List of androgens and anabolic steroids

For chemically related esters, see list of androgen esters.

Testosterone.

Steroid ring system.

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

• Testosterone derivatives: direct 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-Ethynylated/vinylated 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 article 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.

Testosterone derivatives

Non-17α-Alkylated

Compound	Chemical name	Structure	Marketed	Prohormone-like	Prodrug
Testosterone	Androst-4-en-17β-ol-3-one		✓	–	–
4-Hydroxytestosterone	4-Hydroxytestosterone		–	–	–
11-Ketotestosterone	11-Ketotestosterone		–	–	–
Boldenone	Δ1-Testosterone		✓	–	–
Clostebol	4-Chlorotestosterone		✓	–	–
4-Androstenediol	4-Androstenediol		–	✓	–
4-Dehydroepiandrosterone (4-DHEA)	4-Dehydroepiandrosterone		–	✓	–
5-Androstenedione	5-Androstenedione		–	✓	–
5-Dehydroandrosterone (5-DHA)	5-Dehydroandrosterone		–	✓	–
11β-Hydroxyandrostenedione (11β-OHA4)	11β-Hydroxy-4-androstenedione		–	✓	–
Adrenosterone (11-ketoandrostenedione, 11-KA4)	11-Keto-4-androstenedione		–	✓	–
Androstenediol (5-androstenediol, A5)	5-Androstenediol		–	✓	–
Androstenedione (4-androstenedione, A4)	4-Androstenedione		–	✓	–
Atamestane	1-Methyl-δ1-4-androstenedione		–	✓	–
Boldione (1,4-androstadienedione)	δ1-4-Androstenedione		–	✓	–
Dehydroepiandrosterone (DHEA, 5-DHEA; prasterone, androstenolone)	5-Dehydroepiandrosterone		✓	✓	–
Exemestane	6-Methylidene-δ1-4-androstenedione		✓	✓	–
Formestane	4-Hydroxy-4-androstenedione		✓	✓	–
Plomestane	10-Propargyl-4-androstenedione		–	✓	–
Cloxotestosterone	Testosterone 17-chloral hemiacetal ether		✓	–	✓
Quinbolone	Δ1-Testosterone 17β-cyclopentenyl enol ether		✓	–	✓
Silandrone	Testosterone 17β-trimethylsilyl ether		–	–	✓

17α-Alkylated

See also: 17α-Alkylated anabolic steroid

Compound	Chemical name	Structure	Marketed	Prohormone-like	Prodrug
Bolasterone	7α,17α-Dimethyltestosterone		✓	–	–
Calusterone	7β,17α-Dimethyltestosterone		✓	–	–
Chlorodehydromethyltestosterone (CDMT)	4-Chloro-17α-methyl-δ1-testosterone		✓	–	–
Enestebol	4-Hydroxy-17α-methyl-δ1-testosterone		–	–	–
Ethyltestosterone	17α-Ethyltestosterone		–	–	–
Fluoxymesterone	9α-Fluoro-11β-hydroxy-17α-methyltestosterone		✓	–	–
Formebolone	2-Formyl-11α-hydroxy-17α-methyl-δ1-testosterone		✓	–	–
Hydroxystenozole	17α-Methyl-2'H-androsta-2,4-dieno[3,2-c]pyrazol-17β-ol		–	–	–
Metandienone (methandienone, methandrostenolone)	17α-Methyl-δ1-testosterone		✓	–	–
Methylclostebol (chloromethyltestosterone)	4-Chloro-17α-methyltestosterone, (CMT		–	–	–
Methyltestosterone	17α-Methyltestosterone		✓	–	–
Oxymesterone	4-Hydroxy-17α-methyltestosterone		✓	–	–
Tiomesterone (thiomesterone)	1α,7α-Diacetylthio-17α-methyltestosterone		✓	–	–
Chlorodehydromethylandrostenediol (CDMA)	4-Chloro-17α-methyl-δ1-4-androstenediol		–	✓	–
Chloromethylandrostenediol (CMA)	4-Chloro-17α-methyl-4-androstenediol		–	✓	–
Methandriol (methylandrostenediol)	17α-Methyl-5-androstenediol		✓	✓	–
Methyltestosterone 3-hexyl ether	17α-Methyl-4-hydro-δ3,5-testosterone 3-hexyl ether?		✓	–	✓
Penmesterol (penmestrol)	17α-Methyl-4-hydro-δ3,5-testosterone 3-cyclopentyl ether?		✓	–	✓

