Norelgestromin/ethinylestradiol

Norelgestromin/ethinylestradiol
Combination of
NorelgestrominProgestogen
EthinylestradiolEstrogen
Names
Trade namesOrtho Evra, Xulane, Evra
IUPAC name
  • (3Z,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;(8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
Clinical data
Pregnancy
category
  • US: N (Not classified yet)
  • Contraindicated
Routes of
use		Transdermal (patch)
External links
AHFS/Drugs.comProfessional Drug Facts
US NLMNorelgestromin/ethinylestradiol
MedlinePlusa602006
Legal
License data
Legal status
Identifiers
CAS Number
  • 53016-31-2 checkY
  • 57-63-6 checkY
PubChem CID
DrugBank
ChemSpider
  • None
UNII
KEGG
ATC code
Chemical and physical data
FormulaC41H53NO4
Molar mass623.878 g·mol−1
3D model (JSmol)
SMILES
  • CCC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=NO)CCC34.CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)O
InChI
  • InChI=1S/C21H29NO2.C20H24O2/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;1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h2,13,16-19,23-24H,3,5-12H2,1H3;1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/b22-15-;/t16-,17+,18+,19-,20-,21-;16-,17-,18+,19+,20+/m01/s1
  • Key:KBFRRZPPJPKFHQ-WKXKRCMPSA-N
Main article: Contraceptive patch

Norelgestromin/ethinylestradiol, sold under the brand name Ortho Evra among others, is a contraceptive patch containing the progestin norelgestromin and the estrogen ethinylestradiol.[3][4] As of December 2016, the product Ortho Evra has been discontinued in the U.S. while the product Xulane continues to be marketed.[5][3][6]

The most common side effects include headache, nausea (feeling sick), breast tenderness, and irregular uterine bleeding.[4][3]

Norelgestromin/ethinylestradiol was approved for medical use in the United States in November 2001, and in the European Union in August 2002.[7][4]

Norelgestromin/ethinylestradiol is a transdermal patch (a patch that delivers a medicine across the skin).[4] For the first three weeks of the menstrual cycle a new patch should be applied every week, followed by a fourth week, which is patch-free.[4] The patch-free interval must not be longer than seven days; otherwise, additional non-hormonal contraceptive methods must be used, such as condoms.[4] Transdermal patches must always be applied on the same day of the week to the buttock, abdomen (belly), upper arm or upper back.[4] The same area of skin should not be used for two consecutive patches.[4] Norelgestromin/ethinylestradiol may work less well in women weighing 198 pounds (90 kg) or more.[4]

Medical uses

In the United States norelgestromin/ethinylestradiol is indicated for the prevention of pregnancy in women with a BMI < 30 kg/m2 for whom a transdermal delivery system is an appropriate method of contraception.[3]

In the European Union, norelgestromin/ethinylestradiol is indicated for use as female contraception.[4]

Society and culture

Cost

The cost in the U.S. of this medication is $46 (USD) for 1 transdermal extended release film 35 mcg-150 mcg/24 hr[8]

  • Norelgestromin/ethinylestradiol costs (US)
  • Norelgestromin/ethinylestradiol prescriptions (US)

See also

References

  1. ↑ "Evra Product information". Health Canada. 21 June 2018. Archived from the original on 18 February 2020. Retrieved 17 February 2020.
  2. ↑ "Evra transdermal patch - Summary of Product Characteristics (SmPC)". (emc). 26 June 2020. Archived from the original on 24 October 2020. Retrieved 4 July 2020.
  3. 1 2 3 4 "Xulane- norelgestromin and ethinyl estradiol patch". DailyMed. 7 April 2020. Archived from the original on 6 July 2020. Retrieved 4 July 2020.
  4. 1 2 3 4 5 6 7 8 9 10 "Evra EPAR". European Medicines Agency (EMA). Archived from the original on 12 November 2020. Retrieved 4 July 2020. Text was copied from this source which is © European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
  5. ↑ "Ortho Evra (norelgestromin/ethinyl estradiol transdermal system) Initial U.S. Approval: 2001". DailyMed. 12 July 2018. Archived from the original on 5 July 2020. Retrieved 4 July 2020.
  6. ↑ "Ortho Evra: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 5 July 2020. Retrieved 4 July 2020.
  7. ↑ "Drug Approval Package: Ortho EVRA (Norelgestromin/Ethinyl Estradiol Transdermal System NDA #21-180". U.S. Food and Drug Administration (FDA). Archived from the original on 5 July 2020. Retrieved 4 July 2020.
  8. ↑ "Ortho Evra Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 7 September 2015. Retrieved 30 March 2021.


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