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Tolrestat

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Chemical compound Pharmaceutical compound
Tolrestat
Skeletal formula of tolrestat
Ball-and-stick model of the tolrestat molecule
Clinical data
ATC code
Legal status
Legal status
  • Withdrawn from market
Identifiers
IUPAC name
  • N-{carbothioyl}-N-methylglycine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H14F3NO3S
Molar mass357.35 g·mol
3D model (JSmol)
SMILES
  • CN(CC(=O)O)C(=S)C1=CC=CC2=C1C=CC(=C2C(F)(F)F)OC
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)
  • Key:LUBHDINQXIHVLS-UHFFFAOYSA-N
  (what is this?)  (verify)

Tolrestat (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 discontinued by Wyeth in 1997 because of the risk of severe liver toxicity and death. It was sold under the tradename Alredase.

References

  1. Sestanj K, Bellini F, Fung S, et al. (March 1984). "N-thioxomethyl]- N-methylglycine (Tolrestat), a potent, orally active aldose reductase inhibitor". J. Med. Chem. 27 (3): 255–6. doi:10.1021/jm00369a003. PMID 6422042.
  2. Kador PF, Kinoshita JH, Sharpless NE (July 1985). "Aldose reductase inhibitors: a potential new class of agents for the pharmacological control of certain diabetic complications". J. Med. Chem. 28 (7): 841–9. doi:10.1021/jm00145a001. PMID 3925146.
Oral diabetes medication, insulins and insulin analogs, and other drugs used in diabetes (A10)
Insulins / insulin analogs
fast-acting
short-acting
long-acting
ultra-long-acting
inhalable
  • Exubera
  • Afrezza
Non-insulins
Insulin sensitizers
Biguanides
TZDs/"glitazones" (PPAR)
Dual PPAR agonists
Amylin analogs and DACRAs
Secretagogues
KATP
Sulfonylureas
Meglitinides/"glinides"
GLP-1 receptor agonists
GLP1 poly-agonist peptides
DPP-4 inhibitors/"gliptins"
Other
Aldose reductase inhibitors
Alpha-glucosidase inhibitors
SGLT2 inhibitors/"gliflozins"
Other
Combinations


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