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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

tolrestat is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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
Search Google for chemical match using the InChIKey LUBHDINQXIHVLS-UHFFFAOYSA-N
Search Google for chemicals with the same backbone LUBHDINQXIHVLS
Search PubMed clinical trials tolrestat
Search PubMed titles tolrestat
Search PubMed titles/abstracts tolrestat
SynPHARM 79711 (in complex with aldo-keto reductase family 1 member B)
UniChem Compound Search for chemical match using the InChIKey LUBHDINQXIHVLS-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey LUBHDINQXIHVLS-UHFFFAOYSA-N
Wikipedia Tolrestat

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MedChemExpress
Tolrestat (links to external site)
Cat. No. HY-16500