Norgesterone

Norgesterone

Clinical data
Trade names	Vestalin (with EE)
Other names	Norvinodrel; Vinylestrenolone; Vinilestrenolone; Vinylnoretynodrel; 17α-Vinylestr-5(10)-en-17-ol-3-one; 17α-Vinyl-δ5(10)-19-nortestosterone
Routes of administration	By mouth
Drug class	Progestogen; Progestin
ATC code	None
Identifiers
IUPAC name (8R,9S,13S,14S,17R)-17-ethenyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number	13563-60-5
PubChem CID	65606
ChemSpider	59047
UNII	YFS274763Y
CompTox Dashboard (EPA)	DTXSID60159482
Chemical and physical data
Formula	C20H28O2
Molar mass	300.442 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC12CCC3C(C1CCC2(C=C)O)CCC4=C3CCC(=O)C4
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/h3,16-18,22H,1,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1 Key:YPVUHOBTCWJYNQ-SLHNCBLASA-N

Norgesterone, also known as norvinodrel or vinylestrenolone and sold under the brand name Vestalin, is a progestin medication which was formerly used in birth control pills for women but is now no longer marketed. It was used in combination with the estrogen ethinylestradiol. It is taken by mouth.

Norgesterone 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 no androgenic activity.

Norgesterone was first described in 1962. It is no longer available.

Medical uses

Norgesterone was used in combination with ethinylestradiol in birth control pills to prevent pregnancy. It is no longer available.

Pharmacology

Pharmacodynamics

Norgesterone is a progestogen, and hence is an agonist of the progesterone receptor. Unlike related progestins, it is virtually devoid of androgenic activity in animal assays.

Chemistry

Norgesterone, also known as 17α-vinyl-δ⁵⁽¹⁰⁾-19-nortestosterone or as 17α-vinylestr-5(10)-en-17β-ol-3-one, is a synthetic estrane steroid and a derivative of testosterone and 19-nortestosterone.Analogues of norgesterone include norvinisterone (17α-vinyl-19-nortestosterone) and vinyltestosterone (17α-vinyltestosterone).

History

Norgesterone was first described in 1962.

Society and culture

Generic names

Norgesterone is the generic name of the drug and its INN. It has also been referred to as norvinodrel, vinylestrenolone, and vinylnoretynodrel.

Brand names

Norgesterone was marketed in combination with ethinylestradiol, an estrogen, as a birth control pill under the brand name Vestalin.

Availability

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