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Tolrestat

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Chemical compound

Pharmaceutical compound

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Legal status	Withdrawn from market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^Y
PubChemCID	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)

Tolrestat (INN;AY-27773) is analdose 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 byWyeth in 1997 because of the risk of severe liver toxicity and death. It was sold under the tradenameAlredase.

References

[edit]

^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.

Oraldiabetes medication,insulins andinsulin analogues, and other drugs used in diabetes (A10)

Insulins andinsulin analogues

Fast-acting	Insulin aspart Insulin glulisine Insulin lispro
Short-acting	Regular insulin^#
Long-acting	Insulin detemir^# Insulin glargine^# (+lixisenatide) NPH insulin Lente insulin^‡ Ultralente insulin^‡
Ultra-long-acting	Insulin degludec^# (+insulin aspart,+liraglutide) Insulin icodec^† (+semaglutide)
Inhalable	Exubera^‡ Afrezza
Oral	Insulin tregopil^†

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Non-insulins

Insulin sensitizers

Biguanides	Buformin^‡ Metformin^# Phenformin^‡
TZDs ("-glitazones") andPPAR agonists	Ciglitazone^§ Darglitazone^§ Englitazone^§ Lobeglitazone Netoglitazone^§ Pioglitazone Rivoglitazone^† Rosiglitazone Troglitazone^‡
Dual PPAR agonists	Aleglitazar^† Muraglitazar^§ Saroglitazar Tesaglitazar^§
Amylin analogues andDACRAs	Cagrilintide^§ Pramlintide

Secretagogues

K⁺_ATP

Sulfonylureas	1st generation:Acetohexamide Carbutamide Chlorpropamide Glycyclamide Metahexamide Tolazamide Tolbutamide 2nd generation:Glibenclamide (glyburide) Glibornuride Glicaramide Gliclazide^# Glimepiride Glipizide Gliquidone Glisoxepide Glyclopyramide
Meglitinides ("-glinides")	Mitiglinide Nateglinide Repaglinide

GLP-1 receptor agonists

GLP1 poly-agonist peptides	Mazdutide (GLP-1/GCGR) Retatrutide^§ (GLP-1/GIP/GCGR) Tirzepatide (GLP-1/GIP)

DPP-4 inhibitors ("-gliptins")

Other

Aldose reductase inhibitors	Epalrestat Fidarestat^§ Ranirestat^† Tolrestat^‡ Zenarestat^§
Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose
SGLT2 inhibitors ("-gliflozins")	Canagliflozin Dapagliflozin Empagliflozin^# Ertugliflozin Ipragliflozin Luseogliflozin Remogliflozin^§ Sergliflozin^§ Sotagliflozin Tofogliflozin^† Velagliflozin
Other	Benfluorex^‡ Bromocriptine Imeglimin

Combinations

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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