Human Drug Metabolism: An Introduction, Second Edition

Human Drug Metabolism: An Introduction, Second Edition

Volumn , Issue , 2010, Pages

  Coleman, Michael D ^a  

^a ASTON UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

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EID: 84891583384     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470689332     Document Type: Book

References (163)

1. Ayrton A. and Morgan, P. Role of transport proteins in drug discovery and development: a pharmaceutical perspective. Xenobiotica, 38: 676-708, 2008.
2. van Grevenynghe, J. et al., Polycyclic Aromatic Hydrocarbons Inhibit Differentiation of Human Monocytes into Macrophages. J. Immunol. 170: 2374-2381, 2003.
3. Josephy, P.D. et al.,'Phase I'and'Phase II'metabolism: terminology that we should phase out? Drug Met Rev 37: 575-580, 2005.
4. Pombo, M. and Castro-Feijoo, L. Endocrine disruptors. J Ped Endocrinol Met 18: 1145-1155, 2005.
5. Zhang, L. et al., A regulatory viewpoint on transporter-based drug interactions. Xenobiotica, 38: 709-724, 2008.
6. Anzenbacher, P. et al., Active sites of Cytochromes P450: What are they like? Acta Chim. Slov. 55: 63-66, 2008.
7. Bikádi, Z. and Hazai, E. In silico description of differential enantioselectivity in methoxychlor O-demethylation by CYP2C enzymes. Biochimica et Biophysica Acta 1780: 1070-1079, 2008.
8. Cashman, J.R. The implications of polymorphisms in mammalian flavin-containing monooxygenases in drug discovery and development. DDT 9: 13, 2004.
9. Finn, R.D. et al., Defining the in vivo role for cytochrome b 5 in cytochrome P450 function through the conditionalhepatic deletion of microsomal cytochrome b5. J. Biol. Chem. 283: 31385-31393, 2008.
10. Gonzalez, F.J. Role of cytochromes P450 in chemical toxicity and oxidative stress: studies with CYP2E1. Mutation Res. 569: 101-110, 2005.
11. Guengerich, F.P. et al., Evidence for a role of a perferryl-oxygen complex, FeO3 • in the N-oxygenation of amines by cytochrome P450 enzymes. Mol. Pharmacol. 51: 147-151, 1997.
12. Guengerich, F.P. Cytochrome p450: what have we learned and what are the future issues? Drug Met. Rev. 36: 159-197, 2004.
13. Guengerich, F.P. and Isin, E.M. Mechanisms of Cytochrome P450 Reactions Acta Chim. Slov. 55: 7-19, 2008.
14. Hu, Y. and Kupfer, D. Metabolism of the endocrine disruptor pesticide-methoxychlor by human P450s: pathways involving a novel catechol metabolite. Drug Metab. Disp. 30: 1035-1042, 2002.
15. Lamb, D.C. et al., Cytochromes P450 and drug discovery. Current Opinion in Biotechnology 18: 504-512, 2007.
16. Lewis, D.F.V. et al., Human cytochromes P450 in the metabolism of drugs: new molecular models of enzyme-substrate interactions. Exp. Op. Drug Met. & Tox. 4: 1181-1186, 2008.
17. Luo, G. CYP3A4 induction by xenobiotics: biochemistry, experimental methods and impact on drug discovery and development. Curr. Drug Met. 5: 483-505, 2004.
18. Matsunaga, N. The Molecular Mechanism Regulating 24-Hour Rhythm of CYP2E1 Expression in the Mouse Liver Hepatology 48: 240-251, 2008
19. Mitchell, S.C. Flavin Mono-Oxygenase (FMO)-The'other'oxidase. Current Drug Metabolism. 9: 1-4, 2008.
20. Nebert, D.W. Role of aryl hydrocarbon receptor-mediated induction of the CYP1 enzymes in environmental toxicity and cancer. J. Biol. Chem. 279 (23): 23847-23850, 2004.
