Norelgestromin

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. The medication is available in combination with an estrogen and is not available alone. It is used as a patch that is applied to the skin.

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)
MetabolismLiver (oxime to ketone reaction, hydroxylation, conjugation)
Metabolites• Levonorgestrel
Elimination half-life17–37 hours
ExcretionUrine and feces
Identifiers
  • (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)
  • 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=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)

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

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

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