List of androgens/anabolic steroids

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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):

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[edit]

Compound Chemical name Structure Marketed
Testosterone Androst-4-en-17β-ol-3-one Testosteron.svg
4-Hydroxytestosterone 4-Hydroxytestosterone 4-hydroxytestosterone.png
11-Ketotestosterone 11-Ketotestosterone 11-Ketotestosterone.svg
Boldenone Δ1-Testosterone Boldenone.png
Clostebol 4-Chlorotestosterone Clostebol.svg

Prohormone-like[edit]

Compound Chemical name Structure Marketed
4-Androstenediol 4-Androstenediol 4-Androstenediol.svg
4-Dehydroepiandrosterone (4-DHEA) 4-Dehydroepiandrosterone 3beta-Hydroxyandrost-4-en-17-one.png
5-Androstenedione 5-Androstenedione 5-Androstenedione.svg
5-Dehydroandrosterone (5-DHA) 5-Dehydroandrosterone Dehydroandrosterone.svg
11β-Hydroxyandrostenedione (11β-OHA4) 11β-Hydroxy-4-androstenedione 11β-Hydroxyandrostenedione.svg
Adrenosterone (11-ketoandrostenedione, 11-KA4) 11-Keto-4-androstenedione Adrenosterone.png
Androstenediol (5-androstenediol, A5) 5-Androstenediol 5-Androstenediol.png
Androstenedione (4-androstenedione, A4) 4-Androstenedione Androstendion.svg
Atamestane 1-Methyl-δ1-4-androstenedione Atamestane.svg
Boldione (1,4-androstadienedione) δ1-4-Androstenedione Boldione.png
Dehydroepiandrosterone (DHEA, 5-DHEA; prasterone, androstenolone) 5-Dehydroepiandrosterone Dehydroepiandrosteron.svg
Exemestane 6-Methylidene-δ1-4-androstenedione Exemestane.svg
Formestane 4-Hydroxy-4-androstenedione Formestane.svg
Plomestane 10-Propargyl-4-androstenedione Plomestane.svg

Prodrugs[edit]

Ethers[edit]

Compound Chemical name Structure Marketed
Cloxotestosterone Testosterone 17-chloral hemiacetal ether Cloxotestosterone.svg
Quinbolone Δ1-Testosterone 17β-cyclopentenyl enol ether Quinbolone.png
Silandrone Testosterone 17β-trimethylsilyl ether Silandrone.png

Dihydrotestosterone derivatives[edit]

Compound Chemical name Structure Marketed
Dihydrotestosterone (DHT;) androstanolone, stanolone) 4,5α-Dihydrotestosterone Androstanolone.svg
1-Testosterone (dihydro-1-testosterone, dihydroboldenone) 4,5α-Dihydro-δ1-testosterone 1-testosterone.png
11-Ketodihydrotestosterone (11-KDHT) 11-Keto-4,5α-dihydrotestosterone 11-Ketodihydrotestosterone.svg
Drostanolone 2α-Methyl-4,5α-dihydrotestosterone Drostanolone New-And-Improved.png
Epitiostanol (epithioandrostanol) 2α,3α-Epithio-3-deketo-4,5α-dihydrotestosterone Epitiostanol.png
Mesterolone 1α-Methyl-4,5α-dihydrotestosterone Mesterolone.svg
Metenolone (methenolone, methylandrostenolone) 1-Methyl-4,5α-dihydro-δ1-testosterone Metenolone.svg
Nisterime 2α-Chloro-4,5α-dihydrotestosterone 3-O-(p-nitrophenyl)oxime Nisterime.svg
Stenbolone 2-Methyl-4,5α-dihydro-δ1-testosterone Stenbolone.svg

Prohormone-like[edit]