21. Nishikawa, A. Cigarette smoking, metabolic activation and carcinogenesis. Curr. Drug Met. 5: 363-373, 2004.
22. Otyepka, M. et al., What common structural features and variations of mammalian P450s are known to date? Biochimica et Biophysica Acta 1770: 376-389, 2007.
23. Rahnasto, M. et al., Identification of inhibitors of the nicotine metabolising CYP2A6 enzyme-an in silico approach. The Pharmacogenomics Journal 8: 328-338, 2008.
24. Redlich, G. et al., Distinction between Human Cytochrome P450 (CYP) Isoforms and Identification of New Phosphorylation Sites by Mass Spectrometry. J. Proteome Res. 7 (11): 4678-4688, 2008.
25. Skopalik, J. et al., Flexibility of human cytochromes P450: Molecular Dynamics Reveals differences between CYPs 3A4, 2C9, and 2A6, which correlate with their substrate preferences J. Phys. Chem. B 112: 8165-8173, 2008.
26. Szczesna-Skorupa, E. and Kemper, B. Proteasome inhibition compromises direct retention of cytochrome P450 2C2 in the endoplasmic reticulum Exp. Cell Res 314: 3221-3231, 2008.
27. Wade, R.C. Multiple molecular recognition mechanisms. Cytochrome P450-A case study. Biochimica et Biophysica Acta 1754: 239-244, 2005.
28. Williams, P.A. et al., Crystal structure of human cytochrome P4502C9 with bound warfarin. Nature 424: 464-468, 2003.
29. Zanger, U.M. et al., Functional pharmacogenetics/genomics of human cytochromes P450 involved in drug biotransformation. Anal. Bioanal. Chem. 392: 1093-1108, 2008.
30. Bolt, H.M. Rifampicin, a keystone inducer of drug metabolism: from Herbert Remmer's pioneering ideas to modern concepts. Drug Met. Rev. 36: 497-509, 2004.
31. Handschin, C. and Meyer, U.A. Induction of drug metabolism: the role of nuclear receptors. Pharmacol. Rev. 55: 649-673, 2003.
32. Haslam, I.S. et al., Induction of P-glycoprotein expression and function in human intestinal epithelial cells (T84). Biochem. Pharmacol. 76: 850-861, 2008.
33. Kang, H.J. et al., BRCA1 Modulates Xenobiotic Stress-inducible Gene Expression by Interacting with ARNT in HumanBreast Cancer Cells J. Biol. Chem. 281: 14654-14662, 2006.
34. Kanebratt, K.P.B. et al., Healthy Subjects: Determination Using the Karolinska Cocktail and the Endogenous CYP3A4 Marker 4 β-Hydroxycholesterol. Clin. Pharm. Ther. 84: 589-594, 2008.
35. Mannel, M. Drug interactions with St John's Wort-mechanisms and clinical implications. Drug Safety 27: 773-797, 2004.
36. Matsunaga, N. et al., The Molecular Mechanism Regulating 24-Hour Rhythm of CYP2E1 Expression in the Mouse Liver. Hepatology 48: 240-251, 2008.
37. Robertson, P. and Hellriegel, E.T. Clinical Pharmacokinetic Profile of modafinil. Clin Pharmacokinet 42: 123-137, 2003.
38. Patsalos, P.N. et al., The importance of drug interactions in epilepsy therapy. Epilepsia 43: 365-385, 2002.
39. Szczesna-Skorupa, E. and Kemper, B. Proteasome inhibition compromises direct retention of cytochrome P450 2C2 in the endoplasmic reticulum. Exp. Cell Res. 314: 3221-3231, 2008.
40. Tong-Liu, Y. et al., Drugs as CYP3A probes, inducers,and inhibitors. Drug Metabolism Reviews, 39: 699-721, 2007.
41. Yoshinari, K. et al., Omeprazole transactivates human CYP1A1 and CYP1A2 expression through the common regulatory region containing multiple xenobiotic-responsive elements. Biochem. Pharmacol. 76: 139-145, 2008.
42. Bailey, D.G. et al., Naringin is a Major and Selective Clinical Inhibitor of Organic Anion-Transporting Polypeptide 1A2 (OATP1A2) in Grapefruit Juice. Clin. Pharm. & Ther. 81: 495-502, 2007.
