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List of androgens/anabolic steroids

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 derivativesEdit

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-likeEdit

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  

ProdrugsEdit

EthersEdit

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

Dihydrotestosterone derivativesEdit

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-likeEdit

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  

ProdrugsEdit

EthersEdit

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 dimersEdit

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) derivativesEdit

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-likeEdit

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  

ProdrugsEdit

EstersEdit

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

17α-Alkylated testosterone derivativesEdit

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-likeEdit

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  

ProdrugsEdit

EthersEdit

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 derivativesEdit

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  

ProdrugsEdit

Azine dimersEdit

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 derivativesEdit

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-likeEdit

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

ProdrugsEdit

EstersEdit

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

17α-Vinylated testosterone derivativesEdit

Compound Chemical name Structure Marketed
Vinyltestosterone 17α-Ethenyltestosterone  

17α-Vinylated 19-nortestosterone derivativesEdit

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

CommentaryEdit

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 derivativesEdit

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

17α-Ethynylated 19-nortestosterone derivativesEdit

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  

ProdrugsEdit

EthersEdit

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

EstersEdit

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 estersEdit

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

CommentaryEdit

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 alsoEdit

NotesEdit

? = Chemical names that are unverified.

ReferencesEdit

  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 readingEdit