Mechanism-based inhibition of CYP450: An indicator of drug-induced hepatotoxicity

Current Drug Metabolism

Volumn 14, Issue 9, 2013, Pages 921-945

  Feng, Shan ^a   He, Xin ^a  

^a TIANJIN UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

CYP450; CYP450 RNA or protein induction; GSH depletion; Hepatotoxicity; Immune response; Mechanism based inhibition; Reactive metabolites

Indexed keywords

AMIODARONE; AMPRENAVIR; ANGELICIN; BERGAPTEN; CARBON DISULFIDE; CLOPIDOGREL; CLOZAPINE; CYTOCHROME P450; DICLOFENAC; DIHYDRALAZINE; DISULFIRAM; FLUOXETINE; FURAN DERIVATIVE; HALOTHANE; HUMAN IMMUNODEFICIENCY VIRUS PROTEINASE INHIBITOR; IRINOTECAN; ISONIAZID; METHOXSALEN; NEFAZODONE; PAROXETINE; PSORALEN; RITONAVIR; TACRINE; TAMOXIFEN; THIAMAZOLE; TICLOPIDINE; TIENILIC ACID; UNINDEXED DRUG; VERAPAMIL; ZILEUTON;

AGRANULOCYTOSIS; ALANINE AMINOTRANSFERASE BLOOD LEVEL; ALLERGIC REACTION; ALZHEIMER DISEASE; ANXIETY DISORDER; ARTICLE; ASTHMA; BREAST CANCER; CELL STRESS; CHOLESTATIC HEPATITIS; COVALENT BOND; DEPRESSION; DRUG MECHANISM; DRUG METABOLISM; HEPATITIS; HLA SYSTEM; HUMAN; HYPERTRANSAMINASEMIA; IMMUNE RESPONSE; IN VITRO STUDY; JAUNDICE; LIVER INJURY; LIVER NECROSIS; LIVER TOXICITY; MACROMOLECULE; METABOLITE; NEUTROPENIA; NONHUMAN; OBSESSIVE COMPULSIVE DISORDER; OXIDATIVE STRESS; PANIC; PROTEIN DEPLETION; PROTEIN EXPRESSION; QUANTITATIVE ANALYSIS; SCHIZOPHRENIA; SIDE EFFECT; SUICIDE SUBSTRATE; TOXIC HEPATITIS;

ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; DRUG-INDUCED LIVER INJURY; DRUG-RELATED SIDE EFFECTS AND ADVERSE REACTIONS; HUMANS; PHARMACEUTICAL PREPARATIONS;

EID: 84887886007     PISSN: 13892002     EISSN: 18755453     Source Type: Journal    
DOI: 10.2174/138920021131400114     Document Type: Article

References (229)

1. Björnsson, E. Review article: drug-induced liver injury in clinical practice. Aliment Pharmacol. Ther., 2010, 32, 3-13.
2. Amacher, D.E. The primary role of hepatic metabolism in idiosyncratic drug-induced liver injury. Expert. Opin. Drug. Metab. Toxicol., 2012, 8, 335-347.
3. Zhou, S.; Chan, E.; Duan, W.; Huang, M.; Chen, Y.Z. Drug bioactivation, covalent binding to target proteins and toxicity relevance. Drug Metab. Rev., 2005, 37, 41-213.
4. Zhou, S. Separation and detection methods for covalent drugprotein adducts. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 2003, 797, 63-90.
5. Takakusa, H.; Masumoto, H.; Mitsuru, A.; Okazaki, O.; Sudo, K. Markers of electrophilic stress caused by chemically reactive metabolites in human hepatocytes. Drug Metab. Dispos., 2008, 36, 816-823.
6. Usui, T.; Mise, M.; Hashizume, T.; Yabuki, M.; Komuro, S. Evaluation of the potential for drug-induced liver injury based on in vitro covalent binding to human liver proteins. Drug Metab. Dispos., 2009, 37, 2383-2392.
7. Obach, R.S.; Kalgutkar, A.S.; Soglia, J.R.; Zhao, S.X. Can in vitro metabolism-dependent covalent binding data in liver microsomes distinguish hepatotoxic from nonhepatotoxic drugs? An analysis of 18 drugs with consideration of intrinsic clearance and daily dose. Chem. Res. Toxicol., 2008, 21, 1814-1822.
8. Kalgutkar, A.S.; Didiuk, M.T. Structural alerts, reactive metabolites, and protein covalent binding: how reliable are these attributes as predictors of drug toxicity? Chem. Biodivers., 2009, 6, 2115-2137.
9. Tang, W.; Lu, A.Y. Metabolic bioactivation and drug-related adverse effects: current status and future directions from a pharmaceutical research perspective. Drug Metab. Rev., 2010, 42, 225-249.
10. Lammert, C.; Bjornsson, E.; Niklasson, A.; Chalasani, N. Oral medications with significant hepatic metabolism at higher risk for hepatic adverse events. Hepatology, 2010, 51, 615-620.
11. McConn, D.J.; Zhao, Z. Integrating in vitro kinetic data from compounds exhibiting induction, reversible inhibition and mechanismbased inactivation: in vitro study design. Curr. Drug Metab., 2004, 5, 141-146.
12. Nakayama, S.; Takakusa, H.; Watanabe, A.; Miyaji, Y.; Suzuki, W.; Sugiyama, D.p.; Shiosakai, K.; Honda, K.; Okudaira, N.; Izumi, T.; Okazaki, O. Combination of GSH trapping and timedependent inhibition assays as a predictive method of drugs generating highly reactive metabolites. Drug Metab. Dispos., 2011, 39, 1247-1254.
13. Miyaji, Y.; Makino, C.; Kurihara, A.; Suzuki, W.; Okazaki, O. In vitro evaluation of the potential for drug-induced toxicity based on (35)S-labeled glutathione adduct formation and daily dose. Bioanalysis, 2012, 4, 263-269.
14. Obermayer-Straub, P.; Strassburg, C.P.; Manns, M.P. Target proteins in human autoimmunity: cytochromes P450 and UDP-glucuronosyltransferases. Can. J. Gastroenterol., 2000, 14, 429-439.
15. Boitier, E.; Beaune, P. Xenobiotic-metabolizing enzymes as autoantigens in human autoimmune disorders. An update. Clin. Rev. Allergy Immunol., 2000, 18, 215-239.
16. Masubuchi, Y.; Horie, T. Mechanism-based inactivation of cytochrome P450s 1A2 and 3A4 by dihydralazine in human liver microsomes. Chem. Res. Toxicol., 1999, 12, 1028-1032.
17. Belloc, C.; Gauffre, A.; Andre, C.; Beaune, P.H. Epitope mapping of human CYP1A2 in dihydralazine-induced autoimmune hepatitis. Pharmacogenetics, 1997, 7, 181-186.
18. Pariente, E.A.; Pessayre, D.; Bernuau, J.; Degott, C.; Benhamou, J.P. Dihydralazine hepatitis: report of a case and review of the literature. Digestion, 1983, 27, 47-52.
19. Machnik, G.; Bergert A.; Justus, J.; Kunze P.; Müller, R.; Reinhardt, M.; Schulz, H.; Stein, G.; Thiele, R.; Drug-induced hepatitis after dihydralazine treatment with fatal consequences. Zentralbl Allg. Pathol., 1988, 134, 167-177.
20. Nataf, J.; Bernuau, J.; Larrey, D.; Guillin, M.C.; Rueff, B.; Benhamou J.P. A new anti-liver microsome antibody: a specific marker of dihydralazine-induced hepatitis. Gastroenterology, 1986, 90, 1751.
21. Bourdi, M.; Gautier, J.C.; Mircheva, J.; Larrey, D.; Guillouzo, A.; Andre, C.; Belloc, C.; Beaune, P. H. Anti-liver microsomes autoantibodies and dihydralazine-induced hepatitis: specificity of autoantibodies and inductive capacity of the drug. Mol. Pharmacol., 1992, 42, 280-285.
22. Bourdi, M.; Tinel, M.; Beaune, P.H.; Pessayre, D. Interactions of dihydralazine with cytochromes P4501A: a possible explanation for the appearance of anti-cytochrome P4501A2 autoantibodies. Mol. Pharmacol., 1994, 45, 1287-1295.