43. Buckley, N.A. and McManus, P.R. Fatal toxicity of serotoninergic and other antidepressant drugs: analysis of United Kingdom mortality data. Brit. Med. J. 325: 1332-1333, 2002.
44. Chavez, M.L. et al., Evidence-based drug-herbal interactions Life Sciences 78: 2146-2157, 2006.
45. Coleman, M.D. and Taylor, C.T. Effects of dihydrolipoic acid (DHLA), lipoic acid, N-acetyl cysteine and ascorbate on xenobiotic-mediated methaemoglobin formation in human erythrocytes in-vitro. Env. Tox. Pharmacol. 14: 121-127, 2003.
46. Coleman, M.D. and Tingle, M.D. The use of a metabolic inhibitor to reduce dapsone-dependent haematological toxicity. Drug Dev. Res. 25: 1-16, 1992.
47. Coleman, M.D. et al., The use of cimetidine to reduce dapsone-dependent methaemoglobinaemia in dermatitis herpetiformis patients. Brit. J. Clin. Pharmac. 34: 244-249, 1992.
48. Englund, G. et al., Association between the number of coadministered P-glycoprotein inhibitors and serum digoxin levels in patients on therapeutic drug monitoring. BMC Medicine 2: 1-7. 2004.
49. Fallowfield, L. et al., Quality of life of postmenopausal women in the Arimidex, Tamoxifen, Alone or in Combination (ATAC) Adjuvant Breast Cancer Trial. J. Clin. Oncol. 22: 4261-4271, 2004.
50. Glaeser, H. et al., Intestinal Drug Transporter Expression and the Impact of Grapefruit Juice in Humans Clin. Pharm. & Ther 81: 362-370, 2007.
51. Gurley, B.J. et al., Clinical assessment of CYP2D6-mediated herb-drug interactions in humans: Effects of milk thistle, black cohosh, goldenseal, kava kava, St. John's Wort, and Echinacea. Mol Nutr Food Res. 52: 755-763, 2008.
52. Howell, A. et al., Results of the ATAC (Arimidex, Tamoxifen, Alone or in Combination) trial after completion of 5 years'adjuvant treatment for breast cancer. Lancet 365 (9453): 60-62, 2005.
53. Isoherranen, N. et al., Qualitative analysis of the role of metabolites in inhibitory drug-drug interactions: Literature Evaluation Based on the Metabolism and Transport Drug Interaction Database Chem. Res. Toxicol. 22: 294-298, 2009.
54. Johnson, W.W. Cytochrome P450 inactivation by pharmaceuticals and phytochemicals: therapeutic relevance Drug Metabolism Reviews. 40: 101-147, 2008
55. Kalgutkar, A.S. et al., Bioactivation of the nontricyclic antidepressant nefazodone to a reactive quinone-imine species in human liver microsomes and recombinant cytochrome P450 3A4. Drug Metab. Disp 33: 243-253, 2005.
56. Kawazoe, H. et al., Change of the blood concentration of tacrolimus after the switch from fluconazole to voriconazole in patients receiving allogeneic hematopoietic stem cell transplantation. Biol. Pharm. Bull. 29 (12): 2528-2531, 2006.
57. Meregalli, P.G. et al., Pregnancy and the risk of torsades de pointes in congenital long-QT syndrome. Neth Heart J. 16: 422-425, 2008.
58. Ngo, N. et al., Identification of a cranberry juice product that inhibits enteric cyp3a-mediated first-pass metabolism in humans. Drug Metab Dispos. 37: 514-522, 2009.
59. Pal, D. and Mitra, A.K. CYP3A4-mediated drug-herbal interactions. Life Sciences 78: 2131-2145, 2006.
60. Spina, E. et al., Clinically relevant pharmacokinetic drug interactions with second generation antidepressants: an update. Clin. Thera. 30: 1206-1227, 2008.
61. Tiwari, A.K. Nilotinib (AMN107, Tasigna1) reverses multidrug resistance by inhibiting the activity of the ABCB1/Pgp and ABCG2/BCRP/MXR transporters. Biochem. Pharmacol. 78: 153-161, 2009.
