|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
|AHFS/Drugs.com||Micromedex Detailed Consumer Information|
|Biological half-life||12–30 hours|
|ATC code||G03AA11 (WHO) G03FA13 (WHO) (only combinations with estrogens)|
|Molar mass||369.497 g/mol|
|(what is this?)|
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 (~22% of an administered dose; deacetylation of norgestimate occurs in the intestines and the liver), as well as levonorgestrel-17-acetate. 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). Moreover, unlike other 19-nortestosterone progestins, norgestimate does not bind to or occupy SHBG itself. In accordance, clinical trials of norgestimate have observed minimal androgenic side effects. The drug is used in combination with ethinyl estradiol as an oral contraceptive. It was introduced in 1986.
- Thomas L. Lemke; David A. Williams (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1316–. ISBN 978-0-7817-6879-5.
- 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.
- 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
- 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.
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