Norgestrel

Norgestrel

File:Levonorgestrel.svg File:Dextronorgestrel.svg
Systematic (IUPAC) name
(8R/S,9S/R,10R/S,13S/R,14S/R,17S/R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a602008
Legal status	US: ℞-only
Pharmacokinetic data
Biological half-life	5–14 hours
Identifiers
CAS Number	6533-00-2 Y
ATC code	G03AA06 (WHO) G03FA10 G03FB01 (only combinations with estrogens)
PubChem	CID: 16051930
ChemSpider	10481953 Y
UNII	3J8Q1747Z2 Y
KEGG	D00954 Y
ChEBI	CHEBI:7630 N
Chemical data
Formula	C21H28O2
Molecular mass	312.446 g/mol
SMILES O=C\1CC[C@H]4C(=C/1)/CC[C@@H]3[C@@H]4CC[C@@]2(CC)[C@H]3CCC2(O)C#C
InChI InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21?/m0/s1 Y Key:WWYNJERNGUHSAO-CULCCENASA-N Y
NY (what is this?)  (verify)

Norgestrel (INN, USAN, BAN, JAN) (brand names Logynon, Nordette, Eugynon, Microgynon, Ovran, Ovranette, Trinordiol, numerous others) is a steroidal progestin that has been used in hormonal contraceptives. It is a mixture of two stereoisomers, dextronorgestrel (CAS# Template:CAS) and levonorgestrel (CAS# Template:CAS). Only levonorgestrel is biologically active. Therefore, while some medications may contain dextronorgestrel, they are often labeled in terms of their levonorgestrel content only, ignoring the inert isomer.

Norgestrel has also been used as an emergency contraceptive in the Yuzpe regimen.

See also

• Elsimar M. Coutinho
• Herchel Smith