62. Barbier, O. et al., Lipid-activated transcription factors control bile acid glucuronidation Mol Cell Biochem. 326: 3-8, 2009.
63. Dourado, D.F.A.R. et al., Glutathione Transferase: New Model for Glutathione Activation. Chem. Eur. J. 14: 9591-9598, 2008.
64. Eklund, B.I. et al., Divergent Activities of Human Glutathione Transferases in the Bioactivation of Azathioprine. Mol. Pharmacol. 70: 747-754, 2006.
65. Gamage, N.U. et al., Structure of a human carcinogen-converting enzyme, SULT1A1-structural and kinetic implications of substrate inhibition. J. Biol. Chem. 278: 7655-7662, 2003.
66. Grahn, E. et al., New crystal structures of human glutathione transferase A1-1 shed light on glutathione binding and the conformation of the C-terminal helix. Acta Cryst. D62: 197-207, 2006.
67. Hein, D.W. Molecular genetics and function of NAT1 and NAT2: role in aromatic amine metabolism and carcinogenesis. Mutation Res. 506-507: 65-77, 2002.
68. Hong, A.L. et al., UDP-Glucuronosyltransferase 1A1 Gene Polymorphisms and Total Bilirubin Levels in an ethnically Diverse Cohort of Women. Drug Metab. Disp. 35: 1254-1261, 2007.
69. Köhle, C. and Bock, K.W. Coordinate regulation of human drug-metabolizing enzymes,and conjugate transporters by the Ah receptor, pregnane Xreceptor and constitutive androstane receptor. Biochem. Pharmacol. 77: 689-699, 2009.
70. Lankisch, T.O. et al., Gilbert's syndrome and hyperbilirubinemia in protease inhibitor therapy-An extended haplotype of genetic variants increases risk in indinavir treatment. Journal of Hepatology 50: 1010-1018, 2009.
71. Luna-Tortos, C. et al., Several major antiepileptic drugs are substrates for human P-glycoprotein. Neuropharmacology 55: 1364-1375, 2008.
72. Meijerman, I. et al., Combined action and regulation of phase II enzymes and multidrug resistance proteins in multidrug resistance in cancer. Cancer Treatment Reviews 34: 505-520, 2008.
73. Perera, M.A. et al., Pharmacogenetic testing for uridine diphosphate glucuronosyltransferase 1A1 polymorphisms: Are we there yet? Pharmacotherapy 28: 755-768, 2008.
74. Sugatani, J. et al., Transcriptional regulation of human UGT1A1 gene expression through distal and proximal promoter motifs: implication of defects in the UGT1A1 gene promoter. Naunyn-Schmiedeberg's Arch Pharmacol. 377: 597-605, 2008.
75. Wang, Z. et al., A novel method for screening the glutathione transferase inhibitors. BMC Biochemistry 10: 1-11, 2009.
76. Allegaert, K. et al., Both postnatal and postmenstrual age contribute to the interindividual variability in tramadol glucuronidation in neonates. Early Human Development 84: 325-330, 2008.
77. Ashrafian, H. et al., Perhexiline. Cardiovascular Drug Reviews 25: 76-97, 2007.
78. Chen, Y.C. et al., Polymorphism of ethanol-metabolism genes and alcoholism: Correlation of allelic variations with the pharmacokinetic and pharmacodynamic consequences. Chemico-Biological Interactions 178: 2-7, 2009.
79. Cropp, C.D. et al., Genetic Variation in Drug Transporters in Ethnic Populations. Clinical Pharm. & Therapeutics 84: 413-416, 2008.
80. Cuisset, T. et al., Comparison of omeprazole and pantoprazole influence on a high 150-mg Clopidogrel maintenance dose: The PACA (Proton Pump Inhibitors And Clopidogrel Association) Prospective Randomized Study. J. Am. Coll. Cardiol 54: 1149-1153, 2009
81. De Leon, J. Atypical antipsychotic dosing: the effect of smoking and caffeine. Psychopharmacol. 55: 491-493, 2004.
82. Dorado, P. et al., CYP2D6 polymorphism: implications for antipsychotic drug response, schizophrenia and personality traits. Pharmacogenomics 8: 1597-1608, 2007.
