etretinate   

GtoPdb Ligand ID: 7599

Synonyms: Ro-109359 | Tegison®
etretinate is an approved drug (FDA (1986))
Compound class: Synthetic organic
Comment: Etretinate is a highly lipophilic second-generation retinoid. Its use has largely been discontinued as it was discovered to be a long-acting teratogen, with detectable levels in plasma up to three years post-therapy.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 35.53
Molecular weight 354.22
XLogP 6.53
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCOC(=O)C=C(C=CC=C(C=Cc1c(C)cc(c(c1C)C)OC)C)C
Isomeric SMILES CCOC(=O)/C=C(/C=C/C=C(/C=C/c1c(C)cc(c(c1C)C)OC)\C)\C
InChI InChI=1S/C23H30O3/c1-8-26-23(24)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(25-7)20(6)19(21)5/h9-15H,8H2,1-7H3/b11-9+,13-12+,16-10+,17-14+
InChI Key HQMNCQVAMBCHCO-DJRRULDNSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1986))
Withdrawn drug? Yes
IUPAC Name
ethyl 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate
International Nonproprietary Names
INN number INN
4658 etretinate
Synonyms
Ro-109359 | Tegison®
Database Links
CAS Registry No. 54350-48-0
ChEMBL Ligand CHEMBL464
DrugBank Ligand DB00926
DrugCentral Ligand 1116
GtoPdb PubChem SID 223365934
PubChem CID 5282375
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Wikipedia Etretinate