4139. Flumethiazide

Nomenclature

CAS number: 148-56-1
6-(Trifluoromethyl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; 6-trifluoromethyl-7-sulfamoyl-4H-1,2,4-benzothiadiazine 1,1-dioxide; 6-trifluoromethyl-7-sulfamyl-1,2,4-benzothiadiazine 1,1-dioxide; trifluoromethylthiazide; Ademol (BMS); Fludemil.
C8H6F3N3O4S2; mol wt 329.28.
C 29.18%, H 1.84%, F 17.31%, N 12.76%, O 19.44%, S 19.48%.

Description and references

Synthesis: Holdrege et al., J. Am. Chem. Soc. 81, 4807 (1959); Yale et al., ibid. 82, 2042 (1960); US 3040042 (1962 to Olin Mathieson); GB 861809 (1961 to SK&F).

Chemical structure

Properties

Crystals, dec 305.4-307.8°. uv max: 278 nm (E1%1cm 335) (50% diglyme + 50% 0.1N HCl). Sparingly sol in water (50 mg/ml in boiling water with decompn); sol in methanol, ethanol, DMF. Practically insol in ethyl acetate, methyl ethyl ketone, benzene, toluene. Unstable in alkaline soln (conversion to precursor α,α,α-trifluoro-3-amino-4,6-disulfamoyltoluene).

Therapeutic Category

Carbonic anhydrase inhibitor.

Keywords

Carbonic Anhydrase Inhibitor