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Importing Wikidata short description: "Chemical compound"
 
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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
⚫
| IUPAC_name = ''N''-{[6-methoxy-5-(trifluoromethyl)-1-naphthyl]carbothioyl}-''N''-methylglycine
| verifiedrevid = 408940699
⚫
| image = Tolrestat.svg
⚫
| IUPAC_name = ''N''-{[6-methoxy-5-(trifluoromethyl)-1-naphthyl]carbothioyl}-''N''-methylglycine
⚫
| CAS_number = 82964-04-3
⚫
| image = Tolrestat.svg
| CAS_supplemental =
| alt = Skeletal formula of tolrestat
⚫
| ATC_prefix = A10
| image2 = Tolrestat 3D ball.png
⚫
| ATC_suffix = XA01
| alt2 = Ball-and-stick model of the tolrestat molecule
⚫
| ATC_supplemental =

⚫
| PubChem = 53359
<!--Clinical data-->
⚫
| DrugBank =
| tradename =
⚫
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫
| pregnancy_US = <!-- A / B / C / D / X -->
⚫
| pregnancy_category=
⚫
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
⚫
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫
| legal_status
⚫
| routes_of_administration =

<!--Pharmacokinetic data-->
⚫
| bioavailability
⚫
| protein_bound
⚫
| metabolism
⚫
| elimination_half-life =
⚫
| excretion =

<!--Identifiers-->
| 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
| KEGG = D02323
| ChEMBL_Ref = {{ebicite|changed|EBI}}
⚫
| chemical_formula =
| ChEMBL = 436
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 48194

<!--Chemical data-->
⚫
| chemical_formula =
| C=16 | H=14 | F=3 | N=1 | O=3 | S=1
| 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
| molecular_weight = 357.34 g/mol
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫
| smiles = CN(CC(=O)O)C(=S)C1=CC=CC2=C1C=CC(=C2C(F)(F)F)OC
| 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)
⚫
| bioavailability =
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫
| protein_bound =
| StdInChIKey = LUBHDINQXIHVLS-UHFFFAOYSA-N
⚫
| metabolism =
⚫
| elimination_half-life =
⚫
| excretion =
⚫
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫
| pregnancy_US = <!-- A / B / C / D / X -->
⚫
| pregnancy_category=
⚫
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
⚫
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫
| legal_status =
⚫
| routes_of_administration =
}}
}}


'''Tolrestat''' ([[International Nonproprietary Name|INN]]) ('''AY-27773''') is an [[aldose reductase inhibitor]]<ref name="pmid6422042">{{cite journal |author=Sestanj K, Bellini F, Fung S, ''et al.'' |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 |year=1984 |month=March |pmid=6422042 |doi= 10.1021/jm00369a003|url=}}</ref> which was approved for the control of certain diabetic complications.<ref name="pmid3925146">{{cite journal |author=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 |year=1985 |month=July |pmid=3925146 |doi= 10.1021/jm00145a001|url=}}</ref>
'''Tolrestat''' ([[International Nonproprietary Name|INN]]) ('''AY-27773''') is an [[aldose reductase inhibitor]]<ref name="pmid6422042">{{cite journal |=Sestanj K, Bellini F, Fung S, |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 |=1984 |pmid=6422042 |doi= 10.1021/jm00369a003}}</ref> which was approved for the control of certain diabetic complications.<ref name="pmid3925146">{{cite journal |=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 |=1985 |pmid=3925146 |doi= 10.1021/jm00145a001}}</ref>


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'''.
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==
==References==
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{{Oral hypoglycemics and insulin analogs}}
{{Oral hypoglycemics and insulin analogs}}


[[Category:Withdrawn drugs]]
[[Category: ]]
[[Category:Acetic acids]]
[[Category:Hepatotoxins]]
[[Category:Naphthol ethers]]
[[Category:Naphthol ethers]]
[[Category:Organofluorides]]
[[Category:]]
[[Category:Thioamides]]
[[Category:Thioamides]]
[[Category:Withdrawn drugs]]




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