Ticlopidine-induced hepatotoxicity in a GSH-depleted rat model

Archives of Toxicology

Volumn 85, Issue 4, 2011, Pages 347-353

  Shimizu, Shinji ^a   Atsumi, Ryo ^a   Nakazawa, Tsunenori ^a   Izumi, Takashi ^a   Sudo, Kenichi ^a   Okazaki, Osamu ^a   Saji, Hideo ^b  

^a DAIICHI SANKYO CO   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Covalent binding; Glutathione; Hepatotoxicity; Iidiosyncratic; Reactive metabolite; Ticlopidine

Indexed keywords

1 AMINOBENZOTRIAZOLE; ALANINE AMINOTRANSFERASE; GLUTATHIONE; TICLOPIDINE;

ALANINE AMINOTRANSFERASE BLOOD LEVEL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; COVALENT BOND; DRUG EFFECT; LIVER NECROSIS; LIVER TOXICITY; MALE; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; BUTHIONINE SULFOXIMINE; DISEASE MODELS, ANIMAL; DRUG SYNERGISM; DRUG THERAPY, COMBINATION; DRUG-INDUCED LIVER INJURY; ENZYME INHIBITORS; GLUTATHIONE; PLATELET AGGREGATION INHIBITORS; PROTEIN BINDING; RATS; TICLOPIDINE; TRIAZOLES;

ANIMALIA; RATTUS;

EID: 79954425508     PISSN: 03405761     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00204-010-0594-9     Document Type: Article

References (43)

