Urinary metabolites of a novel quinoxaline non-nucleoside reverse transcriptase inhibitor in rabbit, mouse and human: identification of fluorine NIH shift metabolites using NMR and tandem MS

References

• BAILLE T., 1994, The role of LC-ionspray MS/MS in studies of drug metabolism and toxicology. In Proceedings of the 42nd A SMS Conference on MS and Allied Topics, Chicago 29 May-3 June 1994, p. 862.
   Google Scholar
• CHU, I., VILLENEUVE, D. C., VIAU, A., BARNES, C. R., BENorr, F. M. and QIN, Y. H., 1984, Metabolism of 1,2,3,4-1,2,3,5-, and 1,2,4,5-tetrachlorobenzene in the rat. Journal of Toxicology and Environmental Health, 13, 777–786.
   PubMed Web of Science ®Google Scholar
• DALY, J. W., JERINA, D. M. and WoKoE, B., 1972, Arene oxides and the NIH shift: the metabolism, toxicity and carcinogenicity of aromatic compounds. Experientia, 28, 1129–1264.
   PubMedGoogle Scholar
• DE HOFFMAN, E., 1996, Tandem mass spectrometry: a primer. Journal of Mass Spectrometry, 31, 129–137.
   Google Scholar
• DEAR, G. J., HARRELSON, J. C., Jos, A. E., JOHNSON, T. E. and PLEASANCE, S., 1995, Identification of urinary and biliary conjugated metabolites of the neuromuscular blocker 51W89 by liquid chromatography/mass spectrometry. Rapid Communications in Mass Spectrometry, 9, 1457–1464.
   PubMed Web of Science ®Google Scholar
• DEAR, G. J., FRASER, I. J., PATEL, D. K., LONG, J. and PLEASANCE, S., 1998a, Use of liquid chromatography-tandem mass spectrometry for the quantitative and qualitative analysis of an anti-psychotic agent and its metabolites in human plasma and urine. Journal of Chromatography A, 794, 27–36.
   PubMed Web of Science ®Google Scholar
• DEAR, G. J., AYRTON, J., PLUMB, R., SWEATMAN, B. C., IsmAii, I. M., FRASER, I. J. and MUTCH, P. J., 1998b, A rapid and efficient approach to metabolite identification using NMR, LC/MS and LC/NMR/Sequential MS. Rapid Communications in Mass Spectrometry, 12, 2023–2030.
   Web of Science ®Google Scholar
• DEAR, G. J., AYRTON, J., PLUMB, R. and FRASER, I. J., 1999, The rapid identification of drug metabolites using capillary liquid chromatography coupled to an ion-trap mass spectrometer. Rapid Communications in Mass Spectrometry, 13, 456–463.
   PubMedGoogle Scholar
• DEN BESTEN C., ELLENBROEK M., VAN DER REE, M. A. E., RIETJENS, I. M. C. M. and VAN BLADEREN P. J., 1992, The involvement of primary and secondary metabolism in the covalent binding of 1,2- and 1,4-dichlorobenzens. Chemico-Biological Interactions, 84, 223–233.
   Google Scholar
• DEN BESTEN, C., SAENN, M. C. C., DE VRIES, E. J. and VAN BLADEREN, P. J., 1991, Metabolic activation of 1,2,4 -trichlorobenzene by rat liver microsomes: a major role for quinone metabolites. Toxicology and Applied Pharmacology, 108, 223–233.
   Google Scholar
• EVERETT, J. R., JENNINos, K. and WOODNUT, G., 1985, 19F-NMR spectroscopy study of the metabolism of flucloxacillin in rat urine. Journal of Pharmacy and Pharmacology, 37, 869–873.
   PubMed Web of Science ®Google Scholar
• GILBERT, P. J., HARTLEY, T. E., TROKE, J. A., TURCAN, R. G., VOSE, C. W. and WATSON, K. V., 1992. Applications of 19F-NMR spectroscopy to the identification of dog urinary metabolites of imirestat, a spirohydantoin aldose reductase inhibitor. Xenobiotica, 22, 775–787.
   PubMed Web of Science ®Google Scholar
• GUROFF, G., DALY, J. W., JEIUNA, D. M., RENSON, J., WITKOP, B. and UDENFRIEND, S., 1967, Hydroxylation-induced migration: the NIH shift. Science, 157, 1524–1530.
   PubMed Web of Science ®Google Scholar
• HOLT, R. M., NEWMAN, M. J., PULLEN, F. S., RICHARDS, D. S. and SWANSON, A. G., 1997, High-performance liquid chromatography NMR spectrometry mass spectrometry - further advances in hyphenated technology. Journal of Mass Spectrometry, 32, 64–70.
   PubMed Web of Science ®Google Scholar
• IsmAIL, I, DEAR, G. J., murco, P. J., DAVIES, L. H., PLUMB, R. and SWEATMAN, B. C., 1999 The urinary metabolism of the novel non-nucleoside reverse transcriptase inhibitor GW420867X in dog, cynomolgus monkey and mini-pig. Xenobiotica, 29, 957–967.
