8949. Sulfinpyrazone

Nomenclature

CAS number: 57-96-5
1,2-Diphenyl-4-[2-(phenylsulfinyl)ethyl]-3,5-pyrazolidinedione; 1,2-diphenyl-3,5-dioxo-4-(2-phenylsulfinylethyl)pyrazolidine; 4-(phenylsulfoxyethyl)-1,2-diphenyl-3,5-pyrazolidinedione; 4-(2-benzenesulfinylethyl)-1,2-diphenylpyrazolidine-3,5-dione; sulfoxyphenylpyrazolidine; G-28315; Anturan (Novartis); Anturane (Novartis); Anturano (Novartis); Enturen (Novartis).
C23H20N2O3S; mol wt 404.48.
C 68.30%, H 4.98%, N 6.93%, O 11.87%, S 7.93%.

Description and references

Prepn: F. Hfliger, US 2700671 (1955 to Geigy AG); R. Pfister, F. Hfliger, Helv. Chim. Acta 44, 232 (1961). Uricosuric effect: J. J. Burns et al., J. Pharmacol. Exp. Ther. 119, 418 (1957). Clinical trial in prevention of sudden cardiac death: Anturane Reinfarction Trial Research Group, N. Engl. J. Med. 298, 289 (1978); 302, 250 (1980); as antithrombotic: R. D. Sautter et al., J. Am. Med. Assoc. 250, 2649 (1983); D. T. Domoto et al., Thromb. Res. 62, 737 (1991). Review: E. H. Margulies, A. M. White, in Pharmacological and Biochemical Properties of Drug Substances vol. 2, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1979) pp 255-278; E. H. Margulies et al., Drugs 20, 179-197 (1980).

Chemical structure

Properties

Crystals from chloroform + heptane, mp 136-137°. Stable to light and air. uv max (1.0N NaOH): 255 nm. Sol in ethyl acetate, chloroform. Slightly sol in water, alcohol, ether, mineral oils, fats.

Derivative

d-Form.

Properties

Crystals from ethanol, mp 130-133°. [α]D22 +67.1° (c = 2.04 in ethanol); [α]D25 +109.3° (c = 0.5 in CHCl3).

Derivative

l-Form.

Properties

Crystals, mp 130-133°. [α]D23 64.2° (c = 2.14 in ethanol); [α]D26 104.5° (c = 0.5 in CHCl3).

Therapeutic Category

Uricosuric; antithrombotic.

Keywords

Antigout; Antithrombotic; Uricosuric