N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen

IC Calder, SJ Hart, K Healey…

Index: Calder, Ian C.; Hart, Sandra J.; Healey, Kevin; Ham, Kathryn N. Journal of Medicinal Chemistry, 1981 , vol. 24, # 8 p. 988 - 993

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Citation Number: 32

Abstract

The decomposition of N-hydroxyacetaminophen has been shown to occur via an initial first- order dehydration step to N-acetyl-p-benzoquinone imine with a rate constant at pH 7.6 of 8.66 X low3 mid and a half-life of 80 min. This is followed by a complex reaction between the quinone imine and the N-hydroxy compound to ultimately yield p-nitrosophenol and acetaminophen. The glucuronide and sulfate conjugates of N-hydroxyacetaminophen ...