23. Fong, S.Y.; Au Yeung, K,L,; Tosh, J.M.; Wing, Y.K. Clozapineinduced toxic hepatitis with skin rash. J. Psychopharmacol., 2005, 19, 107.
24. Erdogan, A.; Kocabasoglu, N.; Yalug, I.; Ozbay, G.; Senturk, H. Management of marked liver enzyme increase during clozapine treatment: a case report and review of the literature. Int. J. Psychiatry Med., 2004, 34, 83-89.
25. Chang, A.; Krygier, D.S.; Chatur, N.; Yoshida, E.M. Clozapineinduced fatal fulminant hepatic failure: a case report. Can. J. Gastroenterol., 2009, 23, 376-378.
26. Pirmohamed, M.; Williams, D.; Madden, S.; Templeton, E.; Park, B.K. Metabolism and bioactivation of clozapine by human liver in vitro. J. Pharmacol. Exp. Ther., 1995, 272, 984-990.
27. Eiermann, B.; Engel, G.; Johansson, I.; Zanger, U.M.; Bertilsson, L. The involvement of CYP1A2 and CYP3A4 in the metabolism of clozapine. Br. J. Clin. Pharmacol., 1997, 44, 439-446.
28. Tugnait, M.; Hawes E.M.; McKay G.; Eichelbaum, M.; Midha, K.K. Characterization of the human hepatic cytochromes P450 involved in the in vitro oxidation of clozapine. Chem. Biol. Interact., 1999, 118,171-189.
29. Watanabe, A.; Nakamura, K.; Okudaira, N.; Okazaki, O.; Sudo, K.I. Risk assessment for drug-drug interaction caused by metabolism-based inhibition of CYP3A using automated in vitro assay systems and its application in the early drug discovery process. Drug Metab. Dispos., 2007, 35, 1232-1238.
30. Lu, Y.; Meng, Q.; Zhang, G.; Bei, X. Clozapine-induced hepatotoxicity in rat hepatocytes by gel entrapment and monolayer culture. Toxicol In vitro., 2008, 22,1754-1760.
31. Masubuchi, N.; Makino, C.; Murayama, N. 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., 2007, 20, 455-464.
32. Choi, S. Nefazodone (Serzone) withdrawn because of hepatotoxicity. CMAJ., 2003, 169, 1187.
33. von Moltke, L.L.; Greenblatt, D.J.; Granda, B.W.; Grassi, J.M.; Schmider, J.; Harmatz, J.S.; Shader, R.I. Nefazodone, metachlorophenylpiperazine, and their metabolites in vitro: cytochromes mediating transformation, and P450-3A4 inhibitory actions. Psychopharmacology, 1999, 145, 113-122.
34. Kalgutkar A.S.; Vaz A.D.; Lame M.E.; Henne K.R.; Soglia J.; Zhao S.X.; Abramov Y.A.; Lombardo F.; Collin C.; Hendsch Z.S.; Hop C.E. Bioactivation of the nontricyclic antidepressant nefazodone to a reactive quinone-imine species in human liver microsomes and recombinant cytochrome P450 3A4. Drug Metab. Dispos., 2005, 33, 243-253.
35. Kalgutkar, A.S.; Obach, R.S.; Maurer, T.S. Mechanism-based inactivation of cytochrome P450 enzymes: chemical mechanisms, structure-activity relationships and relationship to clinical drugdrug interactions and idiosyncratic adverse drug reactions. Curr. Drug Metab., 2007, 8, 407-447.
36. Dykens, J.A.; Jamieson, J.D.; Marroquin, L.D.; Nadanaciva, S.; Xu, J.J.; Dunn, M.C.; Smith, A.R.; Will, Y. In vitro assessment of mitochondrial dysfunction and cytotoxicity of nefazodone, trazodone, and buspirone. Toxicol. Sci., 2008,103, 335-345.
37. Dykens J.A.; Jamieson J.D.; Marroquin L.D.; Nadanaciva S.; Xu J.J.; Dunn M.C.; Smith A.R.; Will Y. In vitro assessment of mitochondrial dysfunction and cytotoxicity of nefazodone, trazodone, and buspirone. Toxicol. Sci., 2008, 103, 335-345.
38. Kim, J.A.; Han, E.; Eun, C.J.; Tak, Y.K.; Song, J.M. Real-time concurrent monitoring of apoptosis, cytosolic calcium, and mitochondria permeability transition for hypermulticolor high-content screening of drug-induced mitochondrial dysfunction-mediated hepatotoxicity. Toxicol. Lett., 2012, 214, 175-181.
39. Kostrubsky, S.E.; Strom, S.C.; Kalgutkar, A.S.; Kulkarni, S.; Atherton, J.; Mireles, R.; Feng, B.; Kubik, R.; Hanson, J.; Urda, E.; Mutlib, A.E. Inhibition of hepatobiliary transport as a predictive method for clinical hepatotoxicity of nefazodone. Toxicol. Sci., 2006, 90, 451-459.
40. Haduch, A.; Bromek, E.; Daniel, W.A. The effect of psychotropic drugs on cytochrome P450 2D (CYP2D) in rat brain. Eur. J. Pharmacol., 2011, 651, 51-58.
41. Gan, T.J. Diclofenac: an update on its mechanism of action and safety profile. Curr. Med. Res. Opin., 2010, 26, 1715-1731.
42. Laine, L.; Goldkind, L.; Curtis, S.P.; Connors, L.G.; Yanqiong, Z.; Cannon, C.P. How common is diclofenac-associated liver injury? Analysis of 17,289 arthritis patients in a long-term prospective clinical trial. Am. J. Gastroenterol., 2009, 104, 356-362.
43. Bhogaraju, A.; Nazeer, S.; A.L-Baghdadi, Y.; Rahman, M.; Wrestler, F.; Patel, N. Diclofenac-associated hepatitis. South Med. J., 1999, 92, 711-713.
44. Shen, S.; Hargus, S.J.; Martin, B.M.; Pohl, L.R. Cytochrome P4502C11 is a target of diclofenac covalent binding in rats. Chem. Res. Toxicol., 1997, 10, 420-423.
45. Masubuchi, Y.; Ose, A.; Horie, T. Mechanism-based inactivation of CYP2C11 by diclofenac. Drug Metab. Dispos., 2001, 29, 1190-1195.
46. Masubuchi, Y.; Ose, A.; Horie T. Diclofenac-induced inactivation of CYP3A4 and its stimulation by quinidine. Drug Metab. Dispos., 2002, 30, 1143-1148.
47. Gómez-Lechón, M.J.; Ponsoda, X.; O'Connor, E.; Donato, T.; Castell, J.V.; Jover, R. Diclofenac induces apoptosis in hepatocytes by alteration of mitochondrial function and generation of ROS. Biochem. Pharmacol., 2003, 66, 2155-2167.
48. Gómez-Lechón, M.J.; Ponsoda, X.; O'Connor, E.; Donato, T.; Jover, R.; Castell, J.V. Diclofenac induces apoptosis in hepatocytes. Toxicol In vitro., 2003, 17, 675-680.
49. Pourahmad, J.; Mortada, Y.; Eskandari, M.R. and Shahraki, J. Involvement of Lysosomal Labilisation and Lysosomal/mitochondrial Cross-Talk in Diclofenac Induced Hepatotoxicity. Iran J. Pharm. Res., 2011, 10, 877-887.
50. Boelsterli, U.A. Diclofenac-induced liver injury: a paradigm of idiosyncratic drug toxicity. Toxicol. Appl. Pharmacol., 2003, 192, 307-322.
51. Aithal, G.P.; Ramsay, L.; Daly, A.K.; Sonchit, N.; Leathart, J.B.; Alexander, G.; Kenna, J.G.; Caldwell, J.; Day, C.P. Hepatic adducts, circulating antibodies, and cytokine polymorphisms in patients with diclofenac hepatotoxicity. Hepatology, 2004, 39, 1430-1440.
52. Yano, A.; Higuchi, S.; Tsuneyama, K.; Fukami, T.; Nakajima, M.; Yokoi, T. Involvement of immune-related factors in diclofenacinduced acute liver injury in mice. Toxicology, 2012, 293, 107-114.
