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HomeProduct name listZopolrestat

Zopolrestat

Zopolrestat Structural

What is Zopolrestat?

Originator

Alond,Pfizer

The Uses of Zopolrestat

Antidiabetic; inhibitor (aldose reductase).

Manufacturing Process

A mixture of 2-methyl-5-trifluoromethylbenzothiazole (1 mole-equivalent), N- bromosuccinimide (1 mole-equivalent), carbon tetrachloride (700 ml) and a catalytic amount of benzoyl peroxide (0.2 g) was refluxed under irradiation by an UV lamp for 14 hours. The reaction mixture was cooled to room temperature, filtered to remove the precipitated succinimide and the filtrate was evaporated to dryness. The resulting solid was chromatographed over silica gel to obtain the 2-bromomethyl-5-trifluoromethyl-benzothiazole. To a mixture of ethyl 4-oxo-3H-phthalazin-1-ylacetate (1 mole-equivalent) and sodium hydride (50% w/w dispersion in mineral oil) in dimethylformamide (150 ml) was added 2-bromomethyl-5-trifluoromethylbenzothiazole (1 mole- equivalent) and the resulting mixture stirred at room temperature for 1 hour. This reaction mixture was poured over ice-water (500 ml); sufficient 10% HCl was added to adjust the pH to about 4.0 and the precipitated crude solid was collected. This was chromatographed over silica gel to obtain the ethyl[4-oxo- 3-(5-trifluoromethylbenzothiazol-2-yl)-3,4-dihydro-phthalazin-1-yl]acetate; MP: 134°-136°C. A solution of methyl or ethyl [4-oxo-3-(5-trifluoromethylbenzothiazol-2-yl)- 3,4-dihydrophthalazin-1-yl]acetate (1 mole-equivalent) in methanol (50 ml)

Therapeutic Function

Aldose reductase inhibitor

Properties of Zopolrestat

Melting point: 197-198℃
Density  1.58
storage temp.  2-8°C
solubility  DMSO: ≥20mg/mL
form  powder
pka pKa (dioxane/water): 5.46 (1:1); 6.38 (2:1)
color  off-white to light brown

Safety information for Zopolrestat

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H301:Acute toxicity,oral
H413:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P273:Avoid release to the environment.

Computed Descriptors for Zopolrestat

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