Epalrestat

Epalrestat
Names

IUPAC name 2-[(5Z)-5-[(E)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
Identifiers
CAS Number	82159-09-9^Y
ChEBI	CHEBI:31539^N
ChEMBL	ChEMBL56337^N
ChemSpider	1285910^N
Jmol interactive 3D	Image Image
KEGG	D01688^Y
PubChem	1584822
UNII	424DV0807X^N
InChI InChI=1S/C15H13NO3S2/c1-10(7-11-5-3-2-4-6-11)8-12-14(19)16(9-13(17)18)15(20)21-12/h2-8H,9H2,1H3,(H,17,18)/b10-7+,12-8+^N Key: CHNUOJQWGUIOLD-SMTGYRLFSA-N^N InChI=1/C15H13NO3S2/c1-10(7-11-5-3-2-4-6-11)8-12-14(19)16(9-13(17)18)15(20)21-12/h2-8H,9H2,1H3,(H,17,18)/b10-7+,12-8+ Key: CHNUOJQWGUIOLD-SMTGYRLFBD
SMILES CC(=CC1=CC=CC=C1)C=C2C(=O)N(C(=S)S2)CC(=O)O O=C(O)CN1C(=O)C(\SC1=S)=C/C(=C/c2ccccc2)C
Properties
Chemical formula	C₁₅H₁₃NO₃S₂
Molar mass	319.401 g/mol
Density	1.43 g/cm³
Melting point	210 °C (410 °F; 483 K)
Boiling point	516.8 °C (962.2 °F; 789.9 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Epalrestat is a noncompetitive and reversible aldose reductase inhibitor used for the treatment of diabetic neuropathy, which is one of the most common long-term complications in patients with diabetes mellitus.^[1]^[2] It is well tolerated, with the most commonly reported adverse effects being gastrointestinal issues such as nausea and vomiting, as well as increases in certain liver enzymes.

Chemically, epalrestat is unusual in that it is a drug that contains a rhodanine group.

Brand names

Aldonil (Zydus Medica), India
Aldorin, Bangladesh
Alrista (marketed and not manufactured by Macleods), India
Epalrica-M (Ordain Global), India
Eparel 50 (Microlabs Ltd), India
Epimeth (Zaiva Lifesciences), India
Eplistat 150 SR (Schem), India
Letostat-SR (Amor Pharmaceuticals), India
Listap-50 (Vivid Biotek), India

References

↑ Ramirez, Mary Ann; Borja, Nancy L (May 2008). "Epalrestat: An Aldose Reductase Inhibitor for the Treatment of Diabetic Neuropathy". Pharmacotherapy 28 (5): 646–655. doi:10.1592/phco.28.5.646.
↑ Steele, John W.; Faulds, Diana; Goa, Karen L. (1993). "Epalrestat". Drugs & Aging 3 (6): 532–555. doi:10.2165/00002512-199303060-00007.

External links

Epalrestat at chemblink.com

Oral anti-diabetic drugs, insulins and insulin analogs, and other drugs used in diabetes (A10)

Insulin

Sensitizers

Biguanides	Metformin^# Buformin<sp>‡ Phenformin^‡

TZDs/"glitazones" (PPAR)	Ciglitazone^§ Darglitazone^§ Englitazone^§ Lobeglitazone Netoglitazone^§ Pioglitazone Rivoglitazone^† Rosiglitazone Troglitazone^‡

Dual PPAR agonists	Aleglitazar^† Muraglitazar^§ Saroglitazar Tesaglitazar^§

Secretagogues

K+ ATP

Sulfonylureas	1st generation: Acetohexamide Carbutamide Chlorpropamide Metahexamide Tolbutamide Tolazamide 2nd generation: Glibenclamide (Glyburide)^# Glibornuride Glicetanile Gliclazide Gliflumide Glipizide Gliquidone Glisoxepide Glyclopyramide Glimepiride

Meglitinides/"glinides"	Nateglinide Repaglinide Mitiglinide

GLP-1 agonists

DPP-4 inhibitors

GPR40 Free fatty acid receptor 1

Fasiglifam^†

Analogs/other insulins

fast-acting (Insulin lispro
Insulin aspart
Insulin glulisine)
short-acting (Regular insulin)
long-acting (Insulin glargine
Insulin detemir
NPH insulin)
ultra-long-acting (Insulin degludec^†)
inhalable Exubera^‡
Afrezza

Other

Aldose reductase inhibitors	Epalrestat Fidarestat^§ Ranirestat^† Tolrestat^‡ Zenarestat^§

Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose

Amylin analog	Pramlintide

Sodium glucose transporter (SGLT2) inhibitors	Canagliflozin Dapagliflozin Empagliflozin Remogliflozin^§ Sergliflozin^§ Tofogliflozin^†

Other	Benfluorex^‡ Bromocriptine

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

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