53. Higuchi, S.; Kobayashi, M.; Yoshikawa, Y.; Tsuneyama, K.; Fukami, T.; Nakajima, M.; Yokoi, T. IL-4 mediates dicloxacillininduced liver injury in mice. Toxicol. Lett., 2011, 200, 139-145.
54. Gardener, I.; Bergin, P.; Stening, P.; Kenna, J.G.; Caldwell, J. Immunochemical detection of covalently modified protein adducts in livers of rats treated with methyleugenol. Chem. Res. Toxicol., 1996, 9,713-721.
55. Pan, S.Y.; Guo, B.F.; Zhang, Y.; Yu, Q.; Yu, Z.L.; Dong, H.; Ye, Y.; Han, Y.F.; Ko, K.M. Tacrine treatment at high dose suppresses the recognition memory in juvenile and adult mice with attention to hepatotoxicity. Basic Clin. Pharmacol. Toxicol., 2011, 108, 421-427.
56. Meng, Q.; Ru, J.; Zhang, G.; Shen, C.; Schmitmeier, S.; Bader, A. Re-evaluation of tacrine hepatotoxicity using gel entrapped hepatocytes. Toxicol. Lett., 2007, 168, 140-147.
57. Alfirevic, A.; Mills, T.; Carr, D.; Barratt, B.J.; Jawaid, A.; Sherwood, J.; Smith, J.C.; Tugwood, J.; Hartkoorn, R.; Owen, A.; Park, K.B.; Pirmohamed, M. Tacrine-induced liver damage: an analysis of 19 candidate genes. Pharmacogenet. Genomics, 2007, 17, 1091-1100.
58. Peng, J.Z.; Remmel, R.P.; Sawchuk, R.J. Inhibition of murine cytochrome P4501A by tacrine: in vitro studies. Drug Metab. Dispos., 2004, 32, 805-812.
59. Pool, W.F.; Woolf, T.F; Reily, M.D.; Caprathe, B.W.; Emmerling, M.R.; Jaen, J.C. Identification of a 3-hydroxylated tacrine metabolite in rat and man: metabolic profiling implications and pharmacology. J. Med..Chem., 1996, 39, 3014-3018.
60. Pool, W.F.; Reily, M.D.; Bjorge, S.M.; Woolf, T.F. Metabolic disposition of the cognition activator tacrine in rats, dogs, and humans. Species comparisons. Drug Metab. Dispos., 1997, 25, 590-597.
61. Spaldin, V.; Madden, S.; Pool, W.F.; Woolf, T.F.; Park, B.K. The effect of enzyme inhibition on the metabolism and activation of tacrine by human liver microsomes. Br. J. Clin. Pharmacol., 1994, 38, 15-22.
62. Woolf, T.F.; Pool, W.F.; Bjorge, S.M.; Chang, T.; Goel, O.P.; Purchase, C.F.; Schroeder, M.C.; Kunze, K.L.; Trager, W.F. Bioactivation and irreversible binding of the cognition activator tacrine using human and rat liver microsomal preparations. Species difference. Drug Metab. Dispos., 1993, 21, 874-882.
63. Simon, T.; Becquemont, L.; Mary-Krause, M.; de Waziers, I, Beaune, P.; Funck-Brentano, C.; Jaillon, P. Combined glutathioneS-transferase M1 and T1 genetic polymorphism and tacrine hepatotoxicity. Clin. Pharmacol. Ther., 2000, 67, 432-437.
64. Lagadic-Gossmann, D.; Rissel, M.; Le Bot, M.A.; Guillouzo, A. Toxic effects of tacrine on primary hepatocytes and liver epithelial cells in culture. Cell Biol. Toxicol., 1998, 14, 361-373.
65. Osseni, R.A.; Debbasch, C.; Christen, M.O.; Rat, P.; Warnet, J.M. Tacrine-induced Reactive Oxygen Species in a Human Liver Cell Line: The Role of Anethole Dithiolethione as a Scavenger. Toxicol. In vitro., 1999, 13, 683-688.
66. Galisteo, M.; Rissel, M.; Sergent, O.; Chevanne, M.; Cillard, J.; Guillouzo, A.; Lagadic-Gossmann, D. Hepatotoxicity of tacrine: occurrence of membrane fluidity alterations without involvement of lipid peroxidation. J. Pharmacol. Exp. Ther., 2000, 294,160-167.
67. Sinz, M.W.; Woolf, T,F. Characterization of the induction of rat microsomal cytochrome P450 by tacrine. Biochem. Pharmacol., 1997, 54, 425-427.
68. Metushi, I.G.; Cai, P.; Zhu, X.; Nakagawa, T.; Uetrecht, J.P. A fresh look at the mechanism of isoniazid-induced hepatotoxicity. Clin. Pharmacol. Ther., 2011, 89, 911-914.
69. Sarich, T.C.; Adams, S.P.; Petricca, G. and Wright, J.M. Inhibition of isoniazid-induced hepatotoxicity in rabbits by pretreatment with an amidase inhibitor. J. Pharmacol. Exp. Ther., 1999, 289, 695-702.
70. Tafazoli, S.; Mashregi, M.; O'Brien, P.J. Role of hydrazine in isoniazid-induced hepatotoxicity in a hepatocyte inflammation model. Toxicol. Appl. Pharmacol., 2008, 229, 94-101.
71. Bhadauria, S.; Mishra, R.; Kanchan, R.; Tripathi, C.; Srivastava, A.; Tiwari, A.; Sharma, S. Isoniazid-induced apoptosis in HepG2 cells: generation of oxidative stress and Bcl-2 down-regulation. Toxicol. Mech. Methods, 2010, 20, 242-251.
72. Zhang, B.; Sun, S.; Shen, L.; Zu, X.; Chen, Y.; Hao, J.; Huang, X.; Feng, F. DNA methylation in the rat livers induced by low dosage isoniazid treatment. Environ. Toxicol. Pharmacol., 2011, 32, 486-490.
73. Zhang, Z.H.; Tang, J.H.; Zhan, Z.L.; Zhang, X.L.; Wu, H.H.; Hou, Y.N. Cellular toxicity of isoniazid together with rifampicin and the metabolites of isoniazid on QSG-7701 hepatocytes. Asian Pac. J. Trop. Med., 2012, 5, 306-309.
74. Wen, X.; Wang, J.S.; Neuvonen, P.J.; Backman, J.T. Isoniazid is a mechanism-based inhibitor of cytochrome P450 1A2, 2A6, 2C19 and 3A4 isoforms in human liver microsomes. Eur. J. Clin. Pharmacol., 2002, 57, 799-804.
75. Polasek, T.M.; Elliot, D.J.; Somogyi, A.A.; Gillam, E.M.; Lewis, B.C.; Miners, J.O. An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid. Br. J. Clin. Pharmacol., 2006, 61, 570-584.
76. Shen, C.; Zhang, H.; Zhang, G.; Meng, Q. Isoniazid-induced hepatotoxicity in rat hepatocytes of gel entrapment culture. Toxicol. Lett., 2006, 167, 66-74.
77. Zhai, Q.; Lu, S.R.; Lin, Y.; Yang, Q.L. and Yu, B. Oxidative stress potentiated by diallylsulfide, a selective CYP2E1 inhibitor, in isoniazid toxic effect on rat primary hepatocytes. Toxicol. Lett., 2008, 183, 95-98.
78. Yue, J.; Peng, R.; Chen, J.; Liu, Y.; Dong, G. Effects of rifampin on CYP2E1-dependent hepatotoxicity of isoniazid in rats. Pharmacol. Res., 2009, 59, 112-119.
79. Fukino, K.; Sasaki, Y.; Hirai, S.; Nakamura, T.; Hashimoto, M.; Yamagishi, F.; Ueno, K. Effects of N-acetyltransferase 2 (NAT2), CYP2E1 and Glutathione-S-transferase (GST) genotypes on the serum concentrations of isoniazid and metabolites in tuberculosis patients. J. Toxicol. Sci., 2008, 33, 187-195.
80. Yue, J.; Peng, R.X.; Yang, J.; Kong, R.; Liu, J. CYP2E1 mediated isoniazid-induced hepatotoxicity in rats. Acta Pharmacol. Sin., 2004, 25, 699-704.
