Epalrestat information

Epalrestat
Names
	Preferred IUPAC name {(5Z)-5-[(2E)-2-Methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl}acetic acid
Identifiers
CAS Number	82159-09-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:31539 ;
ChEMBL	ChEMBL56337 ;
ChemSpider	1266086 ;
ECHA InfoCard	100.200.343
KEGG	D01688 ;
PubChem CID	1549120;
UNII	424DV0807X ;
CompTox Dashboard (EPA)	DTXSID1046479 ;
	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- Key: CHNUOJQWGUIOLD-NFZZJPOKSA-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-NFZZJPOKBR;
	SMILES 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). verify (what is ?) Infobox references

Epalrestat is a carboxylic acid derivative^[1] and 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. It reduces the accumulation of intracellular sorbitol which is believed to be the cause of diabetic neuropathy, retinopathy and nephropathy ^[2]^[3] 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.^[4] Chemically, epalrestat is unusual in that it is a drug that contains a rhodanine group. Aldose reductase is the key enzyme in the polyol pathway whose enhanced activity is the basis of diabetic neuropathy. Aldose reductase inhibitors (ARI) target this enzyme. Out of the many ARIs developed, ranirestat and fidarestat are in the trial stage. Others have been discarded due to unacceptable adverse effects or weak efficacy. Epalrestat is the only ARI commercially available.^[5] It is easily absorbed into the neural tissue^[6] and inhibits the enzyme with minimum side effects.^[7]

^ Terashima, H; Hama, K (1984). "Effects of a new aldose reductase inhibitor on various tissue in vitro". J Pharmacol Exp Ther. 229 (1): 226–230. PMID 6423811.
^ 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. PMID 18447661. S2CID 207233270.
^ Steele, John W.; Faulds, Diana; Goa, Karen L. (1993). "Epalrestat". Drugs & Aging. 3 (6): 532–555. doi:10.2165/00002512-199303060-00007. PMID 8312678.
^ 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. PMID 18447661. S2CID 207233270.
^ Hotta, N; Akanuma, Y; Kawamori, R; Matsuoka, K; Oka, Y; Shichiri, M (July 2006). "Long-Term Clinical Effects of Epalrestat, an". Diabetes Care. 29 (7): 1538–44. doi:10.2337/dc05-2370. PMID 16801576. Retrieved 16 July 2016.
^ Terashima, H; Hama, K; Yamamoto, R; Tsuboshima, M; Kikkawa, R; Hatanaka, I (1984). "Effects of a new aldose reductase inhibitor on various tissues in vitro". J Pharmacol Exp Ther. 229 (1): 226–30. PMID 6423811.
^ Hotta, N; Sakamoto, N; Shigeta, Y; Kikkawa, G; Goto, Y; Diabetic Neuropathy Study (1996). "Clinical investigation of epalrestat, an aldose reductase inhibitor, on diabetic neuropathy in Japan: multicenter study". J Diabetes Complications. 10 (3): 168–72. doi:10.1016/1056-8727(96)00113-4. PMID 8807467.

[1] Terashima, H; Hama, K (1984). "Effects of a new aldose reductase inhibitor on various tissue in vitro". J Pharmacol Exp Ther. 229 (1): 226–230. PMID 6423811.

[2] 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. PMID 18447661. S2CID 207233270.

[3] Steele, John W.; Faulds, Diana; Goa, Karen L. (1993). "Epalrestat". Drugs & Aging. 3 (6): 532–555. doi:10.2165/00002512-199303060-00007. PMID 8312678.

[4] 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. PMID 18447661. S2CID 207233270.

[5] Hotta, N; Akanuma, Y; Kawamori, R; Matsuoka, K; Oka, Y; Shichiri, M (July 2006). "Long-Term Clinical Effects of Epalrestat, an". Diabetes Care. 29 (7): 1538–44. doi:10.2337/dc05-2370. PMID 16801576. Retrieved 16 July 2016.

[6] Terashima, H; Hama, K; Yamamoto, R; Tsuboshima, M; Kikkawa, R; Hatanaka, I (1984). "Effects of a new aldose reductase inhibitor on various tissues in vitro". J Pharmacol Exp Ther. 229 (1): 226–30. PMID 6423811.

[7] Hotta, N; Sakamoto, N; Shigeta, Y; Kikkawa, G; Goto, Y; Diabetic Neuropathy Study (1996). "Clinical investigation of epalrestat, an aldose reductase inhibitor, on diabetic neuropathy in Japan: multicenter study". J Diabetes Complications. 10 (3): 168–72. doi:10.1016/1056-8727(96)00113-4. PMID 8807467.

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