9505. Tolazamide

Nomenclature

CAS number: 1156-19-0
N-[[(Hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methylbenzenesulfonamide; 1-(hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)urea; N-(p-toluenesulfonyl)-N′-hexamethyleniminourea; tolazolamide; U-17835; Tolanase (Pharmacia & Upjohn).
C14H21N3O3S; mol wt 311.40.
C 54.00%, H 6.80%, N 13.49%, O 15.41%, S 10.30%.

Description and references

Prepn: J. B. Wright, GB 887886 (1962 to Upjohn); J. B. Wright, R. E. Willette, J. Med. Pharm. Chem. 5, 815 (1962). Pharmacology: W. E. Dulin et al., Proc. Soc. Exp. Biol. Med. 107, 245 (1961). Mode of action study: Marshall et al., Metab. Clin. Exp. 19, 1046 (1970). Clinical experience and review of early literature: Balodimos, Marble, Curr. Ther. Res. 13, 6-12 (1971). Clinical bioavailability and pharmacokinetics: P. G. Welling et al., J. Pharm. Sci. 71, 1259 (1982). Structural studies: C. H. Koo et al., Arch. Pharmacal Res. 11, 74 (1988). HPLC determn in serum: B. J. Starkey et al., J. Liq. Chromatogr. 12, 1889 (1989). Comprehensive description: J. K. Lee et al., Anal. Profiles Drug Subs. Excip. 22, 489-516 (1993).

Chemical structure

Properties

Crystals, mp 170-173°. Very slightly sol in water; slightly sol in alcohol; sol in acetone; freely sol in chloroform. pKa (25°): 3.6, pKa (37.5°): 5.68. LD50 in rats, mice (mg/kg): >5000 orally, 2239 i.p. (Dulin).

Therapeutic Category

Antidiabetic.

Keywords

Antidiabetic; Sulfonylurea Derivatives