1. SR Davis EP Quinlivan PW Stacpoole JF Gregory III 2006 Plasma glutathione and cystathionine concentrations are elevated but cysteine flux is unchanged by dietary vitamin B-6 restriction in young men and women J Nutr 136 373 378 16424114 1:CAS:528:DC%2BD28Xht1Wis7c%3D (Pubitemid 43228288)
2. R Drew JO Miners 1984 The effects of buthionine sulfoximine (BSO) on glutathione depletion and xenobiotic biotransformation Biochem Pharmacolo 33 2989 2994 10.1016/0006-2952(84)90598-7 1:CAS:528:DyaL2cXmt1ChtLk%3D (Pubitemid 14044593)
3. OW Griffith A Meister 1979 Potent and specific inhibition of glutathione synthesis by buthionine sulfoximine (S-n-butyl homocysteine sulfoximine) J Biol Chem 254 7558 7560 38242 1:CAS:528:DyaE1MXlvVOhu70%3D (Pubitemid 10230219)
4. NT Ha-Duong S Dijols AC Macherey JA Goldstein PM Dansette D Mansuy 2001 Ticlopidine as a selective mechanism-based inhibitor of human cytochrome P450 2C19 Biochemistry 40 12112 12122 11580286 10.1021/bi010254c 1:CAS:528: DC%2BD3MXmvVSgsrc%3D (Pubitemid 32946552)
5. A Hernanz E Fernández-Vivancos C Montiel JJ Vazquez F Arnalich 2000 Changes in the intracellular homocysteine and glutathione content associated with aging Life Sci 67 1317 1324 10972200 10.1016/S0024-3205(00) 00722-0 1:CAS:528:DC%2BD3cXlslCgtr4%3D (Pubitemid 30640819)
6. K Hirata H Takagi M Yamamoto T Matsumoto T Nishiya K Mori S Shimizu H Masumoto Y Okutani 2008 Ticlopidine-induced hepatotoxicity is associated with specific human leukocyte antigen genomic subtypes in Japanese patients: a preliminary case-control study Pharmacogenomics J 8 29 33 17339877 10.1038/sj.tpj.6500442 1:CAS:528:DC%2BD1cXnt1GlsQ%3D%3D
7. C Ip 1984 Comparative effects of antioxidants on enzymes involved in glutathione metabolism Life Sci 34 2501 2506 6727579 10.1016/0024-3205(84)90287- X 1:CAS:528:DyaL2cXkslWhsLs%3D (Pubitemid 14105569)
8. AK Jacobson 2004 Platelet ADP receptor antagonists: ticlopidine and clopidogrel Best Pract Res Clin Haematol 17 55 64 15171957 10.1016/j.beha.2004. 03.002 1:CAS:528:DC%2BD2cXksVansrg%3D (Pubitemid 38780067)
9. BH Lauterburg ME Velez 1988 Glutathione deficiency in alcoholics: risk factor for paracetamol hepatotoxicity Gut 2 1153 1157 10.1136/gut.29.9.1153
10. AP Li 2002 A review of the common properties of drugs with idiosyncratic hepatotoxicity and the "multiple determinant hypothesis" for the manifestation of idiosyncratic drug toxicity Chem Biol Interact 142 7 23 12399152 10.1016/S0009-2797(02)00051-0 1:CAS:528:DC%2BD38XotVKrtrs%3D (Pubitemid 35232550)
11. R Mataix E Ojeda MC Perez S Jimenez 1992 Ticlopidine and severe aplastic anaemia Br J Haematol 80 125 126 1531614 10.1111/j.1365-2141.1992.tb06412.x 1:STN:280:DyaK387mt1Kjsg%3D%3D
12. P Micke KM Beeh R Buhl 2002 Effects of long-term supplementation with whey proteins on plasma glutathione levels of HIV-infected patients Eur J Nutr 4 12 18 10.1007/s003940200001 (Pubitemid 36055989)
13. JR Mitchell DJ Jollow WZ Potter JR Gillette BB Brodie 1973 Acetaminophene-induced hepatic necrosis. IV. Protective role of glutathione J Pharmacol Exp Ther 187 211 217 4746329 1:CAS:528:DyaE2cXislQ%3D
14. M Mizushima N Iwata TT Fujimoto K Ishikawa K Fujimura 2005 Patient characteristics in ticlopidine hydrochloride-induced liver injury: Case-control study Hepatol Res 33 234 240 16112897 10.1016/j.hepres.2005.05.009 1:CAS:528:DC%2BD2MXht1GnurvL (Pubitemid 41794212)
15. T Mizutani H Nomura K Nakanishi S Fujita 1987 Hepatotoxicity of butylated hydroxytoluene and its analogs in mice depleted of hepatic glutathione Toxicol Appl Pharmacol 87 166 176 3798451 10.1016/0041-008X(87)90094-9 1:CAS:528:DyaL2sXhtFCku78%3D (Pubitemid 17004777)
