Norelgestromin

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Norelgestromin
Norelgestromin.svg
Clinical data
Trade names Evra, Ortho Evra
Synonyms Norelgestromine; Levonorgestrel 3-oxime; 17β-Deacetylnorgestimate; 17α-Ethynyl-18-methyl-19-nortestosterone 3-oxime; 17α-Ethynyl-18-methylestr-4-en-17β-ol-3-one 3-oxime
AHFS/Drugs.com International Drug Names
MedlinePlus a602006
Routes of
administration
Transdermal patch
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
Formula C21H29NO2
Molar mass 327.461 g/mol
3D model (JSmol)
 NYesY (what is this?)  (verify)

Norelgestromin, or norelgestromine, is a progestin which is used in the contraceptive patches Evra and Ortho Evra, in combination with the estrogen ethinylestradiol.[1][2]

Pharmacology[edit]

Norelgestromin is a progestogen. It is one of the active metabolites of norgestimate.[3][4] Unlike many related progestins, norelgestromin has negligible androgenic activity.[4]

Chemistry[edit]

Norelgestromin, also known as 17α-ethynyl-18-methyl-19-nortestosterone 3-oxime or as 17α-ethynyl-18-methylestr-4-en-17β-ol-3-one 3-oxime, is a synthetic estrane steroid and a derivative of testosterone.[5] It is a racemic mixture of E and Z isomers, which have approximately the same activity.[6] Norelgestromin is more specifically a derivative of norethisterone (17α-ethynyl-19-nortestosterone) and is a member of the gonane (18-methylestrane) subgroup of the 19-nortestosterone family of progestins.[7][8] It is the C3 oxime derivative of levonorgestrel and the C17β deacetyl derivative of norgestimate and is also known as levonorgestrel 3-oxime and as 17β-deacetylnorgestimate.[9]

History[edit]

Norelgestromin was introduced in 2002.[10]

Society and culture[edit]

Generic name[edit]

Norelgestromin is the generic name of the drug and its INN, USAN, and BAN.[5]

Brand names[edit]

Norelgestromin is marketed under the brand names Evra and Ortho Evra, both in combination with ethinylestradiol.[5]

See also[edit]

References[edit]

  1. ^ Drugs.com: Norelgestromin/Ethinyl Estradiol Patch
  2. ^ 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): 18. ISSN 1472-6874. PMC 2714834Freely accessible. PMID 19566925. doi:10.1186/1472-6874-9-18. 
  3. ^ Annette M. Doherty (2003). Annual Reports in Medicinal Chemistry. Academic Press. pp. 362–. ISBN 978-0-12-040538-1. 
  4. ^ a b Stefan Offermanns; Walter Rosenthal (14 August 2008). Encyclopedia of Molecular Pharmacology. Springer Science & Business Media. pp. 391–. ISBN 978-3-540-38916-3. 
  5. ^ a b c https://www.drugs.com/international/norelgestromin.html
  6. ^ https://www.google.com/patents/US7345183
  7. ^ Mary C. Brucker; Tekoa L. King (8 September 2015). Pharmacology for Women’s Health. Jones & Bartlett Publishers. pp. 368–. ISBN 978-1-284-05748-5. 
  8. ^ Donna Shoupe (7 November 2007). The Handbook of Contraception: A Guide for Practical Management. Springer Science & Business Media. pp. 16–. ISBN 978-1-59745-150-5. 
  9. ^ 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. 
  10. ^ John E. Macor (2012). Annual Reports in Medicinal Chemistry. Academic Press. pp. 620–. ISBN 978-0-12-396492-2.