This article needs attention from an expert in chemicals. The specific problem is: chemical names need verification and correction as necessary.(September 2016) |
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.
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 | ✓ |
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 | – |
Compound | Chemical name | Structure | Marketed |
---|---|---|---|
Cloxotestosterone | Testosterone 17-chloral hemiacetal ether | ✓ | |
Quinbolone | Δ1-Testosterone 17β-cyclopentenyl enol ether | ✓ | |
Silandrone | Testosterone 17β-trimethylsilyl ether | – |
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 | ✓ |
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 | – |
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 | – | |
Compound | Chemical name | Structure | Marketed |
---|---|---|---|
Bolazine (di(drostanolone) azine) | 3,3-[(1E,2E)-1,2-Hydrazinediylidene]di(2α-methyl-5α-androstan-17β-ol)? | ✓ |
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 | – |
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 | – |
Compound | Chemical name | Structure | Marketed |
---|---|---|---|
Bolmantalate (nandrolone adamantoate) | 19-Nortestosterone 17β-adamantoate | ✓ |
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 | ✓ |
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 | ✓ |
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? | ✓ |
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 | ✓ |
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)? | ✓ |
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 | – |
Compound | Chemical name | Structure | Marketed |
---|---|---|---|
Bolenol (ethylnorandrostenol) | 3-Deketo-17α-ethyl-19-nor-5-androstenediol | – |
Compound | Chemical name | Structure | Marketed |
---|---|---|---|
Propetandrol | 17α-Ethyl-19-nortestosterone 3-propionate | ✓ |
Compound | Chemical name | Structure | Marketed |
---|---|---|---|
Vinyltestosterone | 17α-Ethenyltestosterone | – |
Compound | Chemical name | Structure | Marketed |
---|---|---|---|
Norvinisterone (vinylnortestosterone) | 17α-Ethenyl-19-nortestosterone | ✓ |
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]
Compound | Chemical name | Structure | Marketed |
---|---|---|---|
Ethisterone (ethinyltestosterone) | 17α-Ethynyltestosterone | ✓ | |
Danazol (2,3-isoxazolethisterone) | 2,3-Isoxazol-17α-ethynyltestosterone | ✓ |
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 | ✓ |
Compound | Chemical name | Structure | Marketed |
---|---|---|---|
Quingestanol | 4-Hydro-19-nor-δ3,5-testosterone 3-cyclopentyl ether? | – |
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 | ✓ |
Compound | Chemical name | Structure | Marketed |
---|---|---|---|
Quingestanol acetate | 4-Hydro-17α-ethynyl-19-nor-δ3,5-testosterone 3-cyclopentyl ether 17β-acetate? | ✓ |
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]
? = Chemical names that are unverified.
Tetrahydrogestrinone (THG), known by the nickname The Clear, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed for medical use. It was developed by Patrick Arnold and was used by a number of high-profile athletes such as Barry Bonds and Dwain Chambers.
Nandrolone, also known as 19-nortestosterone, is an endogenous androgen. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are now used by oral administration or instead are given by injection into muscle or fat.
Ethylestrenol, also known as ethyloestrenol or ethylnandrol and sold under the brand names Maxibolin and Orabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used in the past for a variety of indications such as to promote weight gain and to treat anemia and osteoporosis but has been discontinued for use in humans. It is still available for veterinary use in Australia and New Zealand however. It is taken by mouth.
Norethandrolone, sold under the brand names Nilevar and Pronabol among others, is an androgen and anabolic steroid (AAS) medication which has been used to promote muscle growth and to treat severe burns, physical trauma, and aplastic anemia but has mostly been discontinued. It is still available for use in France however. It is taken by mouth.
Norethisterone, also known as norethindrone and sold under the brand name Norlutin among others, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication is available in both low-dose and high-dose formulations and both alone and in combination with an estrogen. It is used by mouth or, as norethisterone enanthate, by injection into muscle.
Ethisterone, also known as ethinyltestosterone, pregneninolone, and anhydrohydroxyprogesterone and formerly sold under the brand names Proluton C and Pranone among others, is a progestin medication which was used in the treatment of gynecological disorders but is now no longer available. It was used alone and was not formulated in combination with an estrogen. The medication is taken by mouth.
Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in androgen replacement therapy for low testosterone levels in men but has never been marketed for medical use. It is given as an implant that is placed into fat. As trestolone acetate, an androgen ester and prodrug of trestolone, the medication can also be given by injection into muscle.
Metribolone is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use but has been widely used in scientific research as a hot ligand in androgen receptor (AR) ligand binding assays (LBAs) and as a photoaffinity label for the AR. More precisely, metribolone is the 17α-methylated derivative of trenbolone. It was investigated briefly for the treatment of advanced breast cancer in women in the late 1960s and early 1970s, but was found to produce signs of severe hepatotoxicity at very low dosages, and its development was subsequently discontinued.
Normethandrone, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the treatment of amenorrhea and menopausal symptoms in women. It is taken by mouth.
Altrenogest, sold under the brand names Swinemate and Altren manufactured by Aurora Pharmaceutical and Regumate manufactured by Merck, is a progestin of the 19-nortestosterone group which is widely used in veterinary medicine to suppress or synchronize estrus in horses and pigs. It is available for veterinary use in both Europe and the United States.
Norvinisterone, sold under the brand names Neoprogestin and Nor-Progestelea, is a progestin and androgen/anabolic steroid (AAS) medication which was used in Europe but is now no longer marketed. It is taken by mouth.
Dimethandrolone (DMA), also known by its developmental code name CDB-1321, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under investigation for potential clinical use.
A 17α-alkylated anabolic steroid is a synthetic anabolic–androgenic steroid (AAS) that features an alkyl group, specifically a methyl or ethyl group, at the C17α position. Unlike many other AAS, 17α-alkylated AAS are orally active and do not require intramuscular injection. However, they uniquely possess a high potential for hepatotoxicity, which simultaneously limits their use. In addition, some have a high risk of gynecomastia due to uniquely high estrogenic activity, although this does not apply to 17α-alkylated AAS that are also 4,5α-reduced or 19-demethylated. The prototypical example of a 17α-alkylated AAS is methyltestosterone (17α-methyltestosterone).
Ethyltestosterone, or 17α-ethyltestosterone, also known as 17α-ethylandrost-4-en-17β-ol-3-one or 17α-pregn-4-en-17-ol-3-one, is a synthetic, orally active anabolic–androgenic steroid (AAS) of the 17α-alkylated group related to methyltestosterone which was never marketed. Like methyltestosterone, ethyltestosterone is the parent compound of many AAS. Derivatives of ethyltestosterone include norethandrolone, ethylestrenol (ethylnandrol), norboletone, ethyldienolone, tetrahydrogestrinone, bolenol (ethylnorandrostenol), and propetandrol.
Dimethyltrienolone is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and 17α-alkylated 19-nortestosterone (nandrolone) derivative which was never marketed for medical use. It has among the highest known affinity of any AAS for the androgen receptors, and has been said to be perhaps the most potent AAS to have ever been developed.
Vinyltestosterone is a synthetic anabolic–androgenic steroid (AAS) that was never marketed. However, two 19-nortestosterone derivatives of vinyltestosterone, norvinisterone (17α-vinyl-19-nortestosterone) and norgesterone, have been marketed. They are used as progestins for female hormonal contraception, rather than as AAS.
11β-Methyl-19-nortestosterone (11β-MNT) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed at this time.
5α-Dihydronorethisterone is a major active metabolite of norethisterone (norethindrone). Norethisterone is a progestin with additional weak androgenic and estrogenic activity. 5α-DHNET is formed from norethisterone by 5α-reductase in the liver and other tissues.
17α-Allyl-19-nortestosterone, also known as 3-ketoallylestrenol or as 17α-allylestr-4-en-17β-ol-3-one, is a progestin which was never marketed. It is a combined derivative of the anabolic–androgenic steroid and progestogen nandrolone (19-nortestosterone) and the antiandrogen allyltestosterone (17α-allyltestosterone). The drug is a major active metabolite of allylestrenol, which is thought to be a prodrug of 17α-allyl-19-nortestosterone.
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).