View source for Estropipate

{{short description|Estrogen medication}}
{{Redirect|Ogen|the character in the Japanese anime|Ogen (Basilisk)|the melon cultivar|Galia melon}}
{{Drugbox
| Verifiedfields = verified
| verifiedrevid = 461095715
| IUPAC_name = [(8''R'',9''S'',13''S'',14''S'')-13-Methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6''H''-cyclopenta[''a'']phenanthren-3-yl] hydrogen sulfate; piperazine
| image = Estropipate.png
| width = 250px
| image2 = Estropipate molecule ball.png
| width2 = 250px

<!--Clinical data-->
| tradename = Harmogen, Improvera, Ogen, Ortho-Est, Sulestrex, others
| Drugs.com = {{drugs.com|monograph|estropipate-esterified-estrogens}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = 
| routes_of_administration = [[Oral administration|By mouth]]
| class = [[Estrogen (medication)|Estrogen]]; [[Estrogen ester]]

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 7280-37-7
| ATC_prefix = None
| ATC_suffix = 
| PubChem = 5284555
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB04574
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4447610
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = SVI38UY019
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00948
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4873
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1200980
| synonyms = Piperazine estrone sulfate; Estrone sulfate piperazine salt; Pipestrone

<!--Chemical data-->
| C=22 | H=32 | N=2 | O=5 | S=1 
| SMILES = O=S(=O)(O)Oc1cc4c(cc1)[C@@H]3[C@H]([C@@H]2CCC(=O)[C@@]2(C)CC3)CC4.N1CCNCC1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C18H22O5S.C4H10N2/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19;1-2-6-4-3-5-1/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22);5-6H,1-4H2/t14-,15-,16+,18+;/m1./s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HZEQBCVBILBTEP-ZFINNJDLSA-N
}}

'''Estropipate''', also known as '''piperazine estrone sulfate''' and sold under the brand names '''Harmogen''', '''Improvera''', '''Ogen''', '''Ortho-Est''', and '''Sulestrex''' among others, is an [[estrogen (medication)|estrogen]] medication which is used mainly in [[menopausal hormone therapy]] in the treatment of [[menopause|menopausal]] [[symptom]]s.<ref name="OgenLabel">{{cite web | title = Ogen, estropipate tablets, USP | url = https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/083220s041lbl.pdf | archive-url = https://web.archive.org/web/20170216163640/http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/083220s041lbl.pdf | url-status = dead | archive-date = February 16, 2017 | work = Pharmacia & Upjohn Co | publisher = U.S. Food and Drug Administration | date = December 2004 }}</ref><ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA900|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=900–}}</ref><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA114|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=114–}}</ref><ref name="Publishing2013">{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia | edition = 3rd |url= https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1484|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=1484–}}</ref> It is a [[salt (chemistry)|salt]] of [[estrone sulfate (medication)|estrone sulfate]] and [[piperazine]], and is [[biotransformation|transformed]] into [[estrone (medication)|estrone]] and [[estradiol (medication)|estradiol]] in the body.<ref name="Elks2014" /><ref name="MortonHall2012" /> It is taken [[oral administration|by mouth]].<ref name="OgenLabel" />

==Medical uses==
Estropipate is used to:<ref name="OgenLabel" />{{Additional citation needed|date=March 2018}}

* Alleviate symptoms of [[menopause]] as [[menopausal hormone therapy]]
* Treat some types of [[infertility]]
* Treat some conditions leading to underdevelopment of [[female]] [[sexual characteristics]]
* Treat [[vaginal atrophy]]
* Treat some types of [[breast cancer]] (particularly in men and postmenopausal women)
* Treat [[prostate cancer]]
* Prevent [[osteoporosis]]

{{Estrogen dosages for menopausal hormone therapy}}

===Available forms===
Estropipate was available in the form of 0.75, 1.5, 3, and 6 mg oral tablets and 1.5 mg/gram vaginal cream. Estropipate is no longer available in the United States.

==Pharmacology==

===Pharmacodynamics===
{{See also|Pharmacodynamics of estradiol}}

Estropipate is a [[prodrug]] of [[estrone (medication)|estrone]] and [[estradiol (medication)|estradiol]]. Hence, it is an [[estrogen (medication)|estrogen]], or an [[agonist]] of the [[estrogen receptor]]s.

{{Relative oral potencies of estrogens}}

===Pharmacokinetics===
{{See also|Pharmacokinetics of estradiol}}

Estropipate is [[hydrolysis|hydrolyzed]] into [[estrone (medication)|estrone]] in the body.<ref name="Martindale" /> Estrone can then be [[biotransformation|transformed]] into [[estradiol (medication)|estradiol]] by [[17β-hydroxysteroid dehydrogenase]].

==Chemistry==
{{See also|Estrogen ester|List of estrogen esters}}

==History==
Estropipate was introduced for medical use by [[Abbott Laboratories|Abbott]] in 1968.<ref name="Budoff1983">{{cite book| first = Penny Wise | last = Budoff | name-list-style = vanc |title=No more hot flashes, and other good news|url=https://archive.org/details/nomorehotflashes00budo_1|url-access=registration|date=1 August 1983|publisher=Putnam|isbn=978-0-399-12793-9|page=[https://archive.org/details/nomorehotflashes00budo_1/page/28 28]}}</ref> It was approved by the {{abbrlink|FDA|Food and Drug Administration}} in the [[United States]] in 1991.<ref name="CORE1993">{{cite book|title=P & T.|url=https://books.google.com/books?id=51cVAQAAMAAJ|date=July 1993|publisher=CORE Medical Journals}}</ref>

==Society and culture==

===Generic names===
''Estropipate'' is the [[generic term|generic name]] of the drug and its {{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}, and {{abbrlink|BAN|British Approved Name}}.<ref name="Elks2014" /><ref name="MortonHall2012" /><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA408|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=408–}}</ref><ref name="Martindale">{{cite book | veditors = Sweetman SC |chapter=Sex hormones and their modulators |title=Martindale: The Complete Drug Reference |edition=36th |year=2009 |page=2101 |publisher=Pharmaceutical Press |location=London|isbn=978-0-85369-840-1|url=https://www.medicinescomplete.com/mc/martindale/2009/mg-9020-r.htm}}</ref><ref name="Drugs.com">{{cite web | title = Estropipate | url = https://www.drugs.com/international/estropipate.html | work = Drugs.com }}</ref>

===Brand names===
Estropipate was marketed under the brand names Genoral, Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others.<ref name="Drugs.com" /><ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Martindale" />

===Availability===
Estropipate has been discontinued in the [[United States]]. In the past, estropipate has also been marketed in [[Canada]], the [[United Kingdom]], [[Ireland]], [[Switzerland]], [[Australia]], [[South Africa]], [[Mexico]], and [[Indonesia]].<ref name="Drugs.com" /><ref name="IndexNominum2000" /><ref name="Martindale" />

== References ==
{{Reflist}}

{{Estradiol}}
{{Estrogens and antiestrogens}}
{{Estrogen receptor modulators}}

[[Category:Estranes]]
[[Category:Estrone esters]]
[[Category:Ketones]]
[[Category:Piperazines]]
[[Category:Sulfate esters]]
[[Category:Salts]]
[[Category:Synthetic estrogens]]