Title: Hydroflumethiazide
CAS Registry Number: 135-09-1
CAS Name: 3,4-Dihydro-6-(trifluoromethyl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
Additional Names: 6-trifluoromethyl-3,4-dihydro-7-sulfamoyl-2H-1,2,4-benzothiadiazine 1,1-dioxide; 3,4-dihydro-7-sulfamyl-6-trifluoromethyl-1,2,4-benzothiadiazine 1,1-dioxide; trifluoromethylhydrothiazide; dihydroflumethiazide; methforylthiazidine; metflorylthiazidine
Trademarks: Diucardin (Ayerst); Elodrine; Finuret; Hydol; Hydrenox (Boots); Leodrine (Leo Pharm); NaClex (Glaxo); Rodiuran; Rontyl (Leo Pharm); Saluron (Apothecon); Sisuril; Vergonil
Molecular Formula: C8H8F3N3O4S2
Molecular Weight: 331.29
Percent Composition: C 29.00%, H 2.43%, F 17.20%, N 12.68%, O 19.32%, S 19.36%
Literature References: Synthesis: Holdrege et al., J. Am. Chem. Soc. 81, 4807 (1959); Close et al., ibid. 82, 1132 (1960); Yale et al., ibid. 2042; Novello et al., J. Org. Chem. 25, 970 (1960). Numerous patents, e.g., Lund et al., US 3254076 (1966 to Lövens Kemiske Fabrik). Pharmacology: J. J. Piala et al., J. Pharmacol. Exp. Ther. 134, 273 (1961). Comprehensive description: C. E. Orzech et al., Anal. Profiles Drug Subs. 7, 297-317 (1978).
Properties: Crystals, mp 272-273°. uv max (methanol): 272.5 nm (log e 4.286). Soly in mg/ml at 25°: acetone >100; methanol 58; acetonitrile 43; water 0.3; ether 0.2; benzene <0.1. pK1 8.9; pK2 10.7. Forms water-sol salts with bases. LD50 in mice (mg/kg): >8000 orally, 750 i.v., 6280 i.p. (Piala).
Melting point: mp 272-273°
pKa: pK1 8.9; pK2 10.7
Absorption maximum: uv max (methanol): 272.5 nm (log e 4.286)
Toxicity data: LD50 in mice (mg/kg): >8000 orally, 750 i.v., 6280 i.p. (Piala)
Therap-Cat: Antihypertensive; diuretic.
Keywords: Antihypertensive; Thiazides and Analogs; Diuretic; Thiazides and Analogs. |