Norgestimate

Norgestimate

File:Norgestimate.svg
Systematic (IUPAC) name
(13-ethyl-17-ethynyl-3-hydroxyimino- 1,2,6,7,8,9,10,11,12,14,15,16- dodecahydrocyclopenta[a] phenanthren-17-yl) acetate
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601050
Legal status	US: ℞-only
Pharmacokinetic data
Biological half-life	12–30 hours
Identifiers
CAS Number	35189-28-7 Y
ATC code	G03AA11 (WHO) G03FA13 (only combinations with estrogens)
PubChem	CID: 6540478
IUPHAR/BPS	7091
DrugBank	DB00957 Y
ChemSpider	5022837 Y
UNII	C291HFX4DY Y
KEGG	D05209 Y
ChEBI	CHEBI:50815 Y
ChEMBL	CHEMBL1200934 N
Chemical data
Formula	C23H31NO3
Molecular mass	369.497 g/mol
SMILES O=C(O[C@@]2(C#C)CC[C@H]1[C@H]4[C@H](CC[C@@]12CC)[C@@H]3/C(=C\C(=N\O)CC3)CC4)C
InChI InChI=1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1 Y Key:KIQQMECNKUGGKA-NMYWJIRASA-N Y
NY (what is this?)  (verify)

Not to be confused with norgestomet.

Norgestimate (INN, USAN, BAN) is an acetylated progestin used as an oral contraceptive. It acts as a prodrug to norelgestromin (17-deacetylnorgestimate or levonorgestrel 3-oxime), the primary active metabolite, and levonorgestrel (deacetylation of norgestimate occurs in the intestines and the liver). Unlike levonorgestrel, norgestimate shows high selectivity for the progesterone receptor and low androgenic action due to a large drug-induced elevation in the level of sex hormone-binding globulin (SHBG) (which preferentially binds androgens and thus inhibits their action). In accordance, clinical trials have observed minimal androgenic side effects. Norgestimate and its metabolites themselves, unlike many other progestins, do not bind to SHBG. Norgestimate is used in combination with ethinyl estradiol as an oral contraceptive.

See also

• Desogestrel