Cytochrome P450s and other enzymes in drug metabolism and toxicity

Cytochrome P-450: Structure, Mechanism, and Biochemistry

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Clinical importance of the cytochromes P450

Nebert, D. W., & Russell, D. W. (2002) · The Lancet · doi:10.1016/s0140-6736(02)11203-7 · Cited by 1,414

Broccoli sprouts: An exceptionally rich source of inducers of enzymes that protect against chemical carcinogens

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ACETAMINOPHEN-INDUCED HEPATIC NECROSIS. II. ROLE OF COVALENT BINDING IN VIVO

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DRUG-DRUG INTERACTIONS FOR UDP-GLUCURONOSYLTRANSFERASE SUBSTRATES: A PHARMACOKINETIC EXPLANATION FOR TYPICALLY OBSERVED LOW EXPOSURE (AUCI/AUC) RATIOS

Williams, J. A., Hyland, R., Jones, B. C., Smith, D. A., Hurst, S., Goosen, T. C., Peterkin, V., Koup, J. R., & Ball, S. E. (2004) · Drug Metabolism and Disposition · doi:10.1124/dmd.104.000794 · Cited by 928

Predicting in vivo drug interactions from in vitro drug discovery data

Wienkers, L. C., & Heath, T. G. (2005) · Nature Reviews Drug Discovery · doi:10.1038/nrd1851 · Cited by 904

Human Cytochrome P450 Enzymes

Guengerich, F. P. (1995) · Cytochrome P450 · doi:10.1007/978-1-4757-2391-5_14 · Cited by 728

Drug−Protein Adducts: An Industry Perspective on Minimizing the Potential for Drug Bioactivation in Drug Discovery and Development

Evans, D. C., Watt, A. P., Nicoll-Griffith, D. A., & Baillie, T. A. (2004) · Chemical Research in Toxicology · doi:10.1021/tx034170b · Cited by 706

Mechanism of the Cardiotoxic Actions of Terfenadine

Woosley, R. L. (1993) · JAMA: The Journal of the American Medical Association · doi:10.1001/jama.1993.03500120070028 · Cited by 646

A Comprehensive Listing of Bioactivation Pathways of Organic Functional Groups

Kalgutkar, A., Gardner, I., Obach, R., Shaffer, C., Callegari, E., Henne, K., Mutlib, A., Dalvie, D., Lee, J., Nakai, Y., et al. (2005) · Current Drug Metabolism · doi:10.2174/1389200054021799 · Cited by 616

Elucidating mechanisms of drug-induced toxicity

Liebler, D. C., & Guengerich, F. P. (2005) · Nature Reviews Drug Discovery · doi:10.1038/nrd1720 · Cited by 323

Role of Metabolism in Drug-Induced Idiosyncratic Hepatotoxicity

Walgren, J. L., Mitchell, M. D., & Thompson, D. C. (2005) · Critical Reviews in Toxicology · doi:10.1080/10408440590935620 · Cited by 322

New Concepts in Immunology Relevant to Idiosyncratic Drug Reactions: The “Danger Hypothesis” and Innate Immune System

Uetrecht, J. P. (1999) · Chemical Research in Toxicology · doi:10.1021/tx980249i · Cited by 304

Identification of the Hepatic Protein Targets of Reactive Metabolites of Acetaminophen in Vivoin Mice Using Two-dimensional Gel Electrophoresis and Mass Spectrometry

Qiu, Y., Benet, L. Z., & Burlingame, A. L. (1998) · Journal of Biological Chemistry · doi:10.1074/jbc.273.28.17940 · Cited by 298

Inactivation of the hepatic cytochrome P450 system by conditional deletion of hepatic cytochrome P450 reductase

Henderson, C. J., Otto, D. M. E., Carrie, D., Magnuson, M. A., McLaren, A. W., Rosewell, I., & Wolf, C. R. (2003) · Journal of Biological Chemistry · doi:10.1074/jbc.m212087200 · Cited by 258

Induction of cytochrome P4501A1 by 2,3,7,8-tetrachlorodibenzo-p-dioxin or indolo(3,2-b)carbazole is associated with oxidative DNA damage.

Park, J. Y., Shigenaga, M. K., & Ames, B. N. (1996) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.93.6.2322 · Cited by 254

Oxidation of the antihistaminic drug terfenadine in human liver microsomes. Role of cytochrome P-450 3A(4) in N-dealkylation and C-hydroxylation.

