2008•Synthetic CommunicationsRequires access

Synthesis of Metabolites and Related Substances of Rabeprazole, an Anti-Ulcerative Drug

Ganta Madhusudhan Reddy, Kaga Mukkanti, Boluggodu Vijaya Bhaskar, Padi Pratap Reddy

Abstract

Rabeprazole sodium (Aciphex®) is a gastric proton pump inhibitor used for the prevention and treatment of gastric acid–related diseases. During the synthesis of bulk drug of rabeprazole sodium, we have observed metabolites rabeprazole sulfide and rabeprazole sulfone and related substances rabeprazole-N-oxide, rabeprazole sulfone-N-oxide, N-aralkyl rabeprazole, chloro rabeprazole, and methoxy rabeprazole as impurities in the drug substance. The present work describes the synthesis and characterization of these compounds.

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Key concepts: Rabeprazole, Chemistry, Antiulcer drug, Sulfone, Proton-pump inhibitor, Drug, Organic chemistry, Pharmacology