref name="Krattenmacher2000" /><ref name="Slynd-Label" /><ref name="Stanczyk2007">{{cite book| vauthors = Stanczyk FZ |title=Treatment of the Postmenopausal Woman|chapter=Structure –Function Relationships, Pharmacokinetics, and Potency of Orally and Parenterally Administered Progestogens|year=2007|pages=779–798|publisher=Academic Press |doi=10.1016/B978-012369443-0/50067-3|isbn=978-0-12-369443-0}}</ref> Levels are about 27&nbsp;ng/mL after a single 4&nbsp;mg dose.<ref name="Slynd-Label" /> There is 1.5- to 2-fold accumulation in drospirenone levels with continuous administration, with [[steady state (pharmacokinetics)|steady-state]] levels of drospirenone achieved after 7 to 10&nbsp;days of administration.<ref name="Kuhl2005" /><ref name="Slynd-Label" /><ref name="Krattenmacher2000" /> Peak levels of drospirenone at steady state with 4&nbsp;mg/day drospirenone are about 41&nbsp;ng/mL.<ref name="Slynd-Label" /> With the combination of 30&nbsp;μg/day [[ethinylestradiol]] and 3&nbsp;mg/day drospirenone, peak levels of drospirenone after a single dose are 35&nbsp;ng/mL, and levels at steady state are 60 to 87&nbsp;ng/mL at peak and 20 to 25&nbsp;ng/mL at [[Cmin (pharmacology)|trough]].<ref name="Krattenmacher2000" /><ref name="Kuhl2005" /> The [[pharmacokinetics]] of oral drospirenone are linear with a single dose across a dose range of 1 to 10&nbsp;mg.<ref name="Slynd-Label" /><ref name="Krattenmacher2000" /> Intake of drospirenone with [[food]] does not influence the [[absorption (pharmacokinetics)|absorption]] of drospirenone.<ref name="Slynd-Label" />

====Distribution====
The [[distribution half-life]] of drospirenone is about 1.6 to 2&nbsp;hours.<ref name="Krattenmacher2000" /><ref name="Kuhl2005" /> The apparent [[volume of distribution]] of drospirenone is approximately 4&nbsp;L/kg.<ref name="Slynd-Label" /> The [[plasma protein binding]] of drospirenone is 95 to 97%.<ref name="Slynd-Label" /><ref name="Kuhl2005" /> It is bound to [[human serum albumin|albumin]] and 3 to 5% circulates freely or unbound.<ref name="Slynd-Label" /><ref name="Kuhl2005" /> Drospirenone has no [[affinity (pharmacology)|affinity]] for [[sex hormone-binding globulin]] (SHBG) or [[corticosteroid-binding globulin]] (CBG), and hence is not bound by these [[plasma protein]]s in the circulation.<ref name="Kuhl2005" />

====Metabolism====
The [[metabolism]] of drospirenone is extensive.<ref name="Krattenmacher2000" /> It is [[metabolism|metabolized]] into the [[acid]] form of drospirenone by opening of its [[lactone]] [[ring (chemistry)|ring]].<ref name="Kuhl2005" /><ref name="Slynd-Label" /> The medication is also metabolized by [[redox|reduction]] of its [[double bond]] between the C4 and C5 positions and subsequent [[sulfation]].<ref name="Kuhl2005" /><ref name="Slynd-Label" /> The two major [[metabolite]]s of drospirenone are drospirenone acid and 4,5-dihydrodrospirenone 3-sulfate, and are both formed independently of the [[cytochrome P450]] system.<ref name="Slynd-Label" /><ref name="Krattenmacher2000" /> Neither of these metabolites are known to be [[biological activity|pharmacologically active]].<ref name="Slynd-Label" /> Drospirenone also undergoes [[oxidation|oxidative]] metabolism by [[CYP3A4]].<ref name="Slynd-Label" /><ref name="Krattenmacher2000" /><ref name="Bachmann2009"/><ref name="WiesingerBerse2015"/>

====Elimination====
Drospirenone is [[excretion|excreted]] in [[urine]] and [[feces]], with slightly more excreted in feces than in urine.<ref name="Slynd-Label" /> Only trace amounts of unchanged drospirenone can be found in urine and feces.<ref name="Slynd-Label" /> At least 20 different [[metabolite]]s can be identified in urine and feces.<ref name="Krattenmacher2000" /> Drospirenone and its metabolites are excreted in urine about 38% as [[glucuronide]] [[conjugation (biochemistry)|conjugate]]s, 47% as [[sulfate]] conjugates, and less than 10% in unconjugated form.<ref name="Krattenmacher2000" /> In feces, excretion is about 17% glucuronide conjugates, 20% sulfate conjugates, and 33% unconjugated.<ref name="Krattenmacher2000" />

The [[elimination half-life]] of drospirenone is between 25 and 33&nbsp;hours.<ref name="Slynd-Label" /><ref name="Krattenmacher2000" /><ref name="Kuhl2005" /> The half-life of drospirenone is unchanged with repeated administration.<ref name="Slynd-Label" /> Elimination of drospirenone is virtually complete 10&nbsp;days after the last dose.<ref name="Krattenmacher2000" /><ref name="Slynd-Label" />

