Norgestrel

Norgestrel

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
Legal status	US: ℞-only
Pharmacokinetic data
Biological half-life	5–14 hours
Identifiers
CAS Number	6533-00-2
ATC code	G03AA06 (WHO) G03FA10 G03FB01 (only combinations with estrogens)
PubChem	CID 16051930
ChemSpider	10481953
UNII	3J8Q1747Z2
KEGG	D00954
ChEBI	CHEBI:7630
Chemical data
Formula	C21H28O2
Molar 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 Key:WWYNJERNGUHSAO-CULCCENASA-N
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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# 797-64-8 ) and levonorgestrel (CAS# 797-63-7 ).^[1] Only levonorgestrel is biologically active.^[2] 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.^[3]

See also

• Elsimar M. Coutinho
• Herchel Smith

References

1. Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 442f. ISBN 3-8047-1763-2.
2. Benagiano, G; Carrara, S; Filippi, V (2009). "Safety, efficacy and patient satisfaction with continuous daily administration of levonorgestrel/ethinylestradiol oral contraceptives". Patient preference and adherence 3: 131–43. PMC 2778424. PMID 19936155.
3. Yuzpe, A. A.; Smith, R. P.; Rademaker, A. W. (1982). "A multicenter clinical investigation employing ethinyl estradiol combined with dl-norgestrel as postcoital contraceptive agent". Fertility and Sterility 37 (4): 508–13. PMID 7040117.