View source for Mesterolone

{{Short description|Chemical compound}}
{{Distinguish|Mestanolone}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 458773932
| IUPAC_name = (1''S'',5''S'',8''R'',9''S'',10''S'',13''S'',14''S'',17''S'')-17-hydroxy-1,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[''a'']phenanthren-3-one
| image = Mesterolone.svg
| image_class = skin-invert-image
| width = 225px

<!--Clinical data-->
| tradename = Proviron, others
| Drugs.com = {{drugs.com|international|mesterolone}}
| pregnancy_category = 
| legal_BR = C5
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_US = Schedule III
| legal_CA = Schedule IV
| legal_AU = S4
| routes_of_administration = [[Oral administration|By mouth]]
| class = [[Androgen]]; [[Anabolic steroid]]

<!--Pharmacokinetic data-->
| bioavailability = 3%
| protein_bound = 98% (40% to [[Albumin]], 58% to [[SHBG]])
| metabolism = [[Liver]]
| elimination_half-life = 12-13 hours
| excretion = [[Urine]]

<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 1424-00-6
| ATC_prefix = G03
| ATC_suffix = BB01
| PubChem = 15020
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 14296
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0SRQ75X9I9
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04947
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 258918
| synonyms = NSC-75054; SH-60723; SH-723; 1α-Methyl-4,5α-dihydrotestosterone; 1α-Methyl-DHT; 1α-Methyl-5α-androstan-17β-ol-3-one

<!--Chemical data-->
| C=20 | H=32 | O=2
| SMILES = O=C4C[C@@H]3CC[C@@H]2[C@H](CC[C@]1(C)[C@@H](O)CC[C@H]12)[C@@]3(C)[C@@H](C)C4
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UXYRZJKIQKRJCF-TZPFWLJSSA-N
}}
<!-- Definition and medical uses -->
'''Mesterolone''', sold under the brand name '''Proviron''' among others, is an [[androgen]] and [[anabolic steroid]] (AAS) medication which is used mainly in the treatment of [[hypogonadism|low testosterone levels]].<ref name="Llewellyn2011">{{cite book| vauthors = Llewellyn W |title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT642|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=641–}}</ref><ref name="NieschlagBehre2004">{{cite book| vauthors = Nieschlag E, Behre HM |title=Testosterone: Action, Deficiency, Substitution|url=https://books.google.com/books?id=ZiZ7MWDqo5oC&pg=PA411|date=1 April 2004|publisher=Cambridge University Press|isbn=978-1-139-45221-2|pages=411–}}</ref> It has also been used to treat [[male infertility]], although this use is controversial.<ref name="Llewellyn2011" /><ref name="Hargreave2012">{{cite book| vauthors = Hargreave TB |title=Male Infertility|url=https://books.google.com/books?id=3m_rBwAAQBAJ&pg=PA398|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4471-1029-3|pages=398–399}}</ref><ref name="LipshultzHowards2009">{{cite book| vauthors = Lipshultz LI, Howards SS, Niederberger CS |title=Infertility in the Male|url=https://books.google.com/books?id=D89GbMA8lxkC&pg=PA445|date=24 September 2009|publisher=Cambridge University Press|isbn=978-0-521-87289-8|pages=445–446}}</ref> It is taken [[oral administration|by mouth]].<ref name="Llewellyn2011" />

<!-- Side effects and mechanism of action -->
[[Side effect]]s of mesterolone include [[symptom]]s of [[virilization|masculinization]] like [[acne]], [[pattern hair loss|scalp hair loss]], [[hirsutism|increased body hair growth]], [[voice deepening|voice changes]], and increased [[libido|sexual desire]].<ref name="Llewellyn2011" /> It has no risk of [[hepatotoxicity|liver damage]].<ref name="Llewellyn2011" /><ref name="NieschlagBehre2004" /> The drug is a [[synthetic compound|synthetic]] androgen and anabolic steroid and hence is an [[agonist]] of the [[androgen receptor]] (AR), the [[biological target]] of androgens like [[testosterone]] and [[dihydrotestosterone]] (DHT).<ref name="Llewellyn2011" /><ref name="pmid18500378">{{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = British Journal of Pharmacology | volume = 154 | issue = 3 | pages = 502–521 | date = June 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }}</ref> It has strong [[androgen]]ic effects and weak [[anabolic]] effects, which make it useful for producing masculinization.<ref name="Llewellyn2011" /> The drug has no [[estrogen (medication)|estrogen]]ic effects.<ref name="Llewellyn2011" /><ref name="NieschlagBehre2004" />

