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This is a list ofandrogens/anabolic steroids (AAS) ortestosteronederivatives.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 ofprogestins with mostly only very weak androgenic/anabolic activity. AAS that are listed as marketed may be marketed as one or more esters rather than as the listed AAS itself.
This article pertains tosteroidal androgens;nonsteroidal androgens like theselective androgen receptor modulators (SARMs)andarine andenobosarm (ostarine) are not included here.
* Only present endogenously in trace/very small amounts or present in other species.
| Compound | Chemical name | Structure | Marketed | Prohormone-like | Prodrug |
|---|---|---|---|---|---|
| Testosterone | Androst-4-en-17β-ol-3-one | | ✓ | – | – |
| 4-Hydroxytestosterone | 4-Hydroxytestosterone |  | – | – | – |
| 11-Ketotestosterone | 11-Ketotestosterone |  | – | – | – |
| Boldenone | Δ1-Testosterone |  | ✓ | – | – |
| Clostebol | 4-Chlorotestosterone |  | ✓ | – | – |
| 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 |  | – | ✓ | – |
| Cloxotestosterone | Testosterone 17-chloral hemiacetal ether |  | ✓ | – | ✓ |
| Quinbolone | Δ1-Testosterone 17β-cyclopentenyl enol ether |  | ✓ | – | ✓ |
| Silandrone | Testosterone 17β-trimethylsilyl ether |  | – | – | ✓ |
| Compound | Chemical name | Structure | Marketed | Prohormone-like | Prodrug |
|---|---|---|---|---|---|
| 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, (CMT |  | – | – | – |
| Methyltestosterone | 17α-Methyltestosterone |  | ✓ | – | – |
| Oxymesterone | 4-Hydroxy-17α-methyltestosterone |  | ✓ | – | – |
| Tiomesterone (thiomesterone) | 1α,7α-Diacetylthio-17α-methyltestosterone |  | ✓ | – | – |
| Chlorodehydromethylandrostenediol (CDMA) | 4-Chloro-17α-methyl-δ1-4-androstenediol |  | – | ✓ | – |
| Chloromethylandrostenediol (CMA) | 4-Chloro-17α-methyl-4-androstenediol |  | – | ✓ | – |
| Methandriol (methylandrostenediol) | 17α-Methyl-5-androstenediol |  | ✓ | ✓ | – |
| 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? |  | ✓ | – | ✓ |
| Compound | Chemical name | Structure | Marketed |
|---|---|---|---|
| Vinyltestosterone | 17α-Ethenyltestosterone |  | – |
| Ethisterone (ethinyltestosterone) | 17α-Ethynyltestosterone |  | ✓ |
| Danazol (2,3-isoxazolethisterone) | 2,3-Isoxazol-17α-ethynyltestosterone |  | ✓ |
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 functionalantiandrogen effects due to their potent progestogenic and henceantigonadotropic activity and capacity to suppressgonadal testosterone production.[1]
| Compound | Chemical name | Structure | Marketed | Prohormone-like | Prodrug |
|---|---|---|---|---|---|
| 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 |  | ✓ | – | – |
| 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 |  | – | ✓ | – |
| 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 |  | – | – | ✓ |
| Bolazine (di(drostanolone) azine) | 3,3-[(1E,2E)-1,2-Hydrazinediylidene]di(2α-methyl-5α-androstan-17β-ol)? |  | ✓ | – | ✓ |
| Compound | Chemical name | Structure | Marketed | Prohormone-like | Prodrug |
|---|---|---|---|---|---|
| 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, methyldihydroboldenone) | 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 |  | ✓ | – | – |
| Mebolazine (dimethazine, di(methasterone) azine) | 3,3-[(1E,2E)-1,2-Hydrazinediylidene]di(2α,17α-dimethyl-5α-androstan-17β-ol)? |  | ✓ | – | ✓ |
| Compound | Chemical name | Structure | Marketed | Prohormone-like | Prodrug |
|---|---|---|---|---|---|
| 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 |  | – | – | – |
| 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 (19-nor-DHEA) |  | – | ✓ | – |
| 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 |  | – | ✓ | – |
| Bolmantalate (nandrolone adamantoate) | 19-Nortestosterone 17β-adamantoate |  | ✓ | – | ✓ |
| Compound | Chemical name | Structure | Marketed | Prohormone-like | Prodrug |
|---|---|---|---|---|---|
| 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 |  | – | – | – |
| Bolenol (ethylnorandrostenol) | 3-Deketo-17α-ethyl-19-nor-5-androstenediol |  | – | ✓ | – |
| Propetandrol | 17α-Ethyl-19-nortestosterone 3-propionate |  | ✓ | – | ✓ |
| Compound | Chemical name | Structure | Marketed | Prohormone-like | Prodrug |
|---|---|---|---|---|---|
| Norvinisterone (vinylnortestosterone) | 17α-Ethenyl-19-nortestosterone |  | ✓ | – | – |
| 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 |  | ✓ | – | – |
| Quingestanol | 4-Hydro-19-nor-δ3,5-testosterone 3-cyclopentyl ether? |  | – | – | ✓ |
| 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 |  | ✓ | – | ✓ |
| Quingestanol acetate | 4-Hydro-17α-ethynyl-19-nor-δ3,5-testosterone 3-cyclopentyl ether 17β-acetate? |  | ✓ | – | ✓ |
The 17α-ethenylated (vinylated) testosterone derivativenorvinisterone (vinylnortestosterone) is much more potent as an AAS than the 17α-ethynylated testosterone derivatives and is intermediate in potency between the 17α-ethynylatedprogestins and conventional AAS, with approximately one-third and one-fifth of the respective androgenic and anabolic activity of nandrolone inanimalbioassays.[2]
Vinyltestosterone has been described as a weak AAS, though stronger than its 17α-ethynylated analogueethisterone.[3]
? = Chemical names that are unverified.
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).