List of androgens/anabolic steroids

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):

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-δ9,11-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-δ2,5(10)-epiandrosterone 3-methyl ether
Trendione (nor-4,9,11-androstatrienedione) 19-Nor-δ9,11-4-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-δ3,5-testosterone 3-hexyl ether?
Penmesterol (penmestrol) 17α-Methyl-4-hydro-δ3,5-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-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

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-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

Prodrugs

Ethers

Compound Chemical name Structure Marketed
Quingestanol 4-Hydro-19-nor-δ3,5-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-δ3,5-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

  1. 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.
  2. 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.
  3. 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).

Further reading

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