Mestanolone

Not to be confused with Mesterolone.
Mestanolone
Clinical data
Trade namesAndrostalone, Ermalone, others
Other namesRU-143; Methylandrostanolone; Methyldihydrotestosterone; Methyl-DHT; 17α-Methyl-4,5α-dihydrotestosterone; 17α-Methyl-DHT; 17α-Methyl-5α-androstan-17β-ol-3-one;
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
Drug classAndrogen; Anabolic steroid
ATC code
  • None
Legal status
Legal status
  • US: Schedule III
Pharmacokinetic data
MetabolismLiver
ExcretionUrine
Identifiers
IUPAC name
  • (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.549
Chemical and physical data
FormulaC20H32O2
Molar mass304.474 g·mol−1
3D model (JSmol)
SMILES
  • O=C2C[C@@H]1CC[C@@H]3[C@@H]([C@@]1(C)CC2)CC[C@]4([C@H]3CC[C@@]4(O)C)C
InChI
  • InChI=1S/C20H32O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h13,15-17,22H,4-12H2,1-3H3/t13-,15+,16-,17-,18-,19-,20-/m0/s1 Y
  • Key:WYZDXEKUWRCKOB-YDSAWKJFSA-N Y
 NY (what is this?)  (verify)

Mestanolone, also known as methylandrostanolone and sold under the brand names Androstalone and Ermalone among others, is an androgen and anabolic steroid (AAS) medication which is mostly no longer used.[1][2][3][4] It is still available for use in Japan however.[2][3] It is taken by mouth.[4]

Side effects of mestanolone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[4] It can also cause liver damage.[4] 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).[4][5] It has strong androgenic effects and weak anabolic effects, which make it useful for producing masculine psychological and behavioral effects.[4] The drug has no estrogenic effects.[4]

Mestanolone was discovered in 1935 and was introduced for medical use in the 1950s.[6][7][8][4] In addition to its medical use, mestanolone has been used to improve physique and performance.[4] It was used in East Germany in Olympic athletes as part of a state-sponsored doping program in the 1970s and 1980s.[4] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[4]

  1. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 775–. ISBN 978-1-4757-2085-3.
  2. ^ a b "Mestanolone". Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 655–. ISBN 978-3-88763-075-1.
  3. ^ a b Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  4. ^ a b c d e f g h i j k Llewellyn W (2009). Anabolics. Molecular Nutrition Llc. p. 241. ISBN 978-0967930473.
  5. ^ 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.
  6. ^ Cite error: The named reference pmid8674183 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference RuzickaGoldberg1935 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference pmid14086172 was invoked but never defined (see the help page).
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