Tolrestat

Tolrestat
Clinical data
ATC code	A10XA01 (WHO) ;
Legal status
Legal status	Withdrawn from market;
Identifiers
	IUPAC name N-{[6-methoxy-5-(trifluoromethyl)-1-naphthyl]carbothioyl}-N-methylglycine;
CAS Number	82964-04-3 ;
PubChem CID	53359;
IUPHAR/BPS	7404;
ChemSpider	48194 ;
UNII	0T93LG5NMK;
KEGG	D02323 ;
ChEMBL	ChEMBL436 ;
CompTox Dashboard (EPA)	DTXSID80904890 DTXSID6048834, DTXSID80904890 ;
Chemical and physical data
Formula	C16H14F3NO3S
Molar mass	357.35 g·mol−1
3D model (JSmol)	Interactive image;
	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 ;
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Tolrestat (INN) (AY-27773) is an aldose reductase inhibitor^[1] which was approved for the control of certain diabetic complications.^[2]

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

^ 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.
^ 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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[pmid6422042-1] 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.

[pmid3925146-2] 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.

[1]

[2]

Clinical data


ATC code	A10XA01 (WHO)
Legal status
Legal status	Withdrawn from market
Identifiers
IUPAC name N-{[6-methoxy-5-(trifluoromethyl)-1-naphthyl]carbothioyl}-N-methylglycine
CAS Number	82964-04-3^Y
PubChem CID	53359
IUPHAR/BPS	7404
ChemSpider	48194^N
UNII	0T93LG5NMK
KEGG	D02323^Y
ChEMBL	ChEMBL436^N
CompTox Dashboard (EPA)	DTXSID80904890 DTXSID6048834, DTXSID80904890
Chemical and physical data
Formula	C₁₆H₁₄F₃NO₃S
Molar mass	357.35 g·mol⁻¹
3D model (JSmol)	Interactive image
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)