==Chemistry==
{{See also|Spirolactone|List of progestogens#Spirolactone derivatives|List of steroidal antiandrogens#Spirolactone derivatives}}
{{Spirolactone structures|align=right|caption=[[Chemical structure]]s of [[progesterone (medication)|progesterone]] and [[spirolactone]]s (steroid-17α-spirolactones).}}

Drospirenone, also known as 1,2-dihydrospirorenone or as 17β-hydroxy-6β,7β:15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21-carboxylic acid, γ-lactone, is a [[synthetic compound|synthetic]] [[steroid]]al [[17α-spirolactone]], or more simply a spirolactone.<ref name="Drugs.com" /><ref name="NegwerScharnow2001" /> It is an [[analog (chemistry)|analogue]] of other spirolactones like [[spironolactone]], [[canrenone]], and [[spirorenone]].<ref name="Drugs.com" /><ref name="NegwerScharnow2001" /> Drospirenone differs structurally from spironolactone only in that the C7α [[acetyl]] [[thio-|thio]] [[substituent|substitution]] of spironolactone has been removed and two [[methylene bridge|methylene groups]] have been substituted in at the C6β–7β and C15β–16β positions.<ref name="Carp2015">{{cite book| vauthors = Carp HJ |title= Progestogens in Obstetrics and Gynecology|url=https://books.google.com/books?id=Ik8SCAAAQBAJ&pg=PA115|date=9 April 2015|publisher=Springer|isbn=978-3-319-14385-9|pages=115–}}</ref>

Spirolactones like drospirenone and spironolactone are [[chemical derivative|derivative]]s of [[progesterone (medication)|progesterone]], which likewise has progestogenic and antimineralocorticoid activity.<ref name="pmid15134800">{{cite journal | vauthors = Ménard J | title = The 45-year story of the development of an anti-aldosterone more specific than spironolactone | journal = Molecular and Cellular Endocrinology | volume = 217 | issue = 1–2 | pages = 45–52 | date = March 2004 | pmid = 15134800 | doi = 10.1016/j.mce.2003.10.008 | quote = [Spironolactone] was synthesized after the demonstration of the natriuretic effect of progesterone (Landau et al., 1955). | s2cid = 19701784 }}</ref><ref name="JamesonGroot2010">{{cite book| vauthors = Jameson JL, De Groot LJ |title=Endocrinology - E-Book: Adult and Pediatric|url=https://books.google.com/books?id=W4dZ-URK8ZoC&pg=PA2401|date=18 May 2010|publisher=Elsevier Health Sciences|isbn=978-1-4557-1126-0|pages=2401–|quote=[Spironolactone] is a potent antimineralocorticoid which was developed as a progestational analog [...]}}</ref><ref name="Elsevier2019">{{cite book|title=Aldosterone|url=https://books.google.com/books?id=5daEDwAAQBAJ&pg=PA46|date=23 January 2019|publisher=Elsevier Science|isbn=978-0-12-817783-9|page=46|quote=In addition to spironolactone, which is a derivative of progesterone [...]}}</ref> The loss of the C7α acetylthio group of spironolactone, a compound with negligible progestogenic activity,<ref name="pmid16101407">{{cite journal | vauthors = Hu X, Li S, McMahon EG, Lala DS, Rudolph AE | title = Molecular mechanisms of mineralocorticoid receptor antagonism by eplerenone | journal = Mini Reviews in Medicinal Chemistry | volume = 5 | issue = 8 | pages = 709–718 | date = August 2005 | pmid = 16101407 | doi = 10.2174/1389557054553811 }}</ref><ref name="pmid2744183">{{cite journal | vauthors = Nakajima ST, Brumsted JR, Riddick DH, Gibson M | title = Absence of progestational activity of oral spironolactone | journal = Fertility and Sterility | volume = 52 | issue = 1 | pages = 155–158 | date = July 1989 | pmid = 2744183 | doi = 10.1016/s0015-0282(16)60807-5 | doi-access =  }}</ref> appears to be involved in the restoration of progestogenic activity in drospirenone, as [[SC-5233]], the analogue of spironolactone without a C7α substitution, has potent progestogenic activity similarly to drospirenone.<ref name="pmid13601900">{{cite journal | vauthors = Hertz R, Tullner WW | title = Progestational activity of certain steroid-17-spirolactones | journal = Proceedings of the Society for Experimental Biology and Medicine | volume = 99 | issue = 2 | pages = 451–452 | date = November 1958 | pmid = 13601900 | doi = 10.3181/00379727-99-24380 | s2cid = 20150966 }}</ref>

