Vinyltestosterone

Vinyltestosterone (also known as 17α-vinyltestosterone, 17α-vinylandrost-4-en-17β-ol-3-one, and 17α-hydroxypregna-4,20-dien-3-one) is a synthetic anabolic–androgenic steroid (AAS) that was never marketed.^[1][2] However, two 19-nortestosterone derivatives of vinyltestosterone, norvinisterone (17α-vinyl-19-nortestosterone) and norgesterone (17α-vinyl-δ⁵⁽¹⁰⁾-19-nortestosterone), have been marketed.^[3] They are used as progestins for female hormonal contraception, rather than as AAS.^[3]

Other names17α-Vinyltestosterone; Ethenyltestosterone; 17α-Ethenyltestosterone; 17α-Vinylandrost-4-en-17β-ol-3-one; 17α-Hydroxypregna-4,20-dien-3-one

CAS Number

• 1235-98-9 ^Y

PubChem CID

• 222286

ChemSpider

• 192964

Quick facts Clinical data, Other names ...

Vinyltestosterone

Clinical data
Other names	17α-Vinyltestosterone; Ethenyltestosterone; 17α-Ethenyltestosterone; 17α-Vinylandrost-4-en-17β-ol-3-one; 17α-Hydroxypregna-4,20-dien-3-one
Identifiers
IUPAC name (8R,9S,10R,13S,14S,17S)-17-Ethenyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number	1235-98-9 Y
PubChem CID	222286
ChemSpider	192964
UNII	SGZ6EUF8MU
Chemical and physical data
Formula	C21H30O2
Molar mass	314.469 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]4(C=C)O)C
InChI InChI=1S/C21H30O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h4,13,16-18,23H,1,5-12H2,2-3H3/t16-,17+,18+,19+,20+,21-/m1/s1 Key:ILGPJZIKYMIGMU-SJFWLOONSA-N

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Vinyltestosterone is a relatively weak AAS.^[2][4][5] In one study, it showed approximately one-third and one-fifth of the respective androgenic and anabolic activity of other AAS such as nandrolone (19-nortestosterone), methyltestosterone (17α-methyltestosterone), and ethyltestosterone (17α-ethyltestosterone) in castrated male rats, whereas ethisterone (17α-ethynyltestosterone) showed almost no androgenic and anabolic activity (only 1/20 the anabolic potency of vinyltestosterone).^[4] Additionally, in women with metastatic breast cancer, vinyltestosterone was found to be ineffective in treating the disease (unlike other AAS such as testosterone propionate or fluoxymesterone)^[6] and produced little or no virilization in the women at a dosage of 100 mg intramuscularly three times per week.^[5][7][8]