List of androgens and anabolic steroids

(Redirected from List of androgens/anabolic steroids)

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

Testosterone.

Steroid ring system.

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

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

Testosterone derivatives

Compound	Chemical name	Structure	Marketed
Testosterone	Androst-4-en-17β-ol-3-one		✓
4-Hydroxytestosterone	4-Hydroxytestosterone		–
11-Ketotestosterone	11-Ketotestosterone		–
Boldenone	Δ¹-Testosterone		✓
Clostebol	4-Chlorotestosterone		✓

Prohormone-like

Compound	Chemical name	Structure	Marketed
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		–

Prodrugs

Ethers

Compound	Chemical name	Structure	Marketed
Cloxotestosterone	Testosterone 17-chloral hemiacetal ether		✓
Quinbolone	Δ¹-Testosterone 17β-cyclopentenyl enol ether		✓
Silandrone	Testosterone 17β-trimethylsilyl ether		–

Dihydrotestosterone derivatives

Compound	Chemical name	Structure	Marketed
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		✓

Prohormone-like

Compound	Chemical name	Structure	Marketed
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		–

Prodrugs

Ethers

Compound	Chemical name	Structure	Marketed
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		–

Azine dimers

Compound	Chemical name	Structure	Marketed
Bolazine (di(drostanolone) azine)	3,3-[(1E,2E)-1,2-Hydrazinediylidene]di(2α-methyl-5α-androstan-17β-ol)^?		✓

19-Nortestosterone (nandrolone) derivatives

Compound	Chemical name	Structure	Marketed
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-δ^9,11-testosterone		✓
Trestolone (MENT)	7α-Methyl-19-nortestosterone		–

Prohormone-like

Compound	Chemical name	Structure	Marketed
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		–
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-δ^2,5(10)-epiandrosterone 3-methyl ether		–
Trendione (nor-4,9,11-androstatrienedione)	19-Nor-δ^9,11-4-androstenedione		–

Prodrugs

Esters

Compound	Chemical name	Structure	Marketed
Bolmantalate (nandrolone adamantoate)	19-Nortestosterone 17β-adamantoate		✓

17α-Alkylated testosterone derivatives

Compound	Chemical name	Structure	Marketed
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		–
Methyltestosterone	17α-Methyltestosterone		✓
Oxymesterone	4-Hydroxy-17α-methyltestosterone		✓
Tiomesterone (thiomesterone)	1α,7α-Diacetylthio-17α-methyltestosterone		✓

Prohormone-like

Compound	Chemical name	Structure	Marketed
Chlorodehydromethylandrostenediol (CDMA)	4-Chloro-17α-methyl-δ¹-4-androstenediol		–
Chloromethylandrostenediol (CMA)	4-Chloro-17α-methyl-4-androstenediol		–
Methandriol (methylandrostenediol)	17α-Methyl-5-androstenediol		✓

Prodrugs

Ethers

Compound	Chemical name	Structure	Marketed
Methyltestosterone 3-hexyl ether	17α-Methyl-4-hydro-δ^3,5-testosterone 3-hexyl ether^?		✓
Penmesterol (penmestrol)	17α-Methyl-4-hydro-δ^3,5-testosterone 3-cyclopentyl ether^?		✓

17α-Alkylated dihydrotestosterone derivatives

Compound	Chemical name	Structure	Marketed
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)	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		✓

Prodrugs

Azine dimers

Compound	Chemical name	Structure	Marketed
Mebolazine (dimethazine, di(methasterone) azine)	3,3-[(1E,2E)-1,2-Hydrazinediylidene]di(2α,17α-dimethyl-5α-androstan-17β-ol)^?		✓

17α-Alkylated 19-nortestosterone derivatives

Compound	Chemical name	Structure	Marketed
Dimethyltrienolone (7α,17α-dimethyltrenbolone)	7α,17α-Dimethyl-19-nor-δ^9,11-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-δ^9,11-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-δ^9,11-testosterone		–
Tetrahydrogestrinone (THG)	17α-Ethyl-18-methyl-19-nor-δ^9,11-testosterone		–

Prohormone-like

Compound	Chemical name	Structure	Marketed
Bolenol (ethylnorandrostenol)	3-Deketo-17α-ethyl-19-nor-5-androstenediol		–

Prodrugs

Esters

Compound	Chemical name	Structure	Marketed
Propetandrol	17α-Ethyl-19-nortestosterone 3-propionate		✓

17α-Vinylated testosterone derivatives

Compound	Chemical name	Structure	Marketed
Vinyltestosterone	17α-Ethenyltestosterone		–

17α-Vinylated 19-nortestosterone derivatives

Compound	Chemical name	Structure	Marketed
Norvinisterone (vinylnortestosterone)	17α-Ethenyl-19-nortestosterone		✓

Commentary

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.^[1]

Vinyltestosterone has been described as a weak AAS, though stronger than its 17α-ethynylated analogue ethisterone.^[2]

17α-Ethynylated testosterone derivatives

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

17α-Ethynylated 19-nortestosterone derivatives

Compound	Chemical name	Structure	Marketed
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-δ^9,11-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-δ^9,11-testosterone		✓
Tibolone (7α-methylnoretynodrel)	7α-Methyl-17α-ethynyl-19-nor-δ⁵⁽¹⁰⁾-testosterone		✓

Prodrugs

Ethers

Compound	Chemical name	Structure	Marketed
Quingestanol	4-Hydro-19-nor-δ^3,5-testosterone 3-cyclopentyl ether^?		–

Esters

Compound	Chemical name	Structure	Marketed
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		✓

Ethers and esters

Compound	Chemical name	Structure	Marketed
Quingestanol acetate	4-Hydro-17α-ethynyl-19-nor-δ^3,5-testosterone 3-cyclopentyl ether 17β-acetate^?		✓

Commentary

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.^[3]

See also

Notes

^? = Chemical names that are unverified.

References

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.

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