Anticonvulsant agents

Drug-Induced Liver Disease, Second Edition

Volumn , Issue , 2007, Pages 485-505

  Pirmohamed, Munir ^a   Leeder, Steven J ^b  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b CHILDREN'S MERCY HOSPITALS AND CLINICS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 46349103309     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (158)

1. Chadwick D. Safety and efficacy of vigabatrin and carbamazepine in newly diagnosed epilepsy: a multicentre randomised double-blind study. Vigabatrin European Monotherapy Study Group [see comments]. Lancet 1999; 354:13-19.
2. Stricker BHC. Drug-Induced Hepatic Injury. Amsterdam: Elsevier Science Publishers, 1992.
3. Pellock JM. Carbamazepine side effects in children and adults. Epilepsia 1987; 28:S64-70.
4. Askmark H, Wiholm B. Epidemiology of adverse drug reactions to carbamazepine as seen in a spontaneous reporting system. Acta Neurol Scand 1990; 81:131-40.
5. Døssing M, Andreasen PB. Drug-induced liver disease in Denmark. An analysis of 572 cases of hepatotoxicity reported to the Danish Board of Adverse Reactions to Drugs. Scand J Gastroenterol 1982; 17:205-11.
6. Friis H, Andreasen PB. Drug-induced hepatic injury. An analysis of 1100 cases reported to the Danish Committee on Adverse Drug Reactions between 1978 and 1987. J Intern Med 1992; 232:133-8.
7. Tennis P, Stern RS. Risk of serious cutaneous disorders after initiation of use of phenytoin, carbamazepine, or sodium valproate: a record linkage study. Neurology 1997; 49(2):542-6.
8. Shear NH, Spielberg SP. Anticonvulsant hypersensitivity syndrome. In vitro assessment of risk. J Clin Invest 1988; 82:1826-32.
9. Pirmohamed M, Park BK. Cytochromes P450 and liver injury. In: Cameron RG, Feuer G, de la Iglesia F, eds. Drug-Induced Hepatotoxicity. Berlin: Springer, 1996:341-66.
10. Hadzic N, Portmann B, Davies ET, Mowat AP, Mieli-Vergani G. Acute liver failure induced by carbamazepine. Arch Dis Child 1990; 65:315-7.
11. Syn WK, Naisbitt DJ, Holt AP, Pirmohamed M, Mutimer DJ. Carbamazepine-induced acute liver failure as part of the DRESS syndrome. Int J Clin Pract 2005; 59(8):988-91.
12. Williams RJ, Ruppin DC, Grierson JM, Farrell GC. Carbamazepine hepatitis. The clinicopatholoical spectrum. J Gastroenterol Hepatol 1986; 1:159-68.
13. Levander HG. Granulomatous hepatitis in a patient receiving carbamazepine. Acta Med Scand 1980; 208:333-5.
14. Hopen G, Nesthus I, Laerum OD. Fatal carbamazepine-associated hepatitis. Report of 2 cases. Acta Med Scand 1981; 210:333-5.
15. Soffer EE, Taylor RJ, Bertram PD, Hagitt RC, Levinson MJ. Carbamazepine-induced liver injury. South Med J 1983; 76:681-3.
16. Larrey D, Hadengue A, Pessayre D, Choudat L, Degott C, Benhamou JP. Carbamazepine-induced acute cholangitis. Dig Dis Sci 1987; 32:554-7.
17. Cox NH, Johnston SRD, Marks J, Bates D. Extensive carbamazepine eruption with eosinophilia and pulmonary infiltrate. Postgrad Med J 1988; 64:249-50.
18. Fellows WR. A case of aplastic anemia and pancytopenia with tegretol therapy. Headache 1969; 9:92-5.
19. Ponte CD. Carbamazepine-induced thrombocytopenia, rash, and hepatic dysfunction. Drug Intell Clin Pharmcol 1983; 17:642-4.
20. Imai H, Nakamoto Y, Hirokawa M, Akihama T, Miura AB. Carbamazepine-induced granulomatous necrotizing angiitis with acute renal failure. Nephron 1989; 51:405-8.
