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Xenobiotica
the fate of foreign compounds in biological systems
Volume 29, 1999 - Issue 2
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Research Article

Studies on the metabolism of 4-fluoroaniline and 4-fluoroacetanilide in rat: formation of 4-acetamidophenol (paracetamol) and its metabolites via defluorination and N-acetylation

G. B. SCARFE Biological Chemistry, Division of Biomedical Sciences, Imperial College School of Medicine, BMS Building, South Kensington, London SW7 2AZ, UK
Pages 205-216 | Published online: 22 Sep 2008

References

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  • BOOTH, J. and BOYLAND, E., 1964, The biochemistry of aromatic amines: enzymic N-hydroxylation of arylamines and conversion of arylhydroxylamines into o-aminophenols. Biochemical journal, 91, 362–369.
  • BECKETT, A. H. and BELANGER, P. M., 1976, Metabolic N-oxidation of secondary and primary aromatic amines as a route to ring hydroxylation, to various N-oxygenated products, and to dealkylation of secondary amines.
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  • BOERSMA, M. G., CNUBBEN, N. H. P., VAN BERKEL, W. J. H., BLom, M., VERVOORT, J. and RIETJENS, I. M. C. M., 1993, Role of cytochromes P-450 and flavin-containing monooxygenase in the biotransformation of 4-fluoro-N-methylaniline. Drug Metabolism and Disposition, 21, 218–230.
  • DALY, J. W., GUROFF, G., UDENFR1END, S. and WrricoP, B., 1968, Hydroxylation of alkyl and halogen substituted anilines and acetanilides by microsomal hydroxylases. Biochemical Pharmacology, 17, 31–36.
  • GORROD, J. W. and MANSON, D., 1986, The metabolism of aromatic amines. Xenobiotica, 16, 933-955. RlETJENS, I. M. C. M. and VERVOORT, J., 1989, Microsomal metabolism of fluoroanilines. Xenobiotica, 19, 1297–1305.
  • RlETJENS, I. M. C. M., TYRAKOWSKA, B., VEEGER, C. and VERVOORT, J., 1990, Reaction pathways for biodehalogenation of fluorinated anilines. European Journal of Biochemistry, 194, 945–954.
  • LINDON, J. C., NICHOLSON, J. K. and WILSON, I. D., 1996, Direct coupling of chromatographic separations to NMR spectroscopy. Progress in Nuclear Magnetic Resonance Spectroscopy, 29, 1–49 and passim.
  • RADOMSKI, J. L., 1979, The primary aromatic amines: their biological properties and structure-activity relationships. Annual Reviews in Pharmacological Toxicology, 19, 129–157.
  • SCARFE, G. B., WRIGHT, B., CLAYTON, E., TAYLOR, S., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1998, '9 F-NMR and directly coupled HPLC-NMR-MS investigations into the metabolism of 2-bromo-4-trifluoromethylaniline in the rat: a urinary excretion balance study without the use of radiolabelling. Xenobiotica, 28, 373–388.
  • SHAKA, A. J., KEELER, J. and FREEMAN, R., 1983, Evaluation of a new broad band decoupler sequence: Waltz 16. Journal of Magnetic Resonance, 53, 313–340.
  • STERNSON, L. A. and GAMMANS, R. E., 1974, A mechanistic study of aromatic hydroxylamine rearrangement in the rat. Bioorganic Chemistry, 4, 58–63.

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