List of androgens/anabolic steroids (alternate)

Testosterone.

Steroid ring system.

This is a list of androgens/anabolic steroids (AAS) or testosterone derivatives. Esters are mostly not included in this list; for esters, see here instead. The major classes of testosterone derivatives include the following (as well as combinations thereof):

• Testosterone derivatives: immediate derivatives of testosterone not falling into the groups below
• 4,5α-Reduced/dihydrogenated testosterone derivatives: dihydrotestosterone (DHT) derivatives
• 19-Demethylated testosterone derivatives: 19-nortestosterone (nandrolone) derivatives
• 17α-Alkylated testosterone derivatives: methyltestosterone and ethyltestosterone derivatives
• 17α-Ethenylated/ethynylated testosterone derivatives: ethynyltestosterone (ethisterone) and vinyltestosterone derivatives

The last group consists of progestins with mostly only very weak androgenic/anabolic activity.

AAS that are listed as marketed may be marketed as one or more esters rather than as the listed AAS itself.

This list specifically pertains to steroidal androgens; nonsteroidal androgens like the selective androgen receptor modulators (SARMs) andarine and enobosarm (ostarine) are not included here.

Natural/endogenous

• Marketed
  • Androstenediol (A5; 5-androstenediol)
  • Boldenone (δ¹-T)*
  • Dehydroepiandrosterone (DHEA; prasterone, 5-androstenolone)
  • Dihydrotestosterone (DHT; androstanolone, stanolone)
  • Nandrolone (19-NT; 19-nortestosterone)*
  • Testosterone (T; 4-androstenolone)
• Never marketed
  • 11-Ketodihydrotestosterone (11-KDHT)
  • 11-Ketotestosterone (11-KT)
  • 11β-Hydroxyandrostenedione (11β-OHA4)
  • 19-Nor-5-androstenediol (19-NA5)*
  • Adrenosterone (11-ketoandrostenedione; 11-KA4)
  • Androstenedione (A4; 4-androstenedione)
  • Androsterone
  • Bolandione (19-nor-4-androstenedione)*
  • Dehydroandrosterone (DHA; 5-dehydroandrosterone)
  • Epiandrosterone

* Only present endogenously in trace/very small amounts or present in other species.

Synthetic

Testosterone derivatives

Non-17α-alkylated derivatives

• Marketed
  • Clostebol (4-chloro-T)
  • Cloxotestosterone (T 17-chloral hemiacetal ether)
  • Quinbolone (δ¹-T 17β-cyclopentenyl enol ether)
• Never marketed
  • 4-Hydroxytestosterone (4-hydroxy-T)
  • Boldione (δ¹-4-androstenedione)
  • Silandrone (T 17β-trimethylsilyl ether)

17α-Alkylated derivatives

• Marketed
  • Bolasterone (7α,17α-dimethyl-T)
  • Calusterone (7β,17α-dimethyl-T)
  • Chlorodehydromethyltestosterone (CDMT; 4-chloro-17α-methyl-δ¹-T)
  • Fluoxymesterone (9α-fluoro-11β-hydroxy-17α-methyl-T)
  • Formebolone (2-formyl-11α-hydroxy-17α-methyl-δ¹-T)
  • Metandienone (methandrostenolone; 17α-methyl-δ¹-T)
  • Methandriol (methylandrostenediol; 17α-methyl-5-androstenediol)
  • Methyltestosterone (17α-methyl-T)
  • Methyltestosterone 3-hexyl ether (17α-methyl-T 3-hexyl ether)
  • Oxymesterone (4-hydroxy-17α-methyl-T)
  • Penmesterol (17α-methyl-T 3-cyclopentyl ether)
  • Tiomesterone (1α,7α-diacetylthio-17α-methyl-T)
• Never marketed
  • Chlorodehydromethylandrostenediol (CDMA; 4-chloro-17α-methyl-δ¹-4-androstenediol)
  • Chloromethylandrostenediol (CMA; 4-chloro-17α-methyl-4-androstenediol)
  • Enestebol (4-hydroxy-17α-methyl-δ¹-T)
  • Ethyltestosterone (17α-ethyl-T)
  • Hydroxystenozole (a pyrazole A ring-fused derivative of δ²-T)
  • Methylclostebol (CMT; 4-chloro-17α-methyl-T)

Dihydrotestosterone derivatives

Non-17α-alkylated derivatives

• Marketed
  • Bolazine (an azine dimer prodrug of drostanolone)
  • Drostanolone (2α-methyl-DHT)
  • Epitiostanol (2α,3α-epithio-DHT)
  • Mepitiostane (a 17-ether prodrug of epitiostanol)
  • Mesterolone (1α-methyl-DHT)
  • Metenolone (1-methyl-δ¹-DHT)
  • Stenbolone (2-methyl-δ¹-DHT)
• Never marketed
  • 1-Testosterone (dihydroboldenone; δ¹-DHT)
  • Mesabolone (a 17-ether prodrug of δ¹-DHT)
  • Prostanozol (a 17-ether prodrug of 17α-demethylstanozolol)