21. Levy M, Goodman MW, Van Dyre J, Summer HW. Granulomatous hepatitis secondary to carbamazepine. Ann Intern Med 1981; 95:64-5.
22. Mitchell MC, Boitnott JK, Arregui A, Maddrey WC. Granulomatous hepatitis associated with carbamazepine therapy. Am J Med 1981; 71:733-5.
23. Forbes GM, Jeffrey GP, Shilkin KB, Reed WD. Carbamazepine hepatotoxicity. Another case of the vanihing bile duct syndrome. Gastroenterology 1992; 102:1385-8.
24. Pirmohamed M, Graham A, Roberts P, et al. Carbamazepine-hypersensitivity: assessment of clinical and in vitro chemical cross-reactivity with phenytoin and oxcarbazepine. Br J Clin Pharmacol 1991; 32:741-9.
25. Zimmerman HJ, Ishak KG. Antiepileptic drugs. In: Cameron RG, Feuer G, de la Iglesia F, eds. Drug-Induced Hepatotoxicity. Berlin: Springer, 1996:637-62.
26. Farrell GC. Drug-Induced Liver Disease. Edinburgh: Churchill Livingstone, 1994.
27. Murphy JV, Francisco CB, Roberts C. Fatal hepatorenal failure in 3 patients receiving carbamazepine. Ann Neurol 1991; 30:276-7.
28. Zakrzewska JM, Ivanyi L. In vitro lymphocyte proliferation by carbamazepine, carbamazepine-10,11-epoxide, and oxcarbazepine in the diagnosis of drug-induced hypersensitivity. J Allergy Clin Immunol 1988; 82:110-5.
29. Naisbitt DJ, Britschgi M, Wong G, et al. Hypersensitivity reactions to carbamazepine: characterization of the specificity, phenotype, and cytokine profile of drug-specific T cell clones. Mol Pharmacol 2003; 63(3):732-41.
30. Leeder JS, Riley RJ, Cook VA, Spielberg SP. Human anti-cytochrome P450 antibodies in aromatic anticonvulsant-induced hypersensitivity reactions. J Pharmacol Exp Ther 1992; 263:360-7.
31. Pirmohamed M, Kitteringham NR, Breckenridge AM, Park BK. Detection of an autoantibody directed against human liver microsomal protein in a patient with carbamazepine hypersensitivity. Br J Clin Pharmacol 1992; 33:183-6.
32. Riley RJ, Smith G, Wolf CR, Cook VA, Leeder JS. Human anti-endoplasmic reticulum antibodies produced in aromatic anticonvulsant hypersensitivity reactions recognise rodent CYP3A proteins and a similarly regulated human P450 enzyme(s). Biochem Biophys Res Commun 1993; 191:32-40.
33. Leeder JS, Gaedigk A, Lu X, Cook VA. Epitope mapping studies with human anti-cytochrome P450 3A antibodies. Mol Pharmacol 1996; 49:234-43.
34. Horowitz S, Patwardhan R, Marcus E. Hepatotoxic reactions associated with carbamazepine therapy. Epilepsia 1988; 29:149-54.
35. Shear NH, Bhimji S. Pharmacogenetics and cutaneous drug reactions. Semin Dermatol 1988; 8:219-26.
36. Edwards SG, Hubbard V, Aylett S, Wren D. Concordance of primary generalised epilepsy and carbamazepine hypersensitivity in monozygotic twins. Postgrad Med J 1999; 75:680-1.
37. Gaedigk A, Spielberg SP, Grant DM. Characterization of the microsomal epoxide hydrolase gene in patients with anticonvulsant adverse drug reactions. Pharmacogenetics 1994; 4:142-53.
38. Green VJ, Pirmohamed M, Kitteringham NR, et al. Genetic analysis of microsomal epoxide hydrolase in patients with carbamazepine hypersensitivity. Biochem Pharmacol 1995; 50:1353-9.
39. Pirmohamed M. Genetic factors in the predisposition to drug-induced hypersensitivity reactions. AAPS J 2006; 8(1):E20-6.
