etonogestrel   

GtoPdb Ligand ID: 7590

Synonyms: 3-keto-desogestrel | Implanon® | Nexplanon® | ORG-3236
etonogestrel is an approved drug (FDA (2006), EMA (2009))
Compound class: Synthetic organic
Comment: Etonogestrel is the active metabolite of the inactive prodrug desogestrel.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: etonogestrel

2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 37.3
Molecular weight 324.21
XLogP 3.4
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES C#CC1(O)CCC2C1(CC)CC(=C)C1C2CCC2=CC(=O)CCC12
Isomeric SMILES C#C[C@]1(O)CC[C@@H]2[C@]1(CC)CC(=C)[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12
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
InChI Key GCKFUYQCUCGESZ-BPIQYHPVSA-N
No information available.
Summary of Clinical Use
Etonogestrel is the active progestin in several hormonal contraceptives.
Mechanism Of Action and Pharmacodynamic Effects
Etonogestrel is an agonist of the progesterone receptor. Artificial maintainence of high levels of circulating progesterone feeds back to reduce the frequency of gonadotrophin-releasing hormone (GnRH) pulses which blunts the pre-ovulatory lutenising hormone (LH) surge, and the ovaries cease cyclic ovulation.
External links