Identification of the urinary metabolites of 4-bromoaniline and 4-bromo- [carbonyl - 13 C]-acetanilide in rat

References

• ANDERSON M. M., MAYS, J. B., MITCHUM, R. K AND HINSON, J. A., 1984, Metabolism of 4-nitroaniline by rat liver microsomes. Drug Metabolism and Disposition, 12, 179–185.
   PubMed Web of Science ®Google Scholar
• 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, 362–669.
   PubMed Web of Science ®Google Scholar
• BOYLE, G. W., MCKILLOP, D., PHILLIPS, P. J., HARDING J. R., PICKFORD, R. and McCoamicx A. D., 1993a, Metabolism of casodex in laboratory animals. Xenobiotica, 23, 781–798.
   Google Scholar
• CNUBBEN, H. H. P., VERVOORT, J., VEEGER, C. and RIETJENS, I. M. C. M., 1992, Study on the regioselectivity and mechanism of the aromatic hydroxylation of monofluoroanilines. Chemico-Biological Interactions, 85, 151–172.
   Google Scholar
• CUPID, B. C. BEDDELL, C. R., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1996, Quantitative structure—metabolism relationships for substituted benzoates in the rabbit: prediction of urinary excretion of glycine and glucuronide conjugates. Xenobiotica, 26, 157–176.
   PubMed Web of Science ®Google Scholar
• CUPID, B. C., HOLMES, E., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1999, Quantitative structure—metabolism relationships (QSMR) using computational chemistry: pattern recognition analysis and statistical prediction of phase II conjugation reactions of substituted benzoic acids in the rat. Xenobiotica, 29, 22–42.
   Google Scholar
• EHLHARDT, W. J. and HOWBERT, J. J., 1991, Metabolism and disposition of p-chloroaniline in rat mouse and monkey. Drug Metabolism and Disposition, 19, 366–369
   PubMed Web of Science ®Google Scholar
• EHLHARDT, W. J., WOODLAND, J. M., WORAZALLA, J. F., BEWLEY, J. R., GRINDEY, G. B., TODD, G. C., Tom, J. E. and HOWBERT, J. J., 1992, Comparison of metabolism and toxicity to the structures of the anticancer agent sulofenur and related sulfonylureas. Chemical Research in Toxicology, 5, 667–673.
   PubMedGoogle Scholar
• FRIES, W., KEISE, M. and LENK, W., 1971, Additional route in the metabolism of sulphanilamide. Xenobiotica, 1, 241–256.
   PubMedGoogle Scholar
• GHAURI, F. Y. K., BLACKLEDGE, C. A., GLEN, R. C., LINDON, J. C., BEDELL, C. R., WILSON, I. D. and NICHOLSON, J. K., 1992b, Quantitative structure-metabolism relationships for substituted benzoic acids in the rat: computational chemistry, NMR spectroscopy and pattern recognition studies. Biochemical Pharmacology, 44, 1935–1 946.
   Google Scholar
• GHAURI, F. Y. K., BLACKLEDGE, C. A., GLEN, R. C., SWEATMAN, B. C., LINDON. J. C., BEDDELL, C. R., WILSON, I. D. and NICHOLSON, J. K., 1992a, An approach to a metabolic expert system: structure-metabolism relationships for benzoic acids in the rat. In E. Reid and I. D. Wilson (eds), Methodological Surveys in Biochemistry and Analysis, 20 (Cambridge: Royal Society of Chemistry), pp. 21–28.
   Google Scholar
• GUTMANN, H. R. and ERICKSON, R. R., 1969, The conversion of the carcinogen N-hydroxy-2-fluorenylacetamide to o-amidophenols by rat liver in vitro. Journal of Biological Chemistry, 244, 1729–1740.
