# List of androgens and anabolic steroids

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):
* Testosterone derivatives: direct derivatives of testosterone not falling into the groups below
* 4,5α-Reduced/dihydrogenated testosterone derivatives: dihydrotestosterone (DHT) derivatives
* 19-Demethylated testosterone derivatives: 19-nortestosterone (nandrolone) derivatives
* 17α-Alkylated testosterone derivatives: methyltestosterone and ethyltestosterone derivatives
* 17α-Ethynylated/vinylated testosterone derivatives: ethynyltestosterone (ethisterone) and vinyltestosterone derivatives
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 | Marketed |
| Testosterone | Androst-4-en-17β-ol-3-one | ✓ |
| 4-Hydroxytestosterone | 4-Hydroxytestosterone | – |
| 11-Ketotestosterone | 11-Ketotestosterone | – |
| Boldenone | Δ$^1$-Testosterone | ✓ |
| Clostebol | 4-Chlorotestosterone | ✓ |

### Prohormone-like

| Compound | Chemical name | 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-δ$^1$-4-androstenedione | – |
| Boldione (1,4-androstadienedione) | δ$^1$-4-Androstenedione | – |
| Dehydroepiandrosterone (DHEA, 5-DHEA; prasterone, androstenolone) | 5-Dehydroepiandrosterone | ✓ |
| Exemestane | 6-Methylidene-δ$^1$-4-androstenedione | ✓ |
| Formestane | 4-Hydroxy-4-androstenedione | ✓ |
| Plomestane | 10-Propargyl-4-androstenedione | – |

### Prodrugs
#### Ethers

| Compound | Chemical name | Marketed |
| Cloxotestosterone | Testosterone 17-chloral hemiacetal ether | ✓ |
| Quinbolone | Δ$^1$-Testosterone 17β-cyclopentenyl enol ether | ✓ |
| Silandrone | Testosterone 17β-trimethylsilyl ether | – |

## Dihydrotestosterone derivatives

| Compound | Chemical name | Marketed |
| Dihydrotestosterone (DHT); androstanolone, stanolone) | 4,5α-Dihydrotestosterone | ✓ |
| 1-Testosterone (dihydro-1-testosterone, dihydroboldenone) | 4,5α-Dihydro-δ$^1$-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-δ$^1$-testosterone | ✓ |
| Nisterime | 2α-Chloro-4,5α-dihydrotestosterone 3-O-(p-nitrophenyl)oxime | – |
| Stenbolone | 2-Methyl-4,5α-dihydro-δ$^1$-testosterone | ✓ |

### Prohormone-like

| Compound | Chemical name | Marketed |
| 1-Androsterone (1-Andro, 1-DHEA) | 1-Dehydroepiandrosterone | – |
| 1-Androstenediol (dihydro-1-androstenediol) | 1-Androstenediol (4,5α-dihydro-δ$^1$-4-androstenediol) | – |
| 1-Androstenedione (dihydro-1-androstenedione) | 1-Androstenedione (4,5α-dihydro-δ$^1$-4-androstenedione) | – |
| 5α-Androst-2-en-17-one | 3-Deketo-2-androstenedione (3-deketo-4,5α-dihydro-δ$^2$-4-androstenedione) | – |
| Androsterone | Androsterone | – |
| Epiandrosterone | Epiandrosterone | – |

### Prodrugs
#### Ethers

| Compound | Chemical name | Marketed |
| Mepitiostane | 2α,3α-Epithio-3-deketo-4,5α-dihydrotestosterone 17β-(1-methoxycyclopentane) ether | ✓ |
| Mesabolone | 4,5α-Dihydro-δ$^1$-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 | Marketed |
| Nandrolone (nortestosterone) | 19-Nortestosterone | ✓ |
| 11β-Methyl-19-nortestosterone (11β-MNT) | 11β-Methyl-19-nortestosterone | – |
| Dienolone | 19-Nor-δ$^9$-testosterone | – |
| Dimethandrolone | 7α,11β-Dimethyl-19-nortestosterone | – |
| Norclostebol | 4-Chloro-19-nortestosterone | ✓ |
| Oxabolone | 4-Hydroxy-19-nortestosterone | ✓ |
| Trenbolone (trienolone) | 19-Nor-δ$^{9,11}$-testosterone | ✓ |
| Trestolone (MENT) | 7α-Methyl-19-nortestosterone | – |