81. Rao, U.; Agarwal, A. Amiodarone-induced acute hepatotoxicity. Eur. J. Clin. Pharmacol., 2012, 68, 449-450.
82. Verhovez, A.; Elia, F.; Riva, A.; Ferrari, G.; Aprà, F. Acute liver injury after intravenous amiodarone: a case report. Am. J. Emerg. Med., 2011, 29, 843.e5-6.
83. Kicker, J.S.; Haizlip, J.A.; Buck, M.L. Hepatotoxicity after continuous amiodarone infusion in a postoperative cardiac infant. J. Pediatr. Pharmacol. Ther., 2012, 17, 189-195.
84. Ishida, S.; Sugino, M.; Hosokawa, T.; Sato, T.; Furutama, D.; Fukuda, A.; Kimura, F.; Kuwabara, H.; Shibayama, Y.; Hanafusa, T. Amiodarone-induced liver cirrhosis and parkinsonism: a case report. Clin. Neuropathol., 2010, 29, 84-88.
85. Lahbabi, M.; Aqodad, N.; Ibrahimi, A.; Lahlou, M.; Aqodad, H. Acute hepatitis secondary to parenteral amiodarone does not preclude subsequent oral therapy. World J. Hepatol., 2012, 4, 196-198.
86. Fromenty, B.; Fisch, C.; Labbe, G.; Degott, C.; Deschamps, D.; Berson, A.; Letteron, P.; Pessayre, D. Amiodarone inhibits the mitochondrial beta-oxidation of fatty acids and produces microvesicular steatosis of the liver in mice. J. Pharmacol. Exp. Ther., 1990, 255, 1371-1376.
87. Waldhauser, K.M.; Török, M.; Ha, H.R.; Thomet, U.; Konrad, D.; Brecht, K.; Follath, F.; Krähenbühl, S. Hepatocellular toxicity and pharmacological effect of amiodarone and amiodarone derivatives. J. Pharmacol. Exp. Ther., 2006, 319, 1413-1423.
88. Serviddio, G.; Bellanti, F.; Giudetti, A.M.; Gnoni, G.V.; Capitanio, N.; Tamborra, R.; Romano, A.D.; Quinto, M.; Blonda, M.; Vendemiale, G.; Altomare, E. Mitochondrial oxidative stress and respiratory chain dysfunction account for liver toxicity during amiodarone but not dronedarone administration. Free Radic. Biol. Med., 2011, 51, 2234-2242.
89. McCarthy, T.C.; Pollak, P.T.; Hanniman, E.A.; Sinal, C.J. Disruption of hepatic lipid homeostasis in mice after amiodarone treatment is associated with peroxisome proliferator-activated receptoralpha target gene activation. J. Pharmacol. Exp. Ther., 2004, 311, 864-873.
90. Golli-Bennour, E.E.; Bouslimi, A.; Zouaoui, O.; Nouira, S.; Achour, A.; Bacha, H. Cytotoxicity effects of amiodarone on cultured cells. Exp. Toxicol. Pathol., 2012, 64, 425-430.
91. Ha, H.R.; Bigler, L.; Wendt, B.; Maggiorini, M.; Follath, F. Identification and quantitation of novel metabolites of amiodarone in plasma of treated patients. Eur. J. Pharm. Sci., 2005, 24, 271-279.
92. Ohyama, K.; Nakajima, M.; Suzuki, M.; Shimada, N.; Yamazaki, H.; Yokoi, T. Inhibitory effects of amiodarone and its Ndeethylated metabolite on human cytochrome P450 activities: prediction of in vivo drug interactions. Br. J. Clin. Pharmacol., 2000, 49, 244-253.
93. Polasek, T.M.; Elliot, D.J.; Lewis, B.C.; Miners, J.O. Mechanismbased inactivation of human cytochrome P4502C8 by drugs in vitro. J. Pharmacol. Exp. Ther., 2004, 311, 996-1007.
94. Zahno, A.; Brecht, K.; Morand, R.; Maseneni, S.; Török, M.; Lindinger, P.W.; Krähenbühl, S. The role of CYP3A4 in amiodarone-associated toxicity on HepG2 cells. Biochem. Pharmacol., 2011, 81, 432-441.
95. Lu, J.; Jones, A.D.; Harkema, J.R.; Roth, R.A.; Ganey, P.E. Amiodarone exposure during modest inflammation induces idiosyncrasylike liver injury in rats: role of tumor necrosis factor-alpha. Toxicol. Sci., 2012, 125, 126-133.
96. Fontana, E.; Dansette, P.M.; Poli, S.M. Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity. Curr. Drug Metab., 2005, 6, 413-454.
97. Pinto, A.G.; Wang, Y.H.; Chalasani, N.; Skaar, T.; Kolwankar, D.; Gorski, J.C.; Liangpunsakul, S.; Hamman, M.A.; Arefayene, M.; Hall, S.D. Inhibition of human intestinal wall metabolism by macrolide antibiotics: effect of clarithromycin on cytochrome P450 3A4/5 activity and expression. Clin. Pharmacol. Ther., 2005, 77, 178-188.
98. Fox, J.C.; Szyjkowski, R.S.; Sanderson, S.O.; Levine, R.A. Progressive cholestatic liver disease associated with clarithromycin treatment. J. Clin. Pharmacol., 2002, 42, 676-680.
99. Masiá, M.; Gutiérrez, F.; Jimeno, A.; Navarro, A.; Borrás, J.; Matarredona, J.; Martín-Hidalgo, A. Fulminant hepatitis and fatal toxic epidermal necrolysis (Lyell disease) coincident with clarithromycin administration in an alcoholic patient receiving disulfiram therapy. Arch. Intern. Med., 2002, 162, 474-476.
100. Tietz, A.; Heim, M.H.; Eriksson, U.; Marsch, S.; Terracciano, L.; Krähenbühl, S. Fulminant liver failure associated with clarithromycin. Ann. Pharmacother., 2003, 37, 57-60.
101. Zhou, S.; Yung Chan, S.; Cher Goh, B.; Chan, E.; Duan, W.; Huang, M.; McLeod, H.L. Mechanism-based inhibition of cytochrome P450 3A4 by therapeutic drugs. Clin. Pharmacokinet., 2005, 44, 279-304.
102. Mayhew, B.S.; Jones, D.R.; Hall, S.D. An in vitro model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation. Drug Metab. Dispos., 2000, 28, 1031-1037.
103. Lee, K.S.; Kim, S.K.; Direct and metabolism-dependent cytochrome P450 inhibition assays for evaluating drug-drug interactions. J. Appl. Toxicol. 2013, doi: 10.1002/jat.1720.
104. Cai, Q.; Benson, M.A.; Talbot, T.J.; Devadas, G.; Swanson, H.J.; Olson, J.L.; Kirchner, J.P. Acute hepatitis due to fluoxetine therapy. Mayo Clin. Proc., 1999, 74, 692-694.
105. Ma, B.; Prueksaritanont, T.; Lin, J.H. Drug interactions with calcium channel blockers: possible involvement of metaboliteintermediate complexation with CYP3A. Drug Metab. Dispos., 2000, 28, 125-130.
106. Wang, Y.H.; Jones, D.R.; Hall, S.D. Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab. Dispos., 2004, 32, 259-266.
107. Watanabe, A.; Nakamura, K.; Okudaira, N.; Okazaki, O.; Sudo, K. Risk assessment for drug-drug interaction caused by metabolismbased inhibition of CYP3A using automated in vitro assay systems and its application in the early drug discovery process. Drug Metab. Dispos., 2007, 35, 1232-1238.
108. Odeh, M.; Oliven, A. Verapamil-associated liver injury. Harefuah., 1998, 134, 36-37.
109. Yang, J.; Zhong, J.; Zhou, L.Z.; Hong, T.; Xiao, X.H.; Wen, G.B. Sudden onset agranulocytosis and hepatotoxicity after taking methimazole. Internal Medicine, 2012, 51, 2189-2192.
110. Gallelli, L.; Staltari, O.; Palleria, C.; De Sarro, G.; Ferraro, M. Hepatotoxicity induced by methimazole in a previously healthy patient. Curr. Drug Saf., 2009, 4, 204-206.
111. Woeber, K.A. Methimazole-induced hepatotoxicity. Endocr. Pract., 2002, 8, 222-224.
112. Mizutani, T.; Yoshida, K.; Murakami, M.; Shirai, M.; Kawazoe, S. Evidence for the involvement of N-methylthiourea, a ring cleavage metabolite, in the hepatotoxicity of methimazole in glutathionedepleted mice: structure-toxicity and metabolic studies. Chem. Res. Toxicol., 2000, 13, 170-176.