==History==
Drospirenone was patented in 1976 and introduced for medical use in 2000.<ref name="Ravina2011" /><ref name=Fis2006/> [[Schering AG]] of [[Germany]] has been granted several patents on the production of drospirenone, including WIPO and US patents, granted in 1998 and 2000, respectively.<ref>{{Cite patent|country=WO|number=9806738|title=PROCESS FOR PRODUCING DROSPIRENONE (6ss,7ss;15ss,16ss-DIMETHYLENE-3-OXO-17 alpha -PREGN-4-EN-21,17-CARBOLACTONE, DRSP), AS WELL AS 7 alpha -(3-HYDROXY-1-PROPYL)-6ss,7ss;15ss,16ss-DIMETHYLENE-5ss-ANDROSTANE-3ss,5,17ss-TRIOL (ZK 92836) AND 6ss,7ss;15ss,16ss-DIMETHYLENE-5ss HYDROXY-5-OXO-17 alpha -ANDROSTANE-21, 17-CARBOLACTONE|status=patent|pubdate=|fdate=1997-08-11|pridate=1996-08-12|gdate=1998-02-19|invent1=Mohr|invent2=Nickisch|inventor1-first=Jörg-Thorsten|inventor2-first=Klaus|assign1=Shering AG|url=https://worldwide.espacenet.com/patent/search/family/007803224/publication/WO9806738A1}} {{Webarchive|url=https://web.archive.org/web/20231208183301/https://worldwide.espacenet.com/patent/search/family/007803224/publication/WO9806738A1 |date=8 December 2023 }}</ref><ref>{{Cite patent|country=US|number=6121465|title=Process for production drospirenone and intermediate products of the process|status=patent|pubdate=|fdate=1999-02-11|pridate=1996-08-12|gdate=2000-09-19|invent1=Mohr|invent2=Nickisch|inventor1-first=Joerg-Thorston|inventor2-first=Klaus|assign1=Scheiring AG|assign2=Bayer Schering Pharma|url=https://worldwide.espacenet.com/patent/search/family/007803224/publication/US6121465A}} {{Webarchive|url=https://web.archive.org/web/20231208183300/https://worldwide.espacenet.com/patent/search/family/007803224/publication/US6121465A |date=8 December 2023 }}</ref> It was introduced for medical use in combination with [[ethinylestradiol]] as a [[combined birth control pill]] in 2000.<ref name="Ravina2011">{{cite book| vauthors = Ravina E |title=The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs|url=https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA193|date=11 January 2011|publisher=John Wiley & Sons|isbn=978-3-527-32669-3|pages=193–}}</ref> Drospirenone is sometimes described as a "fourth-generation" progestin based on its time of introduction.<ref name="HatcherM.D.2007">{{cite book |chapter-url=https://books.google.com/books?id=txh0LpjjhkoC&pg=PA196 |title=Contraceptive Technology |vauthors=Nelson AL |publisher=Ardent Media |year=2007 |isbn=978-1-59708-001-9 |veditors=Hatcher RA, Trussell J, Nelson AL, [[Ward Cates|Cates W]], [[Felicia Stewart|Stewart FH]], Kowal D |edition=19th |page=196 |chapter=Combined Oral Contraceptives}}</ref><ref name="RossoZeichner2016">{{cite book |chapter-url=https://books.google.com/books?id=Au8VDAAAQBAJ&pg=PA160 |title=Advances in Acne Management, An Issue of Dermatologic Clinics, E-Book |vauthors=Harper JC |date=20 April 2016 |publisher=Elsevier Health Sciences |isbn=978-0-323-41753-2 |veditors=Del Rosso JQ, Zeichner JA |page=160 |chapter=Use of Oral Contraceptives for Management of Acne Vulgaris}}</ref> The medication was approved for use in [[menopausal hormone therapy]] in combination with [[estradiol (medication)|estradiol]] in 2005.<ref name="Angeliq-Label" /> Drospirenone was introduced for use as a [[progestogen-only birth control pill]] in 2019.<ref name="Slynd-Label" /> A combined birth control pill containing [[estetrol (medication)|estetrol]] and drospirenone was approved in 2021.<ref name="AdisInsight-E4/DRSP">{{Cite web|url=https://adisinsight.springer.com/drugs/800034634|title=Drospirenone/Estetrol - Mithra Pharmaceuticals | work = AdisInsight | publisher = Springer Nature Switzerland AG }}</ref>

