Add time:07/31/2019         Source:sciencedirect.com

The degradation kinetics of fetindomide, a potential prodrug of Mitindomide (cas 10403-51-7), was studied in aqueous solution at 25°C. The hydrolysis of dilute fetindomide solutions maintained between pH 2.5 and 4.5 followed apparent first-order kinetics over several half-lives. At higher pH values (5.0–8.5) the kinetics of degradation were more complex even in dilute solutions. Above pH 8.5, the degradation of fetindomide was too rapid to measure by HPLC without quenching. In addition to these observations, it was found that various buffers showed general base catalysis. The degradation of fetindomide results in the production of formaldehyde which was found to accelerate the degradation of fetindomide. Analysis of the kinetic data obtained from experiments in which formaldehyde was added to aqueous fetindomide solutions, indicated that fetindomide reacts with formaldehyde to form an unstable intermediate, possible a carbinolamine. It is proposed that the intermediate degrades more rapidly than fetindomide which would account for the non-first-order kinetics seen at pH values greater than 4.5 HPLC chromatograms indicated that the degradation products of fetindomide, irrespective of whether formaldehyde was added, were the same under all conditions.

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