Enzymatic characteristics of CYP3A5 and CYP3A4: A comparison of in vitro kinetic and drug–drug interaction patterns

References

• Cook CS, Berry LM, Kim DH, Burton EG. Involvement of CYP3A in the metabolism of eplerenone in humans and dogs: Differential metabolism by CYP3A4 and CYP3A5. Drug Metabolism and Disposition 2002; 30: 1344–1351
   PubMed Web of Science ®Google Scholar
• Domanski TL, He YA, Khan KK, Roussel F, Wang Q, Halpert JR. Phenylalanine and tryptophan scanning mutagenesis of CYP3A4 substrate recognition site residues and effect on substrate oxidation and cooperativity. Biochemistry 2001; 40: 10150–10160
   PubMed Web of Science ®Google Scholar
• Emoto C, Murase S, Sawada Y, Jones BC, Iwasaki K. In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalysed by human cytochrome P450 enzymes: A comparison with SKF-525A and ketoconazole. Drug Metabolism and Pharmacokinetics 2003; 18: 287–295
   PubMedGoogle Scholar
• Emoto C, Murase S, Sawada Y, Iwasaki K. In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations in human liver microsomes: A comparison with SKF-525A. Drug Metabolism and Pharmacokinetics 2005; 20: 351–357
   PubMedGoogle Scholar
• Galetin A, Clarke SE, Houston JB. Multisite kinetic analysis of interactions between prototypical CYP3A4 subgroup substrates: Midazolam, testosterone, and nifedipine. Drug Metabolism and Disposition 2003; 31: 1108–1116
   PubMed Web of Science ®Google Scholar
• Gibbs MA, Thummel KE, Shen DD, Kunze KL. Inhibition of cytochrome P-450 3A (CYP3A) in human intestinal and liver microsomes: Comparison of Ki values and impact of CYP3A5 expression. Drug Metabolism and Disposition 1999; 27: 180–187
   PubMed Web of Science ®Google Scholar
• Guengerich FP. Cytochrome P-450 3A4: Regulation and role in drug metabolism. Annual Reviews in Pharmacology and Toxicology 1999; 39: 1–17
   PubMed Web of Science ®Google Scholar
• Harlow GR, Halpert JR. Alanine-scanning mutagenesis of a putative substrate recognition site in human cytochrome P450 3A4. Role of residues 210 and 211 in flavonoid activation and substrate specificity. Journal of Biological Chemistry 1997; 272: 5396–5402
   PubMed Web of Science ®Google Scholar
• Kenworthy KE, Bloomer JC, Clarke SE, Houston JB. CYP3A4 drug interactions: Correlation of 10 in vitro probe substrates. British Journal of Clinical Pharmacology 1999; 48: 716–727
   PubMed Web of Science ®Google Scholar
• Koch I, Weil R, Wolbold R, Brockmoller J, Hustert E, Burk O, Nuessler A, Neuhaus P, Eichelbaum M, Zanger U, Wojnowski L. Interindividual variability and tissue-specificity in the expression of cytochrome P450 3A mRNA. Drug Metabolism and Disposition 2002; 30: 1108–1114
   PubMed Web of Science ®Google Scholar
• Komori M, Nishio K, Kitada M, Shiramatsu K, Muroya K, Soma M, Nagashima K, Kamataki T. Fetus-specific expression of a form of cytochrome P-450 in human livers. Biochemistry 1990; 29: 4430–4433
   PubMed Web of Science ®Google Scholar
• Krishna DR, Klotz U. Extrahepatic metabolism of drugs in humans. Clinical Pharmacokinetics Concepts 1994; 26: 144–160
   PubMed Web of Science ®Google Scholar
• Kuehl P, Zhang J, Lin Y, Lamba J, Assem M, Schuetz J, Watkins PB, Daly A, Wrighton SA, Hall SD, Maurel P, Relling M, Brimer C, Yasuda K, Venkataramanan R, Strom S, Thummel K, Boguski MS, Schuetz E. Sequence diversity in CYP3A promoters and characterization of the genetic basis of polymorphic CYP3A5 expression. Nature Genetics 2001; 27: 383–391
   PubMed Web of Science ®Google Scholar
• Lewis DF, Eddershaw PJ, Goldfarb PS, Tarbit MH. Molecular modelling of CYP3A4 from an alignment with CYP102: Identification of key interactions between putative active site residues and CYP3A-specific chemicals. Xenobiotica 1996; 26: 1067–1086
   PubMed Web of Science ®Google Scholar
• Maenpaa J, Hall SD, Ring BJ, Strom SC, Wrighton SA. Human cytochrome P450 3A (CYP3A) mediated midazolam metabolism: The effect of assay conditions and regioselective stimulation by alpha-naphthoflavone, terfenadine and testosterone. Pharmacogenetics 1998; 8: 137–155
