Isolation and Characterization of Cetirizine Degradation Product: Mechanism of Cetirizine Oxidation

Abstract

Degradation of cetirizine in polyethylene glycol arose from the reaction between the drug and the reactive peroxide intermediates such as peroxyl radicals formed through oxidation of PEG. Selective oxidation of cetirizine and isolation/characterization of the oxidation product allowed the identification of the oxidation product as cetirizine N-oxide. The mechanism of oxidation is proposed.

Kinetics and mechanism of oxidation of cetirizine hydrochloride, an anti-allergy agent by Mn(VII) in acidic medium

“…1(a), the product was identified as cetirizine N-Oxide. Similar product was predicted by other author (Dyakonov et al, 2010) when cetirizine was oxidized by H 2 O 2 .…”

Non‐target impurity profiling of marketplace Cetirizine using high‐resolution mass spectrometry and multivariate data analysis

“…The interaction between Cetirizine with excipients of polyols has been reported previously . A PEG‐containing matrix was used for Cetirizine formulation in order to develop the highly water‐soluble and sensitive compound in soft gelatin dosage form that has already been found to be unstable during manufacture and storage …”

A Comprehensive Outlook of Synthetic Strategies and Applications of Redox‐Responsive Nanogels in Drug Delivery

“…The short chain aldehydes may form hydroxymethyl derivative of the formulated compound and cross‐link amino groups containing compounds, while carboxylic acids may lower the pH of PEG solution and can degrade compounds susceptible to acid catalyzed hydrolytic degradation . The degradation of cetirizine hydrochloride to N ‐oxide impurity was attributed to the presence of peroxides in the formulation originating from autoxidation of PEG 400 . In another study, Fukuyama et al reported significant racemization of cholecystokinin (formation of undesired R‐enantiomer) receptor antagonist due to the presence of formic acid in PEG 400 formulation .…”