Etonogestrel

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Etonogestrel
Etonogestrel.svg
Clinical data
AHFS/Drugs.com Multum Consumer Information
MedlinePlus a604032
Routes of
administration
Subdermal as slow-release implant
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
  • ℞ (Prescription only)
Pharmacokinetic data
Metabolism Hepatic (P450 3A4)
Biological half-life 25 hours
Excretion Urinary (majority) and fecal
Identifiers
Synonyms 11-methylenelevonorgestrel, 3-keto-desogestrel[1]
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.053.561
Chemical and physical data
Formula C22H28O2
Molar mass 324.457 g/mol
3D model (Jmol)
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Etonogestrel is a steroidal progestin used in hormonal contraceptives, most notably the etonogestrel contraceptive implant (Nexplanon and Implanon) and the contraceptive vaginal ring (NuvaRing).[2][3]

It was first introduced, as Implanon in Indonesia, in 1998,[4][5] and was subsequently marketed in the United Kingdom shortly thereafter[6] and in the United States in 2006.[4][5] Etonogestrel is less androgenic than levonorgestrel and norethisterone,[7][8] and it does not cause a decrease in sex hormone-binding globulin levels,[9] but it is still associated with acne in up to 13% of patients when used as an implant, though this only accounts for 1% of premature removals.[10]

Etonogestrel is the active metabolite of the inactive prodrug desogestrel, one of two third-generation progestins found in some epidemiological studies of combined oral contraceptive pills to be associated with a higher risk of venous thrombosis than combined oral contraceptive pills containing certain second-generation progestins. Because hormones are released continuously from NuvaRing, peak and total estrogen and progestin doses are significantly lower than with combined oral contraceptives, although it is not known whether this lowers the risk of blood clots. It is effective within the first 8 hours of insertion.[10]

References[edit]

  1. ^ Kenneth J. Ryan (1999). Kistner's Gynecology and Women's Health. Mosby. p. 300. ISBN 978-0-323-00201-1. 
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. p. 420. ISBN 978-3-88763-075-1. 
  3. ^ Thomas L. Lemke; David A. Williams (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1409–. ISBN 978-1-60913-345-0. 
  4. ^ a b Helen Carcio; R. Mimi Secor (10 October 2014). Advanced Health Assessment of Women, Third Edition: Clinical Skills and Procedures. Springer Publishing Company. pp. 411–. ISBN 978-0-8261-2308-4. 
  5. ^ a b E. J. Mayeaux (28 March 2012). The Essential Guide to Primary Care Procedures. Lippincott Williams & Wilkins. pp. 589–. ISBN 978-1-4511-5286-9. 
  6. ^ Anna Glasier; Beverly Winikoff (December 1999). Contraception. Health Press. p. 41. ISBN 978-1-899541-18-8. 
  7. ^ F. William Danby (27 January 2015). Acne: Causes and Practical Management. John Wiley & Sons. pp. 77–. ISBN 978-1-118-23277-4. 
  8. ^ David E. Golan (2008). Principles of Pharmacology: The Pathophysiologic Basis of Drug Therapy. Lippincott Williams & Wilkins. pp. 521–. ISBN 978-0-7817-8355-2. 
  9. ^ Leon Speroff; Philip D. Darney (22 November 2010). A Clinical Guide for Contraception. Lippincott Williams & Wilkins. pp. 365–. ISBN 978-1-60831-610-6. 
  10. ^ a b Gretchen M Lentz; Rogerio A. Lobo; David M Gershenson; Vern L. Katz (21 February 2012). Comprehensive Gynecology. Elsevier Health Sciences. pp. 256–. ISBN 0-323-09131-8.