83. Gardiner, S.J. and Begg, E.J. Pharmacogenetics, drug metabolizing enzymes and clinical practice. Pharm Rev. 58: 521-590, 2006.
84. Ginsberg, G. et al., Incorporating pharmacokinetic differences between children and adults in assessing children's risks to environmental toxicants. Toxicology and Applied Pharmacology 198: 164-183, 2004.
85. Isbister, G.K. et al., Paracetamol overdose in a preterm neonate. Arch. Dis. Child Fetal Neonatal Ed. 85: F70-F72, 2001.
86. Jain, M. et al., Microsomal epoxide hydrolase (EPHX1), slow (exon 3, 113His) and fast (exon 4, 139Arg) alleles confer susceptibility to squamous cell esophageal cancer. Toxicol & Applied Pharmacol 230: 247-251, 2008.
87. Jeffery, E.H. and Araya, M. Physiological effects of broccoli consumption. Phytochem. Rev. 8: 283-298, 2009.
88. Kaplan, M. et al., (TA)n UGT 1A1 Promoter Polymorphism: A Crucial Factor in the Pathophysiology of Jaundice in G-6-PD Deficient Neonates. Ped. Res. 61: 727-731, 2007.
89. Kawara, A. et al., CYP2B6 (c.516G > T) and CYP2A6 . * 9B and/or * 17) polymorphisms are independent predictors of efavirenz plasma concentrations in HIV-infected patients. Brit. J. Clin. Pharmacol. 67: 427-436, 2008.
90. Kearns, G.L. et al., Cisapride disposition in neonates and infants: in vivo reflection of cytochrome P450 3A4 ontogeny. Clin. Pharm. & Ther. 74: 312-325, 2003.
91. Keshava, C. et al., CYP3A4 Polymorphisms-Potential Risk factors for breast and Prostate cancer. A HuGE Review. Am. J. Epidemiol. 160: 825-841, 2004.
92. Kirchheiner, J. CYP2D6 Phenotype Prediction From Genotype: Which System Is the Best? Clin. Pharm. Ther. 83: 225-227, 2008.
93. Krähenbühl, S. et al., Acute liver failure in two patients with regular alcohol consumption ingesting paracetamol at therapeutic dosage. Digestion 75: 232-237, 2007.
94. Lankisch, T.O. et al., Gilbert's Syndrome and Irinotecan Toxicity: Combination with UDP-Glucuronosyltransferase 1A7 Variants Increases Risk. Cancer Epidemiol Biomarkers Prev. 17: 695-701, 2008.
95. Lu, Y. and Cederbaum, A.I. CYP2E1 and oxidative liver injury by alcohol. F ree Rad. Biol Medicine 44: 723-738, 2008.
96. O'Donoghue, M.L. et al., Pharmacodynamic effect and clinical efficacy of clopidogrel and prasugrel with or without a proton-pump inhibitor: an analysis of two randomised trials. The Lancet 374: 989-997, 2009.
97. Petersen, K.U. Relevance of metabolic activation pathways: the example of clopidogrel and prasugrel. Arzn.-Forsch. Drug Res 59: 213-227, 2009
98. Santoro, A. et al., Prometheus system: a technological support in liver failure. Transplantation Proceedings 38: 1078-1082, 2006
99. Shebley, M. and Hollenberg, P.F. Mutation of a single residue (K262R) in P450 2B6 leads to loss of mechanism-based inactivation by phencyclidine. Drug Metab Disp. 35: 1365-1371, 2007.
100. Slanar, O. et al., Miotic action of tramadol is determined by CYP2D6 Genotype. Physiol. Res. 56: 129-136, 2007.
101. Stevens, J.C. Developmental changes in human liver CYP2D6 expression. Drug Metab. Disp. 36: 1587-1593, 2008.
102. Swen, J.J. et al., Translating Pharmacogenomics: Challenges on the Road to the Clinic PLoS Med. 8: 1317-1324, 2007.
103. Albertini, R.J. et al., Molecular epidemiological studies in 1,3-butadiene exposed Czech workers: Female-male comparisons Chemico-Biol. Interactions 166: 63-77, 2007.