16. T Mizutani K Satoh H Nomura K Nakanishi 1991 Hepatotoxicity of eugenol in mice depleted of glutathione by treatment with DL-buthionine sulfoximine Res Commun Chem Pathol Pharmacol 71 219 230 2047567 1:CAS:528:DyaK3MXhtlGmu70%3D
17. T Mizutani Y Irie K Nakanishi 1994 Styrene-induced hepatotoxicity in mice depleted of glutahione Res Commun Mol Pathol Pharmacol 86 361 374 7712112 1:CAS:528:DyaK2MXivVWitrg%3D
18. T Mizutani Y Nakahori K Yamamoto 1994 p-Dichlorobenzene-induced hepatotoxicity in mice depleted of glutathione treated with buthionine sulfoximine Toxicology 94 57 67 7801330 10.1016/0300-483X(94)90028-0 1:CAS:528:DyaK2MXitlejtbY%3D (Pubitemid 24381294)
19. T Mizutani M Murakami M Shirai M Tanaka K Nakanishi 1999 Metabolism-dependent hepatotoxicity of Methimazole in mice depleted of glutathione J Appl Toxicol 19 193 198 10362270 10.1002/(SICI)1099-1263(199905/ 06)19:3<193::AID-JAT553>3.0.CO;2-9 1:CAS:528:DyaK1MXjtlantrk%3D (Pubitemid 29225009)
20. CA Mugford M Mortillo BA Mico JB Tarloff 1992 1-Aminobenzotriazole- induced destruction of hepatic and renal cytochromes P450 in male Sprague-Dawley rats Fundam Appl Toxicol 19 43 49 1397800 10.1016/0272-0590(92)90026-E 1:CAS:528:DyaK38XltVGqsbw%3D
21. M Muszkat MY Shapira S Sviri DM Linton Y Caraco 1998 Ticlopidine-induced thrombotic thrombocytopenic purpura Pharmacotherapy 18 1352 1355 9855338 1:STN:280:DyaK1M%2FntV2rsg%3D%3D (Pubitemid 28533892)
22. S Nakamura K Kugiyama S Sugiyama S Miyamoto S Koide H Fukushima O Honda M Yoshimura H Ogawa 2002 Polymorphism in the 5′-flanking region of human glutamate-cysteine ligase modifier subunit gene is associated with myocardial infarction Circulation 105 2968 2973 12081989 10.1161/01.CIR.0000019739.66514.1E 1:CAS:528:DC%2BD38XlslSjsbc%3D (Pubitemid 34693828)
23. T Nishiya K Mori C Hattori K Kai H Kataoka N Masubuchi T Jindo S Manabe 2008 The crucial protective role of glutathione against tienilic acid hepatotoxicity in rats Toxicol Appl Pharmacol 232 280 291 18708081 10.1016/j.taap.2008.06.024 1:CAS:528:DC%2BD1cXhtFyqtrjK
24. Y Nishiya K Hagihara T Ito M Tajima S Miura A Kurihara NA Farid T Ikeda 2009 Mechanism-based inhibition of human cytochrome P450 2B6 by ticlopidine, clopidogrel, and the thiolactone metabolite of prasugrel Drug Metab Dispos 37 589 593 19047469 10.1124/dmd.108.022988 1:CAS:528:DC%2BD1MXislamtLY%3D
25. K Ono K Kurohara M Yoshihara Y Shimamoto M Yamaguchi 1991 Agranulocytosis caused by ticlopidine and its mechanism Am J Hematol 37 239 242 1858780 10.1002/ajh.2830370405 1:STN:280:DyaK3MzhsVGquw%3D%3D
26. E Panak JP Maffrand C Picard-Fraire E Vallée J Blanchard R Roncucci 1983 Ticlopidine: a promise for the prevention and treatment of thrombosis and its complications Haemostasis 13 Suppl 1 1 54 6642292
27. AE Pizarro RJ Andrade M García-Cortés MI Lucena JM Pérez-Moreno M Puertas H Sánchez-Martínez JL Montero JA Durán M Jiménez A Ruiz-Montero MJ Soto-Conesa L Rodrigo R de Francisco R Alcántara R Camargo 2001 Acute hepatitis due to ticlopidine. A report of 12 cases and review of the literature Rev Neurol 33 1014 1020 11785026 1:STN:280:DC%2BD38%2FlvV2ntA%3D%3D (Pubitemid 34137152)
28. MJ Quinn DJ Fitzgerald 1999 Ticlopidine and clopidogrel Circulation 100 1667 1672 10517740 1:CAS:528:DyaK1MXmvFGntLg%3D (Pubitemid 29477278)