==Society and culture==

===Generic names===
''Drospirenone'' is the [[generic term|generic name]] of the drug and its {{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|BAN|British Approved Name}}, and {{abbrlink|JAN|Japanese Accepted Name}}, while ''drospirénone'' is its {{abbrlink|DCF|Dénomination Commune Française}}.<ref name="Drugs.com">drospirenone at Drugs.com: {{Drugs.com|mtm|drospirenone}}</ref> Its name is a shortened form of the name ''1,2-dihydrospirorenone'' or ''dihydrospirenone''.<ref name="Drugs.com" /><ref name="NegwerScharnow2001" /> Drospirenone is also known by its developmental code names ''SH-470'' and ''ZK-30595'' (alone), ''BAY 86-5300'', ''BAY 98-7071'', and ''SH-T-00186D'' (in combination with [[ethinylestradiol]]), ''BAY 86-4891'' (in combination with [[estradiol (medication)|estradiol]]), and ''FSN-013'' (in combination with [[estetrol (medication)|estetrol]]).<ref name="Drugs.com" /><ref name="NegwerScharnow2001">{{cite book| vauthors = Negwer M, Scharnow HG |title=Organic-chemical drugs and their synonyms: (an international survey)|url=https://books.google.com/books?id=1XBqAAAAMAAJ|date=4 October 2001|publisher=Wiley-VCH|isbn=978-3-527-30247-5|page=2539}}</ref><ref name="AdisInsight-EE/DRSP">{{cite web | url=https://adisinsight.springer.com/drugs/800007379 | title=Ethinylestradiol/drospirenone | work = AdisInsight | publisher = Springer Nature Switzerland AG}}</ref><ref name="EE/DRSP/FA">{{cite web | url=https://adisinsight.springer.com/drugs/800032716 | title=Ethinylestradiol/drospirenone/folic acid | work = AdisInsight | publisher = Springer Nature Switzerland AG }}</ref><ref name="EE/DRSP-Low">{{cite web | url=https://adisinsight.springer.com/drugs/800017043 | title=Drospirenone/ethinylestradiol low-dose - Bayer HealthCare Pharmaceuticals | work = AdisInsight | publisher = Springer Nature Switzerland AG}}</ref><ref name="E2/DRSP">{{cite web | url=https://adisinsight.springer.com/drugs/800014148 | title=Estradiol/drospirenone - Bayer HealthCare Pharmaceuticals | work = AdisInsight | publisher = Springer Nature Switzerland AG }}</ref><ref name="AdisInsight-E4/DRSP" />

===Brand names===
Drospirenone is marketed in combination with an estrogen under a variety of brand names throughout the world.<ref name="Drugs.com" /> Among others, it is marketed in combination with [[ethinylestradiol]] under the brand names Yasmin and Yaz, in combination with estetrol under the brand name Nextstellis, and in combination with [[estradiol (medication)|estradiol]] under the brand name Angeliq.<ref name="Drugs.com" /><ref name="AdisInsight-E4/DRSP" />

===Availability===
{{See also|List of progestogens available in the United States}}

Drospirenone is marketed widely throughout the world.<ref name="Drugs.com" />

===Generation===
Drospirenone has been categorized as a "fourth-generation" progestin.<ref name="pmid21414337" />

===Litigation===
Many lawsuits have been filed against [[Bayer]], the manufacturer of drospirenone, due to the higher risk of [[venous thromboembolism]] (VTE) that has been observed with combined birth control pills containing drospirenone and certain other progestins relative to the risk with levonorgestrel-containing combined birth control pills.<ref name="pmid27854556" />

In July 2012, Bayer notified its stockholders that there were more than 12,000 such lawsuits against the company involving Yaz, Yasmin, and other birth control pills with drospirenone.<ref name="Feeley 2012">{{cite news| vauthors = Feeley J, Kresge N |date=31 July 2012|title=Bayer's Yasmin lawsuit settlements rise to $402.6 million|location=New York|work=Bloomberg News|url=https://www.bloomberg.com/news/2012-07-31/bayer-s-yasmin-lawsuit-settlements-rise-to-402-6-million.html|access-date=11 November 2012}}</ref> They also noted that the company by then had settled 1,977 cases for US$402.6 million, for an average of US$212,000 per case, while setting aside US$610.5 million to settle the others.<ref name="Feeley 2012" />

As of 17 July 2015, there have been at least 4,000 lawsuits and claims still pending regarding VTE related to drospirenone.<ref name="Bayer2015">{{Cite web|url=https://www.bayer.com/en/quarterly-reports.aspx|title=Quarterly Reports of Bayer| work = Bayer AG }}</ref> This is in addition to around 10,000 claims that Bayer has already settled without admitting liability.<ref name="Bayer2015" /> These claims of VTE have amounted to US$1.97 billion.<ref name="Bayer2015" /> Bayer also reached a settlement for [[arterial thromboembolic events]], including [[stroke]] and [[heart attack]]s, for US$56.9 million.<ref name="Bayer2015" />

==Research==
{{See also|Estetrol/drospirenone|Ethinylestradiol/drospirenone/prasterone}}

A combination of [[ethinylestradiol/drospirenone/prasterone|ethinylestradiol, drospirenone, and prasterone]] is under development by Pantarhei Bioscience as a combined birth control pill for prevention of pregnancy in women.<ref name="AdisInsight-EE-DRSP-DHEA">{{Cite web|url=https://adisinsight.springer.com/drugs/800026485|title=Drospirenone/estradiol/prasterone - ANI Pharmaceuticals/Pantarhei Bioscience | work = AdisInsight | publisher = Springer Nature Switzerland AG}}</ref> It includes [[prasterone]] (dehydroepiandrosterone; DHEA), an oral [[androgen prohormone]], to [[androgen replacement therapy|replace testosterone]] and avoid [[testosterone deficiency]] caused by suppression of testosterone by ethinylestradiol and drospirenone.<ref name="AdisInsight-EE-DRSP-DHEA" /> As of August 2018, the formulation is in [[Phases of clinical research#Phase II|phase II]]/III [[clinical trial]]s.<ref name="AdisInsight-EE-DRSP-DHEA" />

