3004. Diazoxide

Nomenclature

CAS number: 364-98-7
7-Chloro-3-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide; 3-methyl-7-chloro-1,2,4-benzothiadiazine 1,1-dioxide; SRG-95213; Eudemine (UCB); Hyperstat (Schering-Plough); Mutabase (Schering-Plough); Proglicem (Schering-Plough); Proglycem (Ivax).
C8H7ClN2O2S; mol wt 230.67.
C 41.66%, H 3.06%, Cl 15.37%, N 12.14%, O 13.87%, S 13.90%.

Description and references

ATP-dependent potassium channel agonist; inhibits secretion of insulin from pancreatic beta cells. Prepn: A. A. Rubin et al., Science 133, 2067 (1961); J. G. Topliss et al., US 2986573; eidem, US 3345365 (1961, 1967 both to Schering); Raffa, Monzani, Farmaco Ed. Sci. 17, 244 (1962). Crystal and molecular structure: G. Bandoli, M. Nicolini, J. Cryst. Mol. Struct. 7, 229 (1978). Mechanism of action and metabolism: B. Raju, P. E. Cryer, Am. J. Physiol. Endocrinol. Metab. 288, 80 (2005). Clinical evaluation as an adjuvant in schizophrenia: S. Akhondzadeth et al., J. Clin. Pharm. Ther. 27, 453 (2002); in ischemic preconditioning in coronary artery bypass grafting: X. Wang et al., Eur. J. Cardiothorac. Surg. 24, 967 (2003). Review of effect on insulin secretion: Nutr. Rev. 30, 194-198 (1972); of pharmacology and efficacy in hypertension: J. Koch-Weser, N. Engl. J. Med. 294, 1271-1274 (1976).

Chemical structure

Properties

Crystals from dil alc, mp 330-331°. uv max (methanol): 268 nm (ε 11300). Sol in alcohol and alkaline solns. Pratically insol to sparingly sol in water.

Therapeutic Category

Antihypoglycemic; antihypertensive.

Therapeutic Category (Veterinary)

In treatment of insulinomas.

Keywords

Antihypertensive; Thiazides and Analogs; Antihypoglycemic