6147. Metolazone

Nomenclature

CAS number: 17560-51-9
7-Chloro-1,2,3,4-tetrahydro-2-methyl-3-(2-methylphenyl)-4-oxo-6-quinazolinesulfonamide; 7-chloro-1,2,3,4-tetrahydro-2-methyl-4-oxo-3-o-tolyl-6-quinazolinesulfonamide; 2-methyl-3-o-tolyl-6-sulfamyl-7-chloro-1,2,3,4-tetrahydro-4-quinazolinone; SR-720-22; Metenix (Sanofi-Aventis); Mykrox (Celltech); Xuret (Galen); Zaroxolyn (Teofarma).
C16H16ClN3O3S; mol wt 365.83.
C 52.53%, H 4.41%, Cl 9.69%, N 11.49%, O 13.12%, S 8.77%.

Description and references

Prepn: B. V. Shetty, US 3360518 (1967 to Wallace & Tiernan); B. V. Shetty et al., J. Med. Chem. 13, 886 (1970). Pharmacology: E. Belair et al., Arch. Int. Pharmacodyn. Ther. 177, 71 (1969); E. J. Belair, Res. Commun. Chem. Pathol. Pharmacol. 2, 98 (1971). HPLC determn in urine: D. Farthing et al., J. Chromatogr. 534, 228 (1990). Clinical evaluations as diuretic in chronic renal disease: R. Schoonees et al., N. Y. State J. Med. 71, 566 (1971); in hypertension: C. L. Curry et al., Clin. Ther. 9, 47 (1986); in congestive heart failure: A. Kiyingi et al., Lancet 335, 29 (1990).

Chemical structure

Properties

Crystals from ethanol or butanol, mp 252-254°. LD50 in mice (mg/kg): >5000 orally; >1500 i.p. (Shetty, 1967).

Therapeutic Category

Diuretic; antihypertensive.

Keywords

Antihypertensive; Thiazides and Analogs; Diuretic; Thiazides and Analogs