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):

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

See also: 17α-Alkylated anabolic steroid
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).

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Dieser Artikel behandelt den englischen Dichter, der nicht zu verwechseln ist mit dem Komponisten Samuel Coleridge-Taylor (1875–1912). Samuel Taylor Coleridge, 1795 Samuel Taylor Coleridge [ˈkoʊlərɪdʒ oder ˈkoʊlrɪdʒ] (* 21. Oktober 1772 in Ottery St Mary, Devon; † 25. Juli 1834 in Highgate, London) war ein englischer Dichter der Romantik, Kritiker und Philosoph. Zusammen mit William Wordsworth und Robert Southey gehörte er den sogenannten Lake Poets an. Sein bekanntestes Werk i...