<!-- History, society, and culture -->
Mesterolone was first described by 1966<ref name="BehreWang2004" /> and introduced for medical use by 1967.<ref name="Pergamon1967">{{cite journal|vauthors=Rausch-Stroomann JG, Petry R, Hienz HA|title=The influence of mesterolone on testicular function|journal=Research on Steroids|volume=3|pages=181–184|url=https://books.google.com/books?id=zBVrAAAAMAAJ|year=1967|publisher=Pergamon}}</ref><ref name="Tausk1968">{{cite book | vauthors = Tausk M | chapter = Practically Applicable Results of Twenty Years of Research in Endocrinology | title = Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques | journal = Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progres des Recherches Pharmaceutiques | volume = 12 | pages = 137–164 | year = 1968 | pmid = 4307936 | doi = 10.1007/978-3-0348-7065-8_3 | isbn = 978-3-0348-7067-2 }}</ref> In addition to its medical use, mesterolone has been used to [[performance-enhancing substance|improve physique and performance]], although it is not commonly used for such purposes due to its weak anabolic effects.<ref name="Llewellyn2011" /> The drug is a [[controlled substance]] in many countries and so non-medical use is generally illicit.<ref name="Llewellyn2011" /><ref name="FFFLM2006" />

==Medical uses==
Mesterolone is used in the treatment of [[androgen deficiency]] in male [[hypogonadism]], [[anemia]], and to support [[male fertility]] among other indications.<ref name="Llewellyn2011" /><ref name="AllahbadiaDas2004">{{cite book| vauthors = Allahbadia GN, Das RB |title=The Art and Science of Assisted Reproductive Techniques|url=https://books.google.com/books?id=_ldpcClfnrgC&pg=PA824|date=12 November 2004|publisher=CRC Press|isbn=978-0-203-64051-7|pages=824–}}</ref><ref name="Becker2001">{{cite book| vauthors = Becker KL |title=Principles and Practice of Endocrinology and Metabolism|url=https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1186|year=2001|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-1750-2|pages=1186–}}</ref> It has also been used to treat [[delayed puberty]] in boys.<ref name="HartNewton2012">{{cite book | vauthors = Hart I, Newton RW |title=Endocrinology|url=https://books.google.com/books?id=QbjUBgAAQBAJ&pg=PA119|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-010-9298-2|pages=119–}}</ref> Because it lacks estrogenic effects, mesterolone may be indicated for treating cases of androgen deficiency in which [[breast tenderness]] or [[gynecomastia]] is also present.<ref name="pmid22612692">{{cite journal | vauthors = Corona G, Rastrelli G, Vignozzi L, Maggi M | title = Emerging medication for the treatment of male hypogonadism | journal = Expert Opinion on Emerging Drugs | volume = 17 | issue = 2 | pages = 239–259 | date = June 2012 | pmid = 22612692 | doi = 10.1517/14728214.2012.683411 | s2cid = 22068249 }}</ref> The drug is described as a relatively weak androgen with partial activity and is rarely used for the purpose of [[androgen replacement therapy]], but is still widely used in medicine.<ref name="Llewellyn2011" /><ref name="Becker2001" /><ref name="pmid15297434">{{cite journal | vauthors = Nieschlag E, Behre HM, Bouchard P, Corrales JJ, Jones TH, Stalla GK, Webb SM, Wu FC | display-authors = 6 | title = Testosterone replacement therapy: current trends and future directions | journal = Human Reproduction Update | volume = 10 | issue = 5 | pages = 409–419 | year = 2004 | pmid = 15297434 | doi = 10.1093/humupd/dmh035 | doi-access = free }}</ref><ref name="NieschlagBehre2004" />

Mesterolone is used in [[androgen replacement therapy]] at a dosage of 50 to 100&nbsp;mg 2 to 3&nbsp;times per day.<ref name="RastrelliReisman2019">{{cite book| vauthors = Rastrelli G, Reisman Y, Ferri S, Prontera O, Sforza A, Maggi M, Corona G |title=Sexual Medicine|chapter=Testosterone Replacement Therapy|year=2019|pages=79–93|publisher=Springer |doi=10.1007/978-981-13-1226-7_8|isbn=978-981-13-1225-0|doi-access=free}}</ref>

{{Androgen replacement therapy formulations and dosages used in men}}

==Non-medical uses==
Mesterolone has been used for [[performance-enhancing drug|physique- and performance-enhancing purpose]]s by [[competition|competitive]] [[athlete]]s, [[bodybuilder]]s, and [[powerlifter]]s.<ref name="Llewellyn2011" />

