tolrestat   Click here for help

GtoPdb Ligand ID: 7404

Synonyms: Alredase® | AY-27,773 | AY-27773
Approved drug PDB Ligand
tolrestat is an approved drug
Compound class: Synthetic organic
Comment: Tolrestat is an aldose reductase inhibitor [1] that failed Phase 3 clinical trial in the US and never made it to the clinic. The manufacturer withdrew the drug from other markets due to toxicity concerns.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 81.86
Molecular weight 357.06
XLogP 3.99
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1ccc2c(c1C(F)(F)F)cccc2C(=S)N(CC(=O)O)C
Isomeric SMILES COc1ccc2c(c1C(F)(F)F)cccc2C(=S)N(CC(=O)O)C
InChI InChI=1S/C16H14F3NO3S/c1-20(8-13(21)22)15(24)11-5-3-4-10-9(11)6-7-12(23-2)14(10)16(17,18)19/h3-7H,8H2,1-2H3,(H,21,22)
InChI Key LUBHDINQXIHVLS-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
Withdrawn drug? Yes
IUPAC Name Click here for help
2-[[6-methoxy-5-(trifluoromethyl)naphthalene-1-carbothioyl]-methylamino]acetic acid
International Nonproprietary Names Click here for help
INN number INN
5529 tolrestat
Synonyms Click here for help
Alredase® | AY-27,773 | AY-27773
Database Links Click here for help
CAS Registry No. 82964-04-3
ChEMBL Ligand CHEMBL436
DrugBank Ligand DB02383
DrugCentral Ligand 2704
GtoPdb PubChem SID 178103976
PubChem CID 53359
RCSB PDB Ligand TOL
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SynPHARM 79711 (in complex with aldo-keto reductase family 1 member B)
Wikipedia Tolrestat