Drospirenone has been suggested for potential use as a progestin in [[male hormonal contraception]].<ref name="CorniaAnawalt2005">{{cite journal| vauthors = Cornia PB, Anawalt BD |title=Male hormonal contraceptives: a potentially patentable and profitable product|journal=Expert Opinion on Therapeutic Patents|volume=15|issue=12|year=2005|pages=1727–1737|issn=1354-3776|doi=10.1517/13543776.15.12.1727|s2cid=83941717}}</ref>

Drospirenone has been studied in forms for [[parenteral administration]].<ref name="pmid21729745">{{cite journal | vauthors = Nippe S, General S | title = Parenteral oil-based drospirenone microcrystal suspensions-evaluation of physicochemical stability and influence of stabilising agents | journal = International Journal of Pharmaceutics | volume = 416 | issue = 1 | pages = 181–188 | date = September 2011 | pmid = 21729745 | doi = 10.1016/j.ijpharm.2011.06.036 }}</ref><ref name="pmid22940138">{{cite journal | vauthors = Nippe S, General S | title = Combination of injectable ethinyl estradiol and drospirenone drug-delivery systems and characterization of their in vitro release | journal = European Journal of Pharmaceutical Sciences | volume = 47 | issue = 4 | pages = 790–800 | date = November 2012 | pmid = 22940138 | doi = 10.1016/j.ejps.2012.08.009 }}</ref><ref name="pmid23116659">{{cite journal | vauthors = Nippe S, Preuße C, General S | title = Evaluation of the in vitro release and pharmacokinetics of parenteral injectable formulations for steroids | journal = European Journal of Pharmaceutics and Biopharmaceutics | volume = 83 | issue = 2 | pages = 253–265 | date = February 2013 | pmid = 23116659 | doi = 10.1016/j.ejpb.2012.09.006 }}</ref><ref name="pmid24621345">{{cite journal | vauthors = Nippe S, General S | title = Investigation of injectable drospirenone organogels with regard to their rheology and comparison to non-stabilized oil-based drospirenone suspensions | journal = Drug Development and Industrial Pharmacy | volume = 41 | issue = 4 | pages = 681–691 | date = April 2015 | pmid = 24621345 | doi = 10.3109/03639045.2014.895375 | s2cid = 42932558 }}</ref>

