PMID: 9530978Apr 8, 1998Paper

Aqueous stability of SB 210661: kinetics and primary degradation mechanisms of an N-hydroxyurea-containing 5-lipoxygenase inhibitor

The Journal of Pharmacy and Pharmacology
M McLoughlinN R Palepu

Abstract

SB 210661, (S)-N-hydroxy-N-[2,3-dihydro-6-(2,6-difluorophenylmethoxy)-3-benzo furanyl]urea, is a potent and selective inhibitor of 5-lipoxygenase. Its aqueous stability was primarily evaluated to support development of analytical methods and formulations. The results also add to the growing database on the stability of N-hydroxyurea compounds. Comparison of the stability of SB 210661 with that of two other N-hydroxyurea-containing compounds, zileuton and Abbott-79175, supported a common primary degradative pathway at pH > 5 and different degradative pathways at pH < 5. The pathway at pH > 5 is consistent with the hydrolysis of the N-hydroxyurea group, whereas for SB 210661, the pathway at pH < 5 is consistent with specific acid-catalysed nucleophilic displacement of the N-hydroxyurea group by water.

Citations

Aug 3, 1999·American Journal of Respiratory and Critical Care Medicine·T HisadaK F Chung

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