   PubMed Web of Science ®Google Scholar
• HOLMES, E., SWEATMAN, B. C., BOLLARD, M. E., BLACKLEDGE, C. A., BEDDELL, C. R., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1995, Prediction of urinary sulphate and glucuronide conjugate excretion for substituted phenols in the rat using quantitative structure-metabolism relationships. Xenobiotica, 25, 1269-1 281.
   Google Scholar
• HINSON, J. A., 1983, Reactive metabolites of phenacetin and acetaminophen. A review. Environmental Health Perspectives, 49, 71–79.
   PubMed Web of Science ®Google Scholar
• HUTSON, D. H., LAKEMAN, S. K. and LOGAN, C. J., 1984b, The fate of 4-cyano-N,N-dimethylaniline in rats: a novel involvement of glutathione in the metabolism of aniline. Xenobiotica, 14, 925–934.
   PubMed Web of Science ®Google Scholar
• HUTSON, D. H., LOGAN, C. J. and REGAN, P. D., 1984a, Evidence for the formation of a novel glutathione conjugate in the metabolism of an aromatic amine derivative. Drug Metabolism and Disposition, 12, 523–524.
   PubMedGoogle Scholar
• KIESE, M. and LENK, W., 1969, Oxidation of acetanilides to glycolanilides and oxanilic acids in rabbits. Biochemical Pharmacology, 18, 1325–1333.
   PubMed Web of Science ®Google Scholar
• KIESE, M. and LENK, W., 1970, Hydroxylation of N-(4-chloropheny1)[14Cdacetamide to N-(4-chloropheny1)414 Cdglycolamide in rabbits. Biochimka et Biophysica Ada, 222, 549–551.
   PubMed Web of Science ®Google Scholar
• KIESE, M. and LENK, W., 1971, Metabolites of 4-chloroaniline and chloroacetanilides produced by rabbits and pigs. Biochemical Pharmacology, 20, 379–391.
   PubMed Web of Science ®Google Scholar
• NICHOLLS, A. W., FARRANT, R. D., SHOCKCOR, J. P., UNGER, S. E., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1997a, NMR and HPLC-NMR spectroscopic studies on the metabolism and futile deacetylation of paracetamol metabolites in rat and man. Biochemical Pharmacology, 49, 1155–1164.
   Web of Science ®Google Scholar
• NICHOLLS, A. W., LINDON, J. C., CADDICK, S., FARRANT, R. D., WILSON, I. D. and NICHOLSON, J. K., 1997b, NNIR spectroscopic studies on the metabolism and futile deacetylation of phenacetin in the rat. Xenobiotica, 27, 1175–1186.
   PubMed Web of Science ®Google Scholar
• NICHOLLS, A. W., LINDON, J. C., FARRANT, R. D., SHOCKOR, J. P., WILSON, I. D. and NICHOLSON, J. K., 1999, Directly-coupled HPLC- NNIR spectroscopic studies of metabolism and futile deacetylation of phenacetin in the rat. Journal of Pharmaceutical and Biomedical Analysis, 20, 865–873.
   PubMed Web of Science ®Google Scholar
• RADOMSKI, J. L., 1979, The primary aromatic amines: their biological properties and structure-activity relationships. Annual Reviews in Pharmacological Toxicology, 19, 129–157.
   PubMed Web of Science ®Google Scholar
• RIETVALD, E. C., PLATE, R. and SEUTTER-BERLAGE, F., 1980, Mechanism of formation of mercapturic acids from aromatic aldehydes in vivo. Archives of Toxicology, 52, 199–207.
   Google Scholar
• SCARFE, G. B., CLAYTON, E., WILSON I. D. and NICHOLSON, J. K., 2000, Identification and quantification of metabolites of 2,3,5,6-tetrafiuoro-4-trifluoromethylaniline in rat urine using 19F nuclear magnetic resonance spectroscopy, high performance liquid chromatography-nuclear magnetic resonance spectroscopy and high performance liquid chromatography-mass spectroscopy. Journal of Chromatography B, 748, 311–319.