== References ==
{{Reflist}}

== Further reading ==
{{refbegin|30em}}
* {{cite journal | vauthors = Archer DF | title = Drospirenone and estradiol: a new option for the postmenopausal woman | journal = Climacteric | volume = 10 | issue = Suppl 1 | pages = 3–10 | date = February 2007 | pmid = 17364592 | doi = 10.1080/13697130601114859 | s2cid = 9221524 }}
* {{cite journal | vauthors = Archer DF | title = Drospirenone-containing hormone therapy for postmenopausal women. Perspective on current data | journal = The Journal of Reproductive Medicine | volume = 52 | issue = 2 Suppl | pages = 159–164 | date = February 2007 | pmid = 17477110 }}
* {{cite journal | vauthors = Archer DF | title = Drospirenone, a progestin with added value for hypertensive postmenopausal women | journal = Menopause | volume = 14 | issue = 3 Pt 1 | pages = 352–354 | date = 2007 | pmid = 17414576 | doi = 10.1097/gme.0b013e31804d440b }}
* {{cite journal | vauthors = Batur P, Casey PM | title = Drospirenone Litigation: Does the Punishment Fit the Crime? | journal = Journal of Women's Health | volume = 26 | issue = 2 | pages = 99–102 | date = February 2017 | pmid = 27854556 | doi = 10.1089/jwh.2016.6092 | doi-access = free }}
* {{cite journal | vauthors = Bitzer J, Paoletti AM | title = Added benefits and user satisfaction with a low-dose oral contraceptive containing drospirenone: results of three multicentre trials | journal = Clinical Drug Investigation | volume = 29 | issue = 2 | pages = 73–78 | date = 2009 | pmid = 19133702 | doi = 10.2165/0044011-200929020-00001 | s2cid = 10356578 }}
* {{cite journal | vauthors = Carranza-Lira S | title = Safety, efficacy and patient acceptability of drospirenone and estradiol in the treatment of menopausal vasomotor symptoms: a review | journal = Clinical Interventions in Aging | volume = 4 | issue =  | pages = 59–62 | date = 2009 | pmid = 19503766 | pmc = 2685225 | doi = 10.2147/CIA.S4117 | doi-access = free }}
* {{cite journal | vauthors = Christiansen C | title = Effects of drospirenone/estrogen combinations on bone metabolism | journal = Climacteric | volume = 8 | issue = Suppl 3 | pages = 35–41 | date = October 2005 | pmid = 16203654 | doi = 10.1080/13697130500330283 | s2cid = 42803561 }}
* {{cite journal | vauthors = Dickerson V | title = Quality of life issues. Potential role for an oral contraceptive containing ethinyl estradiol and drospirenone | journal = The Journal of Reproductive Medicine | volume = 47 | issue = 11 Suppl | pages = 985–993 | date = November 2002 | pmid = 12497673 }}
* {{cite journal | vauthors = Fenton C, Wellington K, Moen MD, Robinson DM | title = Drospirenone/ethinylestradiol 3mg/20microg (24/4 day regimen): a review of its use in contraception, premenstrual dysphoric disorder and moderate acne vulgaris | journal = Drugs | volume = 67 | issue = 12 | pages = 1749–1765 | date = 2007 | pmid = 17683173 | doi = 10.2165/00003495-200767120-00007 | s2cid = 46976925 }}
* {{cite journal | vauthors = Foidart JM | title = Added benefits of drospirenone for compliance | journal = Climacteric | volume = 8 | issue = Suppl 3 | pages = 28–34 | date = October 2005 | pmid = 16203653 | doi = 10.1080/13697130500330309 | s2cid = 31883491 }}
* {{cite journal | vauthors = Foidart JM, Faustmann T | title = Advances in hormone replacement therapy: weight benefits of drospirenone, a 17alpha-spirolactone-derived progestogen | journal = Gynecological Endocrinology | volume = 23 | issue = 12 | pages = 692–699 | date = December 2007 | pmid = 18075844 | doi = 10.1080/09513590701582323 | s2cid = 12572825 }}
* {{cite journal | vauthors = Genazzani AR, Mannella P, Simoncini T | title = Drospirenone and its antialdosterone properties | journal = Climacteric | volume = 10 | issue = Suppl 1 | pages = 11–18 | date = February 2007 | pmid = 17364593 | doi = 10.1080/13697130601114891 | s2cid = 24872884 }}
* {{cite journal | vauthors = Han L, Jensen JT | title = Expert opinion on a flexible extended regimen of drospirenone/ethinyl estradiol contraceptive | journal = Expert Opinion on Pharmacotherapy | volume = 15 | issue = 14 | pages = 2071–2079 | date = October 2014 | pmid = 25186109 | doi = 10.1517/14656566.2014.949237 | s2cid = 25338932 }}
* {{cite journal | vauthors = Heinemann LA, Dinger J | title = Safety of a new oral contraceptive containing drospirenone | journal = Drug Safety | volume = 27 | issue = 13 | pages = 1001–1018 | date = 2004 | pmid = 15471507 | doi = 10.2165/00002018-200427130-00003 | s2cid = 1773936 }}
* {{cite journal | vauthors = Idota N, Kobayashi M, Miyamori D, Kakiuchi Y, Ikegaya H | title = Drospirenone detected in postmortem blood of a young woman with pulmonary thromboembolism: A case report and review of the literature | journal = Legal Medicine | volume = 17 | issue = 2 | pages = 109–115 | date = March 2015 | pmid = 25454533 | doi = 10.1016/j.legalmed.2014.10.001 }}
* {{cite journal | vauthors = Keam SJ, Wagstaff AJ | title = Ethinylestradiol/drospirenone: a review of its use as an oral contraceptive | journal = Treatments in Endocrinology | volume = 2 | issue = 1 | pages = 49–70 | date = 2003 | pmid = 15871554 | doi = 10.2165/00024677-200302010-00005 | s2cid = 209144694 }}
