Canagliflozin ring opening

Canagliflozin ring opening is a structurally altered impurity derived from the parent drug via cleavage of the benzimidazole core, resulting in a deoxyglucose moiety conjugated to a substituted phenylacetylene. This compound retains the hydroxyl and amino functionalities critical for SGLT2 binding but exhibits altered stereochemistry at the C-2 position. The ring-opening event introduces a linear aliphatic chain with increased hydrophilicity, distinguishing it from the cyclic parent structure. This impurity arises during forced degradation under acidic conditions and serves as a reference standard for HPLC method validation in API purity assessment.