Etonogestrel

Etonogestrel
Clinical data
Trade namesCirclet, Implanon, Nexplanon, others
Other namesORG-3236; SCH-900702 (with EETooltip ethinylestradiol); 3-Ketodesogestrel; 3-Oxodesogestrel; 11-Methylenelevonorgestrel;[1] 11-Methylene-17α-ethynyl-18-methyl-19-nortestosterone; 11-Methylene-17α-ethynyl-18-methylestr-4-en-17β-ol-3-one
AHFS/Drugs.comProfessional Drug Facts
MedlinePlusa604032
Pregnancy
category
  • AU: B3
Routes of
administration		Subcutaneous implant, vaginal ring
Drug classProgestogen; Progestin
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only[2]
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only[3]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityImplant: 100%[4]
Vaginal ring: 100%[5]
Protein binding≥98% (66% to albumin, 32% to SHBGTooltip sex hormone-binding globulin)[4]
MetabolismLiver (CYP3A4)[4][5]
Elimination half-life21–38 hours[6][7][4][5]
ExcretionUrine (major), feces (minor)[4][5]
Identifiers
IUPAC name
  • (8S,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-11-methylidene-2,6,7,8,9,10,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.053.561
Chemical and physical data
FormulaC22H28O2
Molar mass324.464 g·mol−1
3D model (JSmol)
SMILES
  • CC[C@]12CC(=C)[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
InChI
  • InChI=1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1 Y
  • Key:GCKFUYQCUCGESZ-BPIQYHPVSA-N Y
  (verify)
Etonogestrel birth control implant
Implanon
Background
TypeHormonal
Progestin-only implant
First use1998  Indonesia
SynonymsEtonogestrel contraceptive implant
Trade namesImplanon, Nexplanon, others
AHFS/Drugs.comFDA Professional Drug Information
Failure rates (first year)
Perfect use0.05%[8]
Typical use0.05%[8]
Usage
Duration effect3 to 5 years[9][10]
ReversibilityYes
User remindersRequires removal after the 3–5 years[11]
Advantages and disadvantages
STI protectionNo
WeightMay cause weight gain
Period disadvantagesMay cause irregular or prolonged bleeding
Period advantagesMinimizes pain. In 33% no periods.
BenefitsLong-term contraception.

Etonogestrel is a medication which is used as a means of birth control for women.[4][5][12][13] It is available as an implant placed under the skin of the upper arm under the brand names Nexplanon and Implanon. It is a progestin that is also used in combination with ethinylestradiol, an estrogen, as a vaginal ring under the brand names NuvaRing and Circlet.[14] Etonogestrel is effective as a means of birth control and lasts at least three or four years with some data showing effectiveness for five years.[9][11] Following removal, fertility quickly returns.[15]

Side effects of etonogestrel include menstrual irregularities, breast tenderness, mood changes, acne, headaches, vaginitis, and others.[4] Etonogestrel is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[16] It works by stopping ovulation, thickening the mucus around the opening of the cervix, and altering the lining of the uterus.[17] It has very weak androgenic and glucocorticoid activity and no other important hormonal activity.[16]

Etonogestrel was patented in 1972 and introduced for medical use in 1998.[18][19][20] It became available in the United States in 2006.[18][19] Etonogestrel implants are approved in more than 90 countries and used by about three million women globally as of 2010.[17][21]

A closely related and more widely known and used progestin, desogestrel, is a prodrug of etonogestrel in the body.[16]

  1. ^ Ryan KJ (1999). Kistner's Gynecology and Women's Health. Mosby. p. 300. ISBN 978-0-323-00201-1.
  2. ^ "NEXPLANON : Etonogestrel extended release subdermal implant" (PDF). Pdf.hres.ca. Archived (PDF) from the original on 2022-06-10. Retrieved 2022-06-08.
  3. ^ "List of nationally authorised medicinal products : Active substance: etonogestrel : Procedure no.: PSUSA/00001331/202109" (PDF). Ema.europa.eu. Archived (PDF) from the original on 2022-06-10. Retrieved 2022-06-08.
  4. ^ a b c d e f g "Nexplanon- etonogestrel implant". DailyMed. 18 November 2019. Archived from the original on 10 June 2022. Retrieved 25 September 2020.
  5. ^ a b c d e "NuvaRing- etonogestrel and ethinyl estradiol insert, extended release". DailyMed. 24 January 2020. Archived from the original on 8 August 2020. Retrieved 25 September 2020.
  6. ^ Cite error: The named reference RunnebaumRabe2012 was invoked but never defined (see the help page).
  7. ^ Mosby's GenRx: A Comprehensive Reference for Generic and Brand Prescription Drugs. Mosby. 2001. p. 687. ISBN 978-0-323-00629-3. The elimination half-life for 3-keto-desogestrel is approximately 38 ± 20 hours at steady state.
  8. ^ a b Trussell J (2011). "Contraceptive efficacy" (PDF). In Hatcher RA, Trussell J, Nelson AL, Cates W, Kowal D, Policar MS (eds.). Contraceptive technology (20th revised ed.). New York: Ardent Media. pp. 779–863. ISBN 978-1-59708-004-0. ISSN 0091-9721. OCLC 781956734. Archived (PDF) from the original on 2013-11-12.
  9. ^ a b Hamilton RJ (2016). Tarascon Pocket Pharmacopoeia 2016 Deluxe Lab-Coat Edition. Jones & Bartlett Publishers. p. 392. ISBN 9781284095289. Archived from the original on 2022-06-10. Retrieved 2021-02-18.
  10. ^ Melville C (2015). Sexual and Reproductive Health at a Glance. John Wiley & Sons. p. 21. ISBN 9781118460757. Archived from the original on 2022-06-10. Retrieved 2021-02-18.
  11. ^ a b Cite error: The named reference Lot2016 was invoked but never defined (see the help page).
  12. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. p. 420. ISBN 978-3-88763-075-1. Archived from the original on 2020-01-03. Retrieved 2018-02-21.
  13. ^ Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1409–. ISBN 978-1-60913-345-0. Archived from the original on 9 May 2022. Retrieved 11 October 2016.
  14. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  15. ^ World Health Organization (2015). The selection and use of essential medicines. Twentieth report of the WHO Expert Committee 2015 (including 19th WHO Model List of Essential Medicines and 5th WHO Model List of Essential Medicines for Children). Geneva: World Health Organization. pp. 332–36. hdl:10665/189763. ISBN 9789241209946. ISSN 0512-3054. WHO technical report series;994.
  16. ^ a b c Cite error: The named reference pmid16112947i was invoked but never defined (see the help page).
  17. ^ a b Pattman R, Sankar N, Elawad B, Handy P, Price DA, eds. (2010). Oxford Handbook of Genitourinary Medicine, HIV, and Sexual Health. OUP Oxford. p. 368. ISBN 9780199571666. Archived from the original on 2017-09-24.
  18. ^ a b Cite error: The named reference CarcioANP-BC2014 was invoked but never defined (see the help page).
  19. ^ a b Cite error: The named reference Mayeaux2012 was invoked but never defined (see the help page).
  20. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 480. ISBN 9783527607495. Archived from the original on 2022-05-09. Retrieved 2020-06-06.
  21. ^ Senanayake P, Potts M (2008). Atlas of Contraception, Second Edition (2 ed.). CRC Press. p. 53. ISBN 9780203347324. Archived from the original on 2017-09-24.
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