17α-alkenyl and -alkynyl

Compound	Chemical name	Structure	Marketed
Vinyltestosterone	17α-Ethenyltestosterone		–
Ethisterone (ethinyltestosterone)	17α-Ethynyltestosterone		✓
Danazol (2,3-isoxazolethisterone)	2,3-Isoxazol-17α-ethynyltestosterone		✓

17α-Ethynylated testosterone derivatives are potent progestins with only very weak androgenic/anabolic activity and are used as oral contraceptives or for the treatment of gynecological conditions in women. They are invariably classified as progestins rather than as AAS. However, these progestins are testosterone derivatives and do have significant androgenic/anabolic activity, sometimes producing acne and other mild androgenic effects in women. Conversely, in men, these drugs may actually have functional antiandrogen effects due to their potent progestogenic and hence antigonadotropic activity and capacity to suppress gonadal testosterone production. ^[1]

Dihydrotestosterone derivatives

Non-17α-Alkylated

Compound	Chemical name	Structure	Marketed	Prohormone-like	Prodrug
Dihydrotestosterone (DHT); androstanolone, stanolone)	4,5α-Dihydrotestosterone		✓	–	–
1-Testosterone (dihydro-1-testosterone, dihydroboldenone)	4,5α-Dihydro-δ1-testosterone		–	–	–
11-Ketodihydrotestosterone (11-KDHT)	11-Keto-4,5α-dihydrotestosterone		–	–	–
Drostanolone	2α-Methyl-4,5α-dihydrotestosterone		✓	–	–
Epitiostanol (epithioandrostanol)	2α,3α-Epithio-3-deketo-4,5α-dihydrotestosterone		✓	–	–
Mesterolone	1α-Methyl-4,5α-dihydrotestosterone		✓	–	–
Metenolone (methenolone, methylandrostenolone)	1-Methyl-4,5α-dihydro-δ1-testosterone		✓	–	–
Nisterime	2α-Chloro-4,5α-dihydrotestosterone 3-O-(p-nitrophenyl)oxime		–	–	–
Stenbolone	2-Methyl-4,5α-dihydro-δ1-testosterone		✓	–	–
1-Androsterone (1-Andro, 1-DHEA)	1-Dehydroepiandrosterone		–	✓	–
1-Androstenediol (dihydro-1-androstenediol)	1-Androstenediol (4,5α-dihydro-δ1-4-androstenediol)		–	✓	–
1-Androstenedione (dihydro-1-androstenedione)	1-Androstenedione (4,5α-dihydro-δ1-4-androstenedione)		–	✓	–
5α-Androst-2-en-17-one	3-Deketo-2-androstenedione (3-deketo-4,5α-dihydro-δ2-4-androstenedione)		–	✓	–
Androsterone	Androsterone		–	✓	–
Epiandrosterone	Epiandrosterone		–	✓	–
Mepitiostane	2α,3α-Epithio-3-deketo-4,5α-dihydrotestosterone 17β-(1-methoxycyclopentane) ether		✓	–	✓
Mesabolone	4,5α-Dihydro-δ1-testosterone 17β-(1-methoxycyclohexane) ether		–	–	✓
Prostanozol	2'H-5α-Androst-2-eno[3,2-c]pyrazol-17β-ol 17β-tetrahydropyran ether		–	–	✓
Bolazine (di(drostanolone) azine)	3,3-[(1E,2E)-1,2-Hydrazinediylidene]di(2α-methyl-5α-androstan-17β-ol)?		✓	–	✓

17α-Alkylated

Compound	Chemical name	Structure	Marketed	Prohormone-like	Prodrug
Androisoxazole	17α-Methyl-5α-androstano[3,2-c]isoxazol-17β-ol		✓	–	–
Desoxymethyltestosterone	3-Deketo-17α-methyl-4,5α-dihydro-δ2-testosterone		–	–	–
Furazabol	17α-Methyl-5α-androstano[2,3-c][1,2,5]oxadiazol-17β-ol		✓	–	–
Mestanolone (methyl-DHT)	17α-Methyl-4,5α-dihydrotestosterone		✓	–	–
Methasterone (methyldrostanolone)	2α,17α-Dimethyl-4,5α-dihydrotestosterone		–	–	–
Methyl-1-testosterone (methyldihydro-1-testosterone, methyldihydroboldenone)	17α-Methyl-4,5α-dihydro-δ1-testosterone		–	–	–
Methyldiazinol	3-Azi-17α-methyl-4,5α-dihydrotestosterone		–	–	–
Methylepitiostanol	2α,3α-Epithio-3-deketo-17α-methyl-4,5α-dihydrotestosterone		–	–	–
Methylstenbolone	2,17α-Dimethyl-4,5α-dihydro-δ1-testosterone		–	–	–
Oxandrolone	2-Oxa-17α-methyl-4,5α-dihydrotestosterone		✓	–	–
Oxymetholone	2-Hydroxymethylene-4,5α-dihydro-17α-methyltestosterone		✓	–	–
Stanozolol	17α-Methyl-2'H-5α-androst-2-eno[3,2-c]pyrazol-17β-ol		✓	–	–
Mebolazine (dimethazine, di(methasterone) azine)	3,3-[(1E,2E)-1,2-Hydrazinediylidene]di(2α,17α-dimethyl-5α-androstan-17β-ol)?		✓	–	✓

