8110. Ranitidine

Nomenclature

CAS number: 66357-35-5
N′[2-[[[-5-[(Dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl]-N-methyl-2-nitro-1,1-ethenediamine.
C13H22N4O3S; mol wt 314.40.
C 49.66%, H 7.05%, N 17.82%, O 15.27%, S 10.20%.

Description and references

Histamine H2-receptor antagonist which inhibits gastric acid secretion. Prepn: B. J. Price et al., FR 2384765; eidem, US 4128658 (both 1978 to Allen & Hanburys). HPLC determn in plasma: P. F. Carey, L. E. Martin, J. Liq. Chromatogr. 1979, 1291. HPTLC determn in urine and bioequivalence study: S. A. Shah et al., J. Chromatogr. B 767, 83 (2002). CV determn in pharmaceutical formulations: P. Norouzi et al., J. Pharmacol. Toxicol. Methods 55, 289 (2007). Pharmacological studies: J. Bradshaw et al., Br. J. Pharmacol. 66, 464 (1979); M. J. Daly et al., Gut 21, 408 (1980). Characterization and soly studies of polymorphic forms: M. Mirmehrabi et al., Int. J. Pharm. 282, 73 (2004). Efficacy in treatment of duodenal ulcers: A. Berstad et al., Scand. J. Gastroenterol. 15, 637 (1980); R. P. Walt et al., Gut 22, 49 (1981); of premeal therapy in reduction of heartburn: K. A. Pappa et al., Curr. Ther. Res. 59, 454 (1998). Review of pharmacology and therapeutic use: R. N. Brogden et al., Drugs 24, 267-303 (1982). Comprehensive description: M. Hohnjec et al., Anal. Profiles Drug Subs. 15, 533-561 (1986).

Chemical structure

Properties

Solid, mp 69-70°. Sulfurous odor. Low soly in water. Protect from light.

Derivative

Hydrochloride.

Nomenclature

CAS number: 66357-59-3
AH-19065; Azantac (GSK); Noctone (GEA); Raniben (Firma); Ranidil (Menarini); Raniplex (Solvay); Sostril (Cascan); Taural (Roemmers); Terposen (Vir); Trigger (Polifarma); Ulcex (Guidotti); Ultidine (GSK); Zantac (GSK); Zantic (GSK).
C13H22N4O3S.HCl; mol wt 350.86.
C 44.50%, H 6.61%, N 15.97%, O 13.68%, S 9.14%, Cl 10.10%.

Properties

White to pale yellow solid, mp 133-134°. Slightly bitter taste; sulfurlike odor. Freely sol in acetic acid and water, sol in methanol, sparingly sol in ethanol. Practically insol in chloroform. uv max (isopropanol): 228, 326 nm.

Derivative

Bismuth citrate.

Nomenclature

CAS number: 128345-62-0
Ranitidine bismutrex; GR-122311X; Pylorid (GSK); Tritec (GSK).
C13H22N4O3S.C6H5BiO7; mol wt 712.48.
C 32.03%, H 3.82%, N 7.86%, O 22.46%, S 4.50%, Bi 29.33%.

Description and references

Pharmacology and activity vs Helicobacter sp: R. Stables et al., Aliment. Pharmacol. Ther. 7, 237 (1993).

Therapeutic Category

Antiulcerative.

Therapeutic Category (Veterinary)

Antiulcerative; gastroprokinetic.

Keywords

Antiulcerative; Histamine H2-Receptor Antagonist