Norgestimate

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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
Legal status
Pharmacokinetic data
Biological half-life 12–30 hours
Identifiers
CAS Number 35189-28-7 YesY
ATC code G03AA11 (WHO) G03FA13 (WHO) (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
Molar mass 369.497 g/mol
 NYesY (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 (~22% of an administered dose; deacetylation of norgestimate occurs in the intestines and the liver), as well as levonorgestrel-17-acetate.[1][2] Unlike levonorgestrel, norgestimate shows high selectivity for the progesterone receptor and low androgenic activity in relation to the induction of a large elevation in the level of sex hormone-binding globulin (SHBG) (which preferentially binds androgens and thus inhibits their action).[1][3] Moreover, unlike other 19-nortestosterone progestins, norgestimate does not bind to or occupy SHBG itself.[1] In accordance, clinical trials of norgestimate have observed minimal androgenic side effects.[3] The drug is used in combination with ethinyl estradiol as an oral contraceptive.[4] It was introduced in 1986.[5]

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. ^ IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007). Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy. World Health Organization. pp. 150–151. ISBN 978-92-832-1291-1. 
  3. ^ 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. 
  4. ^ Consumer Drug Information: Ortho Tri-Cyclen
  5. ^ Benno Clemens Runnebaum; Thomas Rabe; Ludwig Kiesel (6 December 2012). Female Contraception: Update and Trends. Springer Science & Business Media. pp. 13–. ISBN 978-3-642-73790-9.