40. Tybring G, von Bahr C, Bertilsson L, Collste H, Glaumann H, Solbrand M. Metabolism of carbamazepine and its epoxide metabolite in human and rat liver in vitro. Drug Metab Dispos 1981; 9:561-4.
41. Eichelbaum M, Thomson T, Tybring G, Bertilsson L. Carbamazepine metabolism in man. Induction and pharmacogenetic aspects. Clin Pharmacokinet 1985; 10:80-90.
42. Kroetz DL, Kerr BM, McFarland LV, Loiseau P, Wilensky AJ, Levy RH. Measurement of in vivo microsomal epoxide hydrolase activity in white subjects. Clin Pharmacol Ther 1993; 53:306-15.
43. Pirmohamed M, Kitteringham NR, Guenthner TM, Breckenridge AM, Park BK. An investigation of the formation of cytotoxic, protein-reactive and stable metabolites from carbamazepine in vitro. Biochem Pharmacol 1992; 43:1675-82.
44. Madden S, Maggs JL, Park BK. Bioactivation of carbamazepine in the rat in vivo. Evidence for the formation of reactive aren oxide(s). Drug Metab Dispos 1996; 24:469-79.
45. Lertratanangkoon K, Horning MG. Metabolism of carbamazepine. Drug Metab Dispos 1982; 10:1-10.
46. Lillibridge JH, Amore BM, Slattery JT, et al. Protein-reactive metabolites of carbamazepine in mouse liver microsomes. Drug Metab Dispos 1996; 24:509-14.
47. Furst SM, Sukhai P, McClelland RA, Uetrecht JP. Covalent binding of carbamazepine oxidative metabolites to neutrophils. Drug Metab Dispos 1995; 23(5):590-4.
48. Ju C, Uetrecht JP. Detection of 2-hydroxyiminostilbene in the urine of patients taking carbamazepine and its oxidation to a reactive iminoquinone intermediate. J Pharmacol Exp Ther 1999; 288:51-6.
49. Pirmohamed M, Kitteringham NR, Breckenridge AM, Park BK. The effect of enzyme induction on the cytochrome P450-mediated bioactivation of carbamazepine by mouse liver microsomes. Biochem Pharmacol 1992; 44:2307-14.
50. Kerr BM, Thummel KE, Wurden CJ, et al. Human liver carbamazepine metabolism. Role of CYP3A4 and CYP2C8 in 10,11-epoxide formation. Biochem Pharmacol 1994; 47:1969-79.
51. Pearce RE, Vakkalagadda GR, Leeder JS. Pathways of carbamazepine bioactivation in vitro I. Characterization of human cytochromes P450 responsible for the formation of 2- and 3-hydroxylated metabolites. Drug Metab Dispos 2002; 30(11):1170-9.
52. Pearce RE, Uetrecht JP, Leeder JS. Pathways of carbamazepine bioactivation in vitro: II. The role of human cytochrome P450 enzymes in the formation of 2-hydroxyiminostilbene. Drug Metab Dispos 2005; 33(12):1819-26.
53. Bernus I, Dickinson RG, Hooper WD, Eadie MJ. Early-stage autoinduction of carbamazepine metabolism in humans. Eur J Clin Pharmacol 1994; 47:355-60.
54. Bu HZ, Kang P, Deese AJ, Zhao P, Pool WF. Human in vitro glutathionyl and protein adducts of carbamazepine-10,11-epoxide, a stable and pharmacologically active metabolite of carbamazepine. Drug Metab Dispos 2005; 33(12):1920-4.
55. Leeder JS. Mechanisms of idiosyncratic hypersensitivity reactions to antiepileptic drugs. Epilepsia 1998; 39(Suppl. 7):S8-16.
56. Mauri-Hellweg D, Bettens F, Mauri D, Brander C, Hunziker T, Pichler WJ. Activation of drug-specific CD4+ and CD8+ T cells in individuals allergic to sulfonamides, phenytoin, and carbamazepine. J Immunol 1995; 155:462-72.
57. Friedmann PS, Strickland I, Pirmohamed M, Park BK. Investigation of mechanisms in toxic epidermal necrolysis induced by carbamazepine. Arch Dermatol 1994; 130:598-604.
