2279. Cimetidine

Nomenclature

CAS number: 51481-61-9
N-Cyano-N′-methyl-N″-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]guanidine; SKF-92334; Aciloc (Orion); Acinil (GEA); Brumetidina (Bruschettini); Cimal (Alpharma); Dyspamet (Goldshield); Stomédine (GSK); Tagamet (GSK); Ulcedin (AGIPS); Ulcimet (Polipharm).
C10H16N6S; mol wt 252.34.
C 47.60%, H 6.39%, N 33.30%, S 12.71%.

Description and references

Competitive histamine H2-receptor antagonist which inhibits gastric acid secretion and reduces pepsin output. Prepn: G. J. Durant et al., BE 804144; eidem, US 3950333 (1974, 1976 both to SK&F); P. Kairisalo, E. Honkanen, Arch. Pharm. 316, 688 (1983). Chemistry, pharmacology and toxicology: R. W. Brimblecombe et al., J. Int. Med. Res. 3, 86 (1975); eidem, Br. J. Pharmacol. 53, 435p (1975). Use in combination with other drugs for cancer treatment: R. D. Thornes et al., Lancet 2, 328 (1982); S. Borgstr"om et al., N. Engl. J. Med. 307, 1080 (1982); 308, 591 (1983). Controlled clinical study in treatment of acute upper gastrointestinal tract bleeding: D. Barer et al., ibid. 1571; for prevention of recurrent duodenal ulcer: S. Sontag et al., ibid. 311, 689 (1984). Immunoregulatory effect: J. L. Jorizzo et al., Ann. Intern. Med. 92, 192 (1980); W. B. White, M. Ballow, N. Engl. J. Med. 312, 198 (1985). In vivo and in vitro effects on angiogenesis and tumor growth: T. Natori et al., Biomed. Pharmacother. 59, 56 (2005). Review of effect on endocrine secretion: C. Scarpignato, G. Bertaccini, Drugs Exp. Clin. Res. 5(4-5), 129-140 (1979). Symposium on clinical efficacy, cytoprotection and antifibrinolytic effects: Scand. J. Gastroenterol. 21, Suppl. 121, 1-62 (1986). Review of safety profile and drug interactions: A. F. Shinn, Drug Saf. 7, 245-267 (1992).

Chemical structure

Properties

Crystals, mp 141-143°. Bitter taste and characteristic odor. Sol in alcohol; very slightly sol in chloroform. Insol in ether. Soly in water at 37°: 1.14%. Soly increased by dil HCl. pKa 6.8. LD50 in mice, rats (mg/kg): 2600, 5000 orally; 150, 106 i.v.; 470, 650 i.p. (Brimblecombe).

Derivative

Hydrochloride.

Nomenclature

CAS number: 70059-30-2
C10H16N6S.HCl; mol wt 288.80.
C 41.59%, H 5.93%, N 29.10%, S 11.10%, Cl 12.28%.

Properties

White, crystalline powder. Very sol in water; sol in alcohol. pKa 7.11.

Therapeutic Category

Antiulcerative.

Therapeutic Category (Veterinary)

Antiulcerative.

Keywords

Antiulcerative; Histamine H2-Receptor Antagonist