Nonenzymatic formation of a novel hydroxylated sulfamethoxazole derivative in human liver microsomes: Implications for bioanalysis of sulfamethoxazole metabolites

Drug Metabolism and Disposition

Volumn 36, Issue 12, 2008, Pages 2424-2428

  Sanderson, Joseph P ^a   Hollis, Frank J ^b   Maggs, James L ^a   Clarke, Stephen E ^b   Naisbitt, Dean J ^a   Park, B Kevin ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINOBENZOTRIAZOLE; 5 HYDROXYSULFAMETHOXAZOLE; ASCORBIC ACID; CYTOCHROME P450 2C9; DEFEROXAMINE; DRUG METABOLITE; EDETIC ACID; FERROUS ION; HYDROGEN PEROXIDE; MANNITOL; SULFAMETHOXAZOLE; SULFAMETHOXAZOLE HYDROXYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG HYDROXYLATION; DRUG METABOLISM; DRUG OXIDATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYPERSENSITIVITY REACTION; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MASS SPECTROMETRY; PEROXIDATION; PRIORITY JOURNAL;

ASCORBIC ACID; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEFEROXAMINE; EDETIC ACID; ENZYME INHIBITORS; FERROUS COMPOUNDS; HUMANS; HYDROGEN PEROXIDE; HYDROXYLATION; KINETICS; MICROSOMES, LIVER; MOLECULAR STRUCTURE; NADP; SULFAMETHOXAZOLE; TANDEM MASS SPECTROMETRY; TRIAZOLES;

EID: 57349115403     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.021246     Document Type: Article

References (28)

