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

Xenobiotica

Volumn 36, Issue 2-3, 2006, Pages 219-233

  Emoto, C ^a   Iwasaki, K ^a  

^a PFIZER INC   (United States)

Author keywords

naphthoflavone; CYP3A4; CYP3A5; Interaction

Indexed keywords

ALPHA NAPHTHOFLAVONE; ALPRAZOLAM; BUSPIRONE; CYTOCHROME P450 3A4; CYTOCHROME P450 3A5; MIDAZOLAM; NIFEDIPINE; PREDNISONE; TERFENADINE; TESTOSTERONE;

ARTICLE; CATALYSIS; DRUG EFFECT; ENZYME ANALYSIS; ENZYME ASSAY; ENZYME MECHANISM; ENZYME SPECIFICITY; ENZYME SUBSTRATE; HUMAN; HUMAN TISSUE; HYDROXYLATION; XENOBIOTIC METABOLISM;

BENZOFLAVONES; BINDING SITES; CATALYSIS; COMPUTER SIMULATION; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME ACTIVATION; KINETICS; MIDAZOLAM; MODELS, CHEMICAL; NIFEDIPINE; PROTEIN BINDING; PROTEIN INTERACTION MAPPING; SUBSTRATE SPECIFICITY; TERFENADINE; TESTOSTERONE;

EID: 33646568084     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.1080/00498250500489968     Document Type: Article

References (31)

