Norgestimate

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Norgestimate
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
Pharmacokinetic data
Biological half-life 12–30 hours
Identifiers
CAS Registry Number 35189-28-7 YesY
ATC code G03AA11 G03FA13 (only combinations with estrogens)
PubChem CID: 6540478
IUPHAR/BPS 7091
DrugBank DB00957 YesY
ChemSpider 5022837 YesY
UNII C291HFX4DY YesY
KEGG D05209 YesY
ChEBI CHEBI:50815 YesY
ChEMBL CHEMBL1200934 N
Chemical data
Formula C23H31NO3
Molecular mass 369.497 g/mol
 N (what is this?)  (verify)
Not to be confused with norgestomet.

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]

See also[edit]

References[edit]

  1. ^ 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. 
  2. ^ 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. 
  3. ^ Consumer Drug Information: Ortho Tri-Cyclen