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
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2006), EMA (2009))
Prodrug desogestrel
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
International Nonproprietary Names
INN number INN
6832 etonogestrel
Synonyms
3-keto-desogestrel | Implanon® | Nexplanon® | ORG-3236
Database Links
CAS Registry No. 54048-10-1
ChEBI CHEBI:50777
ChEMBL Ligand CHEMBL1531
DrugBank Ligand DB00294
DrugCentral Ligand 1110
GtoPdb PubChem SID 223365925
PubChem CID 6917715
Search Google for chemical match using the InChIKey GCKFUYQCUCGESZ-BPIQYHPVSA-N
Search Google for chemicals with the same backbone GCKFUYQCUCGESZ
Search PubMed clinical trials etonogestrel
Search PubMed titles etonogestrel
Search PubMed titles/abstracts etonogestrel
Search UniChem for chemical match using the InChIKey GCKFUYQCUCGESZ-BPIQYHPVSA-N
Search UniChem for chemicals with the same backbone GCKFUYQCUCGESZ
Wikipedia Etonogestrel