58. Park BK, Pirmohamed M, Kitteringham NR. Role of drug disposition in drug hypersensitivity: a chemical, molecular, and clinical perspective. Chem Res Toxicol 1998; 11(9):969-88.
59. Pichler WJ. Delayed drug hypersensitivity reactions. Ann Intern Med 2003; 139(8):683-93.
60. Wu Y, Sanderson JP, Farrell J, et al. Activation of T cells by carbamazepine and carbamazepine metabolites. J Allergy Clin Immunol 2006; 118(1):233-41.
61. Pirmohamed M, Lin K, Chadwick D, Park BK. TNF-alpha promoter region gene polymorphisms in carbamazepine hypersensitive patients Neurology 2001; 56:890-6.
62. Alfirevic A, Mills T, Harrington P, et al. Serious carbamazepine-induced hypersensitivity reactions associated with the HSP70 gene cluster. Pharmacogenet Genomics 2006; 16(4):287-96.
63. Chung WH, Hung SI, Hong HS, et al. Medical genetics: a marker for Stevens-Johnson syndrome. Nature 2004; 428(6982):486.
64. Lonjou C, Thomas L, Borot N, et al. A marker for Stevens-Johnson syndrome ethnicity matters. Pharmacogenomics J 2006; 6(4):265-8.
65. Hung SI, Chung WH, Jee SH, et al. Genetic susceptibility to carbamazepine-induced cutaneous adverse drug reactions. Pharmacogenet Genomics 2006; 16(4):297-306.
66. Isojarvi JIT, Pakarinen AJ, Rautio A, Pelkonen O, Myllyla VV. Liver enzyme induction and serum lipid levels after repacement of carbamazepine with oxcarbazepine. Epilepsia 1994; 35:1217-20.
67. Jensen NO, Dam M, Jakobsen K. Oxcarbazepine in patients hypersensitive to carbamazepine. Ir J Med Sci 1986; 155:297.
68. Beran RG. Cross-reactive skin eruption with both carbamazeepine and oxcarbazepine. Epilepsia 1993; 34:163-5.
69. Haruda F. Phenytoin hypersensitivity: 38 cases. Neurology 1979; 29:1480-5.
70. Mullick FG, Ishak KG. Hepatic injury associated with diphenylhydantoin therapy. A clinicopathological study of 20 cases. Am J Clin Pathol 1980; 74:442-52.
71. Park BK, Wilson AC, Kaatz G, Ohnhaus EE. Enzyme induction by phenobarbitone and vitamin K1 disposition in man. Br J Clin Pharmacol 1984; 18:94-7.
72. Aiges HW, Daum F, Olson M, Kahn E, Teichberg S. The effects of phenobarbital and diphenylhydantoin on liver function and morphology. J Pediatr 1980; 97:22-6.
73. Flowers FP, Araujo OE, Hamm KA. Phenytoin hypersensitivity syndrome. J Emerg Med 1987; 5:103-8.
74. Egerton-vernon JM, Fisk MJ, Snell AP. Phenytoin-induced hepatotoxicity. N Z Med J 1983; 96:467-9.
75. Masso JFM, Carrera N, Zabalza R, Bengoechea MG. Phenytoin (diphenylhydantoin) induced hepatotoxicity. Med Clin 1983; 81:320-1.
76. Smythe MA, Umstead GS. Phenytoin hepatotoxicity. A review of the literature. Drug Intell Clin Pharmcol 1989; 23:13-18.
77. Dreifuss FE, Langer DH. Hepatic considerations in the use of antiepileptic drugs. Epilepsia 1987; 28(Suppl. 2):S23-9.
78. Bryant AE, Dreifuss FE. Hepatotoxicity associated with antiepileptic drug therapy-avoidance, identification and management. CNS Drugs 1995; 4:13-9.
79. Spechler SJ, Sperber H, Doos WG, Koff RS. Cholestasis and toxic epidermal necrolysis associated with phenytoin sodium. The role of bile duct injury. Ann Intern Med 1981; 95:455-6.