104. Alvestad, S. et al., Cross-reactivity pattern of rash from currentaromatic antiepileptic drugs Epilepsy Research 80: 194-200, 2008.
105. Arlt, V.M. et al., Human enzymes involved in the metabolic activation of the environmental contaminant 3-nitrobenzanthrone: evidence for reductive activation by human NADPH: cytochrome P450 reductase. Cancer Res. 63: 2752-2761, 2003.
106. Arlt, V.M. et al., 3-aminobenzanthrone, a human metabolite of the environmental pollutant 3-nitrobenzanthrone, forms DNA adducts after metabolic activation by human and rat liver microsomes: evidence for activation by cytochrome P450 1A1 and P450 1A2. Chem. Res. Toxicol. 17: 1092-1101, 2004.
107. Andrews, N.W. Membrane repair and immunological danger EMBO reports 6: 826-830, 2005.
108. Björnsson, E. Drug-induced liver injury: Hy's rule revisited. Clin. Pharm. Ther. 79: 521-5288, 2006.
109. Björnsson, E. Hepatotoxicity associated with antiepileptic drugs Acta Neurol Scand. 118: 281-290, 2008.
110. Borlak, J. Trovafloxacin: a case study of idiosyncratic or iatrogenic liver toxicity-molecular mechanisms and lessons for pharmacotoxicity. Hum. & Exp. Toxicol 28: 119-121, 2009.
111. Coleman, M.D. Dapsone mediated agranulocytosis: risks, possible mechanisms and prevention. Toxicology 162: 53-60, 2001.
112. Coleman, M.D. and Coleman, N.A. Drug-induced methaemoglobinaemia. Drug Safety 14: 394-405, 1996.
113. Funk, C. et al., Cholestatic potential of troglitazone as a possible factor contributing to troglitazone-induced hepatotoxicity: in vivo and in vitro interaction at the canalicular bile salt export pump (Bsep) in the rat. Mol. Pharmacol. 59: 627-635, 2001.
114. Green, M.D. and Tephly, T.R. Glucuronidation of amine substrates by purified and expressed UDP-glucuronosyltransferase proteins. Drug Metab. Disp. 26: 860-867, 1998.
115. Julie, N.L. et al., Mitochondrial dysfunction and delayed hepatotoxicity: another lesson from troglitazone Diabetologia 51: 2108-2116, 2008.
116. Kassahun, K. et al., Studies on the metabolism of troglitazone to reactive intermediates in vitro and in vivo. Evidence for novel biotransformation pathways involving quinone methide formation and thiazolidinedione ring scission. Chem. Res. Toxicol. 1: 62-70, 2001.
117. Khan, F.D. et al., Effect of Arylhydroxylamine Metabolites of Sulfamethoxazoleand Dapsone on Stress Signal Expression in Human Keratinocytes. J. Pharm. Exp. Ther. 323: 771-777, 2007.
118. Kier, L.D. Applications of microarrays with toxicologically relevant genes (tox genes) for the evaluation of chemical toxicants in Sprague Dawley rats in vivo and human hepatocytes in vitro. Mutation Research 549: 101-113, 2004.
119. Lauer, B. et al., Species-specific toxicity of diclofenac and troglitazone in primary human and rat hepatocytes. Chemico-Biological Interactions 179: 17-24, 2009.
120. Liguori, M.J. et al., Microarray analysis inhuman hepatocytes suggests a mechanism for hepatotoxicity induced by trovafloxacin. Hepatology 41: 177-186, 2005.
121. Mansouri, A. et al., Tacrine inhibits topoisomerases and DNA synthesis to cause mitochondrial DNA depletion and apoptosis in mouse liver. Hepatology 38: 715-725, 2003.
122. Mansur, T. et al., Anticonvulsant hypersensitivity syndrome: clinical and laboratory features International Journal of Dermatology 47: 1184-1189, 2008.
