alitretinoin   

GtoPdb Ligand ID: 2645

Synonyms: 9-cis-retinoic acid | Panretin® | Toctino®
alitretinoin is an approved drug (FDA (1999), EMA (2000))
Comment: Alitretinoin is an important regulator of gene expression during normal growth and development, as well as in neoplasms. Alitretinoin is a retinoid receptor agonist.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 37.3
Molecular weight 300.21
XLogP 6.25
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CC(=CC=CC(=CC(=O)O)C)C=CC1=C(C)CCCC1(C)C
Isomeric SMILES C/C(=C/C=C/C(=C/C(=O)O)/C)/C=C/C1=C(C)CCCC1(C)C
InChI InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+
InChI Key SHGAZHPCJJPHSC-ZVCIMWCZSA-N
Classification
Compound class Metabolite or derivative
Approved drug? Yes (FDA (1999), EMA (2000))
IUPAC Name
(2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid
International Nonproprietary Names
INN number INN
7781 alitretinoin
Synonyms
9-cis-retinoic acid | Panretin® | Toctino®
Database Links
BindingDB Ligand 31892
CAS Registry No. 5300-03-8 (source: Scifinder)
ChEBI CHEBI:50648
ChEMBL Ligand CHEMBL705
DrugBank Ligand DB00523
DrugCentral Ligand 3862
GtoPdb PubChem SID 135651418
NURSA Ligand 10.1621/M4CYJZD9LZ
PubChem CID 449171
RCSB PDB Ligand 9CR
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SynPHARM 6485 (in complex with Retinoid X receptor-α)
Wikipedia Alitretinoin