80. Spielberg SP, Gordon GB, Blake DA, Goldstein DA, Herlong HF. Predisposition to phenytoin hepatotoxicity assessed in vitro. N Engl J Med 1981; 305:722-7.
81. Tomsick RS. The phenytoin syndrome. Cutis 1983; 32:535-7.
82. Vittorio CC, Muglia JJ. Anticonvulsant hypersensitivity syndrome. Arch Intern Med 1995; 155:2285-90.
83. Gennis MA, Vemuri R, Burns EA, Hill JV, Miller MA, Spielberg SP. Familial occurrence of hypersensitivity to phenytoin. Am J Med 1991; 91:631-4.
84. Spielberg SP. In vitro assessment of pharmacogenetic susceptibility to toxic drug metabolites in humans. Fed Proc 1984; 43:2308-13.
85. Kleckner HB, Yakulis V, Heller P. Severe hypersensitivity to diphenylhydantoin with circulating antibodies to the drug. Ann Intern Med 1975; 83:522-3.
86. Spielberg SP, Gordon GB, Blake DA, Mellits ED, Bross DS. Anticonvulsant toxicity in vitro: possible role of arene oxides. J Pharmacol Exp Ther 1981; 217:386-9.
87. Munns AJ, De Voss JJ, Hooper WD, Dickinson RG, Gillam EMJ. Bioactivation of phenytoin by human cytochrome P450: characterization of the mechanism and targets of covalent adduct formation. Chem Res Toxicol 1997; 10:1049-58.
88. Cuttle L, Munns AJ, Hogg NA, et al. Phenytoin metabolism by human cytochrome P450:involvement of P450 3A and 2C forms in secondary metabolism and drug-protein adduct formation. Drug Metab Dispos 2000; 28:945-50.
89. Komatsu T, Yamazaki H, Asahi S, et al. Formation of a dihydroxy metabolite of phenytoin in human liver microsomes/cytosol: roles of cytochromes P450 2C9, 2C19, and 3A4. Drug Metab Dispos 2000; 28:1362-8.
90. Kinobe RT, Parkinson OT, Mitchell DJ, Gillam EM. P450 2C18 catalyzes the metabolic bioactivation of phenytoin. Chem Res Toxicol 2005; 18(12):1868-75.
91. Allabi AC, Gala JL, Horsmans Y. CYP2C9, CYP2C19, ABCB1 (MDR1) genetic polymorphisms and phenytoin metabolism in a Black Beninese population. Pharmacogenet Genomics 2005; 15(11):779-86.
92. Tate SK, Depondt C, Sisodiya SM, et al. Genetic predictors of the maximum doses patients receive during clinical use of the anti-epileptic drugs carbamazepine and phenytoin. Proc Natl Acad Sci USA 2005; 102(15):5507-12.
93. Lee AY, Kim MJ, Chey WY, Choi J, Kim BG. Genetic polymorphism of cytochrome P450 2C9 in diphenylhydantoin-induced cutaneous adverse drug reactions. Eur J Clin Pharmacol 2004; 60(3):155-9.
94. Evans WE, Self TH, Weisburst MR. Phenobarbital-induced hepatic dysfunction. Drug Intell Clin Pharmcol 1976; 10:439-43.
95. Hyson C, Sadler M. Cross sensitivity of skin rashes with antiepileptic drugs. Can J Neurol Sci 1997; 24:245-9.
96. Bourgeois BFD. Valproic acid. Clinical use. In: Levy RH, Mattson RH, Meldrum BS, eds. Antiepileptic Drugs. 4th ed. New York: Raven Press Ltd, 1995:633-40.
97. Dreifuss FE. Valproic acid. Toxicity. In: Levy RH, Mattson RH, Meldrum BS, eds. Antiepileptic Drugs. 4th ed. New York: Raven Press Ltd, 1995:641-8.
98. Sussman NM, McLain LW. A direct hepatotoxic effect of valproic acid. J Am Med Assoc 1979; 242:1173-4.
99. Russo MW, Galanko JA, Shrestha R, Fried MW, Watkins P. Liver transplantation for acute liver failure from drug induced liver injury in the United States. Liver Transpl 2004; 10(8):1018-23.
