Etonorgestrel

Etonorgestrel

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 (8S,9R,10S,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	54048-10-1 Y
PubChem CID	21729469
DrugBank	DB00294 Y
ChemSpider	5292944 Y
UNII	304GTH6RNH
KEGG	D04104 Y
ChEBI	CHEBI:50777 Y
ChEMBL	ChEMBL1531 Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C22H28O2
Molar mass	324.457 g/mol
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 Y Key:GCKFUYQCUCGESZ-BPIQYHPVSA-N Y
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Alonso Alvarado, M.D. [2]

Overview

Etonogestrel is a steroidal progestin used in hormonal contraceptives, most notably the subdermal implant Nexplanon and the vaginal ring NuvaRing.

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.