Trimethoprim: Novel reactive intermediates and bioactivation pathways by cytochrome P450s

Chemical Research in Toxicology

Volumn 21, Issue 11, 2008, Pages 2181-2187

  Damsten, Micaela C ^a   De Vlieger, Jon S B ^a   Niessen, Wilfried M A ^a   Irth, Hubertus ^a   Vermeulen, Nico P E ^a   Commandeur, Jan N M ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

2 QUINONE METHIDE; 4 QUINONE METHIDE; CYTOCHROME P450; CYTOCHROME P450 1A2; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; CYTOCHROME P450 BM3; GLUTATHIONE; IMINOQUINONE METHIDE; QUINONE DERIVATIVE; RECOMBINANT ENZYME; TRIMETHOPRIM; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; DNA ADDUCT; DRUG ACTIVITY; DRUG METABOLISM; GENETIC POLYMORPHISM; HUMAN; HUMAN CELL; LIVER MICROSOME; METABOLITE; NONHUMAN; RAT;

ANTI-BACTERIAL AGENTS; BIOTRANSFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; GLUTATHIONE; HUMANS; MASS SPECTROMETRY; MICROSOMES, LIVER; TRIMETHOPRIM;

BACTERIA (MICROORGANISMS); RATTUS;

EID: 57449084682     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx8002593     Document Type: Article

References (26)