29. T Richter TE Mürdter G Heinkele J Pleiss S Tatzel M Schwab M Eichelbaum UM Zanger 2004 Potent mechanism-based inhibition of human CYP2B6 by clopidogrel and ticlopidine J Pharmacol Exp Ther 308 189 197 14563790 10.1124/jpet.103.056127 1:CAS:528:DC%2BD2cXmsFegsg%3D%3D (Pubitemid 38090717)
30. Q Ruan M Zhu 2010 Investigation of Bioactivation of Ticlopidine Using Linear Ion Trap/Orbitrap Mass Spectrometry and an Improved Mass Defect Filtering Technique Chem Res Toxicol 23 909 917 20297803 10.1021/tx1000046 1:CAS:528:DC%2BC3cXjsFSksrw%3D
31. P Savi JM Herbert 2005 Clopidogrel and ticlopidine: P2Y12 adenosine diphosphate-receptor antagonists for the prevention of atherothrombosis Semin Thromb Hemost 31 174 183 15852221 10.1055/s-2005-869523 1:CAS:528: DC%2BD2MXkvVSnurc%3D (Pubitemid 40605192)
32. J Sedlak RH Lindsay 1968 Estimation of total, protein-bound, and nonprotein sulfhydryl groups in tissue with Ellman's reagent Anal Biochem 25 192 205 4973948 10.1016/0003-2697(68)90092-4 1:CAS:528:DyaF1MXhslCktA%3D%3D
33. S Shimizu R Atsumi K Itokawa M Iwasaki T Aoki C Ono T Izumi K Sudo O Okazaki 2009 Metabolism-dependent hepatotoxicity of amodiaquine in glutathione-depleted mice Arch Toxicol 83 701 707 19479240 10.1007/s00204-009- 0436-9 1:CAS:528:DC%2BD1MXmsFWqu7s%3D
34. S Shimizu R Atsumi T Nakazawa Y Fujimaki K Sudo O Okazaki 2009 Metabolism of ticlopidine in rats: Identification of the main biliary metabolite as a GSH conjugate of S-oxide Drug Metab Dispos 37 1904 1915 19541827 10.1124/dmd.109.027524 1:CAS:528:DC%2BD1MXhtVOrsrbI
35. FJ Staal SW Ela M Roederer MT Anderson LA Herzenberg 1992 Glutathione deficiency and human immunodeficiency virus infection Lancet 339 909 912 1348307 10.1016/0140-6736(92)90939-Z 1:CAS:528:DyaK38XltV2nurw%3D
36. SR Steinhubl WA Tan JM Foody EJ Topol 1999 Incidence and clinical course of thrombotic thrombocytopenic purpura due to ticlopidine following coronary stenting. EPISTENT Investigators. Evaluation of Platelet IIb/IIIa Inhibitor for Stenting JAMA 281 806 810 10071001 10.1001/jama.281.9.806 1:CAS:528: DyaK1MXhvVKrt78%3D (Pubitemid 29113740)
37. H Takikawa 2005 Lessons from ticlopidine-induced liver injury Hepatol Res 33 193 194 16112899 10.1016/j.hepres.2005.06.009 (Pubitemid 41794205)
38. MH Tsai SL Tsai TC Chen YF Liaw 2000 Ticlopidine-induced cholestatic hepatitis with anti-nuclear antibody in serum J Formos Med Assoc 99 866 869 11155780 1:STN:280:DC%2BD3M%2Fptlamug%3D%3D
39. T Usui M Mise T Hashizume M Yabuki S Komuro 2009 Evaluation of the potential for drug-induced liver injury based on in vitro covalent binding to human liver proteins Drug Metab Dispos 37 2383 2392 19720731 10.1124/dmd.109.028860 1:CAS:528:DC%2BD1MXhsFajtr7K
40. SV van Zanten CW McCormic 1996 Antinuclear antibody-positive ticlopidine-induced hepatitis Can J Gastroenterol 10 231 232
41. T Watanabe H Sagisaka S Arakawa Y Shibaya M Watanabe I Igarashi K Tanaka S Totsuka W Takasaki S Manabe 2003 A novel model of continuous depletion of glutathione in mice treated with l-buthionine (S, R)-sulfoximine J Toxicol Science 28 455 463 10.2131/jts.28.455 1:CAS:528:DC%2BD2cXhvFegsr4%3D (Pubitemid 38133224)
42. K Yoneda R Iwamura H Kishi Y Mizukami K Mogami S Kobayashi 2004 Identification of the active metabolite of ticlopidine from rat in vitro metabolites Br J Pharmacol 142 551 557 15148251 10.1038/sj.bjp.0705808 1:CAS:528:DC%2BD2cXltlejtLY%3D (Pubitemid 38869869)
43. SF Zhou JP Liu B Chowbay 2009 Polymorphism of human cytochrome P450 enzymes and its clinical impact Drug Metab Rev 41 89 295 19514967 10.1080/03602530902843483 1:CAS:528:DC%2BD1MXnsVags78%3D