17α-Alkylated derivatives

• Marketed
  • Androisoxazole (an isoxazole A ring-fused derivative of 17α-methyl-DHT)
  • Furazabol (a furan A ring-fused derivative of 17α-methyl-DHT)
  • Mebolazine (an azine dimer prodrug of methasterone)
  • Mestanolone (17α-methyl-DHT)
  • Oxandrolone (2-oxa-17α-methyl-DHT)
  • Oxymetholone (2-hydroxymethylene-17α-methyl-DHT)
  • Stanozolol (a pyrazole A ring-fused derivative of 17α-methyl-DHT)
• Never marketed
  • Desoxymethyltestosterone (3-deketo-17α-methyl-δ²-DHT)
  • Methasterone (2α,17α-dimethyl-DHT)
  • Methyl-1-testosterone (methyldihydroboldenone; 17α-methyl-δ¹-DHT)
  • Methylepitiostanol (2α,3α-epithio-17α-methyl-DHT)
  • Methylstenbolone (2,17α-dimethyl-δ¹-DHT)

19-Nortestosterone derivatives

Non-17α-alkylated derivatives

• Marketed
  • Bolandiol (19-nor-4-androstenediol)
  • Norclostebol (4-chloro-19-NT)
  • Oxabolone (4-hydroxy-19-NT)
  • Trenbolone (δ^9,11-19-NT)
• Never marketed
  • 7α-Methyl-19-nor-4-androstenedione (MENT dione, trestione)
  • 11β-Methyl-19-nortestosterone (11β-MNT; 11β-methyl-19-NT)
  • 19-Nor-5-androstenedione
  • 19-Nor-5-dehydroepiandrosterone (19-nor-DHEA)
  • Bolmantalate (nandrolone adamantoate; 19-NT)
  • Dienedione (δ⁹-19-nor-4-androstenedione)
  • Dienolone (δ⁹-19-NT 17β-adamantoate)
  • Dimethandrolone (7α,11β-dimethyl-19-NT)
  • Methoxydienone (18-methyl-δ^2,5(10)-19-NEA 3β-methyl ether)
  • Trendione (δ^9,11-19-nor-4-androstenedione)
  • Trestolone (MENT; 7α-methyl-19-NT)

17α-Alkylated derivatives

• Marketed
  • Ethylestrenol (ethylnandrol; 3-deketo-17α-ethyl-19-NT)
  • Mibolerone (7α,17α-dimethyl-19-NT)
  • Norethandrolone (17α-ethyl-19-NT)
  • Normethandrone (methylestrenolone; 17α-methyl-19-NT)
  • Propetandrol (17α-ethyl-19-NT 3β-propionate)
• Never marketed
  • Bolenol (3-deketo-17α-ethyl-19-nor-5-androstenediol)
  • Dimethyltrienolone (7α,17α-dimethyl-δ^9,11-19-NT)
  • Ethyldienolone (17α-ethyl-δ⁹-19-NT)
  • Methyldienolone (17α-ethyl-δ⁹-19-NT)
  • Methylhydroxynandrolone (MOHN, MHN; 4-hydroxy-17α-methyl-19-NT)
  • Metribolone (methyltrienolone, R-1881; 17α-methyl-δ^9,11-19-NT)
  • Norboletone (17α-ethyl-18-methyl-19-NT)
  • RU-2309 (18-methylmetribolone, 17α-methyl-THG)
  • Tetrahydrogestrinone (THG; 17α-ethyl-18-methyl-δ^9,11-19-NT)

Other testosterone derivatives

17α-Alkenylated derivatives

• Marketed
  • Norvinisterone (vinylnortestosterone; 17α-ethenyl-19-NT)
• Never marketed
  • Vinyltestosterone (17α-ethenyl-T)

17α-Alkynylated derivatives

• Marketed
  • Danazol (an isoxazole A ring-fused derivative of 17α-ethynyl-T)
  • Ethisterone (17α-ethynyl-T)
  • Gestrinone (17α-ethynyl-18-methyl-δ^9,11-19-NT)
  • Norgestrienone (17α-ethynyl-δ^9,11-19-NT)
  • Tibolone (7α-methyl-17α-ethynyl-δ⁵⁽¹⁰⁾-19-NT)

See also

• List of steroids
• List of designer drugs § Androgens
• List of androgens/anabolic steroids available in the United States

Further reading

• Kicman, A T (2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. ISSN 0007-1188. PMC 2439524. PMID 18500378.
• Fragkaki AG, Angelis YS, Koupparis M, Tsantili-Kakoulidou A, Kokotos G, Georgakopoulos C (2009). "Structural characteristics of anabolic androgenic steroids contributing to binding to the androgen receptor and to their anabolic and androgenic activities. Applied modifications in the steroidal structure". Steroids. 74 (2): 172–97. doi:10.1016/j.steroids.2008.10.016. PMID 19028512. S2CID 41356223.
• McRobb L, Handelsman DJ, Kazlauskas R, Wilkinson S, McLeod MD, Heather AK (2008). "Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay". J. Steroid Biochem. Mol. Biol. 110 (1–2): 39–47. doi:10.1016/j.jsbmb.2007.10.008. PMID 18395441. S2CID 5612000.