Etonogestrel

Etonogestrel
Clinical data
AHFS/Drugs.com	Multum Consumer Information
MedlinePlus	a604032
Routes of; administration	Subdermal as slow-release implant
ATC code	G03AC08 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Hepatic (P450 3A4)
Elimination half-life	25 hours
Excretion	Urinary (majority) and fecal
Identifiers
	IUPAC name (17α)-13-Ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-one;
CAS Number	54048-10-1 ;
PubChem CID	21729469;
IUPHAR/BPS	7590;
DrugBank	DB00294 ;
ChemSpider	5292944 ;
UNII	304GTH6RNH;
KEGG	D04104 ;
ChEBI	CHEBI:50777 ;
ChEMBL	ChEMBL1531 ;
CompTox Dashboard (EPA)	DTXSID9046782 ;
ECHA InfoCard	100.053.561
Chemical and physical data
Formula	C22H28O2
Molar mass	324.457 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C3\C=C2\CC[C@H]1[C@H]4[C@](CC)(C/C(=C)[C@@H]1[C@H]2CC3)[C@@](C#C)(O)CC4;
	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 ; Key:GCKFUYQCUCGESZ-BPIQYHPVSA-N ;
	(verify)

Etonogestrel (INN, USAN, BAN), also known as 11-methylenelevonorgestrel and 3-keto-desogestrel,^[1] is a steroidal progestin used in hormonal contraceptives, most notably the subdermal implants Nexplanon and Implanon and the 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 significantly 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

^ Kenneth J. Ryan (1999). Kistner's Gynecology and Women's Health. Mosby. p. 300. ISBN 978-0-323-00201-1.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. p. 420. ISBN 978-3-88763-075-1.
^ 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.
^ ^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.
^ ^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.
^ Anna Glasier; Beverly Winikoff (December 1999). Contraception. Health Press. p. 41. ISBN 978-1-899541-18-8.
^ F. William Danby (27 January 2015). Acne: Causes and Practical Management. John Wiley & Sons. pp. 77–. ISBN 978-1-118-23277-4.
^ David E. Golan (2008). Principles of Pharmacology: The Pathophysiologic Basis of Drug Therapy. Lippincott Williams & Wilkins. pp. 521–. ISBN 978-0-7817-8355-2.
^ Leon Speroff; Philip D. Darney (22 November 2010). A Clinical Guide for Contraception. Lippincott Williams & Wilkins. pp. 365–. ISBN 978-1-60831-610-6.
^ ^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.

This drug article relating to the genito-urinary system is a stub. You can help Wikipedia by expanding it.

This article about a steroid is a stub. You can help Wikipedia by expanding it.

[Ryan1999-1] Kenneth J. Ryan (1999). Kistner's Gynecology and Women's Health. Mosby. p. 300. ISBN 978-0-323-00201-1.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. p. 420. ISBN 978-3-88763-075-1.

[LemkeWilliams2012-3] 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.

[CarcioANP-BC2014-4] 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.

[Mayeaux2012-5] E. J. Mayeaux (28 March 2012). The Essential Guide to Primary Care Procedures. Lippincott Williams & Wilkins. pp. 589–. ISBN 978-1-4511-5286-9.

[GlasierWinikoff1999-6] Anna Glasier; Beverly Winikoff (December 1999). Contraception. Health Press. p. 41. ISBN 978-1-899541-18-8.

[Danby2015-7] F. William Danby (27 January 2015). Acne: Causes and Practical Management. John Wiley & Sons. pp. 77–. ISBN 978-1-118-23277-4.

[Golan2008-8] David E. Golan (2008). Principles of Pharmacology: The Pathophysiologic Basis of Drug Therapy. Lippincott Williams & Wilkins. pp. 521–. ISBN 978-0-7817-8355-2.

[SperoffDarney2010-9] Leon Speroff; Philip D. Darney (22 November 2010). A Clinical Guide for Contraception. Lippincott Williams & Wilkins. pp. 365–. ISBN 978-1-60831-610-6.

[LentzLobo2012-10] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]