Synthesis and reactions of nitroso sulphamethoxazole with biological nucleophiles: implications for immune mediated toxicity

DJ Naisbitt, PM O'Neill, M Pirmohamed…

Index: Naisbitt, Dean J.; Neill, Paul M.; Pirmohamed, Munir; Park, B. Kevin Bioorganic and Medicinal Chemistry Letters, 1996 , vol. 6, # 13 p. 1511 - 1516

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Citation Number: 57

Abstract

Sulphamethoxazole hydroxylamine (SMX-NHOH) and nitroso sulphamethoxazole (SMX- NO) were prepared bv a modified literature procedure. SMX-NO produced a complex set of unstable intermediates with sulphur nucleophiles, but did not react with amino containing compounds. No reactions were observed between sulphamethoxazole (SMX)/SMX-NHOH and the nucleophiles used in this study. Thus antigens formed from N-oxidation of SMX ...