Norelgestromin

Norelgestromin

Clinical data
Trade names	Evra, Ortho Evra
AHFS/Drugs.com	International Drug Names
MedlinePlus	a602006
Routes of administration	Transdermal patch
ATC code	G03AA13 (WHO) (only combinations with estrogens)
Legal status
Legal status	℞ (Prescription only)
Identifiers
IUPAC name (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
Synonyms	17-Deacetylnorgestimate, levonorgestrel 3-oxime
CAS Number	53016-31-2
PubChem (CID)	62930
DrugBank	DB06713
ChemSpider	56648
UNII	R0TAY3X631
KEGG	D05205
ChEBI	CHEBI:111762
ChEMBL	CHEMBL1200807
Chemical and physical data
Formula	C21H29NO2
Molar mass	327.461 g/mol
3D model (Jmol)	Interactive image
SMILES ON=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)CC)CC4
InChI InChI=1S/C21H29NO2/c1-3-20-11-9-17-16-8-6-15(22-24)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23-24H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1 Key:ISHXLNHNDMZNMC-XUDSTZEESA-N
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Norelgestromin (INN, USAN, BAN), or norelgestromine, also known as 17-deacetylnorgestimate or norgestrel 3-oxime,^[1] is a steroidal progestin of the 19-nortestosterone group used in the contraceptive patch called Evra or Ortho Evra, where it is combined with the estrogen ethinyl estradiol.^[2][3] It is one of the active metabolites of norgestimate.^[4][5] Unlike many other 19-nortestosterone derivatives, norelgestromin has negligible androgenic activity.^[5] The drug was introduced in 2002.^[6]

References

1. 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.
2. Drugs.com: Norelgestromin/Ethinyl Estradiol Patch
3. Crosignani, Pier Giorgio; Nappi, Carmine; Ronsini, Salvatore; Bruni, Vincenzina; Marelli, Silvia; Sonnino, Davide (2009). "Satisfaction and compliance in hormonal contraception: the result of a multicentre clinical study on women's experience with the ethinylestradiol/norelgestromin contraceptive patch in Italy". BMC Women's Health. 9 (1). doi:10.1186/1472-6874-9-18. ISSN 1472-6874.
4. Annette M. Doherty (2003). Annual Reports in Medicinal Chemistry. Academic Press. pp. 362–. ISBN 978-0-12-040538-1.
5. Stefan Offermanns; Walter Rosenthal (14 August 2008). Encyclopedia of Molecular Pharmacology. Springer Science & Business Media. pp. 391–. ISBN 978-3-540-38916-3.
6. John E. Macor (2012). Annual Reports in Medicinal Chemistry. Academic Press. pp. 620–. ISBN 978-0-12-396492-2.