Metabolism-dependent hepatotoxicity of amodiaquine in glutathione-depleted mice

Archives of Toxicology

Volumn 83, Issue 7, 2009, Pages 701-707

  Shimizu, Shinji ^a   Atsumi, Ryo ^a   Itokawa, Kenichi ^a   Iwasaki, Masaru ^a   Aoki, Takanori ^a   Ono, Chiho ^a   Izumi, Takashi ^a   Sudo, Kenichi ^a   Okazaki, Osamu ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

Amodiaquine; Covalent binding; Glutathione; Hepatotoxicity; Idiosyncratic; L Buthionine S,R sulfoxinine; R sulfoxinine

Indexed keywords

ALANINE AMINOTRANSFERASE; AMINOBENZOTRIAZOLE; AMODIAQUINE; BENZOTRIAZOLE DERIVATIVE; BUTHIONINE SULFOXIMINE; CYTOCHROME P450; GLUTATHIONE; LIVER PROTEIN; UNCLASSIFIED DRUG;

ALANINE AMINOTRANSFERASE BLOOD LEVEL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; COVALENT BOND; DRUG METABOLISM; ENZYME ACTIVITY; ISOTOPE LABELING; LIVER NECROSIS; LIVER TOXICITY; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; RISK FACTOR;

ALANINE TRANSAMINASE; AMODIAQUINE; ANIMALS; ANTIMALARIALS; BUTHIONINE SULFOXIMINE; DISEASE MODELS, ANIMAL; DRUG INTERACTIONS; ENZYME INHIBITORS; GLUTATHIONE; HEPATITIS, TOXIC; LETHAL DOSE 50; LIVER DISEASES; MALE; MICE; MICE, INBRED BALB C; MODELS, BIOLOGICAL;

ANIMALIA; MUS;

EID: 67650762537     PISSN: 03405761     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00204-009-0436-9     Document Type: Article

References (28)

1. AF Boyne GL Ellman 1972 A methodology for analysis of tissue sulfhydryl components Anal Biochem 46 639 653 10.1016/0003-2697(72)90335-1
2. JB Clarke JL Maggs NR Kitteringham BK Park 1990 Immunogenicity of amodiaquine in the rat Int Arch Allergy Appl Immunol 91 335 342 (Pubitemid 20295975)
3. JB Clarke K Neftel NR Kitteringham BK Park 1991 Detection of antidrug IgG antibodies in patients with adverse drug reactions to amodiaquine Int Arch Allergy Appl Immunol 95 4 369 375
4. SR Davis EP Quinlivan PW Stacpoole JF Gregory 3rd 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 (Pubitemid 43228288)
5. R Drew JO Miners 1984 The effects of buthionine sulfoximine (BSO) on glutathione depletion and xenobiotic biotransformation Biochem Pharmacol 33 2989 2994 10.1016/0006-2952(84)90598-7
6. 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 (Pubitemid 10230219)
7. AC Harrison NR Kitteringham JB Clarke BK Park 1992 The mechanism of bioactivation and antigen formation of amodiaquine in the rat Biochem Pharmacol 43 1421 1430 10.1016/0006-2952(92)90198-R
8. 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 10.1016/S0024-3205(00)00722-0
9. C Ip 1984 Comparative effects of antioxidants on enzymes involved in glutathione metabolism Life Sci 34 2501 2506 10.1016/0024-3205(84)90287-X
10. H Jewell JL Maggs AC Harrison PM O'Neill JE Ruscoe B Park 1995 Role of hepatic metabolism in the bioactivation and detoxication of amodiaquine Xenobiotica 25 199 217
11. BH Lauterburg ME Velez 1988 Glutathione deficiency in alcoholics: risk factor for paracetamol hepatotoxicity Gut 2 1153 1157 10.1136/gut.29.9.1153 (Pubitemid 18227046)
12. N Masubuchi C Makino N Murayama 2007 Prediction of in vivo potential for metabolic activation of drugs into chemically reactive intermediate: correlation of in vitro and in vivo generation of reactive intermediates and in vitro glutathione conjugate formation in rats and humans Chem Res Toxicol 20 455 464 10.1021/tx060234h
13. P Matzinger 2002 The danger model: a renewed sense of self Science 296 301 305 10.1126/science.1071059
14. 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
15. T Mizutani Y Irie K Nakanishi 1994 Styrene-induced hepatotoxicity in mice depleted of glutahione Res Commun Mol Pathol Pharmacol 86 361 374
16. T Mizutani Y Nakahori K Yamamoto 1994 p-Dichlorobenzene-induced hepatotoxicity in mice depleted of glutathione treated with buthionine sulfoximine Toxicology 94 57 67 10.1016/0300-483X(94)90028-0
17. 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 (Pubitemid 29225009)
18. 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 10.1016/0272-0590(92)90026-E
19. 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 10.1161/01.CIR.0000019739.66514.1E
20. PA Phillips-Howard LJ West 1990 Serious adverse drug reactions to pyrimethamine-sulphadoxine, pyrimethamine-dapsone and to amodiaquine in Britain J R Soc Med 83 82 85 (Pubitemid 20159350)
21. JM Raymond F Dumas C Baldit P Couzigou C Beraud M Amouretti 1989 Fatal acute hepatitis due to amodiaquine J Clin Gastroenterol 11 602 603 10.1097/00004836-198910000-00034
22. RTECS (1985-1986) Registry of toxic effects of chemical substances. RTECS database (available at http://csi.micromedex.com/ )
23. 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 10.1016/0003-2697(68)90092-4
24. S Tafazoli PJ O'Brien 2009 Amodiaquine-induced oxidative stress in a hepatocyte inflammation model Toxicology 256 101 109 10.1016/j.tox.2008.11.006
25. J Uetrecht 1999 New concepts in immunology relevant to idiosyncratic drug reactions: the "danger hypothesis" and innate immune system Chem Res Toxicol 12 387 395 10.1021/tx980249i
26. 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 Sci 28 455 463 10.2131/jts.28.455
27. WM Watkins DG Sixsmith HC Spencer DA Boriga DM Kariuki T Kipingor DK Koech 1984 Effectiveness of amodiaquine as treatment for chloroquine-resistant Plasmodium falciparum infections in Kenya Lancet 8373 357 359 10.1016/S0140-6736(84)90410-0 (Pubitemid 14183278)
28. PA Winstanley AM Breckenridge 1987 Currently important antimalarial drugs Ann Trop Med Parasitol 81 5 619 627 (Pubitemid 18077356)