113. Guo, Z.; Raeissi, S.; White, R.B. and Stevens, J.C. Orphenadrine and methimazole inhibit multiple cytochrome P450 enzymes in human liver microsomes. Drug Metab. Dispos., 1997, 25, 390-393.
114. Mizutani, T.; Murakami, M.; Shirai, M.; Tanaka, M.; Nakanishi, K. Metabolism-dependent hepatotoxicity of methimazole in mice depleted of glutathione. J. Appl. Toxicol., 1999, 19, 193-198.
115. Xie, C.; Zhong, D.F.; Chen, X.Y. Applications of Liquid Chromatography-Tandem Mass Spectrometry to Detection and Characterization of Reactive Metabolites. J. Chinese Mass Spectromet.Soc., 2011, 32, 1-12.
116. Kobayashi, M.; Higuchi, S.; Ide, M.; Nishikawa, S.; Fukami, T.; Nakajima, M.; Yokoi, T. Th2 cytokine-mediated methimazoleinduced acute liver injury in mice. J. Appl. Toxicol., 2012, 32, 823-833.
117. Maseneni, S.; Donzelli, M.; Taegtmeyer, A.B.; Brecht, K.; Krähenbühl, S. Toxicity of clopidogrel and ticlopidine on human myeloid progenitor cells: importance of metabolites. Toxicology, 2012, 299, 139-145.
118. Zapater, P.; Such, J.; Perez-Mateo, M.; Horga, J.F. A new Poisson and Bayesian-based method to assign risk and causality in patients with suspected hepatic adverse drug reactions: a report of two new cases of ticlopidine-induced hepatotoxicity. Drug Saf., 2002, 25, 735-750.
119. Mizushima, M.; Iwata, N.; Fujimoto, T.T.; Ishikawa, K.; Fujimura, K. Patient characteristics in ticlopidine hydrochloride-induced liver injury: Case-control study. Hepatol. Res., 2005, 33, 234-240.
120. Hirata K.; Takagi H.; Yamamoto M.; Matsumoto T.; Nishiya T.; Mori K.; Shimizu S.; Masumoto H.; Okutani Y. Ticlopidineinduced hepatotoxicity is associated with specific human leukocyte antigen genomic subtypes in Japanese patients: a preliminary casecontrol study. Pharmacogenomics J., 2008, 8, 29-33.
121. Tsai, M.H.; Tsai, S.L.; Chen, T.C.; Liaw, Y.F. Ticlopidine-induced cholestatic hepatitis with anti-nuclear antibody in serum. J. Formos Med. Assoc., 2000, 99, 866-869.
122. Pizarro, A.E,; Andrade, R.J.; Garcia-Cortes, M.; Lucena, M.I.; Perez-Moreno, J.M.; Puertas, M.; Sanchez-Martinez, H.; Montero, J.L.; Duran, J.A.; Jimenez, M.; Ruiz-Montero, A.; Soto-Conesa, M.J.; Rodrigo, L.; de Francisco, R.; Alcantara, R.; Camargo, R. Acute hepatitis due to ticlopidine. A report of 12 cases and review of the literature. Rev. Neurol., 2001, 33, 1014-1020.
123. Skurnik, Y.D.; Tchemiak, A.; Edlan, K. and Sthoeger, Z. Ticlopidine-induced cholestatic hepatitis. Ann. Pharmacother., 2003, 37, 371-375.
124. Ariyoshi, N.; Iga, Y.; Hirata, K.; Sato, Y.; Miura, G.; Ishii, I.; Nagamori, S.; Kitada, M. Enhanced susceptibility of HLAmediated ticlopidine-induced idiosyncratic hepatotoxicity by CYP2B6 polymorphism in Japanese. Drug Metab. Pharmacokinet., 2010, 25, 298-306.
125. Ha-Duong, N.T.; Dijols, S.; Macherey, A.C.; Goldstein, J.A.; Dansette, P.M. and Mansuy, D. Ticlopidine as a selective mechanism-based inhibitor of human cytochrome P450 2C19. Biochemistry, 2001, 40, 12112-12122.
126. Nishiya, Y.; Hagihara, K.; Ito, T.; Tajima, M.; Miura, S.; Kurihara, A.; Farid, N.A.; Ikeda, T. Mechanism-based inhibition of human cytochrome P450 2B6 by ticlopidine, clopidogrel, and the thiolactone metabolite of prasugrel. Drug Metab. Dispos., 2009, 37, 589-593.
127. Shimizu, S.; Atsumi, R.; Nakazawa, T.; Izumi, T.; Sudo, K.; Okazaki, O.; Saji, H. Ticlopidine-induced hepatotoxicity in a GSHdepleted rat model. Arch. Toxicol., 2011, 85, 347-353.
128. Beltran-Robles, M.; Marquez Saavedra, E.; Sanchez-Muñoz, D.; Romero-Gomez, M. Hepatotoxicity induced by clopidogrel. J. Hepatol., 2004, 40, 560-562.
129. Ng, J.A.; Goldberg, N.; Tafreshi, M.J. Clopidogrel-induced hepatotoxicity and fever. Pharmacotherapy., 2006, 26, 1023-1026.
130. López-Vicente, J.; Garfia, C.; López-Medrano, F.; Yela, C. Hepatic toxicity and clopidogrel-induced systemic inflammatory response syndrome. Rev. Esp. Cardiol., 2007, 60, 323-324.
131. Kastalli, S.; El Aïdli, S.; Zaïem, A.; ben Abdallah, H.; Daghfous, R. Fatal liver injury associated with clopidogrel. Fundam Clin. Pharmacol., 2010, 24, 433-435.
132. Zhang, H.; Amunugama, H.; Ney, S.; Cooper, N. and Hollenberg, P.F. Mechanism-based inactivation of human cytochrome P450 2B6 by clopidogrel: involvement of both covalent modification of cysteinyl residue 475 and loss of heme. Mol. Pharmacol., 2011, 80, 839-847.
133. Zhang, H.; Lau, W.C.; Hollenberg, P.F. Formation of the thiol conjugates and active metabolite of clopidogrel by human liver microsomes. Mol. Pharmacol., 2012, 82, 302-309.
134. Pariente, E.A.; Andre, C.; Zafrani, E.S.; Metreau, J.M.; Dhumeaux, D.; Berthelot, P. Tienilic acid can induce acute hepatitis, chronic hepatitis and cirrhosis. A report of three cases (author's transl). Gastroenterol. Clin. Biol., 1981, 5, 567-571.
135. Neuberger J.; Williams R. Immune mechanisms in tienilic acid associated hepatotoxicity. Gut, 1989, 30, 515-519.
136. Zuniga, F.I.; Loi, D.; Ling, K.H.; Tang-Liu, D.D. Idiosyncratic reactions and metabolism of sulfur-containing drugs. Expert Opin. Drug Metab. Toxicol., 2012, 8, 467-485.
137. Koen, Y.M.; Sarma, D.; Williams, T.D.; Galeva, N.A.; Obach, R.S.; Hanzlik, R.P. Identification of protein targets of reactive metabolites of tienilic acid in human hepatocytes. Chem. Res. Toxicol., 2012, 25, 1145-1154.
138. Nishiya, T.; Mori, K.; Hattori, C.; Kai, K.; Kataoka, H.; Masubuchi, N.; Jindo, T.; Manabe, S. The crucial protective role of glutathione against tienilic acid hepatotoxicity in rats. Toxicol. Appl. Pharmacol., 2008, 232, 280-291.
139. Mansuy, D. Molecular structure and hepatotoxicity: compared data about two closely related thiophene compounds. J. Hepatol., 1997, 26,22-25.
140. Pacitto, S.R.; Uetrecht, J.P.; Boutros, P.C.; Popovic, M. Changes in gene expression induced by tienilic Acid and sulfamethoxazole: testing the danger hypothesis. J. Immunotoxicol., 2007, 4, 253-266.