1. Coleman MD, Breckenridge AM, and Park BK (1989) Bioactivation of dapsone to a cytotoxic metabolite by human hepatic microsomal enzymes. Br J Clin Pharmacol 28:389-395.
2. Cribb AE, Miller M, Leeder JS, Hill J, and Spielberg SP (1991) Reactions of the nitroso and hydroxylamine metabolites of sulfamethoxazole with reduced glutathione. Implications for idiosyncratic toxicity. Drug Metab Dispos 19:900-906.
3. Cribb AE, Miller M, Tesoro A, and Spielberg SP (1990) Peroxidase-dependent oxidation of sulfonamides by monocytes and neutrophils from humans and dogs. Mol Pharmacol 38:744-751.
4. Cribb AE and Spielberg SP (1990a) Hepatic microsomal metabolism of sulfamethoxazole to the hydroxylamine. Drug Metab Dispos 18:784-787.
5. Cribb AE and Spielberg SP (1990b) An in vitro investigation of predisposition to sulphonamide idiosyncratic toxicity in dogs. Vet Res Commun 14:241-252.
6. Cribb AE and Spielberg SP (1992) Sulfamethoxazole is metabolized to the hydroxylamine in humans. Clin Pharmacol Ther 51:522-526.
7. Cribb AE, Spielberg SP, and Griffin GP (1995) N4-hydroxylation of sulfamethoxazole by cytochrome P450 of the cytochrome P4502C subfamily and reduction of sulfamethoxazole hydroxylamine in human and rat hepatic microsomes. Drug Metab Dispos 23:406-414.
8. Emoto C, Murase S, Sawada Y, and Iwasaki K (2005) In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations in human liver microsomes: a comparison with SKF-525A. Drug Metab Pharmacokinet 20:351-357.
9. Gill HJ, Maggs JL, Madden S, Pirmohamed M, and Park BK (1996) The effect of fluconazole and ketoconazole on the metabolism of sulphamethoxazole. Br J Clin Pharmacol 42:347-353.
10. Gill HJ, Tjia JF, Kitteringham NR, Pirmohamed M, Back DJ, and Park BK (1999) The effect of genetic polymorphisms in CYP2C9 on sulphamethoxazole N-hydroxylation. Pharmacogenetics 9:43-53.
11. Halliwell B and Kaur H (1997) Hydroxylation of salicylate and phenylalanine as assays for hydroxyl radicals: a cautionary note visited for the third time. Free Radic Res 27:239-244.
12. Hamilton GA (1962) Chemical models and mechanisms for oxygenases, in Oxygenases (Hayaishi O ed), pp 419-431, Academic Press, New York.
13. Ingelman-Sundberg M, Kaur H, Terelius Y, Persson JO, and Halliwell B (1991) Hydroxylation of salicylate by microsomal fractions and cytochrome P-450. Lack of production of 2,3-dihydroxybenzoate unless hydroxyl radical formation is permitted. Biochem J 276:753-757.
14. Ito S, Ueno K, Mitarai A, and Sasaki K (1993) Evidence for hydroxyl radicals as an active species generated from Udenfriend's reagent. J Chem Soc Perkin Trans 2:255-259.
15. Johansson I and Ingelman-Sundberg M (1983) Hydroxyl radical-mediated, cytochrome P-450-dependent metabolic activation of benzene in microsomes and reconstituted enzyme systems from rabbit liver. J Biol Chem 258:7311-7316.
16. Lavergne SN, Kurian JR, Bajad SU, Maki JE, Yoder AR, Guzinski MV, Graziano FM, and Trepanier LA (2006) Roles of endogenous ascorbate and glutathione in the cellular reduction and cytotoxicity of sulfamethoxazole- nitroso. Toxicology 222:25-36.
17. Li M, Carlson S, Kinzer JA, and Perpall HJ (2003) HPLC and LC-MS studies of hydroxylation of phenylalanine as an assay for hydroxyl radicals generated from Udenfriend's reagent. Biochem Biophys Res Commun 312:316-322.
18. Mishin VM and Thomas PE (2004) Characterization of hydroxyl radical formation by microsomal enzymes using a water-soluble trap, terephthalate. Biochem Pharmacol 68:747-752.
19. Naisbitt DJ, Gordon SF, Pirmohamed M, Burkhart C, Cribb AE, Pichler WJ, and Park BK (2001) Antigenicity and immunogenicity of sulphamethoxazole: demonstration of metabolism-dependent haptenation and T-cell proliferation in vivo. Br J Pharmacol 133:295-305.
20. Naisbitt DJ, Hough SJ, Gill HJ, Pirmohamed M, Kitteringham NR, and Park BK (1999) Cellular disposition of sulphamethoxazole and its metabolites: implications for hypersensitivity. Br J Pharmacol 126:1393-1407.
21. Naisbitt DJ, O'Neill PM, Pirmohamed M, and Park BK (1996) Synthesis and reactions of nitroso sulphamethoxazole with biological nucleophiles: Implications for immune mediated toxicity. Bioorg Med Chem Lett 6:1511-1516.
22. Rieder MJ, Uetrecht J, Shear NH, and Spielberg SP (1988) Synthesis and in vitro toxicity of hydroxylamine metabolites of sulfonamides. J Pharmacol Exp Ther 244:724-728.
23. Udenfriend S, Clark CT, Axelrod J, and Brodie BB (1954) Ascorbic acid in aromatic hydroxylation. I. A model system for aromatic hydroxylation. J Biol Chem 208:731-739.
24. Vilar FJ, Naisbitt DJ, Park BK, and Pirmohamed M (2003) Mechanisms of drug hypersensitivity in HIV-infected patients: the role of the immune system. J HIV Ther 8:42-47.
25. Vree TB, van der Ven AJ, Verwey-van Wissen CP, van Ewijk-Beneken Kolmer EW, Swolfs AE, van Galen PM, and Amatdjais-Groenen H (1994) Isolation, identification and determination of sulfamethoxazole and its known metabolites in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Appl 658:327-340.
26. Vyas PM, Roychowdhury S, and Svensson CK (2006) Role of human cyclooxygenase-2 in the bioactivation of dapsone and sulfamethoxazole. Drug Metab Dispos 34:16-18.
27. Vyas PM, Roychowdhury S, Woster PM, and Svensson CK (2005) Reactive oxygen species generation and its role in the differential cytotoxicity of the arylhydroxylamine metabolites of sulfamethoxazole and dapsone in normal human epidermal keratinocytes. Biochem Pharmacol 70:275-286.
28. Winter HR, Trapnell CB, Slattery JT, Jacobson M, Greenspan DL, Hooton TM, and Unadkat JD (2004) The effect of clarithromycin, fluconazole, and rifabutin on dapsone hydroxylamine formation in individuals with human immunodeficiency virus infection (AACTG 283). Clin Pharmacol Ther 76:579-587.