==Side effects==
{{See also|Anabolic steroid#Adverse effects}}

[[Side effect]]s of mesterolone include [[virilization]] among others.<ref name="Llewellyn2011" />

==Pharmacology==

===Pharmacodynamics===
Like other AAS, mesterolone is an [[agonist]] of the [[androgen receptor]] (AR).<ref name="Llewellyn2011" /> Mesterolone is described as a very poor [[anabolic]] agent due to inactivation by [[3α-hydroxysteroid dehydrogenase]] (3α-HSD) in [[skeletal muscle]] [[tissue (biology)|tissue]], similarly to DHT and [[mestanolone]] (17α-methyl-DHT).<ref name="Llewellyn2011" /> In contrast, [[testosterone (medication)|testosterone]] is a very poor [[substrate (biochemistry)|substrate]] for 3α-HSD, and so is not similarly inactivated in skeletal muscle.<ref name="Llewellyn2011" /> Because of its lack of potentiation by 5α-reductase in "androgenic" tissues and its inactivation by 3α-HSD in skeletal muscle, mesterolone is relatively low in both its [[androgen]]ic [[potency (pharmacology)|potency]] and its anabolic potency.<ref name="Llewellyn2011" /> However, it does still show a greater ratio of anabolic activity to androgenic activity relative to testosterone.<ref name="Llewellyn2011" />

Mesterolone is not a [[substrate (biochemistry)|substrate]] for [[5α-reductase]], as it is already 5α-reduced, and hence is not potentiated in so-called "androgenic" [[tissue (biology)|tissue]]s such as the [[skin]], [[hair follicle]]s, and [[prostate gland]].<ref name="Llewellyn2011" /> 

Mesterolone is not a substrate for [[aromatase]], and so cannot be converted into an [[estrogen]].<ref name="Llewellyn2011" /> As such, it has no propensity for producing estrogenic [[side effect]]s such as [[gynecomastia]] and [[water retention (medicine)|fluid retention]].<ref name="Llewellyn2011" /> It also has no [[progestogen]]ic activity.<ref name="Llewellyn2011" />

Because mesterolone is not [[17α-alkylated anabolic steroid|17α-alkylated]], it has little or no potential for [[hepatotoxicity]].<ref name="Llewellyn2011" /> However, its risk of deleterious effects on the [[cardiovascular system]] is comparable to that of several other oral AAS.<ref name="Llewellyn2011" />

===Pharmacokinetics===
The C1α [[methyl group]] of mesterolone inhibits its [[liver|hepatic]] [[metabolism]] and thereby confers significant [[oral administration|oral]] activity, although its oral [[bioavailability]] is still much lower than that of 17α-alkylated AAS.<ref name="Llewellyn2011" /> In any case, mesterolone is one of the few non-17α-alkylated AAS that is active with oral ingestion.<ref name="Llewellyn2011" /> Uniquely among AAS, mesterolone has very high [[affinity (pharmacology)|affinity]] for human serum [[sex hormone-binding globulin]] (SHBG), about 440% that of DHT in one study and 82% of that of DHT in another study.<ref name="pmid6539197">{{cite journal | vauthors = Saartok T, Dahlberg E, Gustafsson JA | title = Relative binding affinity of anabolic-androgenic steroids: comparison of the binding to the androgen receptors in skeletal muscle and in prostate, as well as to sex hormone-binding globulin | journal = Endocrinology | volume = 114 | issue = 6 | pages = 2100–2106 | date = June 1984 | pmid = 6539197 | doi = 10.1210/endo-114-6-2100 }}</ref><ref name="Llewellyn2011" /><ref name="pmid7195405">{{cite journal | vauthors = Pugeat MM, Dunn JF, Nisula BC | title = Transport of steroid hormones: interaction of 70 drugs with testosterone-binding globulin and corticosteroid-binding globulin in human plasma | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 53 | issue = 1 | pages = 69–75 | date = July 1981 | pmid = 7195405 | doi = 10.1210/jcem-53-1-69 }}</ref> As a result, it may displace [[endogenous]] testosterone from SHBG and thereby increase free testosterone concentrations, which may in part be involved in its effects.<ref name="Llewellyn2011" />

