Bioactivation of glafenine by human liver microsomes and peroxidases: Identification of electrophilic iminoquinone species and GSH conjugates

Drug Metabolism and Disposition

Volumn 39, Issue 9, 2011, Pages 1511-1521

  Wen, Bo ^a   Moore, David J ^a  

^a HOFFMANN LA ROCHE INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 HYDROXYGLAFENIC ACID; 5 HYDROXYGLAFENINE; BENZENE DERIVATIVE; CYTOCHROME P450; DRUG METABOLITE; GLAFENIC ACID; GLAFENINE; GLAFENINE N OXIDE; HORSERADISH PEROXIDASE; IMINOQUINONE DERIVATIVE; MYELOPEROXIDASE; QUINONE DERIVATIVE; RECOMBINANT CYTOCHROME P450 2C19; RECOMBINANT CYTOCHROME P450 2D6; RECOMBINANT CYTOCHROME P450 3A4; RECOMBINANT ENZYME; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; DRUG ACTIVATION; DRUG CONJUGATION; DRUG HYDROXYLATION; DRUG OXIDATION; DRUG STRUCTURE; ELECTROPHILICITY; ENZYME ACTIVITY; HETEROLOGOUS EXPRESSION; HUMAN; HUMAN CELL; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; LIVER MICROSOME METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; SIGNAL TRANSDUCTION; TANDEM MASS SPECTROMETRY;

CYCLOPHILINS; CYTOCHROME P-450 ENZYME SYSTEM; GLAFENINE; GLUTATHIONE; HUMANS; METABOLIC DETOXICATION, DRUG; MICROSOMES, LIVER; OXIDATION-REDUCTION; PEROXIDASES; PROTEIN BINDING; QUINONES; TANDEM MASS SPECTROMETRY;

ARMORACIA RUSTICANA;

EID: 80051987699     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.111.039396     Document Type: Article

References (23)

