Sulfinpyrazone
Title: Sulfinpyrazone
CAS Registry Number: 57-96-5
CAS Name: 1,2-Diphenyl-4-[2-(phenylsulfinyl)ethyl]-3,5-pyrazolidinedione
Additional Names: 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
Manufacturers' Codes: G-28315
Trademarks: Anturan (Novartis); Anturane (Novartis); Anturano (Novartis); Enturen (Novartis)
Molecular Formula: C23H20N2O3S
Molecular Weight: 404.48
Percent Composition: C 68.30%, H 4.98%, N 6.93%, O 11.87%, S 7.93%
Literature References: Prepn: F. Häfliger, US 2700671 (1955 to Geigy AG); R. Pfister, F. Häfliger, 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).
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.
Melting point: mp 136-137°
Absorption maximum: uv max (1.0N NaOH): 255 nm
 
Derivative Type: d-Form
Properties: Crystals from ethanol, mp 130-133°. [a]D22 +67.1° (c = 2.04 in ethanol); [a]D25 +109.3° (c = 0.5 in CHCl3).
Melting point: mp 130-133°
Optical Rotation: [a]D22 +67.1° (c = 2.04 in ethanol); [a]D25 +109.3° (c = 0.5 in CHCl3)
 
Derivative Type: l-Form
Properties: Crystals, mp 130-133°. [a]D23 -64.2° (c = 2.14 in ethanol); [a]D26 -104.5° (c = 0.5 in CHCl3).
Melting point: mp 130-133°
Optical Rotation: [a]D23 -64.2° (c = 2.14 in ethanol); [a]D26 -104.5° (c = 0.5 in CHCl3)
 
Therap-Cat: Uricosuric; antithrombotic.
Keywords: Antigout; Antithrombotic; Uricosuric.

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