4781. Hydrochlorothiazide

Nomenclature

CAS number: 58-93-5
6-Chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; 6-chloro-3,4-dihydro-7-sulfamoyl-2H-1,2,4-benzothiadiazine 1,1-dioxide; 6-chloro-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide; 3,4-dihydrochlorothiazide; chlorsulfonamidodihydrobenzothiadiazine dioxide; chlorosulthiadil; Dichlotride (Merck & Co.); Disalunil (Berlin-Chemie); Esidrex (Novartis); Esidrix (Novartis); HydroDiuril (Merck & Co.); Hydrosaluric (Merck & Co.); Oretic (Abbott).
C7H8ClN3O4S2; mol wt 297.74.
C 28.24%, H 2.71%, Cl 11.91%, N 14.11%, O 21.49%, S 21.54%.

Description and references

Prepn: de Stevens et al., Experientia 14, 463 (1958); Werner et al., J. Am. Chem. Soc. 82, 1161 (1960); Jones, Novello, US 3025292 (1962 to Merck & Co.); de Stevens, Werner, US 3163645 (1964 to Ciba); Klosa, DE 1163332 (1964); J. S. Irons, T. M. Cook, US 3164588 (1965 to Merck & Co.). Purification: Downing, US 3043840 (1962 to Merck & Co.). LC/MS/MS determn in plasma: F. Liu et al., J. Pharm. Biomed. Anal. 44, 1187 (2007). Toxicity data: J. J. Piala et al., J. Pharmacol. Exp. Ther. 134, 273 (1961). Comprehensive description: H. P. Deppeler, Anal. Profiles Drug Subs. 10, 405-441 (1981). Review of pharmacoogy and clinical experience of combination with valsartan in hypertension: A. J. Wagstaff, Drugs 66, 1881-1901 (2006).

Chemical structure

Properties

White, or practically white, crystalline powder, mp 273-275°. uv max (methanol + trace HCl): 317, 271, 226 nm (A1%1cm 130, 654, 1280). pKa 7.9, 9.2. Sol in sodium hydroxide solution; slightly sol in water. LD50 in mice (mg/kg): 590 i.v.; >8000 orally (Piala).

Therapeutic Category

Diuretic.

Therapeutic Category (Veterinary)

Diuretic.

Keywords

Antihypertensive; Thiazides and Analogs; Diuretic; Thiazides and Analogs