TOL

TOLRESTAT


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Chemical Component Summary

NameTOLRESTAT
Identifiers2-[[6-methoxy-5-(trifluoromethyl)naphthalen-1-yl]carbothioyl-methyl-amino]ethanoic acid
FormulaC16 H14 F3 N O3 S
Molecular Weight357.347
TypeNON-POLYMER
Isomeric SMILESCN(CC(=O)O)C(=S)c1cccc2c1ccc(c2C(F)(F)F)OC
InChIInChI=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)
InChIKeyLUBHDINQXIHVLS-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count38
Chiral Atom Count0
Bond Count39
Aromatic Bond Count11

Drug Info: DrugBank

DrugBank IDDB02383 
NameTolrestat
Groups withdrawn
DescriptionTolrestat (INN) (AY-27773) is an aldose reductase inhibitor which was approved for the control of certain diabetic complications. While it was approved for marketed in several countries, it failed a Phase III trial in the U.S. due to toxicity and never received FDA approval. It was sold under the tradename Alredase but was discontinued by Wyeth in 1997 because of the risk of severe liver toxicity and death.
SynonymsTolrestat
IndicationFor the pharmacological control of certain diabetic complications.
Categories
  • Aldehyde Reductase, antagonists & inhibitors
  • Aldose Reductase Inhibitors
  • Alimentary Tract and Metabolism
  • Drugs Used in Diabetes
  • Enzyme Inhibitors
ATC-CodeA10XA01
CAS number82964-04-3

Drug Targets

NameTarget SequencePharmacological ActionActions
Alcohol dehydrogenase [NADP(+)]MAASCVLLHTGQKMPLIGLGTWKSEPGQVKAAVKYALSVGYRHIDCAAIY...unknown
Aldo-keto reductase family 1 member B10MATFVELSTKAKMPIVGLGTWKSPLGKVKEAVKVAIDAGYRHIDCAYVYQ...unknown
Aldose reductaseMASRLLLNNGAKMPILGLGTWKSPPGQVTEAVKVAIDVGYRHIDCAHVYQ...unknowninhibitor
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL436
PubChem 53359
ChEMBL CHEMBL436
ChEBI CHEBI:48549