Inhibition of cytochrome P-450 3A (CYP3A) in human intestinal and liver microsomes: Comparison of K1 values and impact of CYP3A5 expression

Drug Metabolism and Disposition

Volumn 27, Issue 2, 1999, Pages 180-187

  Gibbs, Megan A ^a   Thummel, Kenneth E ^a   Shen, Danny D ^a   Kunze, Kent L ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; MIDAZOLAM;

ARTICLE; BINDING AFFINITY; BIOAVAILABILITY; CATALYSIS; ENZYME ACTIVITY; ENZYME INHIBITION; GENE EXPRESSION; HYDROXYLATION; INTESTINE ABSORPTION; LIVER MICROSOME; PRIORITY JOURNAL;

ALGORITHMS; ANTIFUNGAL AGENTS; BLOTTING, WESTERN; CYTOCHROME P-450 ENZYME SYSTEM; DNA, COMPLEMENTARY; DRUG INTERACTIONS; ENZYME INHIBITORS; FLUCONAZOLE; HUMANS; INTESTINE, SMALL; KETOCONAZOLE; KINETICS; MICROSOMES; MICROSOMES, LIVER; MIDAZOLAM; MIXED FUNCTION OXYGENASES;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0032956839     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (41)

1. Aoyama T, Yamano S, Waxman DJ, Lapenson DP, Meyer UA, Fischer V, Tyndale R, Inaba T, Kalow W, Gelboin HV and Gonzalez FJ (1989) Cytochrome P450 hPCN3, a novel cytochrome P450IIIA gene product that is differentially expressed in adult human liver. cDNA and deduced amino acid sequence and distinct specificities of cDNA-expressed hPCN1 and hPCN3 for the metabolism of steroid hormones and cyclosporine. J Biol Chem 264:10388-10395.
2. Buters JTM, Korzekwa KR, Kunze KL, Omata Y, Hardwick JP and Gonzalez FJ (1994) cDNA-Directed expression of human cytochrome P450 CYP3A4 using baculovirus. Drug Metab Dispos 22:688-692.
3. DeWaziers I, Cugnenc PH, Yang CS, Leroux J-P and Beaune PH (1990) Cytochrome P450 isoenzymes, epoxide hydrolase and glutathione transferases in rat and human hepatic and extrahepatic tissues. J Pharmacol Exp Ther 253:387-394.
4. Ducharme MP, LH Warbasse and Edwards DJ (1995) Disposition of intravenous and oral cyclosporine after administration with grapefruit juice. Clin Pharmacol Ther 57:485-491.
5. Edgar B, Regårdh CG, Johnsson G, Johansson L, Lundborg P, Löfberg I and Rönn O (1985) Felodipine kinetics in healthy men. Clin Pharmacol Ther 38:205-211.
6. Fahr A (1993) Cyclosporin clinical pharmacokinetics. Clin Pharmacokinet 24:472-495.
7. Fleishaker JC, Pearson PG, Wienkers LC, Pearson LK and Graves GR (1996) Biotransformation of tirilazad in humans: 2. Effect of ketoconazole on tirilazad clearance and oral bioavailability. J Pharmacol Exp Ther 277:991-998.
8. Fromm MF, Busse D, Kroemer HK and Eichelbaum M (1996) Differential induction of prehepatic and hepatic metabolism of verapamil by rifampin. Hepatology 24:796-801.
9. Gallagher EP, Kunze KL, Stapleton PL and Eaton DL (1996) The kinetics of aflatoxin B1 oxidation by human cDNA-expressed and human liver microsomal cytochromes P450 1A2 and 3A4. Toxicol Appl Pharmacol 141:595-606.
10. Ghosal A, Satoh H, Thomas PE, Bush E and Moore D (1996) Inhibition and kinetics of cytochrome P4503A activity in microsomes from rat, human and cDNA-expressed human cytochrome P450. Drug Metab Dispos 24:940-947.
11. Gillam EMJ, Baba T, Kim B-R, Ohmori S and Guengerich FP (1993) Expression of modified human cytochrome P450 3A4 in Escherichia coli and purification and reconstitution of the enzyme. Arch Biochem Biophys 305:123-131.
12. Gillam EMJ, Guo Z, Ueng Y-F, Yamazaki H, Cock I, Reilly PEB, Hooper WD and Guengerich FP (1995) Expression of cytochrome P450 3A5 in Escherichia coli: Effects of 5′ modification, purification, spectral characterization, reconstitution conditions, and catalytic activities. Arch Biochem Biophys 317:374-384.
13. Gomez DY, Wacher VJ, Tomlanovich SJ, Hebert MF and Benet LZ (1995) The effects of ketoconazole on the intestinal metabolism and bioavailability of cyclosporine. Clin Pharmacol Ther 58:15-19.
14. Hebert MF, Roberts JP, Prueksaritanont T and Benet LZ (1992) Bioavailability of cyclosporine with concomitant rifampin administration is markedly less than predicted by hepatic enzyme induction. Clin Pharmacol Ther 52:453-457.
