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| Other names | 17α-Vinyltestosterone; Ethenyltestosterone; 17α-Ethenyltestosterone; 17α-Vinylandrost-4-en-17β-ol-3-one; 17α-Hydroxypregna-4,20-dien-3-one |
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| Chemical and physical data | |
| Formula | C21H30O2 |
| Molar mass | 314.469 g·mol−1 |
| 3D model (JSmol) | |
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Vinyltestosterone (also known as17α-vinyltestosterone,17α-vinylandrost-4-en-17β-ol-3-one, and17α-hydroxypregna-4,20-dien-3-one) is asyntheticanabolic–androgenic steroid (AAS) that was never marketed.[1][2] However, two19-nortestosterone derivatives of vinyltestosterone,norvinisterone (17α-vinyl-19-nortestosterone) andnorgesterone (17α-vinyl-δ5(10)-19-nortestosterone), have been marketed.[3] They are used asprogestins for femalehormonal contraception, rather than as AAS.[3]
Vinyltestosterone is a relatively weak AAS.[2][4][5] In one study, it showed approximately one-third and one-fifth of the respectiveandrogenic andanabolic activity of other AAS such asnandrolone (19-nortestosterone),methyltestosterone (17α-methyltestosterone), andethyltestosterone (17α-ethyltestosterone) incastrated male rats, whereasethisterone (17α-ethynyltestosterone) showed almost no androgenic and anabolic activity (only 1/20 the anabolic potency of vinyltestosterone).[4] Additionally, in women withmetastatic breast cancer, vinyltestosterone was found to be ineffective in treating the disease (unlike other AAS such astestosterone propionate orfluoxymesterone)[6] and produced little or novirilization in the women at a dosage of 100 mgintramuscularly three times per week.[5][7][8]
17α-Vinyltestosterone in large doses manifested weak myotropic and androgenic activities in castrated male rats (1) and proved to be ineffective in the therapy of patients with metastatic breast cancer, in whom it had little or no virilizing effect at a dosage level of 100 mg. intramuscularly three times a week (18).
