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Etonogestrel

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Pharmaceutical compound
Etonogestrel
Clinical data
AHFS/Drugs.comMultum Consumer Information
MedlinePlusa604032
Routes of
administration		Subdermal as slow-release implant
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
MetabolismHepatic (P450 3A4)
Elimination half-life25 hours
ExcretionUrinary (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-cyclopentaphenanthren-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.053.561 Edit this at Wikidata
Chemical and physical data
FormulaC22H28O2
Molar mass324.457 g/mol g·mol
3D model (JSmol)
SMILES
  • O=C3\C=C2\CC14(CC)(C/C(=C)12CC3)(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
  (what is this?)  (verify)

Etonogestrel is a molecule used in hormonal contraceptives, most notably the subdermal implant Implanon and the contraceptive vaginal ring NuvaRing.

Etonogestrel, the specific progestin used in NuvaRing, 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.

See also

Template:Sex hormones


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