Structural Formula Vector Image
Title: Tolazamide
CAS Registry Number: 1156-19-0
CAS Name: N-[[(Hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methylbenzenesulfonamide
Additional Names: 1-(hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)urea; N-(p-toluenesulfonyl)-N¢-hexamethyleniminourea; tolazolamide
Manufacturers' Codes: U-17835
Trademarks: Tolanase (Pharmacia & Upjohn)
Molecular Formula: C14H21N3O3S
Molecular Weight: 311.40
Percent Composition: C 54.00%, H 6.80%, N 13.49%, O 15.41%, S 10.30%
Literature 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).
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).
Melting point: mp 170-173°
pKa: pKa (25°): 3.6, pKa (37.5°): 5.68
Toxicity data: LD50 in rats, mice (mg/kg): >5000 orally, 2239 i.p. (Dulin)
Therap-Cat: Antidiabetic.
Keywords: Antidiabetic; Sulfonylurea Derivatives.

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