* {{cite journal | vauthors = Krattenmacher R | title = Drospirenone: pharmacology and pharmacokinetics of a unique progestogen | journal = Contraception | volume = 62 | issue = 1 | pages = 29–38 | date = July 2000 | pmid = 11024226 | doi = 10.1016/S0010-7824(00)00133-5 }}
* {{cite journal | vauthors = Larivée N, Suissa S, Khosrow-Khavar F, Tagalakis V, Filion KB | title = Drospirenone-containing oral contraceptive pills and the risk of venous thromboembolism: a systematic review of observational studies | journal = BJOG | volume = 124 | issue = 10 | pages = 1490–1499 | date = September 2017 | pmid = 28276140 | doi = 10.1111/1471-0528.14623 | doi-access = free }}
* {{cite journal | vauthors = Lete I, Chabbert-Buffet N, Jamin C, Lello S, Lobo P, Nappi RE, Pintiaux A | title = Haemostatic and metabolic impact of estradiol pills and drospirenone-containing ethinylestradiol pills vs. levonorgestrel-containing ethinylestradiol pills: A literature review | journal = The European Journal of Contraception & Reproductive Health Care | volume = 20 | issue = 5 | pages = 329–343 | date = 2015 | pmid = 26007631 | doi = 10.3109/13625187.2015.1050091 | s2cid = 41601833 }}
* {{cite journal | vauthors = Li J, Ren J, Sun W | title = A comparative systematic review of Yasmin (drospirenone pill) versus standard treatment options for symptoms of polycystic ovary syndrome | journal = European Journal of Obstetrics, Gynecology, and Reproductive Biology | volume = 210 | pages = 13–21 | date = March 2017 | pmid = 27923166 | doi = 10.1016/j.ejogrb.2016.11.013 }}
* {{cite journal | vauthors = Machado RB, Pompei LD, Giribela AG, Giribela CG | title = Drospirenone/ethinylestradiol: a review on efficacy and noncontraceptive benefits | journal = Women's Health | volume = 7 | issue = 1 | pages = 19–30 | date = January 2011 | pmid = 21175386 | doi = 10.2217/whe.10.84 | doi-access = free }}
* {{cite journal | vauthors = Mallareddy M, Hanes V, White WB | title = Drospirenone, a new progestogen, for postmenopausal women with hypertension | journal = Drugs & Aging | volume = 24 | issue = 6 | pages = 453–466 | date = 2007 | pmid = 17571911 | doi = 10.2165/00002512-200724060-00002 | s2cid = 39236155 }}
* {{cite journal | vauthors = Motivala A, Pitt B | title = Drospirenone for oral contraception and hormone replacement therapy: are its cardiovascular risks and benefits the same as other progestogens? | journal = Drugs | volume = 67 | issue = 5 | pages = 647–655 | date = 2007 | pmid = 17385938 | doi = 10.2165/00003495-200767050-00001 | s2cid = 22985078 }}
* {{cite journal | vauthors = Oelkers W | title = Antimineralocorticoid activity of a novel oral contraceptive containing drospirenone, a unique progestogen resembling natural progesterone | journal = The European Journal of Contraception & Reproductive Health Care | volume = 7 | issue = Suppl 3 | pages = 19–26; discussion 42–3 | date = December 2002 | pmid = 12659403 }}
* {{cite journal | vauthors = Oelkers W | title = Drospirenone--a new progestogen with antimineralocorticoid activity, resembling natural progesterone | journal = The European Journal of Contraception & Reproductive Health Care | volume = 5 | issue = Suppl 3 | pages = 17–24 | date = December 2000 | pmid = 11246598 | doi = 10.1080/14730782.2000.12288986 | s2cid = 35051390 }}
* {{cite journal | vauthors = Oelkers W | title = Drospirenone, a progestogen with antimineralocorticoid properties: a short review | journal = Molecular and Cellular Endocrinology | volume = 217 | issue = 1–2 | pages = 255–261 | date = March 2004 | pmid = 15134826 | doi = 10.1016/j.mce.2003.10.030 | s2cid = 19936032 }}
* {{cite journal | vauthors = Oelkers W | title = The renin-aldosterone system and drospirenone | journal = Gynecological Endocrinology | volume = 16 | issue = 1 | pages = 83–87 | date = February 2002 | pmid = 11915587 | doi = 10.1080/gye.16.1.83.87 | s2cid = 32410408 }}
* {{cite journal | vauthors = Oelkers WH | title = Drospirenone in combination with estrogens: for contraception and hormone replacement therapy | journal = Climacteric | volume = 8 | issue = Suppl 3 | pages = 19–27 | date = October 2005 | pmid = 16203652 | doi = 10.1080/13697130500330341 | s2cid = 42837148 }}
* {{cite journal | vauthors = Palacios S, Foidart JM, Genazzani AR | title = Advances in hormone replacement therapy with drospirenone, a unique progestogen with aldosterone receptor antagonism | journal = Maturitas | volume = 55 | issue = 4 | pages = 297–307 | date = November 2006 | pmid = 16949774 | doi = 10.1016/j.maturitas.2006.07.009 | hdl = 2268/9932 | hdl-access = free }}
* {{cite journal | vauthors = Pérez-López FR | title = Clinical experiences with drospirenone: from reproductive to postmenopausal years | journal = Maturitas | volume = 60 | issue = 2 | pages = 78–91 | date = June 2008 | pmid = 18468818 | doi = 10.1016/j.maturitas.2008.03.009 }}
* {{cite journal | vauthors = Rapkin AJ, Sorger SN, Winer SA | title = Drospirenone/ethinyl estradiol | journal = Drugs of Today | volume = 44 | issue = 2 | pages = 133–145 | date = February 2008 | pmid = 18389090 | doi = 10.1358/dot.2008.44.2.1191057 | s2cid = 32413831 }}
