etonogestrel   Click here for help

GtoPdb Ligand ID: 7590

Synonyms: 3-keto-desogestrel | Implanon® | Nexplanon® | ORG-3236
Approved drug
etonogestrel is an approved drug (FDA (2006), EMA (2009))
Compound class: Synthetic organic
Comment: Etonogestrel is the active metabolite of the inactive prodrug desogestrel.
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2D Structure
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Physico-chemical Properties
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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
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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 Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2006), EMA (2009))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
Prodrug desogestrel
IUPAC Name Click here for help
(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 Click here for help
INN number INN
6832 etonogestrel
Synonyms Click here for help
3-keto-desogestrel | Implanon® | Nexplanon® | ORG-3236
Database Links Click here for help
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
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Wikipedia Etonogestrel