123. Matzinger, P. Tolerance, danger, and the extended family. Annu Rev Immunol 12: 991-1045, 1994.
124. Merk, H.F. et al., Skin: Major target organ of allergic reactions to small molecular weight compounds Toxicology & Applied Pharmacol. 224: 313-317, 2007.
125. Noor, F. et al., An integrated approach to improved toxicity prediction for the safety assessment during preclinical drug development using Hep G2 cells. Toxicology & App Pharmacol. 237: 221-231, 2009.
126. Pichler, W.J. Delayed drug hypersensitivity reactions. Ann Int. Med. 139: 683-693, 2003.
127. Pichler, W.J. Drug allergy does not need to involve reactive intermediates: An alternative hypothesis. Toxicology Letters 172S: S1-S240, 2007.
128. Reynisson, J. et al., Mutagenic Potential of Nitrenium Ions of Nitrobenzanthrones: Correlation Between Theory and Experiment. Environ. Mol. Mutagen. 49: 659-667, 2008.
129. Roychowdhury, S. and Svensson, C.K. Mechanisms of doug-induced delayed type hyperaseusitivity reactions in the skin. AAPS J. 7: E834-E846, 2005.
130. Santos, N.A.G. et al., Involvement of oxidative stress in the hepatotoxicity induced by aromatic antiepileptic drugs. Toxicology in Vitro 22: 1820-1824, 2008.
131. Sheen, C.L. Paracetamol toxicity: epidemiology, prevention and costs to the health-care system. Q. J. Med. 95: 609-619, 2002.
132. Stachlewitz, R.F. et al., Development and characterization of a new model of tacrine-induced hepatotoxicity: role of the sympathetic nervous system and hypoxia-reoxygenation. Drug Metab. Disp. 282: 1591-1599, 1997.
133. Suzuki, Y. et al., Carbamazepine-induced drug-induced hypersensitivity syndrome in a 14-year-old Japanese boy Epilepsia, 49: 2118-2121, 2008
134. Talaska, G. Aromatic amines and human urinary bladder cancer: exposure sources and epidemiology. J. ENV. Sci. Health Part C-Env. Carc. & Ecotox. Rev. 21: 29-43, 2003.
135. Vyas, P.M. et al., Enzyme-mediatedprotein haptenation of dapsone and sulfamethoxazole in human keratinocytes: II. Expression and role of flavin-containing monooxygenases andperoxidases. J. Pharmacol. Exp. Ther. 319: 497-505. 2006.
136. Zimmerman, H.J. Hepatotoxicity. The adverse effects of drugs and other chemicals on the liver. 2nd ed. Philadelphia: Lippincott Williams & Wilkins, 1999.
137. Coleman, M.D. and Kuhns, M.K. Methaemoglobin formation by 4-aminopropriophenone in single and dual compartmental systems. Env. Tox. Pharmacol. 7: 75-80, 1999.
138. Grime, K.H. et al., Mechanism-based inhibition of cytochrome P450 enzymes: An evaluation of early decision making in vitro approachesand drug-drug interaction prediction Eur. J Pharm. Sci. 36: 175-191, 2009.
139. Li, A.P. Human hepatocytes: Isolation, cryopreservation and applications in drug development. Chemico-Biol.l Interactions 168: 16-29, 2007.
140. Muruganandan, S. and Sinal, C.J. Mice as Clinically Relevant Models for the Study of Cytochrome P450-dependent Metabolism. Clin. Pharm, & Ther. 83: 818-828, 2008.
141. O'Brien, P.J. et al., High concordance of drug-induced human hepatotoxicity with in vitrocytotoxicity. Arch Toxicol 80: 580-604, 2006.
142. Soars, M.G. et al., The pivotal role of hepatocytes in drug discovery. Chemico-Biol. Interactions 168: 2-15, 2007.
143. Tingle, M.D. et al., Investigation into the role of metabolism in dapsone-induced methaemoglobinaemia using a two-compartment in vitro test system. Brit. J. Clin. Pharmac. 30: 829-838, 1990.
