Norgestimate

Norgestimate
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
Legal status	US: ℞-only;
Pharmacokinetic data
Biological half-life	12–30 hours
Identifiers
CAS Number	35189-28-7
ATC code	G03AA11 (WHO) G03FA13 (WHO) (only combinations with estrogens)
PubChem	CID 6540478
IUPHAR/BPS	7091
DrugBank	DB00957
ChemSpider	5022837
UNII	C291HFX4DY
KEGG	D05209
ChEBI	CHEBI:50815
ChEMBL	CHEMBL1200934
Chemical data
Formula	C23H31NO3
Molar 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 ; Key:KIQQMECNKUGGKA-NMYWJIRASA-N ;
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Norgestimate (INN, USAN, BAN) is an acetylated progestin used as an oral contraceptive.^[1] 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).^[1] 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).^[1]^[2] In accordance, clinical trials have observed minimal androgenic side effects.^[2] Norgestimate and its metabolites themselves, unlike many other progestins, do not bind to SHBG.^[1] Norgestimate is used in combination with ethinyl estradiol as an oral contraceptive.^[3]

References[edit]

^ ^a ^b ^c ^d Thomas L. Lemke; David A. Williams (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1316–. ISBN 978-0-7817-6879-5.
^ ^a ^b Chapdelaine A, Desmarais JL, Derman RJ (1989). "Clinical evidence of the minimal androgenic activity of norgestimate". Int. J. Fertil. 34 (5): 347–52. PMID 2571595.
^ Consumer Drug Information: Ortho Tri-Cyclen

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