19-Nortestosterone (nandrolone) derivatives

Non-17α-alkylated

Compound	Chemical name	Structure	Marketed	Prohormone-like	Prodrug
Nandrolone (nortestosterone)	19-Nortestosterone		✓	–	–
11β-Methyl-19-nortestosterone (11β-MNT)	11β-Methyl-19-nortestosterone		–	–	–
Dienolone	19-Nor-δ9-testosterone		–	–	–
Dimethandrolone	7α,11β-Dimethyl-19-nortestosterone		–	–	–
Norclostebol	4-Chloro-19-nortestosterone		✓	–	–
Oxabolone	4-Hydroxy-19-nortestosterone		✓	–	–
Trenbolone (trienolone)	19-Nor-δ9,11-testosterone		✓	–	–
Trestolone (MENT)	7α-Methyl-19-nortestosterone		–	–	–
7α-Methyl-19-nor-4-androstenedione (MENT dione, trestione)	7α-Methyl-19-nor-4-androstenedione		–	✓	–
19-Nor-5-androstenediol	19-Nor-5-androstenediol		–	✓	–
19-Nor-5-androstenedione	19-Nor-5-androstenedione		–	✓	–
19-Nordehydroepiandrosterone	19-Nor-5-dehydroepiandrosterone (19-nor-DHEA)		–	✓	–
Bolandiol (nor-4-androstenediol)	19-Nor-4-androstenediol		✓	✓	–
Bolandione (nor-4-androstenedione)	19-Nor-4-androstenedione		–	✓	–
Dienedione (nor-4,9-androstadienedione)	19-Nor-δ9-4-androstenedione		–	✓	–
Methoxydienone (methoxygonadiene)	18-Methyl-19-nor-δ2,5(10)-epiandrosterone 3-methyl ether		–	✓	–
Trendione (nor-4,9,11-androstatrienedione)	19-Nor-δ9,11-4-androstenedione		–	✓	–
Bolmantalate (nandrolone adamantoate)	19-Nortestosterone 17β-adamantoate		✓	–	✓

17α-Alkylated

Compound	Chemical name	Structure	Marketed	Prohormone-like	Prodrug
Dimethyltrienolone (7α,17α-dimethyltrenbolone)	7α,17α-Dimethyl-19-nor-δ9,11-testosterone		–	–	–
Dimethyldienolone (7α,17α-dimethyldienolone)	7α,17α-Dimethyl-19-nor-δ9-testosterone		–	–	–
Ethyldienolone	17α-Ethyl-19-nor-δ9-testosterone		–	–	–
Ethylestrenol (ethylnandrol)	17α-Ethyl-3-deketo-19-nortestosterone		✓	–	–
Methyldienolone	17α-Methyl-19-nor-δ9-testosterone		–	–	–
Methylhydroxynandrolone (MOHN, MHN)	4-Hydroxy-17α-methyl-19-nortestosterone		–	–	–
Metribolone (methyltrienolone, R-1881)	17α-Methyl-19-nor-δ9,11-testosterone		–	–	–
Mibolerone	7α,17α-Dimethyl-19-nortestosterone		✓	–	–
Norboletone	17α-Ethyl-18-methyl-19-nortestosterone		–	–	–
Norethandrolone (ethylnandrolone, ethylestrenolone)	17α-Ethyl-19-nortestosterone		✓	–	–
Normethandrone (methylestrenolone, normethisterone)	17α-Methyl-19-nortestosterone		✓	–	–
RU-2309 (18-methymetribolone, 17α-methyl-THG)	17α,18-Dimethyl-19-nor-δ9,11-testosterone		–	–	–
Tetrahydrogestrinone (THG)	17α-Ethyl-18-methyl-19-nor-δ9,11-testosterone		–	–	–
Bolenol (ethylnorandrostenol)	3-Deketo-17α-ethyl-19-nor-5-androstenediol		–	✓	–
Propetandrol	17α-Ethyl-19-nortestosterone 3-propionate		✓	–	✓

