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Mestanolone

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Not to be confused with Mesterolone.
Mestanolone
Clinical data
Trade namesAndrostalone, Ermalone, others
Other namesRU-143; Methylandrostanolone; Methyldihydrotestosterone; Methyl-DHT; 17αあるふぁ-Methyl-4,5αあるふぁ-dihydrotestosterone; 17αあるふぁ-Methyl-DHT; 17αあるふぁ-Methyl-5αあるふぁ-androstan-17βべーた-ol-3-one;
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
Drug classAndrogen; Anabolic steroid
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver
ExcretionUrine
Identifiers
  • (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 Edit this at Wikidata
Chemical and physical data
FormulaC20H32O2
Molar mass304.474 g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:WYZDXEKUWRCKOB-YDSAWKJFSA-N checkY
 ☒NcheckY (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]

Medical uses

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Available forms

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Mestanolone was available in the form of 25 mg sublingual tablets (brand name Ermalone).[9]

Pharmacology

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Pharmacodynamics

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Mestanolone is an AAS, with both androgenic and anabolic effects.[4] It is very similar in its effects to androstanolone (dihydrotestosterone; DHT), and can be thought of as an orally active version of this AAS.[4] Due to inactivation by 3αあるふぁ-hydroxysteroid dehydrogenase (3αあるふぁ-HSD) in skeletal muscle, mestanolone is described as a very poor anabolic agent, similarly to androstanolone and mesterolone.[4] As mestanolone is 5αあるふぁ-reduced, it cannot be aromatized and hence has no propensity for estrogenic side effects such as gynecomastia.[4] The drug also has no progestogenic activity.[4] Like other 17αあるふぁ-alkylated AAS, mestanolone is hepatotoxic.[4]

Pharmacokinetics

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Due to its C17αあるふぁ methyl group, unlike androstanolone, mestanolone is orally active.[4]

Chemistry

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See also: List of androgens/anabolic steroids

Mestanolone, also known as 17αあるふぁ-methyl-4,5αあるふぁ-dihydrotestosterone (17αあるふぁ-methyl-DHT) or as 17αあるふぁ-methyl-5αあるふぁ-androstan-17βべーた-ol-3-one, is a synthetic androstane steroid and a 17αあるふぁ-alkylated derivative of dihydrotestosterone (DHT).[1][4] It differs from DHT only by the presence of the methyl group at the C17αあるふぁ position.[1][4] Close synthetic relatives of mestanolone include oxandrolone (2-oxa-17αあるふぁ-methyl-DHT), oxymetholone (2-hydroxymethylene-17αあるふぁ-methyl-DHT), and stanozolol (a derivative of 17αあるふぁ-methyl-DHT (mestanolone) with a pyrazole ring fused to the A ring).[1][4]

Side effects

[edit]
See also: Anabolic steroid § Adverse effects

Side effects of mestanolone include virilization and hepatotoxicity among others.[4]

History

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Mestanolone was first synthesized in 1935 along with methyltestosterone and methandriol.[6][7] It was developed by Roussel in the 1950s and was introduced for medical use, under the brand names Androstalone and Ermalone, by at least 1960.[4][10][8] It was marketed in Germany.[4] The drug was originally thought to be a potent anabolic agent, but subsequent research showed that it actually has relatively weak anabolic effects and is mostly an androgen.[4] Mestanolone was used as a doping agent in athletes competing in the Olympics from East Germany due to a state-sponsored doping program in the 1970s and 1980s.[4] Its value is said to have been less as a muscle-builder and more as an androgen in the central nervous system and neuromuscular interaction, improving speed, strength, aggression, focus, endurance, and stress resilience.[4] Today, mestanolone has mostly been discontinued in medicine, though it is still available in Japan.[2][3][4]

Society and culture

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Generic names

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Mestanolone is the generic name of the drug and its INNTooltip International Nonproprietary Name, BANTooltip British Approved Name, and JANTooltip Japanese Accepted Name.[1][11]

Brand names

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Mestanolone was marketed under the brand names Andoron, Androstalone, Ermalone, Mesanolon, and Notandron among many others.[4][2][12][3]

Availability

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Mestanolone has mostly been discontinued but remains available in Japan.[2][3][4]

References

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  1. ^ a b c d e 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 c d e "Mestanolone". Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 655–. ISBN 978-3-88763-075-1.
  3. ^ a b c d e "S1. Anabolic Agents". Drugs in Sport: Anti-Doping Prohibited List – via Drugs.com.
  4. ^ a b c d e f g h i j k l m n o p q r s t u v w x y z aa ab ac ad 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. ^ a b Schänzer W (July 1996). "Metabolism of anabolic androgenic steroids". Clinical Chemistry. 42 (7): 1001–1020. doi:10.1093/clinchem/42.7.1001. PMID 8674183.
  7. ^ a b Ruzicka L, Goldberg MW, Rosenberg HR (1935). "Sexualhormone X. Herstellung des 17-Methyl-testosterons und anderer Androsten- und Androstanderivate. Zusammenhänge zwischen chemischer Konstitution und männlicher Hormonwirkung". Helvetica Chimica Acta. 18 (1): 1487–1498. doi:10.1002/hlca.193501801203. ISSN 0018-019X.
  8. ^ a b Arnold A, Potts GO, Beyler AL (December 1963). "The Ratio of Anabolic to Androgenic Activity of 7: 17-Dimethyltestosterone, Oxymesterone, Mestanolone and Fluoxymesterone". The Journal of Endocrinology. 28: 87–92. doi:10.1677/joe.0.0280087. PMID 14086172.
  9. ^ Krüskemper HL (22 October 2013). Anabolic Steroids. Elsevier. pp. 196–. ISBN 978-1-4832-6504-9.
  10. ^ Bishop PM (January 1960). "Male sex hormones". British Medical Journal. 1 (5167): 184–186. doi:10.1136/bmj.1.5167.184. PMC 1966335. PMID 13800998.
  11. ^ "Mestanolone [INN:BAN:JAN]". ChemIDplus. U.S. National Library of Medicine.
  12. ^ Negwer M (1987). Organic-chemical Drugs and Their Synonyms: (an International Survey). VCH Publishers. ISBN 978-0-89573-552-2. Anavormol, Andoron, Androne, Androstalone, Antalon "Kobayashi K.", Assimil, Ermalone, Etnabolate, Hermalone-Glosset, Macrobin (Tabl. -- Syrup), Mesanolon, Mestalone, Mestanolone", Methyantalon, Methybol, 172-Methylandrostanolone, Preroide,. 1045.
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