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Tolrestat

Summary

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

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  • Withdrawn from market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
  • N-{[6-methoxy-5-(trifluoromethyl)-1-naphthyl]carbothioyl}-N-methylglycine
CAS Number
  • 82964-04-3 checkY
PubChem CID
  • 53359
IUPHAR/BPS
  • 7404
ChemSpider
  • 48194 ☒N
UNII
  • 0T93LG5NMK
KEGG
  • D02323 checkY
ChEMBL
  • ChEMBL436 ☒N
CompTox Dashboard (EPA)
  • DTXSID6048834 Edit this at Wikidata
Chemical and physical data
FormulaC16H14F3NO3S
Molar mass357.35 g·mol−1
3D model (JSmol)
  • Interactive image
  • CN(CC(=O)O)C(=S)C1=CC=CC2=C1C=CC(=C2C(F)(F)F)OC
  • 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
 ☒NcheckY (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 edit

  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.