==Chemistry==
{{See also|List of androgens/anabolic steroids}}

Mesterolone, also known as 1α-methyl-4,5α-dihydrotestosterone (1α-methyl-DHT) or as 1α-methyl-5α-androstan-17β-ol-3-one, is a [[synthetic compound|synthetic]] [[androstane]] [[steroid]] and [[chemical derivative|derivative]] of DHT.<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=PA775|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=775–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA656|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=656–}}</ref><ref name="Llewellyn2011" /> It is specifically DHT with a [[methyl group]] at the C1α position.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> Closely related AAS include [[metenolone]] and its [[ester]]s [[metenolone acetate]] and [[metenolone enanthate]].<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> The [[antiandrogen]] [[rosterolone]] (17α-propylmesterolone) is also closely related to mesterolone.<ref name="pmid1788861">{{cite journal | vauthors = Brooks JR, Primka RL, Berman C, Krupa DA, Reynolds GF, Rasmusson GH | title = Topical anti-androgenicity of a new 4-azasteroid in the hamster | journal = Steroids | volume = 56 | issue = 8 | pages = 428–433 | date = August 1991 | pmid = 1788861 | doi = 10.1016/0039-128x(91)90031-p | s2cid = 21500107 }}</ref>

==History==
Mesterolone was developed in the 1960s<ref name="Carruthers2006">{{cite book| vauthors = Carruthers M |title=Androgen Deficiency in the Adult Male: Causes, Diagnosis and Treatment|url=https://books.google.com/books?id=YFYgyAEACAAJ|year=2006|publisher=CRC Press|isbn=978-0-367-80018-5|pages=137–178}}</ref> and was first described by 1966.<ref name="BehreWang2004">{{cite book| vauthors = Behre HM, Wang C, Handelsman DJ, Nieschlag E |title=Testosterone|chapter=Pharmacology of testosterone preparations|year=2004|pages=405–444|publisher=Cambridge University Press |doi=10.1017/CBO9780511545221.015|isbn=9780521833806}}</ref><ref name="pmid6014248">{{cite journal | vauthors = Neumann F, Wiechert R, Kramer M, Raspé G | title = [Experimental animal studies with a new androgen--mesterolone (1-alpha-methyl-5-alpha-androstan-17-beta-ol-one)] | language = de | journal = Arzneimittel-Forschung | volume = 16 | issue = 4 | pages = 455–458 | date = April 1966 | pmid = 6014248 }}</ref><ref name="LaschetNiermann1967">{{cite journal| vauthors = Laschet U, Niermann H, Laschet L, Paarmann HF |title=Mesterolone, a potent oral active androgen without gonadotropin inhibition|journal=Acta Endocrinologica|volume=56|issue=1_Suppl|year=1967|pages=S55|issn=0804-4643|doi=10.1530/acta.0.056S055}}</ref><ref name="pmid4307936">{{cite book | vauthors = Tausk M | chapter = Practically Applicable Results of Twenty Years of Research in Endocrinology | title = Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques | journal = Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progres des Recherches Pharmaceutiques | volume = 12 | pages = 137–164 | date = 1968 | pmid = 4307936 | doi = 10.1007/978-3-0348-7065-8_3 | isbn = 978-3-0348-7067-2 }}</ref> It was introduced for medical use by [[Schering AG|Schering]] under the brand name Proviron by 1967.<ref name="Pergamon1967"/><ref name="Tausk1968" /> The well-established brand name Proviron had previously been used by Schering for [[testosterone propionate]] starting in 1936.<ref name="NieschlagNieschlag2017">{{cite book| vauthors = Nieschlag E, Nieschlag S |title=Testosterone|chapter=The History of Testosterone and The Testes: From Antiquity to Modern Times|year=2017|pages=1–19|publisher=Springer |doi=10.1007/978-3-319-46086-4_1|isbn=978-3-319-46084-0|doi-access=free}}</ref> Following the introduction of mesterolone as Proviron, Schering continued to market testosterone propionate under the brand name Testoviron.<ref name="NieschlagNieschlag2017" /> A number of sources incorrectly state that mesterolone was synthesized or introduced for medical use in 1934.<ref name="Carruthers2006" /><ref name="Llewellyn2011" /><ref name="Hohl2017">{{cite book| vauthors = Hohl A |title=Testosterone: From Basic to Clinical Aspects|url=https://books.google.com/books?id=Et6TDgAAQBAJ&pg=PA204|date=6 April 2017|publisher=Springer|isbn=978-3-319-46086-4|pages=204–}}</ref><ref name="KalinchenkoTyuzikov2017">{{cite book| vauthors = Kalinchenko S, Tyuzikov I, Mskhalaya G, Tishova Y |title=Testosterone|chapter=Testosterone Therapy: Oral Androgens|year=2017|pages=203–224|publisher=Springer |doi=10.1007/978-3-319-46086-4_10|isbn=978-3-319-46084-0|doi-access=free}}</ref>

