Preferred orientations in the binding of 4'-hydroxyacetanilide (acetaminophen) to cytochrome P450 1A1 and 2B1 isoforms as determined by 13C- and 15N-NMR relaxation studies.

@article{Myers1994PreferredOI,
  title={Preferred orientations in the binding of 4'-hydroxyacetanilide (acetaminophen) to cytochrome P450 1A1 and 2B1 isoforms as determined by 13C- and 15N-NMR relaxation studies.},
  author={Timothy G. Myers and Kenneth E. Thummel and Thomas F Kalhorn and Sidney D. Nelson},
  journal={Journal of medicinal chemistry},
  year={1994},
  volume={37 6},
  pages={860-7}
}
The widely used analgesic/antipyretic agent 4'-hydroxyacetanilide (acetaminophen, APAP) is oxidized by cytochromes P450 to a potent cytotoxin, N-acetyl-p-benzoquinone imine (NAPQI), and a nontoxic catechol, 3',4'-dihydroxyacetanilide (3-hydroxyacetaminophen, 3-OH-APAP). There are marked differences in the ratios of these two products formed from different isoforms of cytochrome P450. For example, the ratio of NAPQI to 3-OH-APAP formed by rat liver CYP1A1 was found to be approximately 3:1… CONTINUE READING