Norelgestromin

Norelgestromin
Clinical data
Trade namesEvra, Ortho Evra, Xulane, others
Other namesNorelgestromine; NGMN; RWJ-10553; 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.comInternational Drug Names
MedlinePlusa602006
License data
Routes of
administration		Transdermal patch
Drug classProgestogen; Progestin
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding99% (to albumin but not to SHBGTooltip sex hormone-binding globulin)[1][2][3]
MetabolismLiver (oxime to ketone reaction, hydroxylation, conjugation)[4]
Metabolites• Levonorgestrel[4]
Elimination half-life17–37 hours[1][3]
ExcretionUrine and feces[4]
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.170.714
Chemical and physical data
FormulaC21H29NO2
Molar mass327.468 g·mol−1
3D model (JSmol)
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 Y
  • Key:ISHXLNHNDMZNMC-XUDSTZEESA-N Y
  (verify)

Norelgestromin, or norelgestromine, sold under the brand names Evra and Ortho Evra among others, is a progestin medication which is used as a method of birth control for women.[5][6][7] The medication is available in combination with an estrogen and is not available alone.[5] It is used as a patch that is applied to the skin.[6][7]

Side effects of the combination of an estrogen and norelgestromin include menstrual irregularities, headaches, nausea, abdominal pain, breast tenderness, mood changes, and others.[4] Norelgestromin is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[8][9] It has very weak androgenic activity and no other important hormonal activity.[8][9]

Norelgestromin was introduced for medical use in 2002.[10] It is sometimes referred to as a "third-generation" progestin.[11][12] Norelgestromin is marketed widely throughout the world.[5] It is available as a generic medication.[13]

  1. ^ a b "PREFEST (estradiol/norgestimate) tablets" (PDF). Teva Pharmaceuticals. U.S. Food and Drug Administration. November 2017.
  2. ^ "ORTHO-CYCLEN and ORTHO TRI-CYCLEN (norgestimate/ethinyl estradiol) tablets, for oral use" (PDF). Janssen Pharmaceuticals, Inc. U.S. Food and Drug Administration. August 2017.
  3. ^ a b Cite error: The named reference pmid16112947 was invoked but never defined (see the help page).
  4. ^ a b c d Cite error: The named reference OrthoEvraLabel was invoked but never defined (see the help page).
  5. ^ a b c Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  6. ^ a b "Norelgestromin/Ethinyl Estradiol Patch". Drugs.com.
  7. ^ a b Crosignani PG, Nappi C, Ronsini S, Bruni V, Marelli S, Sonnino D (June 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. doi:10.1186/1472-6874-9-18. PMC 2714834. PMID 19566925.
  8. ^ a b Cite error: The named reference Doherty2003 was invoked but never defined (see the help page).
  9. ^ a b Cite error: The named reference OffermannsRosenthal2008 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference Macor2012 was invoked but never defined (see the help page).
  11. ^ Borgelt LM (2010). Women's Health Across the Lifespan: A Pharmacotherapeutic Approach. ASHP. pp. 294–. ISBN 978-1-58528-194-7.
  12. ^ Vaamonde D, du Plessis SS, Agarwal A (7 March 2016). Exercise and Human Reproduction: Induced Fertility Disorders and Possible Therapies. Springer. pp. 288–. ISBN 978-1-4939-3402-7.
  13. ^ "First Generic Ortho Evra Patch Launched". Medical Professionals Reference (MPR). Haymarket Media, Inc. 17 April 2014.
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