==Society and culture==

===Generic names===
''Mesterolone'' 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|DCIT|Denominazione Comune Italiana}}, while ''mestérolone'' is its {{abbrlink|DCF|Dénomination Commune Française}}.<ref name="Elks2014" /><ref name="IndexNominum2000" /><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=PA177|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=176–177}}</ref><ref name="Drugs.com">{{Cite web|url=https://www.drugs.com/international/mesterolone.html|title = Mesterolone}}</ref>

===Brand names===
Mesterolone is marketed mainly under the brand name Proviron.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Drugs.com" /><ref name="Llewellyn2011" />

===Availability===
Mesterolone is available widely throughout the world, including in the [[United Kingdom]], [[Australia]], and [[South Africa]], as well as many non-[[English language|English]]-speaking countries.<ref name="IndexNominum2000" /><ref name="Drugs.com" /> It is not available in the [[United States]], [[Canada]], or [[New Zealand]].<ref name="IndexNominum2000" /><ref name="Drugs.com" /> The drug has never been marketed in the United States.<ref name="Hohl2017" />

===Legal status===
Mesterolone, along with other AAS, is a [[Controlled Substances Act#Schedule III controlled substances|schedule III]] [[controlled substance]] in the [[United States]] under the [[Controlled Substances Act]] and a [[Controlled Drugs and Substances Act#Schedule IV|schedule IV]] controlled substance in [[Canada]] under the [[Controlled Drugs and Substances Act]].<ref name="FFFLM2006">{{cite book|vauthors = Karch SB|title=Drug Abuse Handbook, Second Edition|url=https://books.google.com/books?id=ZjrMBQAAQBAJ&pg=PA30|date=21 December 2006|publisher=CRC Press|isbn=978-1-4200-0346-8|pages=30–}}</ref><ref name="LilleySnyder2016">{{cite book| vauthors = Lilley LL, Snyder JS, Collins SR |title=Pharmacology for Canadian Health Care Practice|url=https://books.google.com/books?id=dNgoDwAAQBAJ&pg=PA50|date=5 August 2016|publisher=Elsevier Health Sciences|isbn=978-1-77172-066-3|pages=50–}}</ref>

==Research==
In one small scale clinical trial of depressed patients, an improvement of symptoms which included anxiety, lack of drive and desire was observed.<ref name="pmid6431212">{{cite journal | vauthors = Itil TM, Michael ST, Shapiro DM, Itil KZ | title = The effects of mesterolone, a male sex hormone in depressed patients (a double blind controlled study) | journal = Methods and Findings in Experimental and Clinical Pharmacology | volume = 6 | issue = 6 | pages = 331–337 | date = June 1984 | pmid = 6431212 }}</ref> In patients with [[dysthymia]], [[unipolar depression|unipolar]], and [[bipolar depression]] significant improvement was observed.<ref name="pmid6431212" /> In this series of studies, mesterolone lead to a significant decrease in [[luteinizing hormone]] and [[testosterone]] levels.<ref name="pmid6431212" /> In another study, 100&nbsp;mg [[mesterolone cipionate]] was administered twice monthly.<ref name="pmid883846">{{cite journal | vauthors = Kövary PM, Lenau H, Niermann H, Zierden E, Wagner H | title = Testosterone levels and gonadotrophins in Klinefelter's patients treated with injections of mesterolone cipionate | journal = Archives for Dermatological Research | volume = 258 | issue = 3 | pages = 289–294 | date = May 1977 | pmid = 883846 | doi = 10.1007/bf00561132 | s2cid = 1222130 }}</ref> With regards to plasma testosterone levels, there was no difference between the treated versus untreated group, and baseline luteinizing hormone levels were minimally affected.<ref name="pmid883846" />

== References ==
{{Reflist|30em}}

== Further reading ==
{{refbegin}}
* {{cite book | vauthors = Morrison MC |title=Hormones, Gender and the Aging Brain: The Endocrine Basis of Geriatric Psychiatry |publisher=Cambridge University Press |location=Cambridge, UK |year=2000 |page=134 |isbn=0-521-65304-5 |url=https://books.google.com/books?id=I7QsN6hx8IQC}}
{{refend}}

== External links ==
* [https://anabolic.org/proviron-mesterolone/ Proviron (mesterolone) - William Llewellyn's Anabolic.org] {{Webarchive|url=https://web.archive.org/web/20160923141415/http://anabolic.org/proviron-mesterolone/ |date=2016-09-23 }}.


{{Androgens and antiandrogens}}
{{Androgen receptor modulators}}

[[Category:Secondary alcohols]]
[[Category:Anabolic–androgenic steroids]]
[[Category:Androstanes]]
[[Category:Ketones]]