   PubMed Web of Science ®Google Scholar
• JERINA, D. M. and DALY, J. W., 1974, Arene oxides: a new aspect of drug metabolism. Science, 185, 573–582.
   PubMed Web of Science ®Google Scholar
• KOERTS, J., SOFFERS, A. E. M. F., VERVOOT, J., DE JAGER, A. and RIETJENS, I. M. C. M., 1998, Occurrence of the NIH shift upon the cytochrome P450-catalyzed in vivo and in vitro aromatic ring hydroxylation of fluorobenzenes. Chemical Research in Toxicology, 11, 503–512.
   Google Scholar
• KOHLI, J., JoNEs, D. and SAFE, S., 1976, The metabolism of higher chlorinated benzene isomers. Canadian Journal of Biochemistry, 54, 203–208.
   PubMedGoogle Scholar
• KORZEKWA, K., TRAGER, W., GOUTERMAN M., SPANGLER, D. and LOEW, G. H., 1985, Cytochrome P450 mediated aromatic oxidation: a theoretical study. Journal of the American Chemical Society, 107, 4273–4279.
   Google Scholar
• LINIDON, J. C., NICHOLSON, J. K., SIDELMANN, U. G. and WILSON, I. D., 1997, Directly coupled HPLC-NMR and its application to drug metabolism. Drug Metabolism Reviews, 29, 705–746.
   PubMedGoogle Scholar
• NICHOLSON, J. K. and WILSON, I. D., 1989, High resolution proton magnetic resonance spectroscopy of biological fluids. Progress in NMR Spectroscopy, 21, 449–501.
   Web of Science ®Google Scholar
• PLUMB, R. S., AYRTON, J., DEAR, G. J., SWEATMAN, B. C. and IsmAit, I. M., 1999, The use of preparative high performance liquid chromatography with tandem mass spectrometric directed fraction collection for the isolation and characterisation of drug metabolites in urine by nuclear magnetic resonance spectroscopy/sequential mass spectrometry. Rapid Communications in Mass Spec-trometry, 13, 845–854.
   PubMedGoogle Scholar
• PULLEN, F. S., SWANSON, A. G., NEWMAN, M. J. and RICHARDS, D. S., 1995, On-line liquid chromatography nuclear magnetic resonance mass spectrometry - a powerful spectroscopic tool for the analysis of mixtures of pharmaceutical interest. Rapid Communications in Mass Spectrometry, 9, 1003–1006.
   Web of Science ®Google Scholar
• SAFE, S., JONES, D. and HUTZINGER, O., 1976, Metabolism of 4,4'-dihalogenobiphenyls. Journal of the Chemical Society, Perkin Transactions, 1, 357–359.
   Google Scholar
• SAKAMOTO, K., NAKAMURA, Y., AIKOH, S., BABA, T., PERREGAARD, J., PEDERSEN, H., MOLTZEN, K., MULFORD, D. J. and YAMAGUCHI, T., 1995, Metabolism of sertindole: identification of the metabolites in rat and dog, and species comparison of liver microsomal metabolism. Xenobiotica, 25, 1327–1343.
   PubMed Web of Science ®Google Scholar
• SCHWARTZ, H., CRu, I., VILLENEUVE, D. C. and BENou, F. M., 1987, Metabolism of 1,2,3,4-, 1,2,3,5-, and 1,2,4,5 -tetrachlorobenzene in the squirrel monkey. Journal of Toxicology and Environmental Health, 22, 341–350.
   PubMed Web of Science ®Google Scholar
• SHOCKCOR, J. P., UNGER, S. E., WILSON, I. D., FOXALL, P. J. D., NICHOLSON, J. K. and LINDON, J. C., 1996, Combined HPLC, NMR spectroscopy, and ion-trap mass spectrometrywith application to the detection and characterisation of xenobiotic and endogenous metabolites in human urine. Analytical Chemistry, 68, 4431–4435.
   Google Scholar
• SPRAUL, M., HOFFMAN, M., LINDON, J. C., FARRANT, R. D., SEDDON, M., NICHOLSON, J. K. and WILSON, I. D., 1994, Evaluation of liquid chromatography coupled with high field 11-1-NMR spectroscopy for drug metabolism detection and characterisation; the identification of paracetamol metabolites in urine and bile. NMR BioMedicine, 7, 295–303.
   PubMed Web of Science ®Google Scholar
• VIALANEDC, J. P., MALET -MARTINO, M. C., HOFFMAN, J. S., Pius, J. and MARTINO, R., 1987, Direct detection of new flucytosine metabolites in human biofluids by 19F nuclear magnetic resonance. Drug Metabolism and Disposition, 5, 718–724.
   Google Scholar
• WADE, K. E., TROKE, J., MACDONALD, C. M., WILSON, I. D. and NICHOLSON, J. K., 1988,19F studies of the metabolism of trifluoro-methylaniline. In E. Reid, J. D. Robinson and I. D. Wilson (eds), Bioanalysis of Drug Metabolites (London: Plenum).
   Google Scholar