141. Lecoeur, S.; Bonierbale, E.; Challine, D.; Gautier, J.C.; Valadon, P.; Dansette, P. M.; Catinot, R.; Ballet, F.; Mansuy, D.; Beaune, P.H. Specificity of in vitro covalent binding of tienilic acid metabolites to human liver microsomes in relationship to the type of hepatotoxicity: comparison with two directly hepatotoxic drugs. Chem. Res. Toxicol., 1994, 7, 434-442.
142. Nishiya, T.; Kato, M.; Suzuki, T.; Maru, C.; Kataoka, H.; Hattori, C.; Mori, K.; Jindo, T.; Tanaka, Y.; Manabe, S. Involvement of cytochrome P450-mediated metabolism in tienilic acid hepatotoxicity in rats. Toxicol. Lett., 2008, 183, 81-89.
143. Watkins, P.B.; Dube, L.M.; Walton-Bowen, K.; Cameron, C.M.; Kasten, L.E. Clinical pattern of zileuton-associated liver injury: results of a 12-month study in patients with chronic asthma. Drug Saf., 2007, 30, 805-815.
144. Joshi, E.M.; Heasley, B.H.; Chordia, M.D.; Macdonald, T.L. In vitro metabolism of 2-acetylbenzothiophene: relevance to zileuton hepatotoxicity. Chem. Res. Toxicol., 2004, 17, 137-143.
145. Joshi E.M.; Heasley B.H.; Macdonald T.L. 2-ABT-S-oxide detoxification by glutathione S-transferases A1-1, M1-1 and P1-1: implications for toxicity associated with zileuton. Xenobiotica, 2009, 39, 197-204.
146. Li, F.; Chordia, M.D.; Woodling, K.A.; Macdonald, T.L. Irreversible alkylation of human serum albumin by zileuton metabolite 2-acetylbenzothiophene- S-oxide: a potential model for hepatotoxicity. Chem. Res. Toxicol., 2007, 20, 1854-1861.
147. Lu, P.; Schrag, M.L.; Slaughter, D.E.; Raab, C.E.; Shou, M.; Rodrigues, A.D. Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. Drug Metab Dispos., 2003, 31, 1352-1360.
148. Habibollahi, P.; Mahboobi, N.; Esmaeili, S.; Safari, S.; Dabbagh, A.; Alavian, S.M. Halothane-induced hepatitis: A forgotten issue in developing countries: Halothane-induced hepatitis. Hepat. Mon., 2011, 11, 3-6.
149. Otedo, A.E. Halothane induced hepatitis: case report. East Afr. Med. J., 2004, 81, 538-539.
150. Kumar, G.P.; Bhat, V.J.; Sowdi, V. Fulminant hepatic failure following halothane anaesthesia. J. Clin. Forensic Med., 2005, 12, 271-273.
151. Qureshi, M.A.; Saeed, F.; Hussain, T. Halothane induced fulminant hepatic failure. J. Coll. Physicians Surg. Pak., 2007, 17, 103-104.
152. Madan, A.; Parkinson, A. Characterization of the NADPHdependent covalent binding of [14C]halothane to human liver microsomes: a role for cytochrome P4502E1 at low substrate concentrations. Drug Metab. Dispos., 1996, 24, 1307-1313.
153. Spracklin, D.K.; Hankins, D.C.; Fisher, J.M.; Thummel, K.E.; Kharasch, E.D. Cytochrome P450 2E1 is the principal catalyst of human oxidative halothane metabolism in vitro. J. Pharmacol. Exp. Ther., 1997, 281, 400-411.
154. Kharasch, E.D.; Hankins, D.C.; Fenstamaker, K.; Cox, K. Human halothane metabolism, lipid peroxidation, and cytochromes P(450)2A6 and P(450)3A4. Eur. J. Clin. Pharmacol., 2000, 55, 853-859.
155. Bourdi, M.; Chen, W.; Peter, R.M.; Martin, J.L.; Buters, J.T.; Nelson, S.D.; Pohl, L.R. Human cytochrome P450 2E1 is a major autoantigen associated with halothane hepatitis. Chem. Res. Toxicol., 1996, 9, 1159-1166.
156. Odaka, Y.; Takahashi, T.; Yamasaki, A.; Suzuki, T.; Fujiwara, T.; Yamada, T.; Hirakawa, M.; Fujita, H.; Ohmori, E.; Akagi, R. Prevention of halothane-induced hepatotoxicity by hemin pretreatment: protective role of heme oxygenase-1 induction. Biochem. Pharmacol., 2000, 59, 871-880.
157. Masubuchi, Y.; Horie, T. Toxicological significance of mechanism-based inactivation of cytochrome p450 enzymes by drugs. Crit. Rev. Toxicol., 2007, 37, 389-412.
158. Oropeza-Hernández, L.F.; Quintanilla-Vega, B.; Reyes-Mejía, R.A.; Serrano, C.J.; García-Latorre, E.A.; Dekant, W.; Manno, M.; Albores, A. Trifluoroacetylated adducts in spermatozoa, testes, liver and plasma and CYP2E1 induction in rats after subchronic inhalatory exposure to halothane. Toxicol. Lett., 2003, 144, 105-116.
159. Knutsen, B. Complications of antabuse treatment. Tidsskr Nor Laegeforen, 1949, 69, 436-437.
160. Björnsson, E.; Nordlinder, H.; Olsson, R. Clinical characteristics and prognostic markers in disulfiram-induced liver injury. J. Hepatol., 2006, 44, 791-797.
161. Berlin, R.G. Disulfiram hepatotoxicity: a consideration of its mechanism and clinical spectrum. Alcohol Alcohol, 1989, 24, 241-246.
162. Eliasson, E.; Stål, P.; Oksanen, A.; Lytton, S. Expression of autoantibodies to specific cytochromes P450 in a case of disulfiram hepatitis. J. Hepatol., 1998, 29, 819-825
163. Martini, R.; Ingelman-Sundberg, M.; Murray, M. Pretranslational and posttranslational regulation of rat hepatic CYPs 3A2 and 2E1 by disulfiram. Biochem. Pharmacol., 1997, 54,1323-1329.
164. Cvek, B. TNF-alpha could be responsible for disulfiram-mediated hepatotoxicity. J. Hepatol., 2008, 49, 865-866.
165. Pan, J.; Hong, J.Y.; Li, D.; Schuetz, E.G.; Guzelian, P.S.; Huang, W.; Yang, C.S. Regulation of cytochrome P450 2B1/2 genes by diallyl sulfone, disulfiram, and other organosulfur compounds in primary cultures of rat hepatocytes. Biochem. Pharmacol., 1993, 45, 2323-2329.
166. Colakoglu, O.; Tankurt, E.; Unsal, B.; Ugur, F.; Kupelioglu, A.; Buyrac, Z.; Akpinar, Z. Toxic hepatitis associated with paroxetine. Int. J. Clin. Pract., 2005, 59, 861-862.
167. Azaz-Livshits, T.; Hershko, A.; Ben-Chetrit, E. Paroxetine associated hepatotoxicity: a report of 3 cases and a review of the literature. Pharmacopsychiatry, 2002, 35, 112-115.
168. Odeh, M.; Misselevech, I.; Boss, J.H.; Oliven, A. Severe hepatotoxicity with jaundice associated with paroxetine. Am. J. Gastroenterol., 2001, 96, 2494-2496.
169. Helmchen, C.; Boerner, R.J.; Meyendorf, R.; Hegerl, U. Reversible hepatotoxicity of paroxetine in a patient with major depression. Pharmacopsychiatry, 1996, 29, 223-226.
170. Cadranel, J.F.; Di Martino, V.; Cazier, A.; Pras, V.; Bachmeyer, C.; Olympio, P.; Gonzenbach, A.; Mofredj, A.; Coutarel, P.; Devergie, B.; Biour, M. Atrium and paroxetine-related severe hepatitis. J. Clin. Gastroenterol., 1999, 28, 52-55.
171. Zhao, S.X.; Dalvie, D.K.; Kelly, J.M.; Soglia, J.R.; Frederick, K.S.; Smith, E.B.; Obach, R.S.; Kalgutkar, A.S. NADPH-dependent covalent binding of [3H]paroxetine to human liver microsomes and S-9 fractions: identification of an electrophilic quinone metabolite of paroxetine. Chem. Res. Toxicol., 2007, 20,1649-1657.
172. Zourková, A.; Hadasová, E. Paroxetine-induced conversion of cytochrome P450 2D6 phenotype and occurence of adverse effects. Gen. Physiol. Biophys., 2003, 22,103-113.
