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A stability-indicating high-performance liquid chromatography method to quantify 2-(2,4-difluorophenyl)-4,5,6,7-tetrafluoroisoindoline-1,3-dione (NSC-726796) and its three main degradation products was developed. This method was used to investigate its degradation kinetics and mechanism. The reaction follows first-order kinetics and appears to be base catalyzed with the maximum stability at pH 1. The products were identified as 2-(2,4-difluorophenylcarbamoyl)-3,4,5,6-tetrafluorobenzoic acid (NSC-749820), 2,4-difluoroaniline, and tetrafluorophthalic acid. The parent drug, NSC-726796, was also found to react with methanol and ethanol. NSC-726796 demonstrates antiangiogenic activity, however, when its degradant NSC749820 does not show antiangiogenic activity.
| Authors: | Duoli Guo, James P. Cain, Sean O’Connell, Erin R. Gardner, Steven Pisle, William D. Figg, S. Esmail Tabibi, Samuel H. Yalkowsky | |
| Journal: | AAPS PharmSciTech | |
| Year: | 2012 | |
| DOI: | 10.1208/s12249-012-9784-5 | |
| Publication date: | 03-05-2012 |
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