Tolrestat

Tolrestat (INN) (AY-27773) is an aldose reductase inhibitor[1] which was approved for the control of certain diabetic complications.[2]

Tolrestat
Clinical data
ATC code
Legal status
Legal status
  • Withdrawn from market
Identifiers
IUPAC name
  • N-{[6-methoxy-5-(trifluoromethyl)-1-naphthyl]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−1
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) N
  • Key:LUBHDINQXIHVLS-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

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-[5-(trifluoromethyl)-6-methoxy-1-naphthalenyl]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.


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