1120. Benzthiazide

Nomenclature

CAS number: 91-33-8
6-Chloro-3-[[(phenylmethyl)thio]methyl]-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; 3-[(benzylthio)methyl]-6-chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; 3-[(benzylthio)methyl]-6-chloro-7-sulfamoyl-2H-benzo-1,2,4-thiadiazine 1,1-dioxide; 6-chloro-7-sulfamoyl-3-benzylthiomethyl-2H-1,2,4-benzothiadiazine 1,1-dioxide; benzothiazide; Exna (Wyeth); Fovane (Pfizer).
C15H14ClN3O4S3; mol wt 431.94.
C 41.71%, H 3.27%, Cl 8.21%, N 9.73%, O 14.82%, S 22.27%.

Description and references

Prepn: J. M. McManus et al., 136th Am. Chem. Soc. Meet. (Atlantic City, Sept. 1959) Abstr. of Papers, pp 13-O; W. M. McLamore, G. D. Laubach, DE 1137740; eidem, US 3440244 (1962, 1969 both to Pfizer). Pharmacology, toxicity: S. Y. P'an et al., J. Pharmacol. Exp. Ther. 128, 122 (1960).

Chemical structure

Properties

Crystals from acetone, mp 231-232° (U.S. patent); also reported as mp 238-239° (P'an). Bitter taste. Practically insol in water. Sol in alkaline solns. LD50 in mice, rats (mg/kg): >5000, >10000 orally; 410, 422 i.v. (P'an).

Therapeutic Category

Diuretic, antihypertensive.

Keywords

Antihypertensive; Thiazides and Analogs; Diuretic; Thiazides and Analogs