Norgesterone

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.^[1][2][3][4] It was used in combination with the estrogen ethinylestradiol.^[2][3][4] It is taken by mouth.^[5][6]

Norgesterone

Clinical data
Trade names	Vestalin (with EETooltip ethinylestradiol)
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 is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.^[7] It has no androgenic activity.^[7]

Norgesterone was first described in 1962.^[8][9] It is no longer available.^[10]

Medical uses

Norgesterone was used in combination with ethinylestradiol in birth control pills to prevent pregnancy.^[2] It is no longer available.^[10]

Pharmacology

Pharmacodynamics

Norgesterone is a progestogen, and hence is an agonist of the progesterone receptor.^[7] Unlike related progestins, it is virtually devoid of androgenic activity in animal assays.^[7]

Chemistry

See also: List of progestogens and List of androgens/anabolic steroids

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.^[1] Analogues of norgesterone include norvinisterone (17α-vinyl-19-nortestosterone) and vinyltestosterone (17α-vinyltestosterone).^[1]

History

Norgesterone was first described in 1962.^[8][9]

Society and culture

Generic names

Norgesterone is the generic name of the drug and its INNTooltip International Nonproprietary Name.^[1] It has also been referred to as norvinodrel, vinylestrenolone, and vinylnoretynodrel.^[1][11]

Brand names

Norgesterone was marketed in combination with ethinylestradiol, an estrogen, as a birth control pill under the brand name Vestalin.^[2][3][4]

Availability

Norgesterone is no longer marketed and hence is no longer available in any country.^[10]