1. Baillie TA and Davis M.R. (1993) Mass spectrometry in the analysis of Hydroxy2′Glutathione conjugates. Biol Mass Spectrom 22:319-325. (Pubitemid 23165443)
2. Boyer J., Lafargue J.P., Person B., Boisserie P, and Saint-André J.D. (1984) [Fatal acute hepatitis after taking glafenine]. Gastroenterol Clin Biol 8:91-92.
3. Brissot P., Gie S., Colobert A., Delamaire D., Cartier F, and Bourel M. (1982) [A new case of hepatitis due to glafenine]. Gastroenterol Clin Biol 6:948.
4. Caballería Rovíra E., Offso Ubeda R.M., Arago López JV, and Sanchís Closa A. (1992) Hepatotoxicity caused by glafenin. Apropos of 2 cases. Rev Clin Esp 191:166-168.
5. Dieckhaus C.M., Fernandez-Metzler C.L., King R., Krolikowski PH, and Baillie, T.A. (2005) Chem Res Toxicol 18:630-638.
6. Kang P., Dalvie D., Smith E, and Renner M. (2009) Bioactivation of lumiracoxib by peroxidases and human liver microsomes: Identification of multiple quinone imine intermediates and GSH adducts. Chem Res Toxicol 22:106-117.
7. Li Y., Slatter J.G., Zhang Z., Li Y., Doss G.A., Braun M.P., Stearns R.A., Dean D.C., Baillie TA, and Tang W. (2008) In vitro metabolic activation of lumiracoxib in rat and human liver preparations. Drug Metab Dispos 36:469-473. (Pubitemid 351185763)
8. Poon G.K., Chen Q., Teffera Y., Ngui J.S., Griffin P.R., Braun M.P., Doss G.A., Freeden C., Stearns R.A., Evans D.C., et al. (2001) Bioactivation of diclofenac via benzoquinone imine intermediatesidentification of urinary mercapturic acid derivatives in rats and humans. Drug Metab Dispos 29:1608-1613. (Pubitemid 33111594)
9. Pottier J., Busigny M, and Raynaud J.P. (1979) Biotransformations of glafenine in the rat and in man. Eur J Drug Metab Pharmacokinet 4:109-115. (Pubitemid 9223237)
10. Rodrigues A.D. (1999) Integrated cytochrome P450 reaction phenotyping: attempting to bridge the gap between cDNA- Expressed cytochromes P450 and native human liver microsomes. Biochem Pharmacol 57:465-480.
11. Shen S., Marchick M.R., Davis M.R., Doss GA, and Pohl L.R. (1999) Metabolic activation of diclofenac by human cytochrome P450 3A4: role of 5- Hydroxydiclofenac. Chem Res Toxicol 12:214-222. (Pubitemid 29096071)
12. Stricker B.H., Blok AP, and Bronkhorst F.B. (1986) Glafenine- Associated hepatic injury. Analysis of 38 cases and review of the literature. Liver 6:63-72. (Pubitemid 16021401)
13. Stricker B.H., De Groot RR, and Wilson J.H. (1990) Anaphylaxis to glafenine. Lancet 336:943-944. (Pubitemid 20351208)
14. Tang W., Stearns R.A., Bandiera S.M., Zhang Y., Raab C., Braun M.P., Dean D.C., Pang J., Leung K.H., Doss G.A., et al. (1999) Studies on cytochrome P-450- 450Mediated bioactivation of diclofenac in rats and in human hepatocytes: identification of glutathione conjugated metabolites. Drug Metab Dispos 27:365-372. (Pubitemid 29114244)
15. Van der Klauw M.M., Stricker B.H., Herings R.M., Cost W.S., Valkenburg HA, and Wilson J.H. (1993) A population based case- Cohort study of drug- Cohort study of drugInduced anaphylaxis. Br J Clin Pharmacol 35:400-408. (Pubitemid 23103381)
16. Van der Klauw M.M., Wilson JH, and Stricker B.H. (1996) Drug- Associated anaphylaxis: 20 years of reporting in The Netherlands (1974- Associated anaphylaxis: 20 years of reporting in The Netherlands (19741994) and review of the literature. Clin Exp Allergy 26:1355-1363. (Pubitemid 27019790)
17. Verhamme M., De Wolf-Peeters C, and Van Steenbergen W. (1984) Hepatic injury due to glafenine. Report of two cases and review of the literature. Neth J Med 27:35-39. (Pubitemid 14159765)
18. Vermerie N., Kusielewicz D., Tod M., Nicolas P., Perret G., Fauvelle F, and Petitjean O. (1992) Pharmacokinetics of glafenine and glafenic acid in patients with cirrhosis, compared to healthy volunteers. Fundam Clin Pharmacol 6:197-203.
19. Wen B., Coe K.J., Rademacher P., Fitch W.L., Monshouwer M, and Nelson S.D. (2008a) Comparison of in vitro bioactivation of flutamide and its cyano analogue: Evidence for reductive activation by human NADPH: Evidence for reductive activation by human NADPHCytochrome P450 reductase. Chem Res Toxicol 21:2393-2406.
20. Wen B., Ma L., Nelson SD, and Zhu M. (2008b) High- Throughput screening and characterization of reactive metabolites using polarity switching of hybrid triple quadrupole linear ion trap mass spectrometry. Anal Chem 80:1788-1799. (Pubitemid 351429586)
21. Wen B., Ma L., Rodrigues AD, and Zhu M. (2008c) Detection of novel reactive metabolites of trazodone: evidence for CYP2D6- Mediated bioactivation of m- Mediated bioactivation of mChlorophenylpiperazine. Drug Metab Dispos 36:841-850. (Pubitemid 351574881)
22. Ypma R.T., Festen JJ, and De Bruin C.D. (1978) Hepatotoxicity of glafenine. Lancet 2:480-481. (Pubitemid 9033278)
23. Yu L.J., Chen Y., Deninno M.P., O'Connell TN, and Hop C.E. (2005) Identification of a novel glutathione adduct of diclofenac, 4′-hydroxy- Hydroxy2′-glutathion- Hydroxy2′GlutathionDeschloro- Hydroxy2′GlutathionDeschloroDiclofenac, upon incubation with human liver microsomes. Drug Metab Dispos 33:484-488. (Pubitemid 40393189)