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

Xenobiotica

Volumn 30, Issue 4, 2000, Pages 407-426

  Dear, G J ^a   Ismail, I M ^a   Mutch, P J ^a   Plumb, R S ^a   Davies, L H ^a   Sweatman, B C ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 ETHYL 7 FLUORO 3 OXO 3 4 DIHYDRO 2H QUINOXALINE CARBOXYLIC ACID ISOPROPYLESTER; CYSTEINE; DRUG METABOLITE; FLUORINE; GLUCURONIDE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ADULT; ANIMAL EXPERIMENT; ARTICLE; BIOTRANSFORMATION; DRUG BLOOD LEVEL; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG URINE LEVEL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN EXPERIMENT; MASS SPECTROMETRY; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; RABBIT;

ANIMALIA; ORYCTOLAGUS CUNICULUS;

EID: 0034055226     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.1080/004982500237604     Document Type: Article

References (30)

1. Baille T., 1994, The role of LC-ionspray MS/MS in studies of drug metabolism and toxicology. In Proceedings of the 42nd ASMS Conference on MS and Allied Topics, Chicago 29 May-3 June 1994, p. 862.
2. Chu, I., Villeneuve, D. C., Viau, A., Barnes, C. R., Benoit, 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.
3. Daly, J. W., Jerina, D. M. and Witkop, B., 1972, Arene oxides and the NIH shift; The metabolism, toxicity and carcinogenicity of aromatic compounds. Experientia, 28, 1129-1264.
4. De Hoffman, E., 1996, Tandem mass spectrometry: a primer. Journal of Mass Spectrometry, 31, 129-137.
5. Dear, G. J., Harrelson, J. C., Jones, 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.
6. 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.
7. Dear, G. J., Ayrton, J., Plumb, R., Sweatman, B. C., Ismail, 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.
8. 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.
9. 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.
10. Den Besten, C., Smink, 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.
11. 19F-NMR spectroscopy study of the metabolism of flucloxacillin in rat urine. Journal of Pharmacy and Pharmacology, 37, 869-873.
12. 19F-NMR spectroscopy to the identification of dog urinary metabolites of imirestat, a spirohydantoin aldose reductase inhibitor. Xenobiotica, 22, 775-787.
13. Guroff, G., Daly, J. W., Jerina, D. M., Renson, J., Witkop, B. and Udenfriend, S., 1967, Hydroxylation-induced migration: the NIH shift. Science, 157, 1524-1530.
14. 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.
15. Ismail, I, Dear, G. J., Mutch, 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.
16. Jerina, D. M. and Daly, J. W., 1974, Arene oxides: a new aspect of drug metabolism. Science, 185, 573-582.
17. 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.
18. Kohli, J., Jones, D. and Safe, S., 1976, The metabolism of higher chlorinated benzene isomers. Canadian Journal of Biochemistry, 54, 203-208.
19. 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.
20. Lindon, 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.
21. Nicholson, J. K. and Wilson, I. D., 1989, High resolution proton magnetic resonance spectroscopy of biological fluids. Progress in NMR Spectroscopy, 21, 449-501.
22. Plumb, R. S., Ayrton, J., Dear, G. J., Sweatman, B. C. and Ismail, 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 Spectrometry, 13, 845-854.
23. 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.
24. Safe, S., Jones, D. and Hutzinger, O., 1976, Metabolism of 4,4′-dihalogenobiphenyls. Journal of the Chemical Society, Perkin Transactions, 1, 357-359.
25. 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.
26. Schwartz, H., Chu, I., Villeneuve, D. C. and Benoit, 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.
27. 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 spectrometry with application to the detection and characterisation of xenobiotic and endogenous metabolites in human urine. Analytical Chemistry, 68, 4431-4435.
28. 1 H-NMR spectroscopy for drug metabolism detection and characterisation; the identification of paracetamol metabolites in urine and bile. NMR BioMedicine, 7, 295-303.
29. 19F nuclear magnetic resonance. Drug Metabolism and Disposition, 5, 718-724.
30. 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).