tolrestat

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 408940699

| IUPAC_name = N-{[6-methoxy-5-(trifluoromethyl)-1-naphthyl]carbothioyl}-N-methylglycine

| image = Tolrestat structure.svg

| alt = Skeletal formula of tolrestat

| image2 = Tolrestat 3D ball.png

| alt2 = Ball-and-stick model of the tolrestat molecule

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Withdrawn from market

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| IUPHAR_ligand = 7404

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 82964-04-3

| ATC_prefix = A10

| ATC_suffix = XA01

| ATC_supplemental =

| PubChem = 53359

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 0T93LG5NMK

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D02323

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 436

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 48194

| chemical_formula =

| C=16 | H=14 | F=3 | N=1 | O=3 | S=1

| smiles = CN(CC(=O)O)C(=S)C1=CC=CC2=C1C=CC(=C2C(F)(F)F)OC

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = LUBHDINQXIHVLS-UHFFFAOYSA-N

}}

Tolrestat (INN; AY-27773) is an aldose reductase inhibitor{{cite journal |vauthors=Sestanj K, Bellini F, Fung S, etal |title=N-[5-(trifluoromethyl)-6-methoxy-1-naphthalenyl]thioxomethyl]- N-methylglycine (Tolrestat), a potent, orally active aldose reductase inhibitor |journal=J. Med. Chem. |volume=27 |issue=3 |pages=255–6 |date=March 1984 |pmid=6422042 |doi= 10.1021/jm00369a003}} which was approved for the control of certain diabetic complications.{{cite journal |vauthors=Kador PF, Kinoshita JH, Sharpless NE |title=Aldose reductase inhibitors: a potential new class of agents for the pharmacological control of certain diabetic complications |journal=J. Med. Chem. |volume=28 |issue=7 |pages=841–9 |date=July 1985 |pmid=3925146 |doi= 10.1021/jm00145a001}}

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.