Norvinisterone

Norvinisterone

Clinical data
Trade names	Neoprogestin, Nor-Progestelea
Other names	Vinylnortestosterone; SC-4641; 17α-Vinyl-19-nortestosterone; 17α-Vinylestr-4-en-17β-ol-3-one
Routes of administration	By mouth
Drug class	Progestogen; Progestin; Androgen; Anabolic steroid
ATC code	None
Identifiers
IUPAC name (8R,9S,10R,13S,14S,17R)-17-ethenyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number	6795-60-4
PubChem CID	65588
ChemSpider	59030
UNII	7Q843V12Q0
Chemical and physical data
Formula	C20H28O2
Molar mass	300.442 g·mol−1
3D model (JSmol)	Interactive image
Melting point	169 to 171 °C (336 to 340 °F)
SMILES O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@](O)(\C=C)CC[C@H]3[C@@H]1CC2)C)CC4
InChI InChI=1S/C20H28O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h3,12,15-18,22H,1,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1 Key:VOJYZDFYEHKHAP-XGXHKTLJSA-N

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.

Norvinisterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has androgenic activity.

Norvinisterone was synthesized in 1953. It is no longer available.

Medical uses

Norvinisterone was used in hormonal contraception to prevent pregnancy.

Pharmacology

Pharmacodynamics

Norvinisterone is a progestogen. It appears to be quite androgenic, with about one-third and one-fifth of the androgenic and anabolic activity, respectively, of nandrolone in animal bioassays. However, it has also been reported to have little anabolic activity.

Chemistry

Norvinisterone, also known as 17α-vinyl-19-nortestosterone or as 17α-vinylestr-4-en-17β-ol-3-one, is a synthetic estrane steroid and a derivative of testosterone and 19-nortestosterone.Analogues of norvinisterone include the progestin norgesterone and the AAS vinyltestosterone.

History

Norvinisterone was synthesized in 1953 and was studied in humans by 1960.

Society and culture

Generic names

Norvinisterone is the generic name of the drug and its INN. It is also known as vinylnortestosterone and is known by its developmental code name SC-4641.

Brand names

Norvinisterone was marketed under the brand names Neoprogestin and Nor-Progestelea by Syntex.

Availability

Norgesterone is no longer marketed and hence is no longer available in any country.