8089. Rabeprazole

Nomenclature

CAS number: 117976-89-3
2-[[[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole; pariprazole.
C18H21N3O3S; mol wt 359.44.
C 60.15%, H 5.89%, N 11.69%, O 13.35%, S 8.92%.

Description and references

Partially reversible gastric proton pump inhibitor. Prepn: S. Souda et al., EP 268956; eidem, US 5045552 (1988, 1991 both to Eisai). Pharmacology: H. Goto et al., Arzneim.-Forsch. 41, 635 (1991). Mode of action: M. Morii, N. Takeguchi, J. Biol. Chem. 268, 21553 (1993). HPLC determn in plasma: H. Nakai et al., J. Chromatogr. B 660, 211 (1994). Clinical pharmacokinetics: S. Yasuda et al., Int. J. Clin. Pharmacol. Ther. 32, 466 (1994). Review of clinical trials in acid peptic diseases: M. L. Cloud et al., Dig. Dis. Sci. 43, 993-1000 (1998); of pharmacology and clinical experience in gastro-esophageal reflux disease: B. Thjodleifsson, Expert Opin. Pharmacother. 5, 137-149 (2004).

Chemical structure

Properties

White crystals from CH2Cl2/ether, mp 99-100° (dec).

Derivative

Sodium salt.

Nomenclature

CAS number: 117976-90-6
E-3810; Aciphex (Eisai); Pariet (Eisai).
C18H20N3NaO3S; mol wt 381.42.
C 56.68%, H 5.29%, N 11.02%, Na 6.03%, O 12.58%, S 8.41%.

Properties

White crystals from ether, mp 140-141° (dec). Very sol in water, methanol; freely sol in ethanol, chloroform, ethyl acetate. Insol in ether, n-hexane.

Therapeutic Category

Antiulcerative.

Keywords

Antiulcerative; Gastric Proton Pump Inhibitor