100. Bjornsson E, Olsson R. Suspected drug-induced liver fatalities reported to the WHO database. Dig Liver Dis 2006; 38(1):33-8.
101. Dreifuss FE, Santilli N, Langer DH, Sweeney KP, Moline KA, Menander KB. Valproic acid hepatic fatalities: a retrospective review. Neurology 1987; 37:379-85.
102. Dreifuss FE, Langer DH, Moline KA, Maxwell JE. Valproic acid hepatic fatalities. II. U.S. experience since 1984. Neurology 1989; 39:201-7.
103. Bryant AE, Dreifuss FE. Valproic acid hepatic fatalities. III. U.S. experience since 1986. Neurology 1996; 46:465-9.
104. Kay JDS, Hilton-Jones D, Hyman N. Valproate toxicity and ornithine carbamoltransferase deficiency. Lancet 1986; ii:1283-4.
105. Eadie MJ, McKinnon GE, Dunston PR, McLaughlin D, Dickinson RG. Valproate metabolism during hepatotoxicity associated with the drug. Q J Med 1990; 284:1229-40.
106. Tokatli A, Coskun S, Cataltepe S, Ozalp I. Valproate-induced lethal hyperammonemic coma in a carrier of ornithine transcarbamylase deficiency. J Inherit Metab Dis 1991; 14:836-7.
107. Honeycutt D, Callahan K, Rutledge L, Wans B. Heterozygotic ornithine transcarbamylase deficiency presenting as symptomatic hyperammonemia durining initiation of valproate treatment. Neurology 1992; 42:666.
108. Zimmerman HJ, Ishak KG. Valproate-induced hepatic injury: analysis of 23 fatal cases. Hepatology 1982; 2:591-7.
109. Suchy FJ, Balistreri WF, Buchino JJ, et al. Acute hepatic failure associated with the use of sodium valproate. N Engl J Med 1979; 300:962-6.
110. Scheffner D, König S, Rauterberg-Ruland I, Kochen W, Hofmann WJ, Unkelbach S. Fatal liver failure in 16 children with valproate therapy. Epilepsia 1988; 29:530-42.
111. Kondo T, Kaneko S, Otani K, et al. Associations between risk factors for valproate hepatotoxicity and altered valproate metabolism. Epilepsia 1992; 33:172-7.
112. Anderson GD, Acheampong AA, Wilensky AJ, Levy RH. Effect of valproate dose on formation of hepatotoxic metabolites. Epilepsia 1992; 33:736-42.
113. Millington DS, Bohan TP, Roe CR, Yergey AL, Liberato DJ. Valproylcarnitine: a novel drug metabolite identified by fast atom bombardment and thermospray liquid chromatography-mass spectrometry. Clin Chim Acta 1985; 145:69-76.
114. Li J, Norwood DL, Mao L-F, Schulz H. Mitochondrial metabolism of valproic acid. Biochemistry 1991; 30:388-94.
115. Ponchaut S, Draye JP, Veitch K. In vitro effects of valproate and valproate metabolites on mitochondrial oxidations: relevance of CoA sequestration to the observed inhibitions. Biochem Pharmacol 1992; 43:2435-42.
116. Bjorge SM, Baillie TA. Inhibition of medium-chain fatty acid β-oxidation in vivo by valproic acid and its unsaturated metabolite, 2-n-propyl-4-pentenoic acid. Biochem Biophys Res Commun 1985; 132:245-52.
117. Kesterson JW, Granneman GR, Machinist JM. The hepatotoxicity of valproic acid and its metabolites in rats I. Toxicologic, biochemical and histopathologic studies. Hepatology 1984; 4:1143-52.
118. Granneman GR, Wang SI, Kesterson JW, Machinist JM. The hepatotoxicity of valproic acid and its metabolites in rats. II. Intermediary and valproic acid metabolism. Hepatology 1984; 4:1153-8.
119. Kingsley E, Gray PD, Tolman KG, Tweedale R. The toxicity of the metabolites of sodium valproate in cultured hepatocytes. J Clin Pharmacol 1983; 23:178-85.