Yun, C. H., Okerholm, R. A., & Guengerich, F. P. (1993) · Drug Metabolism and Disposition · doi:10.1016/s0090-9556(25)07393-3 · Cited by 229

Minimising the potential for metabolic activation in drug discovery

Kalgutkar, A. S., & Soglia, J. R. (2005) · Expert Opinion on Drug Metabolism & Toxicology · doi:10.1517/17425255.1.1.91 · Cited by 229

Glutathione conjugate mediated toxicities*1

Monks, T. J. (1990) · Toxicology and Applied Pharmacology · doi:10.1016/0041-008x(90)90100-9 · Cited by 228

Human Cytochrome P450 Enzymes

Guengerich, F. P. (2007) · Cytochrome P450 · doi:10.1007/0-387-27447-2_10 · Cited by 220

Liver-specific Deletion of the NADPH-Cytochrome P450 Reductase Gene

Gu, J., Weng, Y., Zhang, Q.-Y., Cui, H., Behr, M., Wu, L., Yang, W., Zhang, L., & Ding, X. (2003) · Journal of Biological Chemistry · doi:10.1074/jbc.m303125200 · Cited by 214

Oxidation of trichloroethylene by liver microsomal cytochrome P-450: evidence for chlorine migration in a transition state not involving trichloroethylene oxide

Miller, R. E., & Guengerich, F. P. (1982) · Biochemistry · doi:10.1021/bi00534a041 · Cited by 214

CYP2E1-dependent toxicity and oxidative stress in HepG2 cells,

Cederbaum, A. (2001) · Free Radical Biology and Medicine · doi:10.1016/s0891-5849(01)00743-2 · Cited by 208

Anti-liver endoplasmic reticulum autoantibodies are directed against human cytochrome P-450IA2. A specific marker of dihydralazine-induced hepatitis.

Bourdi, M., Larrey, D., Nataf, J., Bernuau, J., Pessayre, D., Iwasaki, M., Guengerich, F. P., & Beaune, P. H. (1990) · Journal of Clinical Investigation · doi:10.1172/jci114660 · Cited by 207

Targeted Disruption of the Microsomal Epoxide Hydrolase Gene

Miyata, M., Kudo, G., Lee, Y.-H., Fernandez-Salguero, P., Kimura, S., Gonzalez, F. J., Yang, T. J., & Gelboin, H. V. (1999) · Journal of Biological Chemistry · doi:10.1074/jbc.274.34.23963 · Cited by 199

Cytochrome P450: What Have We Learned and What Are the Future Issues?

Peter Guengerich, F. (2004) · Drug Metabolism Reviews · doi:10.1081/dmr-120033996 · Cited by 193

Paracelsus: Herald of Modern Toxicology

Borzelleca, J. F. (2000) · Toxicological Sciences · doi:10.1093/toxsci/53.1.2 · Cited by 171

Activation of Heterocyclic Aromatic Amines by Rat and Human Liver Microsomes and by Purified Rat and Human Cytochrome P450 1A2

Turesky, R. J., Constable, A., Richoz, J., Varga, N., Markovic, J., Martin, M. V., & Guengerich, F. P. (1998) · Chemical Research in Toxicology · doi:10.1021/tx980022n · Cited by 170

Statins induce apoptosis in rat and human myotube cultures by inhibiting protein geranylgeranylation but not ubiquinone

Johnson, T. E., Zhang, X. D., Bleicher, K. B., Dysart, G. R., Loughlin, A. F., Schaefer, W. H., & Umbenhauer, D. R. (2004) · Toxicology and Applied Pharmacology · doi:10.1016/j.taap.2004.04.010 · Cited by 144

Toxicological profile for trichloroethylene

Williams-Johnson, M. M. (1997) · Cited by 139

Function of human cytochrome P450s: Characterization of the orphans

Guengerich, F. P., Wu, Z., & Bartleson, C. (2005) · Biochemical and Biophysical Research Communications · doi:10.1016/j.bbrc.2005.08.079 · Cited by 133

“Phase I and Phase II” Drug Metabolism: Terminology that we Should Phase Out?

Josephy, P. D., Guengerich, F. P., & Miners, J. O. (2005) · Drug Metabolism Reviews · doi:10.1080/03602530500251220 · Cited by 128

Reaction of aflatoxin B 1 exo -8,9-epoxide with DNA: Kinetic analysis of covalent binding and DNA-induced hydrolysis

Johnson, W. W., & Guengerich, F. P. (1997) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.94.12.6121 · Cited by 126

Use of Terfenadine and Contraindicated Drugs

Thompson, D. (1996) · JAMA · doi:10.1001/jama.1996.03530410053033 · Cited by 109

Human variability in CYP3A4 metabolism and CYP3A4-related uncertainty factors for risk assessment

Dorne, J. L. C. M., Walton, K., & RENWICK, A. G. (2003) · Food and Chemical Toxicology · doi:10.1016/s0278-6915(02)00209-0 · Cited by 94

