Mesterolone

Not to be confused with Mestanolone.
Mesterolone
Clinical data
Trade namesProviron, others
Other namesNSC-75054; SH-60723; SH-723; 1α-Methyl-4,5α-dihydrotestosterone; 1α-Methyl-DHT; 1α-Methyl-5α-androstan-17β-ol-3-one
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
Drug classAndrogen; Anabolic steroid
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability3%
Protein binding98% (40% to Albumin, 58% to SHBG)
MetabolismLiver
Elimination half-life12-13 hours
ExcretionUrine
Identifiers
  • (1S,5S,8R,9S,10S,13S,14S,17S)-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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.014.397 Edit this at Wikidata
Chemical and physical data
FormulaC20H32O2
Molar mass304.474 g·mol−1
3D model (JSmol)
  • 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
  • InChI=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 checkY
  • Key:UXYRZJKIQKRJCF-TZPFWLJSSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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 low testosterone levels.[2][3] It has also been used to treat male infertility, although this use is controversial.[2][4][5] It is taken by mouth.[2]

Side effects of mesterolone include symptoms of masculinization like acne, scalp hair loss, increased body hair growth, voice changes, and increased sexual desire.[2] It has no risk of liver damage.[2][3] The drug is a 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).[2][6] It has strong androgenic effects and weak anabolic effects, which make it useful for producing masculinization.[2] The drug has no estrogenic effects.[2][3]

Mesterolone was first described by 1966[7] and introduced for medical use by 1967.[8][9] In addition to its medical use, mesterolone has been used to improve physique and performance, although it is not commonly used for such purposes due to its weak anabolic effects.[2] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[2][10]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  2. ^ a b c d e f g h i j Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 641–. ISBN 978-0-9828280-1-4.
  3. ^ a b c Nieschlag E, Behre HM (1 April 2004). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 411–. ISBN 978-1-139-45221-2.
  4. ^ Hargreave TB (6 December 2012). Male Infertility. Springer Science & Business Media. pp. 398–399. ISBN 978-1-4471-1029-3.
  5. ^ Lipshultz LI, Howards SS, Niederberger CS (24 September 2009). Infertility in the Male. Cambridge University Press. pp. 445–446. ISBN 978-0-521-87289-8.
  6. ^ Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
  7. ^ Cite error: The named reference BehreWang2004 was invoked but never defined (see the help page).
  8. ^ Rausch-Stroomann JG, Petry R, Hienz HA (1967). "The influence of mesterolone on testicular function". Research on Steroids. 3. Pergamon: 181–184.
  9. ^ Tausk M (1968). "Practically Applicable Results of Twenty Years of Research in Endocrinology". Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Vol. 12. pp. 137–164. doi:10.1007/978-3-0348-7065-8_3. ISBN 978-3-0348-7067-2. PMID 4307936. {{cite book}}: |journal= ignored (help)
  10. ^ Cite error: The named reference FFFLM2006 was invoked but never defined (see the help page).