120. Rettenmeier AW, Prickett KS, Gordon WP, et al. Studies on the biotransformation in the perfused rat liver of 2-n-propyl-4-pentenoic acid, a metabolite of the antiepileptic drug valproic acid. Evidence for the formation of chemically reactive intermediates. Drug Metab Dispos 1985; 13:81-96.
121. Baillie TA. Metabolic activation of valproic acid and drug-mediated hepatotoxicity. Role of the terminal olefin, 2-n-propyl-4-pentenoic acid. Chem Res Toxicol 1988; 1:195-9.
122. Rettie AE, Rettenmeier AW, Howald WN, Baillie TA. Cytochrome P-450-catalyzed formation of Δ4-VPA, a toxic metabolite of valproic acid. Science 1987; 235:890-3.
123. Sadeque AJM, Fisher MB, Korzekwa KR, Gonzalez FJ, Rettie AE. Human CYP2C9 and CYP2A6 mediate formation of the hepatotoxin 4-ene-valproic acid. J Pharmacol Exp Ther 1997; 283:698-703.
124. Levy RH, Rettemeier AW, Anderson GD, et al. Effect of polytherapy with phenytoin, carbamazepine, and stirpentol on formation of 4-ene-valproate, a hepatotoxic metabolite of valproic acid. Clin Pharmacol Ther 1990; 48:225-35.
125. Donato MT, Gómez-Lechón MJ, Castell JV. Effect of model inducers on cytochrome P450 activities of human hepatocytes in primary culture. Drug Metab Dispos 1995; 23:553-8.
126. Chang TKH, Yu L, Maurel P, Waxman DJ. Enhanced cyclophosphamide and ifosfamide activation in primary human hepatocyte cultures: response to cytochrome P-450 inducers and autoinduction by oxazaphosphorines. Cancer Res 1997; 57:1946-54.
127. Wrighton SA, Brian WR, Sari M-A, et al. Studies on the expression and metabolic capabilities of human liver cytochrome P450IIIA5 (HLp3). Mol Pharmacol 1990; 38:207-13.
128. Ho PC, Abbott FS, Zanger UM, Chang TK. Influence of CYP2C9 genotypes on the formation of a hepatotoxic metabolite of valproic acid in human liver microsomes. Pharmacogenomics J 2003; 3(6):335-42.
129. Waxman DJ, Azaroff L. Phenobarbital induction of cytochrome P-450 gene expression. Biochem J 1992; 281:577-92.
130. Leeder JS, Kearns GL. Pharmacogenetics in pediatrics. Implications for practice. Pediatr Clin North Am 1997; 44:55-77.
131. Shen DD, Pollack GM, Cohen ME, Duffner P, Lacey D, Ryan-Dudek P. Effect of age on the serum metabolite pattern of valproic acid in epileptic children. Epilepsia 1984; 25:674.
132. Gopaul S, Farrell K, Abbott F. Effects of age and polytherapy, risk factors of valproic acid (VPA) hepatotoxicity, on the excretion of thiol conjugates of (E)-2,4-diene VPA in people with epilepsy taking VPA. Epilepsia 2003; 44(3):322-8.
133. Kochen W, Schneider A, Ritz A. Abnormal metabolism of valproic acid in fatal hepatic failure. Eur J Pediatr 1983; 141:30-5.
134. Paganini M, Zaccara G, Moroni F, et al. Lack of relationship between sodium valproate-induced adverse effects and the plasma concentration of its metabolite 2-propylpenten-4-oic acid. Eur J Clin Pharmacol 1987; 32:219-22.
135. Tennison MB, Miles MV, Pollack GM, Thorn MD, Dupuis RE. Valproate metabolites and hepatotoxicity in an epileptic population. Epilepsia 1988; 29:543-7.
136. Siemes H, Nau H, Schultze K, et al. Valproate (VPA) metabolites in various clinical conditions of probable VPA-associated hepatotoxicity. Epilepsia 1993; 34:332-46.
137. Fromenty B, Pessayre D. Inhibition of mitochondrial b-oxidation as a mechanism of hepatotxicity. Pharmacol Ther 1995; 67:101-54.
