6005. Methyclothiazide

Nomenclature

CAS number: 135-07-9
6-Chloro-3-(chloromethyl)-3,4-dihydro-2-methyl-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; 6-chloro-3-chloromethyl-3,4-dihydro-2-methyl-7-sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide; 6-chloro-3-chloromethyl-2-methyl-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide; Aquatensen (Mallinckrodt); Duretic; Enduron (Abbott); Enduronum (Abbott); Naturon.
C9H11Cl2N3O4S2; mol wt 360.24.
C 30.01%, H 3.08%, Cl 19.68%, N 11.66%, O 17.77%, S 17.80%.

Description and references

Prepn: Close et al., J. Am. Chem. Soc. 82, 1132 (1960). Description: Ford, Curr. Ther. Res. 2, 422 (1960). Comprehensive description: J. A. Raihle, Anal. Profiles Drug Subs. 5, 307-326 (1976).

Chemical structure

Properties

Crystals from alcohol + water, mp 225°. uv max (methanol): 226, 267, 311 nm (ε 39300, 21250, 3300). pKa 9.4. Very sol in acetone, pyridine; slightly sol in methanol, ethanol. Almost insol in water, chloroform, benzene.

Therapeutic Category

Diuretic; antihypertensive.

Keywords

Antihypertensive; Thiazides and Analogs; Diuretic; Thiazides and Analogs