173. Fisher, B.; Costantino, J.P.; Redmond, C.K.; Fisher, E.R.; Wickerham, D.L.; Cronin, W.M. Endometrial cancer in tamoxifentreated breast cancer patients: findings from the National Surgical Adjuvant Breast and Bowel Project (NSABP) B-14. J. Natl. Cancer Inst., 1994, 86, 527-537.
174. Tryndyak, V.P.; Muskhelishvili, L.; Kovalchuk, O.; Rodriguez-Juarez, R.; Montgomery, B.; Churchwell, M.I.; Ross, S.A.; Beland, F.A.; Pogribny, I.P. Effect of long-term tamoxifen exposure on genotoxic and epigenetic changes in rat liver: implications for tamoxifen-induced hepatocarcinogenesis. Carcinogenesis, 2006, 27, 1713-1720.
175. Kärki, A.; Mäntylä, E.; Hirsimäki, Y.; Karlsson, S.; Toikkanen, S.; Hirsimäki, P. Comparison of the effects of tamoxifen and toremifene on rat hepatocarcinogenesis. Arch. Toxicol., 2000, 74, 249-256.
176. Park, B.K.; Kitteringham, N.R.; Maggs, J.L.; Pirmohamed, M.; Williams, D.P. The role of metabolic activation in drug-induced hepatotoxicity. Annu. Rev. Pharmacol. Toxicol., 2005, 45, 177-202.
177. Schild, L.J.; Divi, R.L.; Beland, F.;, Churchwell, M.I.; Doerge, D.R.; Gamboa da, C.G.; Marques, M.M.; Poirier, M.C. Formation of tamoxifen-DNA adducts in multiple organs of adult female cynomolgus monkeys dosed with tamoxifen for 30 days. Cancer Res., 2003, 63, 5999-6003.
178. White, I.N. The tamoxifen dilemma. Carcinogenesis, 1999, 20, 1153-1160.
179. Phillips, D.H. Understanding the genotoxicity of tamoxifen? Carcinogenesis, 2001, 22, 839-849.
180. Zhao, X.J.; Jones, D.R.; Wang, Y.H.; Grimm, S.W.; Hall, S.D. Reversible and irreversible inhibition of CYP3A enzymes by tamoxifen and metabolites. Xenobiotica, 2002, 32, 863-878.
181. Sridar, C.; Kent, U.M.; Notley, L.M.; Gillam, E.M.; Hollenberg, P.F. Effect of tamoxifen on the enzymatic activity of human cytochrome CYP2B6. J. Pharmacol. Exp. Ther., 2002, 301, 945-952.
182. Floren, L.C.; Hebert, M.F.; Venook, A.P.; Jordan, V.C.; Cisneros, A.; Somberg, K.A. Tamoxifen in liver disease: potential exacerbation of hepatic dysfunction. Ann. Oncol., 1998, 9, 1123-1126.
183. Parvez, S.; Tabassum, H.; Rehman, H.; Banerjee, B.D.; Athar, M.; Raisuddin, S. Catechin prevents tamoxifen-induced oxidative stress and biochemical perturbations in mice. Toxicology, 2006, 225, 109-118.
184. Tabassum H.;, Rehman H.; Banerjee B.D.; Raisuddin S.; Parvez S. Attenuation of tamoxifen-induced hepatotoxicity by taurine in mice. Clin. Chim. Acta, 2006, 370,129-136.
185. Sane, R.S.; Buckley, D.J.; Buckley, A.R.; Nallani, S.C.; Desai, P.B. Role of human pregnane X receptor in tamoxifen-and 4-hydroxytamoxifen-mediated CYP3A4 induction in primary human hepatocytes and LS174T cells. Drug Metab. Dispos., 2008, 36, 946-954.
186. Hanioka, N.; Ozawa, S.; Jinno, H.; Tanaka-Kagawa, T.; Nishimura, T.; Ando, M.; Sawada Ji, J. Interaction of irinotecan (CPT-11) and its active metabolite 7-ethyl-10-hydroxycamptothecin (SN-38) with human cytochrome P450 enzymes. Drug Metab. Dispos., 2002, 30, 391-396.
187. Basseville, A.; Preisser, L.; de Carné Trécesson, S.; Boisdron-Celle, M.; Gamelin, E.; Coqueret, O.; Morel, A. Irinotecan induces steroid and xenobiotic receptor (SXR) signaling to detoxification pathway in colon cancer cells. Mol. Cancer., 2011, 10, 80.
188. Choti, M.A. Chemotherapy-associated hepatotoxicity: do we need to be concerned. Ann. Surg. Oncol., 2009, 16, 2391-2394.
189. Ma, D.; Zhang, X.C.; Yand, D.Y.; Liu, J.H.; Su, J. Association of UGT1A1*28 Polymorphism with Toxicity and Efficacy of Innotecan in Chinese Patients. J. Sun Yat-sen Univ. Med. Sci., 2011, 32, 495-499.
190. Baumgaertner, I.; Ratziu, V.; Vaillant, J.C.; Hannoun, L.; Poynard, T.; André, T. Hepatotoxicity of metastatic colorectal cancer chemotherapy: systematic review. Bull. Cancer, 2010, 97, 559-569.
191. Núñez, M.J.; Martín-Carbonero, L.; Moreno, V., Valencia, E.; Garcia-Samaniego; J.; Castillo, J.G.; Barreiro, P.; González-Lahoz, J.; Soriano, V. Impact of antiretroviral treatment-related toxicities on hospital admissions in HIV-infected patients. AIDS Res. Hum. Retroviruses, 2006, 22, 825-829.
192. Heil, E.L.; Townsend, M.L.; Shipp, K.; Clarke, A.; Johnson, M.D. Incidence of Severe Hepatotoxicity Related to Antiretroviral Therapy in HIV/HCV Coinfected Patients. AIDS Res. Treat., 2010, 856542.
193. Jülg, B.; Bogner, J.R.; Goebel, F.D. Severe hepatotoxicity associated with the combination of enfuvirtide and tipranavir/ritonavir: case report. AIDS, 2006, 20, 1563.
194. Merchante, N.; López-Cortés, L.F.; Delgado- Fernández, M.; Ríos-Villegas, M.J.; Márquez-Solero, M.; Merino, D.; Pasquau, J.; García-Figueras, C.; Martínez-Perez, M.A.; Omar, M.; Rivero, A.; Macías, J.p.; Mata, R.; Pineda, J.A. Liver toxicity of antiretroviral combinations including fosamprenavir plus ritonavir 1400/100mg once daily in HIV/hepatitis C virus-coinfected patients. AIDS Patient Care STDS, 2011, 25, 395-402.
195. Shibuyama, S.; Gevorkyan, A.; Yoo, U.; Tim, S.; Dzhangiryan, K.; Scott, J.D. Understanding and avoiding antiretroviral adverse events. Curr. Pharm. Des., 2006, 12, 1075-1090.
196. Sulkowski, M.S. Drug-induced liver injury associated with antiretroviral therapy that includes HIV-1 protease inhibitors. Clin. Infect. Dis., 2004, 38 Suppl 2, S90-97.
197. Bruno, R.; Sacchi, P.; Maiocchi, L.; Patruno, S.; Filice, G. Hepatotoxicity and antiretroviral therapy with protease inhibitors: A review. Dig. Liver Dis., 2006, 38, 363-373.
198. Servoss, J.C.; Kitch, D.W.; Andersen, J.W.; Reisler, R.B.; Chung, R.T.; Robbins, G.K. Predictors of antiretroviral-related hepatotoxicity in the adult AIDS Clinical Trial Group (1989-1999). J. Acquir. Immune Defic. Syndr., 2006, 43, 320-323.
199. Zucker, S.D.; Qin, X.; Rouster, S.D.; Yu, F.; Green, R.M.; Keshavan, P.; Feinberg, J.; Sherman, K.E. Mechanism of indinavirinduced hyperbilirubinemia. Proc. Natl. Acad. Sci. U. S. A., 2001, 98, 12671-12676.
200. Viengchareun, S.; Caron, M.; Auclair, M.; Kim, M.J.; Frachon, P.; Capeau, J.; Lombès, M.; Lombès, A. Mitochondrial toxicity of indinavir, stavudine and zidovudine involves multiple cellular targets in white and brown adipocytes. Antivir. Ther., 2007, 12, 919-929.