Compound Chemical name Structure Marketed
1-Androsterone (1-Andro, 1-DHEA) 1-Dehydroepiandrosterone 1-Androsterone.svg
1-Androstenediol (dihydro-1-androstenediol) 1-Androstenediol (4,5α-dihydro-δ1-4-androstenediol) 1-Androstenediol.svg
1-Androstenedione (dihydro-1-androstenedione) 1-Androstenedione (4,5α-dihydro-δ1-4-androstenedione) 1-Androstenedione.svg
5α-Androst-2-en-17-one 3-Deketo-2-androstenedione (3-deketo-4,5α-dihydro-δ2-4-androstenedione) 5alpha-androst-2-ene-17-one.svg
Androsterone Androsterone Androsterone.png
Epiandrosterone Epiandrosterone Epiandrosterone.png

Prodrugs[edit]

Ethers[edit]

Compound Chemical name Structure Marketed
Mepitiostane 2α,3α-Epithio-3-deketo-4,5α-dihydrotestosterone 17β-(1-methoxycyclopentane) ether Mepitiostane.png
Mesabolone 4,5α-Dihydro-δ1-testosterone 17β-(1-methoxycyclohexane) ether Mesabolone.png
Prostanozol 2'H-5α-Androst-2-eno[3,2-c]pyrazol-17β-ol 17β-tetrahydropyran ether Prostanozol.png

Azine dimers[edit]

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

19-Nortestosterone (nandrolone) derivatives[edit]

Compound Chemical name Structure Marketed
Nandrolone (nortestosterone) 19-Nortestosterone Nandrolone.svg
11β-Methyl-19-nortestosterone (11β-MNT) 11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone.svg
Dienolone 19-Nor-δ9-testosterone Dienolone structure.png
Dimethandrolone 7α,11β-Dimethyl-19-nortestosterone Dimethandrolone structure.svg
Norclostebol 4-Chloro-19-nortestosterone Norclostebol.svg
Oxabolone 4-Hydroxy-19-nortestosterone Oxabolone.svg
Trenbolone (trienolone) 19-Nor-δ9,11-testosterone Trenbolone.svg
Trestolone (MENT) 7α-Methyl-19-nortestosterone Trestolone structure.svg

Prohormone-like[edit]

Compound Chemical name Structure Marketed
7α-Methyl-19-nor-4-androstenedione (MENT dione, trestione) 7α-Methyl-19-nor-4-androstenedione 7α-Methyl-19-norandrostenedione.svg
19-Nor-5-androstenediol 19-Nor-5-androstenediol 19-Nor-5-androstenediol.svg
19-Nor-5-androstenedione 19-Nor-5-androstenedione 19-Nor-5-androstenedione.svg
19-Nordehydroepiandrosterone 19-Nor-5-dehydroepiandrosterone
Bolandiol (nor-4-androstenediol) 19-Nor-4-androstenediol Bolandiol.svg
Bolandione (nor-4-androstenedione) 19-Nor-4-androstenedione 19-norandrostenedione.png
Dienedione (nor-4,9-androstadienedione) 19-Nor-δ9-4-androstenedione Dienedione.svg
Methoxydienone (methoxygonadiene) 18-Methyl-19-nor-δ2,5(10)-epiandrosterone 3-methyl ether Methoxydienone.svg
Trendione (nor-4,9,11-androstatrienedione) 19-Nor-δ9,11-4-androstenedione Trendione.svg

Prodrugs[edit]

Esters[edit]

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

17α-Alkylated testosterone derivatives[edit]