1. Cook CS, Berry LM, Kim DH, Burton EG. 2002. Involvement of CYP3A in the metabolism of eplerenone in humans and dogs: Differential metabolism by CYP3A4 and CYP3A5. Drug Metabolism and Disposition 30:1344-1351.
2. Domanski TL, He YA, Khan KK, Roussel F, Wang Q, Halpert JR. 2001. Phenylalanine and tryptophan scanning mutagenesis of CYP3A4 substrate recognition site residues and effect on substrate oxidation and cooperativity. Biochemistry 40:10150-10160.
3. Emoto C, Murase S, Sawada Y, Jones BC, Iwasaki K. 2003. 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 18:287-295.
4. Emoto C, Murase S, Sawada Y, Iwasaki K. 2005. In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations in human liver microsomes: A comparison with SKF-525A. Drug Metabolism and Pharmacokinetics 20:351-357.
5. Galetin A, Clarke SE, Houston JB. 2003. Multisite kinetic analysis of interactions between prototypical CYP3A4 subgroup substrates: Midazolam, testosterone, and nifedipine. Drug Metabolism and Disposition 31:1108-1116.
6. Gibbs MA, Thummel KE, Shen DD, Kunze KL. 1999. 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 27:180-187.
7. Guengerich FP. 1999. Cytochrome P-450 3A4: Regulation and role in drug metabolism. Annual Reviews in Pharmacology and Toxicology 39:1-17.
8. Harlow GR, Halpert JR. 1997. 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 272:5396-5402.
9. Kenworthy KE, Bloomer JC, Clarke SE, Houston JB. 1999. CYP3A4 drug interactions: Correlation of 10 in vitro probe substrates. British Journal of Clinical Pharmacology 48:716-727.
10. Koch I, Weil R, Wolbold R, Brockmoller J, Hustert E, Burk O, Nuessler A, Neuhaus P, Eichelbaum M, Zanger U, Wojnowski L. 2002. Interindividual variability and tissue-specificity in the expression of cytochrome P450 3A mRNA. Drug Metabolism and Disposition 30:1108-1114.
11. Komori M, Nishio K, Kitada M, Shiramatsu K, Muroya K, Soma M, Nagashima K, Kamataki T. 1990. Fetus-specific expression of a form of cytochrome P-450 in human livers. Biochemistry 29:4430-4433.
12. Krishna DR, Klotz U. 1994. Extrahepatic metabolism of drugs in humans. Clinical Pharmacokinetics Concepts 26:144-160.
13. 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. 2001. Sequence diversity in CYP3A promoters and characterization of the genetic basis of polymorphic CYP3A5 expression. Nature Genetics 27:383-391.
14. Lewis DF, Eddershaw PJ, Goldfarb PS, Tarbit MH. 1996. Molecular modelling of CYP3A4 from an alignment with CYP102: Identification of key interactions between putative active site residues and CYP3A-specific chemicals. Xenobiotica 26:1067-1086.
15. Maenpaa J, Hall SD, Ring BJ, Strom SC, Wrighton SA. 1998. Human cytochrome P450 3A (CYP3A) mediated midazolam metabolism: The effect of assay conditions and regioselective stimulation by alpha-naphthoflavone, terfenadine and testosterone. Pharmacogenetics 8:137-155.
16. Nakajima M, Tane K, Nakamura S, Shimada N, Yamazaki H, Yokoi T. 2002. 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 91:952-963.
17. Nelson DR, Koymans L, Kamataki T, Stegeman JJ, Feyereisen R, Waxman DJ, Waterman MR, Gotoh O, Coon MJ, Estabrook RW, Gunsalus IC, Nebert DW. 1996. P450 superfamily: Update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics 6:1-42.
18. Patki KC, Von Moltke LL, Greenblatt DJ. 2003. 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 31:938-944.
19. Racha JK, Zhao ZS, Olejnik N, Warner N, Chan R, Moore D, Satoh H. 2003. 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 18:128-138.
20. Rendic S. 2002. Summary of information on human CYP enzymes: Human P450 metabolism data. Drug Metabolism Reviews 34:83-448.
21. Schrag ML, Wienkers LC. 2001. Triazolam substrate inhibition: Evidence of competition for heme-bound reactive oxygen within the CYP3A4 active site. Drug Metabolism and Disposition 29:70-75.
22. Shimada T, Yamazaki H, Mimura M, Inui Y, Guengerich FP. 1994. 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 270:414-423.
23. Shou M, Grogan J, Mancewicz JA, Krausz KW, Gonzalez FJ, Gelboin HV, Korzekwa KR. 1994. Activation of CYP3A4: Evidence for the simultaneous binding of two substrates in a cytochrome P450 active site. Biochemistry 33:6450-6455.
24. Smith DA, Ackland MJ, Jones BC. 1997. Properties of cytochrome P450 isoenzymes and their substrates part 2: Properties of cytochrome P450 substrates. Drug Discovery Today 2:479-486.
25. Spatzenegger M, Jaeger W. 1995. Clinical importance of hepatic cytochrome P450 in drug metabolism. Drug Metabolism Reviews 27:397-417.
26. Ueng YF, Kuwabara T, Chun YJ, Guengerich FP. 1997. Cooperativiry in oxidations catalysed by cytochrome P450 3A4. Biochemistry 36:370-381.
27. Wang H, Dick R, Yin H, Licad-Coles E, Kroetz DL, Szklarz G, Harlow G, Halpert JR, Correia MA. 1998. Structure-function relationships of human liver cytochromes P450 3A: Aflatoxin B1 metabolism as a probe. Biochemistry 37:12536-12545.
28. Wang RW, Newton DJ, Liu N, Atkins WM, Lu AY. 2000. Human cytochrome P-450 3A4: In vitro drug-drug interaction patterns are substrate-dependent. Drug Metabolism and Disposition 28:360-366.
29. Westlind A, Malmebo S, Johansson I, Otter C, Andersson TB, Ingelman-Sundberg M, Oscarson M. 2001. Cloning and tissue distribution of a novel human cytochrome p450 of the CYP3A subfamily, CYP3A43. Biochemical and Biophysical Research Communications 281:1349-1355.
30. Wrighton SA, Brian WR, Sari MA, Iwasaki M, Guengerich FP, Raucy JL, Molowa DT, Vandenbranden M. 1990. Studies on the expression and metabolic capabilities of human liver cytochrome P450IIIA5 (HLp3). Molecular Pharmacology 38:207-213.
31. Wrighton SA, Stevens JC. 1992. The human hepatic cytochromes P450 involved in drug metabolism. 1992. Critical Reviews in Toxicology 22:1-21.