110. Acifran

Nomenclature

CAS number: 72420-38-3
4,5-Dihydro-5-methyl-4-oxo-5-phenyl-2-furancarboxylic acid; 2-methyl-2-phenyl-3(2H)-furanone-5-carboxylic acid; AY-25712; Reductol (Wyeth-Ayerst).
C12H10O4; mol wt 218.21.
C 66.05%, H 4.62%, O 29.33%.

Description and references

Prepd (not claimed): I. L. Jirkovsky et al., US 4169202; prepn and resolution of enantiomers: eidem, US 4244958 (1979, 1981 both to American Home); I. L. Jirkovsky, M. N. Cayen, J. Med. Chem. 25, 1154 (1982). Metabolism and pharmacokinetics in dogs and rats: M. N. Cayen et al., Xenobiotica 16, 251 (1986). LC determn in serum: R. Gonzalez, D. Thibeault, Clin. Biochem. 16, 244 (1983). Clinical evaluation in hyperlipoproteinemia: D. B. Hunninghake et al., Clin. Pharmacol. Ther. 38, 313 (1985); J. C. LaRosa et al., Artery 14, 338 (1987).

Chemical structure

Properties

Crystals, mp 176°. uv max (methanol): 281 nm (ε 7960). LD50 orally in rats: 3 g/kg (Jirkovsky, 1982).

Derivative

()-Form.

Nomenclature

CAS number: 77103-92-5

Properties

mp 87-89°. [α]D25 144.7° (c = 2 in methanol).

Derivative

(+)-Form.

Nomenclature

CAS number: 77103-91-4

Properties

mp 87-89°. [α]D25 +146.4° (c = 2 in methanol).

Therapeutic Category

Antilipemic.

Keywords

Antilipemic