Title: Nizatidine
CAS Registry Number: 76963-41-2
CAS Name: N-[2-[[[2-[(Dimethylamino)methyl]-4-thiazolyl]methyl]thio]ethyl]-N¢-methyl-2-nitro-1,1-ethenediamine
Additional Names: N-[4-(6-methylamino-7-nitro-2-thia-5-aza-6-heptene-1-yl)-2-thiazolylmethyl]-N,N-dimethylamine
Manufacturers' Codes: LY-139037; ZE-101; ZL-101
Trademarks: Axid (Lilly); Calmaxid (Lilly); Cronizat (Caber); Distaxid (Norgine); Gastrax (Asche); Nizax (Lilly); Nizaxid (Norgine)
Molecular Formula: C12H21N5O2S2
Molecular Weight: 331.46
Percent Composition: C 43.48%, H 6.39%, N 21.13%, O 9.65%, S 19.35%
Literature References: Histamine H2-receptor antagonist related to ranitidine, q.v. Prepn: R. P. Pioch, EP 49618; idem, US 4375547 (1982, 1983 both to Eli Lilly). General pharmacology in animals: K. Bemis et al., Arzneim.-Forsch. 39, 240 (1989). Pharmacokinetics and gastric acid suppression in humans: J. T. Callaghan et al., Clin. Pharmacol. Ther. 37, 162 (1985). Study of effect on hepatic drug metabolism in humans: J. W. Secor et al., Br. J. Clin. Pharmacol. 20, 710 (1985). Disposition and metabolism in humans: M. P. Knadler et al., Drug Metab. Dispos. 14, 175 (1986). Symposium on pharmacology and clinical studies: Scand. J. Gastroenterol. 22, Suppl. 136, 1-88 (1987). Comprehensive description: T. J. Wozniak, Anal. Profiles Drug Subs. 19, 397-427 (1990).
Properties: Crystals from ethanol-ethyl acetate, mp 130-132°. uv max (methanol): 240, 325 nm (e 8400, 19600); (water): 260, 314 nm (e 11820, 15790). pKa1 2.1; pKa2 6.8. Partition coefficient (octanol/water): 0.3 (pH 7.4). Soly (mg/ml): chloroform >100; methanol 50.0-100.0; water 10.0-33.3; isopropanol 3.33-5.0; ethyl acetate 1.0-2.0; benzene, diethyl ether, octanol <0.5. LD50 in mice, rats (mg/kg): 265, >300 i.v.; 1685, 1680 orally (Pioch).
Melting point: mp 130-132°
pKa: pKa1 2.1; pKa2 6.8
Log P: Partition coefficient (octanol/water): 0.3 (pH 7.4)
Absorption maximum: uv max (methanol): 240, 325 nm (e 8400, 19600); (water): 260, 314 nm (e 11820, 15790)
Toxicity data: LD50 in mice, rats (mg/kg): 265, >300 i.v.; 1685, 1680 orally (Pioch)
Therap-Cat: Antiulcerative.
Keywords: Antiulcerative; Histamine H2-Receptor Antagonist. |