Add time:08/04/2019         Source:sciencedirect.com

HPLC analysis of drug products containing Bisoprolol fumarate (cas 104344-23-2) and lactose revealed the presence of N-formylbisoprolol, which is a final product of the Maillard reaction. Formulations containing secondary amines and reducing carbohydrates are prone to the condensation of amine and carbonyl functional groups and formation of glycosylamines in pharmaceutically relevant conditions. Further rearrangement occurs in the presence of a nucleophile and leads to the formation of 1-deoxy-1-amino-2-ketose also known as the Amadori Rearrangement Product (ARP). The influence of water content, carbohydrate, and lubricant types on the reaction rate was tested. The reaction progress was monitored by HPLC and UV–Vis spectrophotometry. The structures of intermediates were confirmed by the LC/MS2 analysis. N-formylbisoprolol – the final reaction product – was synthesised and characterised by LC/MS2, H1 and C13 NMR.

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