201. McRae, M.P.; Lowe, C.M.; Tian, X.; Bourdet, D.L.; Ho, R.H.; Leake, B.F.; Kim, R.B.; Brouwer, K.L.; Kashuba, A.D. Ritonavir, saquinavir, and efavirenz, but not nevirapine, inhibit bile acid transport in human and rat hepatocytes. J. Pharmacol. Exp. Ther., 2006, 318, 1068-1075.
202. McRae, M.; Rezk, N.L.; Bridges, A.S.; Corbett, A.H.; Tien, H.C.; Brouwer, K.L.; Kashuba, A.D. Plasma bile acid concentrations in patients with human immunodeficiency virus infection receiving protease inhibitor therapy: possible implications for hepatotoxicity. Pharmacotherapy, 2010, 30, 17-24.
203. Koudriakova, T.; Iatsimirskaia, E.; Utkin, I.; Gangl, E.; Vouros, P.; Storozhuk, E.; Orza, D.; Marinina, J.; Gerber, N. Metabolism of the human immunodeficiency virus protease inhibitors indinavir and ritonavir by human intestinal microsomes and expressed cytochrome P4503A4/3A5: mechanism-based inactivation of cytochrome P4503A by ritonavir. Drug Metab. Dispos., 1998, 26, 552-561.
204. Ernest II, C.S.;, Hall, S.D.; Jones, D.R. Mechanism-based inactivation of CYP3A by HIV protease inhibitors. J. Pharmacol. Exp. Ther., 2005, 312, 583-591.
205. Denissen, J.F.; Grabowski, B.A.; Johnson, M.K.; Buko, A.M.; Kempf, D.J.; Thomas, S.B.; Surber, B.W. Metabolism and disposition of the HIV-1 protease inhibitor ritonavir (ABT-538) in rats, dogs, and humans. Drug Metab. Dispos., 1997, 25, 489-501.
206. Chiba, M.; Nishime, J.A.; Neway, W.; Lin, Y.; Lin, J.H. Comparative in vitro metabolism of indinavir in primates-a unique stereoselective hydroxylation in monkey. Xenobiotica, 2000, 30, 117-129.
207. Li, F.; Lu, J.; Ma, X. Metabolomic screening and identification of the bioactivation pathways of ritonavir. Chem. Res. Toxicol., 2011, 24, 2109-2114.
208. Liu, L.; Mugundu, G.M.; Kirby, B.J.; Samineni, D.; Desai, P.B.; Unadkat, J.D. Quantification of human hepatocyte cytochrome P450 enzymes and transporters induced by HIV protease inhibitors using newly validated LC-MS/MS cocktail assays and RT-PCR. Biopharm. Drug Dispos., 2012, 33, 207-217.
209. Koenigs, L.L.; Trager, W.F. Mechanism-based inactivation of cytochrome P450 2B1 by 8-methoxypsoralen and several other furanocoumarins. Biochemistry, 1998, 37,13184-13193.
210. Baumgart, A.; Schmidt, M.; Schmitz, H.J.; Schrenk, D. Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes. Biochem. Pharmacol., 2005, 69, 657-667.
211. Stephens, R.B.; Cooper, A. Hepatitis from 5-methoxypsoralen occurring in a patient with previous flucloxacillin hepatitis. Australas J. Dermatol., 1999, 40, 217-219.
212. Koenigs, L.L.; Peter, R.M.; Thompson, S.J.; Rettie, A.E.; Trager, W.F. Mechanism-based inactivation of human liver cytochrome P450 2A6 by 8-methoxypsoralen. Drug Metab. Dispos., 1997, 25, 1407-1415.
213. Koenigs, L.L.; Trager, W.F. Mechanism-based inactivation of P450 2A6 by furanocoumarins. Biochemistry, 1998, 37, 10047-10061.
214. von Weymarn, L.B.; Zhang, Q.Y.; Ding, X.; Hollenberg, P.F. Effects of 8-methoxypsoralen on cytochrome P450 2A13. Carcinogenesis, 2005, 26, 621-629.
215. Pariser, D.M.; Wyles, R.J. Toxic hepatitis from oral methoxsalen photochemotherapy (PUVA). J. Am. Acad. Dermatol., 1980, 3, 248-250.
216. Nyfors, A; Dahl-Nyfors, B.; Hopwood, D. Liver biopsies from patients with psoriasis related to photochemotherapy (PUVA): findings before and after 1 year of therapy in twelve patients. A blind study and review of literature on hepatotoxicity of PUVA. J. Am. Acad. Dermatol., 1986, 14, 43-48.
217. Wang, X.; Lou, Y.J.; Wang, M.X.; Shi, Y.W.; Xu, H.X.; Kong, L.D. Furocoumarins affect hepatic cytochrome P450 and renal organic ion transporters in mice. Toxicol. Lett., 2012, 209, 67-77.
218. Nam, S.W.; Baek, J.T.; Lee, D.S.; Kang, S.B.; Ahn, B.M.; Chung, K.W. A case of acute cholestatic hepatitis associated with the seeds of Psoralea corylifolia (Boh-Gol-Zhee). Clin. Toxicol., 2005, 43, 589-591.
219. Cheung, W.I.; Tse, M.L.; Ngan, T.; Lin, J.; Lee, W.K.; Poon, W.T.; Mak, T.W.; Leung, V.K.; Chau, T.N. Liver injury associated with the use of Fructus Psoraleae (Bol-gol-zhee or Bu-gu-zhi) and its related proprietary medicine. Clin. Toxicol. (Phila)., 2009, 47, 683-685.
220. Ortiz de Montellano, P.R. Cytochrome P450 Structure, Mechanism, and Biochemistry, 3rd ed.; Kluwer Academic/Plenum Publishers: New York, 2004.
221. Hari Kumar, K.B.; Kuttan, R. Inhibition of drug metabolizing enzymes (cytochrome P450) in vitro as well as in vivo by Phyllanthus amarus Schum & Thonn. Biol. Pharm. Bull., 2006, 29, 1310-1313.
222. Gu, X.S.; Manautou, J.E. Molecular mechanisms underlying chemical liver injury. Expert Rev. Mol. Med., 2012, 14, e4.
223. Settivari, R.S.; Evans, T.J.; Rucker, E.; Rottinghaus, G.E.; Spiers, D.E. Effect of ergot alkaloids associated with fescue toxicosis on hepatic cytochrome P450 and antioxidant proteins. Toxicol. Appl. Pharmacol., 2008, 227,347-356.
224. Polasek, T.M.; Miners J.O. In vitro approaches to investigate mechanism-based inactivation of CYP enzymes. Expert Opin. Drug Met., 2007, 3, 321-329.
225. Metushi, I.G.; Sanders C, Lee, W.M.; Uetrecht, J. Detection of anti-isoniazid and anti-cyp antibodies in patients with isoniazidinduced liver failure. Hepatology, 2013, doi: 10.1002/hep.26564.
226. Masini, A.; Gallesi, D.; Giovannini, F.; Trenti, T.; Ceccarelli, D. Membrane potential of hepatic mitochondria after acute cocaine administration in rats-the role of mitochondrial reduced glutathione. Hepatology, 1997, 25, 385-390.
227. Liu, Y.L.; Roebuck, B.D.; Yager, J.D.; Groopman, J.D.; Kensler, T.W. Protection by 5-(2-pyrazinyl)-4-methyl-1,2-dithiol-3-thione (oltipraz) against the hepatotoxicity of aflatoxin B1 in the rat. Toxicol. Appl. Pharmacol., 1988, 93, 442-451.
228. Dimova, S.; Koleva, M.; Rangelova, D.; Stoythchev, T. Effect of nifedipine, verapamil, diltiazem and trifluoperazine on acetaminophen toxicity in mice. Arch. Toxicol., 1995, 70: 112-118.
229. Zhou, S.; Chan, E.; Lim, L.Y.; Boelsterli, U.A.; Li, S.C.; Wang, J.; Zhang, Q.; Huang, M.; Xu, A. Therapeutic Drugs that Behave as Mechanism-Based Inhibitors of Cytochrome P450 3A4. Curr. Drug Metab., 2004, 5, 415-442.