* {{cite journal | vauthors = Rapkin AJ, Winer SA | title = Drospirenone: a novel progestin | journal = Expert Opinion on Pharmacotherapy | volume = 8 | issue = 7 | pages = 989–999 | date = May 2007 | pmid = 17472544 | doi = 10.1517/14656566.8.7.989 | s2cid = 6954183 }}
* {{cite journal | vauthors = Rapkin RB, Creinin MD | title = The combined oral contraceptive pill containing drospirenone and ethinyl estradiol plus levomefolate calcium | journal = Expert Opinion on Pharmacotherapy | volume = 12 | issue = 15 | pages = 2403–2410 | date = October 2011 | pmid = 21877996 | doi = 10.1517/14656566.2011.610791 | s2cid = 40231903 }}
* {{cite journal | vauthors = Rübig A | title = Drospirenone: a new cardiovascular-active progestin with antialdosterone and antiandrogenic properties | journal = Climacteric | volume = 6 | issue = Suppl 3 | pages = 49–54 | date = October 2003 | pmid = 15018248 }}
* {{cite journal | vauthors = Scheinfeld NS | title = Yaz (3 mg drospirenone/20 microg ethinyl estradiol) | journal = Skinmed | volume = 6 | issue = 6 | pages = 289 | date = 2007 | pmid = 17975349 | doi = 10.1111/j.1540-9740.2007.07338.x }}
* {{cite journal | vauthors = Sehovic N, Smith KP | title = Risk of venous thromboembolism with drospirenone in combined oral contraceptive products | journal = The Annals of Pharmacotherapy | volume = 44 | issue = 5 | pages = 898–903 | date = May 2010 | pmid = 20371756 | doi = 10.1345/aph.1M649 | s2cid = 8248469 }}
* {{cite journal | vauthors = Shulman LP | title = A review of drospirenone for safety and tolerability and effects on endometrial safety and lipid parameters contrasted with medroxyprogesterone acetate, levonorgestrel, and micronized progesterone | journal = Journal of Women's Health | volume = 15 | issue = 5 | pages = 584–590 | date = June 2006 | pmid = 16796485 | doi = 10.1089/jwh.2006.15.584 }}
* {{cite journal | vauthors = Simoncini T, Genazzani AR | title = A review of the cardiovascular and breast actions of drospirenone in preclinical studies | journal = Climacteric | volume = 13 | issue = 1 | pages = 22–33 | date = February 2010 | pmid = 19938948 | doi = 10.3109/13697130903437375 | s2cid = 4306359 }}
* {{cite journal | vauthors = Sitruk-Ware R | title = Pharmacology of different progestogens: the special case of drospirenone | journal = Climacteric | volume = 8 | issue = Suppl 3 | pages = 4–12 | date = October 2005 | pmid = 16203650 | doi = 10.1080/13697130500330382 | s2cid = 24205704 }}
* {{cite journal | vauthors = Thorneycroft IH | title = Evolution of progestins. Focus on the novel progestin drospirenone | journal = The Journal of Reproductive Medicine | volume = 47 | issue = 11 Suppl | pages = 975–980 | date = November 2002 | pmid = 12497671 }}
* {{cite journal | vauthors = Toni I, Neubert A, Botzenhardt S, Gratzki N, Rascher W | title = Venous thromboembolism in adolescents associated with drospirenone-containing oral contraceptives - two case reports | journal = Klinische Padiatrie | volume = 225 | issue = 5 | pages = 266–267 | date = September 2013 | pmid = 23975850 | doi = 10.1055/s-0033-1353169 | s2cid = 19085818 }}
* {{cite journal | vauthors = White WB | title = Drospirenone with 17beta-estradiol in the postmenopausal woman with hypertension | journal = Climacteric | volume = 10 | issue = Suppl 1 | pages = 25–31 | date = February 2007 | pmid = 17364595 | doi = 10.1080/13697130601114933 | s2cid = 9451771 }}
* {{cite journal | vauthors = Whitehead M | title = Hormone replacement therapy with estradiol and drospirenone: an overview of the clinical data | journal = The Journal of the British Menopause Society | volume = 12 | issue = Suppl 1 | pages = 4–7 | date = March 2006 | pmid = 16513012 | doi = 10.1258/136218006775992185 | s2cid = 38095916 }}
* {{cite journal | vauthors = Wu CQ, Grandi SM, Filion KB, Abenhaim HA, Joseph L, Eisenberg MJ | title = Drospirenone-containing oral contraceptive pills and the risk of venous and arterial thrombosis: a systematic review | journal = BJOG | volume = 120 | issue = 7 | pages = 801–810 | date = June 2013 | pmid = 23530659 | doi = 10.1111/1471-0528.12210 | s2cid = 206904730 | doi-access = free }}
* {{cite journal | vauthors = Zhao X, Zhang XF, Zhao Y, Lin X, Li NY, Paudel G, Wang QY, Zhang XW, Li XL, Yu J | title = Effect of combined drospirenone with estradiol for hypertensive postmenopausal women: a systemic review and meta-analysis | journal = Gynecological Endocrinology | volume = 32 | issue = 9 | pages = 685–689 | date = September 2016 | pmid = 27176003 | doi = 10.1080/09513590.2016.1183629 | s2cid = 9116138 }}
* {{cite journal | vauthors =  | title = Drospirenone in HRT? | journal = Drug and Therapeutics Bulletin | volume = 47 | issue = 4 | pages = 41–44 | date = April 2009 | pmid = 19357298 | doi = 10.1136/dtb.2009.03.0011 | s2cid = 1909717 }}
{{refend}}

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[[Category:Antimineralocorticoids]]
[[Category:Drugs developed by Bayer]]
[[Category:Cyclopropanes]]
[[Category:Enantiopure drugs]]
[[Category:Enones]]
[[Category:Hormonal contraception]]
[[Category:Lactones]]
[[Category:Pregnanes]]
[[Category:Progestogens]]
[[Category:Spiro compounds]]
[[Category:Spirolactones]]
[[Category:Steroidal antiandrogens]]