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82159-09-9

Basic Information
CAS No.: 82159-09-9
Name: Epalrestat
Molecular Structure:
Molecular Structure of 82159-09-9 (Epalrestat)
Formula: C15H13NO3S2
Molecular Weight: 319.39
Synonyms: 2-[(5Z)-5-[(E)-2-methyl-3-phenyl-prop-2-enylidene]-4-oxo-2-sulfanylidene-thiazolidin-3-yl]acetic acid;3-Thiazolidineacetic acid,5-[(2E)-2-methyl-3-phenyl-2-propenylidene]- 4-oxo-2-thioxo-,(5Z)-;3-Thiazolidineacetic acid, 5-(2-methyl-3-phenyl-2-propenylidene)-4-oxo-2-thioxo-, (E,E)-;Kinedak;Epalrestat (JAN);5-((Z,E)-beta-Methylcinnamylidene)-4-oxo-2-thioxo-3-thiazolidineacetic acid;Epalrestat [INN];Kinedak (TN);Ono 2235;Epalrestatum [Latin];Properties: orange red crystalline powder, with special odor;Epalrestate;Epatrestat;
EINECS: 675-018-0
Density: 1.43 g/cm3
Melting Point: 210-217 °C
Boiling Point: 516.8 °C at 760 mmHg
Flash Point: 266.4 °C
Solubility:
Appearance: Deep red acicular crystal
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 115.00000
LogP: 2.85660
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Chemistry

IUPAC Name:  2-[(5Z)-5-[(E)-2-Methyl-3-phenylprop-2-enylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetic acid
Following is the structure of Epalrestat (82159-09-9):
             
Molecular Formula: C15H13NO3S2
Molecular Weight of Epalrestat (82159-09-9): 319.4 g/mol
RTECS: XJ5131855
Merck: 12,3640
Solubility: Soluble in water
Index of Refraction: 1.705 
Density: 1.43 g/cm3
Flash Point: 266.4 °C
Melting Point: 210-217 °C
Surface Tension: 75.3 dyne/cm
Enthalpy of Vaporization: 83.06 kJ/mol
Boiling Point of Epalrestat (82159-09-9): 516.8 °C at 760 mmHg
Vapour Pressure of Epalrestat (82159-09-9): 1.66E-11 mmHg at 25 °C 
Product Categories: Treatment of diabetic neuropathy; API's
Canonical SMILES: CC(=CC1=CC=CC=C1)C=C2C(=O)N(C(=S)S2)CC(=O)O
Isomeric SMILES: C/C(=C\C1=CC=CC=C1)/C=C\2/C(=O)N(C(=S)S2)CC(=O)O
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-
InChIKey: CHNUOJQWGUIOLD-NFZZJPOKSA-N

Uses

 Epalrestat (82159-09-9) is used as aldose reductase inhibitor, can reversibly inhibit the glucose into sorbitol and the role of aldose reductase. Obstacle for diabetic nerve endings caused by symptoms, vibration sense abnormalities, abnormal changes in heart rate improved.

Production

 Benzene, formaldehyde, ethanol, sodium hydroxide and water mixture, 0 ~ 5 ℃ dropping propionaldehyde, dripping finished in 25 ~ 30 ℃ reaction. Add water, extracted with ether. Extract drying, vacuum distillation, collecting 148 ~ 151 ℃ / 5kPa distillate, may 2 - methyl -3 - phenyl-acrolein (Ⅰ), yield 83.5%.
Dioxane soluble in carbon disulfide, and concentrated ammonia, and stirring at -5 ℃, dropping sodium glycine response. Evaporated and after adding sodium chloroacetate solution at room temperature reaction. Evaporated, add water and concentrated hydrochloric acid, boiling water bath heating. Filter set crystal, recrystallized with ethanol, may 3 - carboxymethyl-rhodanine, the yield of 76.4%. 3 - carboxymethyl rhodanine, 2 - methyl -3 - phenyl-acrolein, anhydrous sodium acetate and glacial acetic acid with the return. Cool to room temperature, add water, refrigerator overnight. Filtration, ethanol recrystallization, were dark red needle-like crystals Epalrestat yield of 65%, melting point 210 ~ 217 ℃.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 1gm/kg (1000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.
mouse LD50 intraperitoneal 687mg/kg (687mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.
mouse LD50 intravenous 255ug/kg (0.255mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.
mouse LD50 oral 3200mg/kg (3200mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.
mouse LD50 subcutaneous > 3gm/kg (3000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.
rat LD50 intraperitoneal 922gm/kg (922000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.
rat LD50 intravenous 255ug/kg (0.255mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.
rat LD50 oral 5300ug/kg (5.3mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.
rat LD50 subcutaneous > 3gm/kg (3000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 201, 1992.

Specification

 Epalrestat , its cas register number is 82159-09-9. It also can be called {(5Z)-5-[(2E)-2-Methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}acetic acid ; 5-((Z,E)-beta-Methylcinnamylidene)-4-oxo-2-thioxo-3-thiazolidineacetic acid ; and Epalrestatum . Epalrestat (82159-09-9) should be stored in original container in a cool dark place.