Norgestimate

Norgestimate

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601050
ATC code	G03AA11 (WHO) G03FA13 (WHO) (only combinations with estrogens)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Biological half-life	12–30 hours
Identifiers
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
Synonyms	ORF-10131
CAS Number	35189-28-7 Y
PubChem CID	6540478
IUPHAR/BPS	7091
DrugBank	DB00957 Y
ChemSpider	5022837 Y
UNII	C291HFX4DY
KEGG	D05209 Y
ChEBI	CHEBI:50815 Y
ChEMBL	CHEMBL1200934 N
Chemical and physical data
Formula	C23H31NO3
Molar mass	369.497 g/mol
3D model (Jmol)	Interactive image
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?)

Norgestimate (INN, USAN, BAN) (brand names Ortho-Cyclen, Ortho Tri-Cyclen, Previfem, Sprintec, Prefest, others) is a steroidal progestin of the 19-nortestosterone group that is used in combination with ethinylestradiol as an oral contraceptive and in combination with estradiol in menopausal hormone replacement therapy. It is a prodrug, mainly of norelgestromin, but also of levonorgestrel in small amounts.

Norgestimate, unlike other 19-nortestosterone derivatives such as levonorgestrel, shows high selectivity for the progesterone receptor (PR) and low androgenic activity. Moreover, norgestimate and its main active metabolite norelgestromin do not bind to or occupy sex hormone-binding globulin (SHBG). In accordance, clinical trials of norgestimate have observed minimal androgenic side effects.

The relative binding affinity of norgestimate and its metabolite norelgestromin for the rat prostatic androgen receptor (AR) are 0.3% and 1.3% of those of dihydrotestosterone (DHT), respectively, whereas the respective values for levonorgestrel and gestodene are 22.0% and 15.4%. Moreover, the ratios of AR to PR binding are 219 for norgestimate and 48 for its metabolite norelgestromin, whereas the ratios of progesterone, levonorgestrel, and gestodene are 93, 11, and 28, respectively.