1. Niemi, M., Kajosaari, L. I., Neuvonen, M., Backman, J. T., and Neuvonen, P. J. (2004) The CYP2C8 inhibitor trimethoprim increases the plasma concentrations of repaglinide in healthy subjects. Br. J. Clin. Pharmacol. 57, 441-447.
2. Frisch, J. M. (1973) Clinical experience with adverse reactions to trimethoprim-sulfamethoxazole. J. Infect. Dis. 128, 607-612.
3. Haaverstad, R., and Kannelonning, K. S. (1984) Fatal agranulocytosis and toxic liver damage after use of trimethoprim-sulfamethoxazole. Tidsskr. Nor Laegeforen. 104, 741-742.
4. Keisu, M., Wiholm, B. E., and Palmblad, J. (1990) Trimethoprim- sulphamethoxazole-associated blood dyscrasias. Ten years' experience of the Swedish spontaneous reporting system. J. Intern. Med. 228, 353-360.
5. Williamson, G. D., and Crowe, G. R. (1972) Trimethoprim-sulphamethoxazole mixtures and agranulocytosis. Med. J. Aust. 2, 1506-1507.
6. Medina, I., Mills, J., Leoung, G., Hopewell, P. C., Lee, B., Modin, G., Benowitz, N., and Wofsy, C. B. (1990) Oral therapy for Pneumocystis carinii pneumonia in the acquired immunodeficiency syndrome. A controlled trial of trimethoprim-sulfamethoxazole versus trimethoprim-dapsone. N. Engl. J. Med. 323, 776-782.
7. Pirmohamed, M., Alfirevic, A., Vilar, J., Stalford, A., Wilkins, E. G., Sim, E., and Park, B. K. (2000) Association analysis of drug metabolizing enzyme gene polymorphisms in HIV-positive patients with co-trimoxazole hypersensitivity. Pharmacogenetics 10, 705-713.
8. Kielhofner, M. A. (1990) Trimethoprim- sulfamethoxazole: Pharmacokinetics, clinical uses, and adverse reactions. Tex. Heart Inst. J. 17, 86-93.
9. Nwokolo, C., Byrne, L., and Misch, K. J. (1988) Toxic epidermal necrolysis occurring during treatment with trimethoprim alone. Br. Med. J. (Clin. Res. Ed.) 296, 970.
10. Das, G., Bailey, M. J., and Wickham, J. E. (1988) Toxic epidermal necrolysis and trimethoprim. Br. Med J. (Clin. Res. Ed.) 296, 1604-1605.
11. Hawkins, T., Carter, J. M., Romeril, K. R., Jackson, S. R., and Green, G. J. (1993) Severe trimethoprim induced neutropenia and thrombocytopenia. N. Z. Med. J. 106, 251-252.
12. Meshi, T., and Sato, Y. (1972) Studies on sulfamethoxazole-trimethoprim. Absorption, distribution, excretion and metabolism of trimethoprim in rat. Chem. Pharm. Bull. (Tokyo) 20, 2079-2090.
13. Van, T., Klooster, G. A., Kolker, H. J., Woutersen-Van Nijnanten, F. M., Noordhoek, J., and Van Miert, A. S. (1992) Determination of trimethoprim and its oxidative metabolites in cell culture media and microsomal incubation mixtures by high-performance liquid chromatography. J. Chromatogr. 579, 354-360.
14. Schwartz, D. E., Vetter, W., and Englert, G. (1970) Trimethoprim metabolites in rat, dog and man: Qualitative and quantitative studies. Arzneimittelforschung 20, 1867-1871.
15. Brooks, M. A., De Silva, J. A., and D'aroconte, L. (1973) Determination of trimethoprim and its N-oxide metabolites in urine of man, dog, and rat by differential pulse polarography. J. Pharm. Sci. 62, 1395-1397.
16. Lai, W. G., Zahid, N., and Uetrecht, J. P. (1999) Metabolism of trimethoprim to a reactive iminoquinone methide by activated human neutrophils and hepatic microsomes. J. Pharmacol. Exp. Ther. 291, 292-299.
17. Wen, X., Wang, J. S., Backman, J. T., Laitila, J., and Neuvonen, P. J. (2002) Trimethoprim and sulfamethoxazole are selective inhibitors of CYP2C8 and CYP2C9, respectively. Drug Metab. Dispos. 30, 631-635.
18. Damsten, M. C., Van Vugt-Lussenburg, B. M., Zeldenthuis, T., De Vlieger, J. S., Commandeur, J. N., and Vermeulen, N. P. (2008) Application of drug metabolising mutants of cytochrome P450 BM3 (CYP102A1) as biocatalysts for the generation of reactive metabolites. Chem.-Biol. Interact. 171, 96-107.
19. Baillie, T. A., and Davis, M. R. (1993) Mass spectrometry in the analysis of glutathione conjugates. Biol. Mass Spectrom. 22, 319-325.
20. Rooseboom, M., Commandeur, J. N., Floor, G. C., Rettie, A. E., and Vermeulen, N. P. (2001) Selenoxidation by flavin-containing monooxygenases as a novel pathway for beta-elimination of selenocysteine Se-conjugates. Chem. Res. Toxicol. 14, 127-134.
21. Appiah-Opong, R., Commandeur, J. N., Van Vugt-Lussenburg, B., and Vermeulen, N. P. (2007) Inhibition of human recombinant cytochrome P450s by curcumin and curcumin decomposition products. Toxicology 235, 83-91.
22. Gillam, E. M., Guo, Z., and Guengerich, F. P. (1994) Expression of modified human cytochrome P450 2E1 in Escherichia coli, purification, and spectral and catalytic properties. Arch. Biochem. Biophys. 312, 59-66.
23. Rostami-Hodjegan, A., and Tucker, G. T. (2007) Simulation and prediction of in vivo drug metabolism in human populations from in vitro data. Nat. Rev. Drug Discovery 6, 140-148.
24. Ingelman-Sundberg, M. (2001) Pharmacogenetics: An opportunity for a safer and more efficient pharmacotherapy. J. Intern. Med. 250, 186-200.
25. Pirmohamed, M., and Park, B. K. (2003) Cytochrome P450 enzyme polymorphisms and adverse drug reactions. Toxicology 192, 23-32.
26. Pirmohamed, M., and Park, B. K. (2001) Genetic susceptibility to adverse drug reactions. Trends Pharmacol. Sci. 22, 298-305.