Norelgestromin/ethinylestradiol

Norelgestromin/ethinylestradiol
Ortho Evra brand of birth control patch
Combination of
NorelgestrominProgestogen
EthinylestradiolEstrogen
Names
Trade namesOrtho Evra, Xulane, Evra, others[1]
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
Main usesPregnancy prevention[2]
Side effectsHeadache, nausea, breast tenderness, irregular uterine bleeding, blood clots[2][3]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • US: N (Not classified yet)
  • Contraindicated
Routes of
use		Transdermal (patch)
External links
AHFS/Drugs.comProfessional Drug Facts
MedlinePlusa602006
Legal
License data
Legal status
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

Norelgestromin/ethinylestradiol, sold under the brand name Evra among others, is a type of birth control patch used to prevent pregnancy.[2] Other benefits include the ability to determine when periods occur, improved acne, and less PMS.[6] It is generally applied to the skin for a week at a time for three weeks, followed by a fourth week patch-free.[2] If the patch-free interval is longer than seven days, additional birth control, such as condoms, should be used.[2] Patches should be applied the same day of the week to altering areas of the buttock, abdomen, upper arm, or upper back.[2]

Common side effects include headache, nausea, breast tenderness, and irregular uterine bleeding.[2][3] Use is not recommended in those with liver problems, migraines with aura, or at risk of blood clots.[2] Those at risk of blood clots include those over 35 years old who smoke.[3] It works less well in those weighing more than 90 kilograms (200 lb) or with a BMI ≥ 30 kg/m2.[2][3] It contains the progestin, norelgestromin and the estrogen, ethinylestradiol.[3][2]

The combination was approved for medical use in the United States in 2001 and Europe in 2002.[7][8][2] A generic version became available in 2014.[6] They are used by about 0.4% of women not wanting to become pregnant in the United States.[9] In the United States it costs about 35 USD per month as of 2024.[10] As of 2016, the brand Ortho Evra has been discontinued in the United States while other brands continues to be marketed.[11][3]

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.[2]

Society and culture

Cost

The cost in the U.S. of this medication is about $46 (USD) for 1 month of transdermal extended release film 35 mcg-150 mcg/24 hr[12]

See also

References

  1. ↑ "DailyMed - Search Results for Norelgestromin_and_ethinyl_estradiol". dailymed.nlm.nih.gov. Archived from the original on 1 January 2022. Retrieved 19 February 2024.
  2. 1 2 3 4 5 6 7 8 9 10 11 12 "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.
  3. 1 2 3 4 5 6 7 "Xulane- norelgestromin and ethinyl estradiol patch". DailyMed. 7 April 2020. Archived from the original on 6 July 2020. Retrieved 4 July 2020.
  4. ↑ "Evra Product information". Health Canada. 2018-06-21. Archived from the original on 18 February 2020. Retrieved 17 February 2020.
  5. ↑ "Evra transdermal patch - Summary of Product Characteristics (SmPC)". (emc). 26 June 2020. Archived from the original on 24 October 2020. Retrieved 4 July 2020.
  6. 1 2 Cason, Patty; Cwiak, Carrie; Kowal, Deborah; Edelman, Alison (26 September 2023). "12". Contraceptive Technology (22 ed.). Jones & Bartlett Learning. pp. 359–405. ISBN 978-1-284-25503-4. Retrieved 18 February 2024.
  7. ↑ "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.
  8. ↑ "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.
  9. ↑ Cason, Patty; Cwiak, Carrie; Kowal, Deborah; Edelman, Alison (26 September 2023). "5". Contraceptive Technology. Jones & Bartlett Learning. pp. 125–163. ISBN 978-1-284-25503-4. Retrieved 18 February 2024.
  10. ↑ "Xulanegeneric Ortho Evra". GoodRx. Archived from the original on 9 May 2023. Retrieved 18 February 2024.
  11. ↑ "Ortho Evra: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on 5 July 2020. Retrieved 4 July 2020.
  12. ↑ "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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