Etonogestrel

Etonogestrel

Systematic (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
Clinical data
AHFS/Drugs.com	Multum Consumer Information
MedlinePlus	a604032
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only ℞ (Prescription only)
Routes of administration	Subdermal as slow-release implant
Pharmacokinetic data
Metabolism	Hepatic (P450 3A4)
Biological half-life	25 hours
Excretion	Urinary (majority) and fecal
Identifiers
CAS Number	54048-10-1 Y
ATC code	G03AC08 (WHO)
PubChem	CID: 21729469
IUPHAR/BPS	7590
DrugBank	DB00294 Y
ChemSpider	5292944 Y
UNII	304GTH6RNH Y
KEGG	D04104 Y
ChEBI	CHEBI:50777 Y
ChEMBL	CHEMBL1531 Y
Chemical data
Formula	C22H28O2
Molecular mass	324.457 g/mol
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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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. It is effective within the first 24 hours.