tenidap   Click here for help

GtoPdb Ligand ID: 2395

PDB Ligand
Compound class: Synthetic organic
Comment: Tenidap is a dual COX/5-LOX inhibitor [4]. It was a clinical candidate with anti-inflammatory/anti-rheumatic potential, but development was terminated due to liver and kidney toxicity [1-2].
The INN record for tenidap provides the IUPAC name (Z)-5-chloro-3-(α-hydroxy-2-thenylidene)-2-oxo-1-indolinecarboxamide. The SMILES obtained by coverting this IUPAC using OPSIN match PubChem CID 60712, however this CID does not include the Z configuration that was specified in the INN's IUPAC name.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 113.56
Molecular weight 320.75
XLogP 3.2
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Clc1ccc2c(c1)c(C(=O)c1cccs1)c(n2C(=O)N)O
Isomeric SMILES c1csc(c1)C(=O)c1c(n(c2c1cc(cc2)Cl)C(=O)N)O
InChI InChI=1S/C14H9ClN2O3S/c15-7-3-4-9-8(6-7)11(13(19)17(9)14(16)20)12(18)10-2-1-5-21-10/h1-6,19H,(H2,16,20)
InChI Key IZSFDUMVCVVWKW-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
5-chloro-2-hydroxy-3-(thiophene-2-carbonyl)indole-1-carboxamide
International Nonproprietary Names Click here for help
INN number INN
6421 tenidap
Database Links Click here for help
CAS Registry No. 120210-48-2 (source: Scifinder)
ChEBI CHEBI:35847
ChEMBL Ligand CHEMBL1908355
DrugCentral Ligand 4728
GtoPdb PubChem SID 135651243
PubChem CID 60712
RCSB PDB Ligand I2U
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UniChem Compound Search for chemical match using the InChIKey IZSFDUMVCVVWKW-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey IZSFDUMVCVVWKW-UHFFFAOYSA-N
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Tenidap (links to external site)
Cat. No. 2580