2193. Chlorthalidone

Nomenclature

CAS number: 77-36-1
2-Chloro-5-(2,3-dihydro-1-hydroxy-3-oxo-1H-isoindol-1-yl)benzenesulfonamide; 2-chloro-5-(1-hydroxy-3-oxo-1-isoindolinyl)benzenesulfonamide; 3-hydroxy-3-(4-chloro-3-sulfamylphenyl)phthalimidine; 2-chloro-5-(3-hydroxy-1-oxoisoindolin-3-yl)benzenesulfonamide; 1-oxo-3-(3-sulfamyl-4-chlorophenyl)-3-hydroxyisoindoline; 3-(4′-chloro-3′-sulfamoylphenyl)-3-hydroxyphthalimidine; 1-keto-3-(3′-sulfamyl-4′-chlorophenyl)-3-hydroxyisoindoline; chlorphthalidolone; phthalamudine; phthalamodine; G-33182; Higroton (Novartis); Hydro-long (Sanorania); Hygroton (Novartis); Thalitone (Boehringer, Ing.).
C14H11ClN2O4S; mol wt 338.77.
C 49.64%, H 3.27%, Cl 10.47%, N 8.27%, O 18.89%, S 9.47%.

Description and references

Prepn: Graf et al., Helv. Chim. Acta 42, 1085 (1959); US 3055904 (1962 to Geigy). Activity and side effects: Holtmeier et al., Med. Welt 1967, 1384; Zsoter et al., J. Pharmacol. Exp. Ther. 180, 723 (1972). Metabolism: Beisenherz et al., Arch. Int. Pharmacodyn. Ther. 161, 76 (1966). Comprehensive description: J. M. Singer et al., Anal. Profiles Drug Subs. 14, 1-36 (1985).

Chemical structure

Properties

Crystals from 50% acetic acid, dec 224-226°. mp range may extend from 218 to 264° on slow heating. Can form a monohydrate. uv max (methanol): <220 nm. Soly in water: 12 mg/100 ml (20°); 27 mg/100 ml (37°); in 0.1N Na2CO3: 577 mg/100 ml (20°); 990 mg/100 ml (37°). More sol in aq solns of NaOH. Soluble in warm ethanol; slightly sol in ether.

Therapeutic Category

Diuretic; antihypertensive.

Therapeutic Category (Veterinary)

Diuretic.

Keywords

Antihypertensive; Thiazides and Analogs; Diuretic; Thiazides and Analogs