### Prohormone-like

| Compound | Chemical name | 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-δ$^9$-4-androstenedione | – |
| Methoxydienone (methoxygonadiene) | 18-Methyl-19-nor-δ$^{2,5(10)}$-epiandrosterone 3-methyl ether | – |
| Trendione (nor-4,9,11-androstatrienedione) | 19-Nor-δ$^{9,11}$-4-androstenedione | – |

### Prodrugs
#### Esters

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

## 17α-Alkylated testosterone derivatives

| Compound | Chemical name | Marketed |
| Bolasterone | 7α,17α-Dimethyltestosterone | ✓ |
| Calusterone | 7β,17α-Dimethyltestosterone | ✓ |
| Chlorodehydromethyltestosterone (CDMT) | 4-Chloro-17α-methyl-δ$^1$-testosterone | ✓ |
| Enestebol | 4-Hydroxy-17α-methyl-δ$^1$-testosterone | – |
| Ethyltestosterone | 17α-Ethyltestosterone | – |
| Fluoxymesterone | 9α-Fluoro-11β-hydroxy-17α-methyltestosterone | ✓ |
| Formebolone | 2-Formyl-11α-hydroxy-17α-methyl-δ$^1$-testosterone | ✓ |
| Hydroxystenozole | 17α-Methyl-2'H-androsta-2,4-dieno[3,2-c]pyrazol-17β-ol | – |
| Metandienone (methandienone, methandrostenolone) | 17α-Methyl-δ$^1$-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 | Marketed |
| Chlorodehydromethylandrostenediol (CDMA) | 4-Chloro-17α-methyl-δ$^1$-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-δ$^{3,5}$-testosterone 3-hexyl ether$^?$ | | ✓ |
| Penmesterol (penmestrol) | 17α-Methyl-4-hydro-δ$^{3,5}$-testosterone 3-cyclopentyl ether$^?$ | | ✓ |

## 17α-Alkylated dihydrotestosterone derivatives

| Compound | Chemical name | Marketed |
| Androisoxazole | 17α-Methyl-5α-androstano[3,2-c]isoxazol-17β-ol | ✓ |
| Desoxymethyltestosterone | 3-Deketo-17α-methyl-4,5α-dihydro-δ$^2$-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-δ$^1$-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-δ$^1$-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 | Marketed |
| Dimethyltrienolone (7α,17α-dimethyltrenbolone) | 7α,17α-Dimethyl-19-nor-δ$^{9,11}$-testosterone | – |
| Dimethyldienolone (7α,17α-dimethyldienolone) | 7α,17α-Dimethyl-19-nor-δ$^9$-testosterone | – |
| Ethyldienolone | 17α-Ethyl-19-nor-δ$^9$-testosterone | – |
| Ethylestrenol (ethylnandrol) | 17α-Ethyl-3-deketo-19-nortestosterone | ✓ |
| Methyldienolone | 17α-Methyl-19-nor-δ$^9$-testosterone | – |
| Methylhydroxynandrolone (MOHN, MHN) | 4-Hydroxy-17α-methyl-19-nortestosterone | – |
| Metribolone (methyltrienolone, R-1881) | 17α-Methyl-19-nor-δ$^{9,11}$-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-δ$^{9,11}$-testosterone | – |
| Tetrahydrogestrinone (THG) | 17α-Ethyl-18-methyl-19-nor-δ$^{9,11}$-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.
Vinyltestosterone has been described as a weak AAS, though stronger than its 17α-ethynylated analogue ethisterone.

## 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 | 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-δ$^{9,11}$-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-δ$^{9,11}$-testosterone | ✓ |
| Tibolone (7α-methylnoretynodrel) | 7α-Methyl-17α-ethynyl-19-nor-δ$^{5(10)}$-testosterone | ✓ |

### Prodrugs
#### Ethers

| Compound | Chemical name | Structure | Marketed |
| Quingestanol | 4-Hydro-19-nor-δ$^{3,5}$-testosterone 3-cyclopentyl ether$^?$ | | – |

#### Esters

| Compound | Chemical name | 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-δ$^{3,5}$-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.