Kinetics and Mechanism of Hydrolysis of Aflatoxin B1 exo-8,9-Epoxide and Rearrangement of the Dihydrodiol

Johnson, W. W., Harris, T. M., & Guengerich, F. P. (1996) · Journal of the American Chemical Society · doi:10.1021/ja960525k · Cited by 94

Inhibition of Terfenadine Metabolism

Kivistö, K. T., Neuvonen, P. J., & Klotz, U. E. (1994) · Clinical Pharmacokinetics · doi:10.2165/00003088-199427010-00001 · Cited by 84

Reaction of Aflatoxin B 1 Oxidation Products with Lysine

Guengerich, F. P., Arneson, K. O., Williams, K. M., et al. (2002) · Chemical Research in Toxicology · doi:10.1021/tx010156s · Cited by 73

Human variability in polymorphic CYP2D6 metabolism: is the kinetic default uncertainty factor adequate?

Dorne, J. L. C. M., Walton, K., Slob, W., & RENWICK, A. G. (2002) · Food and Chemical Toxicology · doi:10.1016/s0278-6915(02)00117-5 · Cited by 70

Acetaminophen structure-toxicity studies: In vivo covalent binding of a nonhepatotoxic analog, 3-hydroxyacetanilide

Roberts, S., Price, V. F., & Jollow, D. J. (1990) · Toxicology and Applied Pharmacology · doi:10.1016/0041-008x(90)90181-s · Cited by 68

Reduction of Aflatoxin B1 Dialdehyde by Rat and Human Aldo-keto Reductases

Guengerich, F. P., Cai, H., McMahon, M. J., Hayes, J. D., Sutter, T. R., Groopman, J. D., Deng, J. Z., & Harris, T. M. (2001) · Chemical Research in Toxicology · doi:10.1021/tx010005p · Cited by 66

Principles of covalent binding of reactive metabolites and examples of activation of bis-electrophiles by conjugation

Guengerich, F. P. (2004) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2004.07.035 · Cited by 61

The microsomal metabolism and site of covalent binding to protein of 3'-hydroxyacetanilide, a nonhepatotoxic positional isomer of acetaminophen.

Streeter, A. J., Bjorge, S. M., Axworthy, D. B., Nelson, S. D., & Baillie, T. A. (1984) · Drug Metabolism and Disposition · doi:10.1016/s0090-9556(25)07764-5 · Cited by 58

Metabolic activation of pesticides with proestrogenic activity.

Kupfer, D., & Bulger, W. H. (1987) · PubMed · Cited by 55

Activation of Dihaloalkanes by Thiol-dependent Mechanisms

Guengerich, F. P. (2003) · BMB Reports · doi:10.5483/bmbrep.2003.36.1.020 · Cited by 48

Is Neurotoxicity Associated with Environmental Trichloroethylene (TCE)?

Kilburn, K. H. (2002) · Archives of Environmental Health An International Journal · doi:10.1080/00039890209602925 · Cited by 29

Reaction of Trichloroethylene Oxide with Proteins and DNA: Instability of Adducts and Modulation of Functions

Cai, H., & Guengerich, F. P. (2000) · Chemical Research in Toxicology · doi:10.1021/tx000185n · Cited by 24

Historical Perspectives on Conjugation-Dependent Bioactivation of Foreign Compounds

Miller, J. A., & Surht, Y.-J. (1994) · Advances in pharmacology · doi:10.1016/s1054-3589(08)61027-3 · Cited by 22

The DNA cleavage reaction of topoisomerase II: wolf in sheep's clothing

Deweese, J. E., & Osheroff, N. (2009) · Nucleic Acids Research · doi:10.1093/nar/gkn937 · Cited by 462

Therapeutic advances of miRNAs: A preclinical and clinical update

Chakraborty, C., Sharma, A. R., Sharma, G., & Lee, S.-S. (2021) · Journal of Advanced Research · doi:10.1016/j.jare.2020.08.012 · Cited by 402

Cytochrome P450: taming a wild type enzyme

Jung, S. T., Lauchli, R., & Arnold, F. H. (2011) · Current Opinion in Biotechnology · doi:10.1016/j.copbio.2011.02.008 · Cited by 293

Potential of insulin nanoparticle formulations for oral delivery and diabetes treatment.

Wong, C. Y., Al-Salami, H., & Dass, C. R. (2017) · Journal of Controlled Release · doi:10.1016/j.jconrel.2017.09.003 · Cited by 257

Application of PBPK modeling to predict human intestinal metabolism of CYP3A substrates – An evaluation and case study using GastroPlus™

Heikkinen, A. T., Baneyx, G., Caruso, A., & Parrott, N. (2012) · European Journal of Pharmaceutical Sciences · doi:10.1016/j.ejps.2012.06.013 · Cited by 76