138. Kassahun K, Farrell K, Abbott FS. Identification and characterization of the glutathione and N-acetylcysteine conjugates of (E)-2-propyl-2,4-pentadienoic acid, a toxic metabolite of valproic acid, in rats and humans. Drug Metab Dispos 1991; 19:525-35.
139. Kassahun K, Abbott FS. In vivo formation of the thiol conjugates of reactive metabolites of 4-ene-VPA and its analogue 4-pentenoic acid. Drug Metab Dispos 1993; 21:1098-106.
140. Gopaul SV, Farrell K, Abbott FS. Identification and characterization of N-acetylcysteine conjugates of valproic acid in humans and animals. Drug Metab Dispos 2000; 28:823-32.
141. Pellock JM, Brodie MJ. Felbamate: 1997 update. Epilepsia 1997; 38:1261-4.
142. Pellock JM. Felbamate. Epilepsia 1999; 40(Suppl. 5):S57-62.
143. O’Neil MG, Perdun CS, Wilson MB, McGown ST, Patel S. Felbamate-associated fatal acute hepatic necrosis. Neurology 1996; 46:1457-9.
144. Thompson CD, Kinter MT, Macdonald TL. Synthesis and in vitro reactivity of 3-carbamoyl-2- phenylproprionaldehyde and 2-phenylpropenal: putative reactive metabolites of felbamate. Chem Res Toxicol 1996; 9:1225-9.
145. Thompson CD, Gulden PH, Macdonald TL. Identification of modified atropaldehyde mercapturic acids in rat and human urine after felbamate administration. Chem Res Toxicol 1997; 10:457-62.
146. Thompson CD, Barthen MT, Hopper DW, et al. Quantification in patient urine samples of felbamate and three metabolites: acid carbamate and two mercapturic acids. Epilepsia 1999; 40:769-76.
147. Kapetanovic IM, Torchin CD, Strong JM, et al. Reactivity of atropaldehyde, a felbamate metabolite in human liver tissue in vitro. Chem Biol Interact 2002; 142(1-2):119-34.
148. Popovic M, Nierkens S, Pieters R, Uetrecht J. Investigating the role of 2-phenylpropenal in felbamate-induced idiosyncratic drug reactions. Chem Res Toxicol 2004; 17(12):1568-76.
149. Buchanan N. Lamotrigine: clinical experience in 200 patients with epilepsy with follow-up to four years. Seizure 1996; 5:209-14.
150. Dooley J, Camfield P, Gordon K, Camfield C, Wirrell E, Smith E. Lamotrigine-induced rash in children. Neurology 1996; 46:240-2.
151. Schlienger RG, Knowles SR, Shear NH. Lamotrigine-associated anticonvulsant hypersensitivity syndrome. Neurology 1998; 51:1172-5.
152. Makin AJ, Fitt S, Williams R, Duncan JS. Fulminant hepatic failure induced by lamotrigine. Br Med J 1995; 311:292.
153. Arnon R, DeVivo D, Defelice AR, Kazlow PG. Acute hepatic failure in a child treated with lamotrigine. Pediatr Neurol 1998; 18:251-3.
154. Overstreet K, Costanza C, Behling C, Hassanin T, Masliah E. Fatal progressive hepatic necrosis associated with lamotrigine treatment: a case report and literature review. Dig Dis Sci 2002; 47(9):1921-5.
155. Sachs B, Ronnau AC, von Schmiedeberg S, Ruzicka T, Gleichmann E, Schuppe HC. Lamotrigineinduced Stevens-Johnson syndrome: demonstration of specific lymphocyte reactivity in vitro. Dermatology 1997; 195:60-4.
156. Yuen AWC, Land G, Weatherley BC, Peck AW. Sodium valproate acutely inhibits lamotrigine metabolism. Br J Clin Pharmacol 1992; 33:511-3.
157. Brody MJ. Lamotrigine. Lancet 1992; 339:1397-400.
158. Maggs JL, Naisbitt DJ, Tettey JNA, Pirmohamed M, Park BK. Metabolism of lamotrigine to a reactive arene oxide intermediate. Chem Res Toxicol 2000; 13:1075-81.