144. Tsaioun, K. et al., ADDME-Avoiding Drug Development Mistakes Early: central nervous system drug discovery perspective. BMC Neurology 9 (Suppl 1): 1-11, 2009.
145. Uno, S. et al., CYP1A1 and CYP1A2 expression: Comparing'humanized'mouse lines and wild-type mice; comparing human and mouse hepatoma-derived cell lines. Tox. & Appl. Pharmacol. 237: 119-126, 2009.
146. Zhang, L. et al., A regulatory viewpoint on transporter-based drug interactions. Xenobiotica, 38: 709-724, 2008.
147. Zolnik, B.S. and Sadrieh, N. Regulatory perspective on the importance of ADME assessment of nanoscale materialcontaining drugs. Advanced Drug Delivery Rev. 61: 422-427, 2009.
148. Antia, U. et al., Metabolic interactions between piperazine-based'party pill'drugs J. Pharm. Pharmacol. 61: 877-882, 2009.
149. Antia, U. et al., Pharmacokinetics of'party pill'drug N-benzylpiperazine (BZP) in healthy human participants. Forensic Science International 186: 63-67, 2009.
150. Antoniou, T. and Tseng, A.L. Interactions between recreational drugs and antiretroviral agents. A nn. Pharmacother. 36: 1598-1613, 2002.
151. Casey Laizure, S. et al., Cocaethylene metabolism and interaction with cocaine and ethanol: role of carboxylesterases. Drug Metab. Disp. 31: 16-20, 2003.
152. Holmquist, G.L. Opioid Metabolism and Effects of Cytochrome P450 PharmD. Pain Med. 10: S20-s29, 2009.
153. Kharasch, E.D. et al., Methadone metabolism and clearance are induced by nelfinavir despite inhibition of cytochrome P4503A (CYP3A) activity. Drug and Alcohol Dependence 101: 158-168, 2009.
154. Moody, D.E. et al., The in vivo response of novel buprenorphine metabolites, M1 and M3 to antiviral inducers and inhibitors of buprenorphine metabolism. Basic & Clinical Pharmacology & Toxicology, 105: 211-215, 2009.
155. Perfetti, X. et al., Neurotoxic Thioether Adducts of 3,4-Methylenedioxymethamphetamine Identified in Human Urine After Ecstasy Ingestion. Drug Met. Disp 37: 1448-1455, 2009.
156. Rook, E.J. et al., Population pharmacokinetics of heroin and its major metabolites. Clin. Pharmakinet. 45: 401-417, 2006.
157. Sauer, C. et al., Investigations on the cytochrome P450 (CYP) isoenzymes involved in the metabolism of the designer drugs N-(1-phenyl cyclohexyl)-2-ethoxyethanamine and N-(1-phenylcyclohexyl)-2-methoxyethanamine. Biochem. Pharmacol. 77: 444-450, 2009.
158. Shebley, S. and Hollenburg, P.F., Mutation of a single residue (K262R) in P450 2B6 leads to loss of mechanism-based inactivation by phencyclidine. Drug Metab. Disp. 35: 1365-1371, 2007.
159. Sun, H. et al., Cocaine metabolism accelerated by a re-engineered human butyrylcholinesterase. Pharm Exper. Ther. 302 (2): 710-716, August 2002.
160. de la Torre, R. and Farré, M. Neurotoxicity of MDMA (ecstasy): the limitations of scaling from animals to humans. Trends Pharm. Sci. 25: 505-508, 2004.
161. Totah, R.H. et al., Role of CYP2B6 in Stereoselective Human Methadone Metabolism Anesthesiology 108: 363-74, 2008.
162. 'The Vikings'Douglas, K. et al., dir. Richard Fleischer: running time 116 min; Metro-Goldwyn-Mayer, Released June 1958. WARNING: re-enacting the feasting scene is both sexist and may result in serious personal injury.
163. Zwisler, S.T. et al., The Hypoalgesic Effect of Oxycodone in Human Experimental Pain Models in Relation to the CYP2D6 Oxidation Polymorphism. Basic & Clinical Pharmacology & Toxicology 104: 335-344, 2009.