Compound Chemical name Structure Marketed
Bolasterone 7α,17α-Dimethyltestosterone Bolasterone.png
Calusterone 7β,17α-Dimethyltestosterone Calusterone.svg
Chlorodehydromethyltestosterone (CDMT) 4-Chloro-17α-methyl-δ1-testosterone 4-Chlorodehydromethyltestosterone.png
Enestebol 4-Hydroxy-17α-methyl-δ1-testosterone Enestebol.png
Ethyltestosterone 17α-Ethyltestosterone Ethyltestosterone structure.png
Fluoxymesterone 9α-Fluoro-11β-hydroxy-17α-methyltestosterone Fluoxymesterone structure.svg
Formebolone 2-Formyl-11α-hydroxy-17α-methyl-δ1-testosterone Formebolone.png
Hydroxystenozole 17α-Methyl-2'H-androsta-2,4-dieno[3,2-c]pyrazol-17β-ol Hydroxystenozole.png
Metandienone (methandienone, methandrostenolone) 17α-Methyl-δ1-testosterone Metandienone.svg
Methylclostebol (chloromethyltestosterone) 4-Chloro-17α-methyltestosterone Methylclostebol.svg
Methyltestosterone 17α-Methyltestosterone Methyltestosterone.svg
Oxymesterone 4-Hydroxy-17α-methyltestosterone Oxymesterone.png
Tiomesterone (thiomesterone) 1α,7α-Diacetylthio-17α-methyltestosterone Tiomesterone structure.svg

Prohormone-like[edit]

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

Prodrugs[edit]

Ethers[edit]

Compound Chemical name Structure Marketed
Methyltestosterone 3-hexyl ether 17α-Methyl-4-hydro-δ3,5-testosterone 3-hexyl ether? Methyltestosterone 3-hexyl ether.svg
Penmesterol (penmestrol) 17α-Methyl-4-hydro-δ3,5-testosterone 3-cyclopentyl ether? Penmesterol.svg

17α-Alkylated dihydrotestosterone derivatives[edit]

Compound Chemical name Structure Marketed
Androisoxazole 17α-Methyl-5α-androstano[3,2-c]isoxazol-17β-ol Androisoxazole.png
Desoxymethyltestosterone 3-Deketo-17α-methyl-4,5α-dihydro-δ2-testosterone Desoxymethyltestosterone.png
Furazabol 17α-Methyl-5α-androstano[2,3-c][1,2,5]oxadiazol-17β-ol Furazabol.png
Mestanolone (methyl-DHT) 17α-Methyl-4,5α-dihydrotestosterone Mestanolone.png
Methasterone (methyldrostanolone) 2α,17α-Dimethyl-4,5α-dihydrotestosterone Methasterone.png
Methyl-1-testosterone (methyldihydro-1-testosterone) 17α-Methyl-4,5α-dihydro-δ1-testosterone Methyl-1-testosterone.svg
Methyldiazinol 3-Azi-17α-methyl-4,5α-dihydrotestosterone Methyldiazirinol.svg
Methylepitiostanol 2α,3α-Epithio-3-deketo-17α-methyl-4,5α-dihydrotestosterone Methylepitiostanol.svg
Methylstenbolone 2,17α-Dimethyl-4,5α-dihydro-δ1-testosterone Methylstenbolone.png
Oxandrolone 2-Oxa-17α-methyl-4,5α-dihydrotestosterone Oxandrolone.svg
Oxymetholone 2-Hydroxymethylene-4,5α-dihydro-17α-methyltestosterone Oxymetholone.svg
Stanozolol 17α-Methyl-2'H-5α-androst-2-eno[3,2-c]pyrazol-17β-ol Stanozolol.svg

Prodrugs[edit]

Azine dimers[edit]

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)? Mebolazine.png

17α-Alkylated 19-nortestosterone derivatives[edit]