   PubMedGoogle Scholar
• Nakajima M, Tane K, Nakamura S, Shimada N, Yamazaki H, Yokoi T. Evaluation of approach to predict the contribution of multiple cytochrome P450s in drug metabolism using relative activity factor: Effects of the differences in expression levels of NADPH-cytochrome P450 reductase and cytochrome b5 in the expression system and the differences in the marker activities. Journal of Pharmaceutical Science 2002; 91: 952–963
   PubMed Web of Science ®Google Scholar
• Nelson DR, Koymans L, Kamataki T, Stegeman JJ, Feyereisen R, Waxman DJ, Waterman MR, Gotoh O, Coon MJ, Estabrook RW, Gunsalus IC, Nebert DW. P450 superfamily: Update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics 1996; 6: 1–42
   PubMedGoogle Scholar
• Patki KC, Von Moltke LL, Greenblatt DJ. In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes p450: Role of cyp3a4 and cyp3a5. Drug Metabolism and Disposition 2003; 31: 938–944
   PubMed Web of Science ®Google Scholar
• Racha JK, Zhao ZS, Olejnik N, Warner N, Chan R, Moore D, Satoh H. Substrate dependent inhibition profiles of fourteen drugs on CYP3A4 activity measured by a high throughput LCMS/MS method with four probe drugs, midazolam, testosterone, nifedipine and terfenadine. Drug Metabolism and Pharmacokinetics 2003; 18: 128–138
   PubMedGoogle Scholar
• Rendic S. Summary of information on human CYP enzymes: Human P450 metabolism data. Drug Metabolism Reviews 2002; 34: 83–448
   PubMed Web of Science ®Google Scholar
• Schrag ML, Wienkers LC. Triazolam substrate inhibition: Evidence of competition for heme-bound reactive oxygen within the CYP3A4 active site. Drug Metabolism and Disposition 2001; 29: 70–75
   PubMed Web of Science ®Google Scholar
• Shimada T, Yamazaki H, Mimura M, Inui Y, Guengerich FP. Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians. Journal of Pharmacology and Experimental Therapeutics 1994; 270: 414–423
   PubMed Web of Science ®Google Scholar
• Shou M, Grogan J, Mancewicz JA, Krausz KW, Gonzalez FJ, Gelboin HV, Korzekwa KR. Activation of CYP3A4: Evidence for the simultaneous binding of two substrates in a cytochrome P450 active site. Biochemistry 1994; 33: 6450–6455
   PubMed Web of Science ®Google Scholar
• Smith DA, Ackland MJ, Jones BC. Properties of cytochrome P450 isoenzymes and their substrates part 2: Properties of cytochrome P450 substrates. Drug Discovery Today 1997; 2: 479–486
   Web of Science ®Google Scholar
• Spatzenegger M, Jaeger W. Clinical importance of hepatic cytochrome P450 in drug metabolism. Drug Metabolism Reviews 1995; 27: 397–417
   PubMed Web of Science ®Google Scholar
• Ueng YF, Kuwabara T, Chun YJ, Guengerich FP. Cooperativity in oxidations catalysed by cytochrome P450 3A4. Biochemistry 1997; 36: 370–381
   PubMed Web of Science ®Google Scholar
• Wang H, Dick R, Yin H, Licad-Coles E, Kroetz DL, Szklarz G, Harlow G, Halpert JR, Correia MA. Structure–function relationships of human liver cytochromes P450 3A: Aflatoxin B1 metabolism as a probe. Biochemistry 1998; 37: 12536–12545
   PubMed Web of Science ®Google Scholar
• Wang RW, Newton DJ, Liu N, Atkins WM, Lu AY. Human cytochrome P-450 3A4: In vitro drug–drug interaction patterns are substrate-dependent. Drug Metabolism and Disposition 2000; 28: 360–366
   PubMed Web of Science ®Google Scholar
• Westlind A, Malmebo S, Johansson I, Otter C, Andersson TB, Ingelman-Sundberg M, Oscarson M. Cloning and tissue distribution of a novel human cytochrome p450 of the CYP3A subfamily, CYP3A43. Biochemical and Biophysical Research Communications 2001; 281: 1349–1355
   PubMed Web of Science ®Google Scholar
• Wrighton SA, Brian WR, Sari MA, Iwasaki M, Guengerich FP, Raucy JL, Molowa DT, Vandenbranden M. Studies on the expression and metabolic capabilities of human liver cytochrome P450IIIA5 (HLp3). Molecular Pharmacology 1990; 38: 207–213
   PubMed Web of Science ®Google Scholar
• Wrighton SA, Stevens JC. The human hepatic cytochromes P450 involved in drug metabolism. 1992. Critical Reviews in Toxicology 1992; 22: 1–21
   PubMed Web of Science ®Google Scholar