17α-alkenyl and -alkynyl

Compound	Chemical name	Structure	Marketed	Prohormone-like	Prodrug
Norvinisterone (vinylnortestosterone)	17α-Ethenyl-19-nortestosterone		✓	–	–
Norethisterone (norethindrone)	17α-Ethynyl-19-nortestosterone		✓	–	–
Etynodiol (ethynodiol, 3β-hydroxynorethisterone)	17α-Ethynyl-3-deketo-3β-hydroxy-19-nortestosterone		–	–	–
Gestrinone (ethylnorgestrienone, R-2323)	17α-Ethynyl-18-methyl-19-nor-δ9,11-testosterone		✓	–	–
Levonorgestrel ((−)-norgestrel)	(−)-17α-Ethynyl-18-methyl-19-nortestosterone		✓	–	–
Lynestrenol (3-deketonorethisterone)	17α-Ethynyl-3-deketo-19-nortestosterone		✓	–	–
Norgestrel (18-methylnorethisterone)	17α-Ethynyl-18-methyl-19-nortestosterone		✓	–	–
Norgestrienone (ethynyltrenbolone)	17α-Ethynyl-19-nor-δ9,11-testosterone		✓	–	–
Tibolone (7α-methylnoretynodrel)	7α-Methyl-17α-ethynyl-19-nor-δ5(10)-testosterone		✓	–	–
Quingestanol	4-Hydro-19-nor-δ3,5-testosterone 3-cyclopentyl ether?		–	–	✓
Etynodiol diacetate (ethynodiol diacetate)	17α-Ethynyl-3-deketo-3β-hydroxy-19-nortestosterone 3β,17β-diacetate		✓	–	✓
Norethisterone acetate (norethindrone acetate)	17α-Ethynyl-19-nortestosterone 17β-acetate		✓	–	✓
Norethisterone enanthate (norethindrone enanthate)	17α-Ethynyl-19-nortestosterone 17β-enanthate		✓	–	✓
Quingestanol acetate	4-Hydro-17α-ethynyl-19-nor-δ3,5-testosterone 3-cyclopentyl ether 17β-acetate?		✓	–	✓

The 17α-ethenylated (vinylated) testosterone derivative norvinisterone (vinylnortestosterone) is much more potent as an AAS than the 17α-ethynylated testosterone derivatives and is intermediate in potency between the 17α-ethynylated progestins and conventional AAS, with approximately one-third and one-fifth of the respective androgenic and anabolic activity of nandrolone in animal bioassays. ^[2]

Vinyltestosterone has been described as a weak AAS, though stronger than its 17α-ethynylated analogue ethisterone. ^[3]

See also

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

Notes

^? = Chemical names that are unverified.

References

1. Paulsen, C. Alvin; Leach, Robert B.; Lanman, John; Goldston, Norman; Maddock, W. O.; Heller, Carl G. (1962). "Inherent Estrogenicity of Norethindrone and Norethynodrel: Comparison with Other Synthetic Progestins and Progesterone1". The Journal of Clinical Endocrinology & Metabolism. 22 (10): 1033–1039. doi:10.1210/jcem-22-10-1033. ISSN   0021-972X. PMID   13942007. Androgenic effects were absent for each of the compounds in the doses administered as judged by: (a) marked decrease in libido and sexual potentia in each of 21 normal male subjects receiving norethynodrel, norethindrone and norethandrolone; (b) failure to increase libido and sexual potentia in each of four hypogonadotrophic eunuchoidal men receiving norethandrolone (each had previously responded to testosterone administration); (c) no virilization of 14 of 15 postmenopausal women receiving the three progestins (one who was taking norethandrolone at the dose level of 30 mg daily noted lowering in the pitch of her voice during the second month of therapy).
2. Saunders, Francis J.; Drill, Victor A. (1956). "The Myotrophic and Androgenic Effects of 17-Ethyl-19-Nortestosterone and Related Compounds". Endocrinology. 58 (5): 567–572. doi:10.1210/endo-58-5-567. ISSN   0013-7227. PMID   13317831.
3. LEWIS RA, DeMAJO S, ROSEMBERG E (1949). "The effects of 17-vinyl testosterone upon the rat adrenal". Endocrinology. 45 (6): 564–70. doi:10.1210/endo-45-6-564. PMID   15402199.

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.