   Google Scholar
• SCARFE, G. B., LINDON, J. C., NICHOLSON, J. K., WRIGHT, B., CLAYTON, E. and WILSON, I. D., 1999b, Investigation of the quantitative metabolic fate and urinary excretion of 3-methy1-4-trifluoromethylaniline and 3-methyl-4-trifluoromethylacetanilde in the rat. Drug Metabolism and Disposition, 27, 1171–1178.
   PubMed Web of Science ®Google Scholar
• SCARFE, G. B., TUGNAIT, M., WILSON, I. D. and NICHOLSON, J. K., 1999a, Studies on the metabolism of 4-fluoroaniline and 4-fluoroacetanilide in rat: formation of 4-actamidophenol (paracetamol) and its metabolites via defluorination and N-acetylation. Xenobiotica, 29, 205–216.
   PubMed Web of Science ®Google Scholar
• SCARFE, G. B., WILSON, I. D., SPRAUL, M., HOFMANN, M, BRAUMAN, U., LINDON. J. C. and NICHOLSON, J. K., 1997, Application of directly coupled high performance liquid chromatography-nuclear magnetic resonance-mass spectrometry to the detection and characterisation of the metabolites of 2-bromo-4-trifluoromethylaniline in rat urine. Analytical Communications, 34, 37–39.
   Google Scholar
• SCARFE, G. B., WRIGHT G. B., CLAYTON, E., TAYLOR S., WILSON, I. D., LINDON, J. C. and NICHOLSON, J. K., 1998, 19F-NMR and directly coupled HPLC-NMR-MS investigations into the metabolism of 2-bromo-4-trifluromethylathline in the rat: urinary excretion balance study without the use of radiolabelling. Xenobiotica, 28, 373–388.
   Google Scholar
• SCHRODER, H., LEWKONIA, R. M. and PRICE-EVANS, D. A., 1973, Metabolism of salicylazosulfapyridine in healthy subjects and patients with ulcerative colitis. Clinical Pharmacology and Therapeutics, 14, 802–809.
   Google Scholar
• SCINMZ, M., SCHMOLDT, A., DONN, F. and BECKER, H., 1988, The pharmacokinetics of flutamide and its major metabolites after a single oral dose and during chronic treatment. European Journal of Clinical Pharmacology, 34, 633–636.
   PubMedGoogle Scholar
• SEUTTER-BERLAGE, F., RIETVELD, E. C., PLATE, R. and KIPPERT, P. J. M, 1982, Mercapturic acids as metabolites of aromatic aldehydes and alcohols. In R. Snyder, D. V. Parke, J. Koesis, D. J. Jollow and G. G. Gibson (eds), Biological Reactive Intermediates IIA: Chemical Mechanisms and Biological Effects (New York: Plenum), pp. 359–368.
   Google Scholar
• SILVERMAN, R. B., 1992, The Organic Chemistry of Drug Design and Drug Action (San Diego: Academic Press), pp. 277–351.
   Google Scholar
• STERNSON, L. A. and GAMMANS, R. E., 1974, A mechanisitic study of aromatic hydroxylamine rearrangement in the rat. Bioinorganic Chemistry, 4, 58–63.
   Google Scholar
• WADE, K. E., TROKE, J., MACDONALD, C. M., WILSON. I. D. and NICHOLSON, J. K., 1988, NNIR studies of the metabolism of trifluoromethylaniline. In E. Reid, J. D. Robinson and I. D. Wilson (eds), Methodological Surveys in Biochemistry and Analysis, 18 (New York: Plenum), pp. 383–388.
   Google Scholar
• WILSON, I. D., MACDONALD, C. M., FROMSON, J. M., TROKE, J. A. and HILLBECK, D., 1985, Species differences in the metabolism of HC-p-trifluoromethylaniline: production of an oxanilic acid as the major metabolite by the rat. Biochemical Pharmacology, 34, 2025–2028.
   PubMed Web of Science ®Google Scholar