Compound Chemical name Structure Marketed
Dimethyltrienolone (7α,17α-dimethyltrenbolone) 7α,17α-Dimethyl-19-nor-δ9,11-testosterone 7a17a-dimethyltrenbolone.png
Dimethyldienolone (7α,17α-dimethyldienolone) 7α,17α-Dimethyl-19-nor-δ9-testosterone Dimethyldienolone.svg
Ethyldienolone 17α-Ethyl-19-nor-δ9-testosterone Ethyldienolone.png
Ethylestrenol (ethylnandrol) 17α-Ethyl-3-deketo-19-nortestosterone Ethylestrenol.svg
Methyldienolone 17α-Methyl-19-nor-δ9-testosterone Methyldienolone.svg
Methylhydroxynandrolone (MOHN, MHN) 4-Hydroxy-17α-methyl-19-nortestosterone Methylhydroxynandrolone.svg
Metribolone (methyltrienolone, R-1881) 17α-Methyl-19-nor-δ9,11-testosterone Metribolone.png
Mibolerone 7α,17α-Dimethyl-19-nortestosterone Mibolerone structure.png
Norboletone 17α-Ethyl-18-methyl-19-nortestosterone Norboletone.svg
Norethandrolone (ethylnandrolone, ethylestrenolone) 17α-Ethyl-19-nortestosterone Norethandrolone structure.png
Normethandrone (methylestrenolone, normethisterone) 17α-Methyl-19-nortestosterone Methylestrenolone.png
RU-2309 (18-methymetribolone, 17α-methyl-THG) 17α,18-Dimethyl-19-nor-δ9,11-testosterone RU-2309.svg
Tetrahydrogestrinone (THG) 17α-Ethyl-18-methyl-19-nor-δ9,11-testosterone Tetrahydrogestrinone.png

Prohormone-like[edit]

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

Prodrugs[edit]

Esters[edit]

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

17α-Vinylated testosterone derivatives[edit]

Compound Chemical name Structure Marketed
Vinyltestosterone 17α-Ethenyltestosterone Norvinisterone.svg

17α-Vinylated 19-nortestosterone derivatives[edit]

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

Commentary[edit]

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[edit]

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

17α-Ethynylated 19-nortestosterone derivatives[edit]

Compound Chemical name Structure Marketed
Norethisterone (norethindrone) 17α-Ethynyl-19-nortestosterone Norethisterone.svg
Etynodiol (ethynodiol, 3β-hydroxynorethisterone) 17α-Ethynyl-3-deketo-3β-hydroxy-19-nortestosterone Etynodiol.svg
Gestrinone (ethylnorgestrienone, R-2323) 17α-Ethynyl-18-methyl-19-nor-δ9,11-testosterone Gestrinone.svg
Levonorgestrel ((−)-norgestrel) (−)-17α-Ethynyl-18-methyl-19-nortestosterone Levonorgestrel.svg
Lynestrenol (3-deketonorethisterone) 17α-Ethynyl-3-deketo-19-nortestosterone Lynestrenol.svg
Norgestrel (18-methylnorethisterone) 17α-Ethynyl-18-methyl-19-nortestosterone Levonorgestrel.svgDextronorgestrel.svg
Norgestrienone (ethynyltrenbolone) 17α-Ethynyl-19-nor-δ9,11-testosterone Norgestrienone.svg
Tibolone (7α-methylnoretynodrel) 7α-Methyl-17α-ethynyl-19-nor-δ5(10)-testosterone Tibolone.svg

Prodrugs[edit]

Ethers[edit]

Compound Chemical name Structure Marketed
Quingestanol 4-Hydro-19-nor-δ3,5-testosterone 3-cyclopentyl ether? Quingestanol structure.svg

Esters[edit]

Compound Chemical name Structure Marketed
Etynodiol diacetate (ethynodiol diacetate) 17α-Ethynyl-3-deketo-3β-hydroxy-19-nortestosterone 3β,17β-diacetate Ethynodiol diacetate.svg
Norethisterone acetate (norethindrone acetate) 17α-Ethynyl-19-nortestosterone 17β-acetate Norethisterone acetate.svg
Norethisterone enanthate (norethindrone enanthate) 17α-Ethynyl-19-nortestosterone 17β-enanthate Norethindrone enanthate.svg

Ethers and esters[edit]

Compound Chemical name Structure Marketed
Quingestanol acetate 4-Hydro-17α-ethynyl-19-nor-δ3,5-testosterone 3-cyclopentyl ether 17β-acetate? Quingestanol acetate.svg

Commentary[edit]

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[edit]

Notes[edit]

? = Chemical names that are unverified.

References[edit]

  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[edit]