15. Holtbecker N, Fromm M, Kroemer HK, Ohnhaus EE and Heidemann H (1996) The nifedipine-rifampin interaction. Evidence for induction of gut wall metabolism. Drug Metab Dispos 24:1121-1123.
16. Imaoka S, Imai Y, Shimada T and Funae Y (1992) Rote of phospholipids in reconstituted cytochrome P450 3A form and mechanism of their activation of catalytic activity. Biochemistry 31:6063-6069.
17. Jounäidi Y, Hyrailles V, Gervot L and Maurel P (1996) Detection of a CYP3A5 allelic variant: A candidate for the polymorphic expression of the protein? Biochem Biophys Res Comm 221: 466-470.
18. Kerr BM, Thummel KE, Wurden CJ, Klein SM, Kroetz DL, Gonzalez FJ and Levy RH (1994) Human liver carbamazepine metabolism. Role of CYP3A4 and CYP2C8 in 10, 11-epoxide formation. Biochem Pharmacol 47:1969-1976.
19. Kharasch ED and Thummel KE (1993) Human alfentanil metabolism by cytochrome P450 3A3/4. An explanation for the interindividual variability in alfentanil clearance? Anesthesia & Analgesia 76: 1033-1039.
20. Kolars JC, Awni WM, Merion RM and Watkins PB (1991) First-pass metabolism of cyclosporin by the gut. Lancet 338:1488-1490.
21. Kunze KL, Wienkers LC, Thummel KE and Trager WF (1995) Warfarin-fluconazole I. Inhibition of the human cytochrome P450-dependent metabolism of warfarin by fluconazole: In vitro studies. Drug Metab Dispos 24:414-421.
22. Kupferschmidt HHT, Ha HR, Ziegler WH, Meier PJ and Krähenbühl S (1995) Interaction between grapefruit juice and midazolam in humans. Clin Pharmacol Ther 58:20-28.
23. Lalonde RL, Lessard D and Gaudreault J (1996) Population pharmacokinetics of terfenadine. Pharmaceut Res 13:832-838.
24. Lampen A. Christians U, Guengerich FP, Watkins PB, Kolars JC, Bader A, Gonschior A-K, Dralle H, Hackbarth I and Sweing K-F (1995) Metabolism of the immunosuppressant tacrolimus in the small intestine: Cytochrome P450, drug interactions, and interindividual variability. Drug Metab Dispos 23:1315-1324.
25. Lown KS, Kolars JC, Thummel KE, Barnett JL, Kunze KL, Wrighton SA and Watkins PB (1994) Interpatient heterogeneity in expression of CYP3A4 and CYP3A5 in small bowel: Lack of prediction by the erythromycin breath test. Drug Metab Dispos 22:947-955.
26. Lowry OH, Rosebrough NJ, Farr AL and Randall RJ (1951) Protein measurement with the folin phenol reagent. J Biol Chem 193:265-275.
27. McTavish D and Sorkin EM (1989) Verapamil: An updated review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in hypertension. Drugs 38:19-76.
28. Paine MF, Khalighi M, Fisher JM, Shen DD, Kunze KL, Marsh CL, Perkins JD, and Thummel KE (1997) Characterization of inter- and intra-intestinal differences in human CYP3A-dependent metabolism. J Pharmacol Exp Ther 283:1552-1562.
29. Paine MF, Shen DD, Kunze KL, Perkins JD, Marsh CL, McVicar JP, Barr DM, Gillies BS, and Thummel KE (1996) First-pass metabolism of midazolam by the human intestine. Clin Pharmacol Ther 60:14-24.
30. Segel IH (1975) Enzyme Kinetics: Behavior and Analysis of Rapid Equilibrium and Steady-State Enzyme Systems. New York: John Wiley and Sons, Inc.
31. Shimada T, Yamazaki H, Mimura M, Inui Y, and Guengerich FP (1994) Interindividual variations in human liver cytochrome P450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther 270:414-423.
32. Shou M, Grogan J, Mancewicz JA, Krausz KW, Gonzalez FJ, Gelboin HV, and Korzekwa KR (1994) Activation of CYP3A4: Evidence for the simultaneous binding of two substrates in a cytochrome P450 active site. Biochemistry 33:6450-6455.
33. Smith MT, Eadie MJ, and Brophy TOR (1981) The pharmacokinetics of midazolam in man. Eur J Clin Pharmacol 19:271-278.
34. Thummel KE, O'Shea D, Paine MF, Shen DD, Kunze KL, Perkins JD, and Wilkinson GR (1996) Oral first-pass elimination of midazolam involves both gastrointestinal and hepatic CYP3A-mediated metabolism. Clin Pharmacol Ther 59:491-502.
35. Thummel KE, Shen DD, Podoll TD, Kunze KL, Trager WF, Bacchi CE, Marsh CL, McVicar JP, Barr DM, Perkins JD, and Carithers Jr RL (1994) Use of midazolam as a human cytochrome P450 3A probe. II. Characterization of inter- and intra-individual hepatic P4503A variability after liver transplantation. J Pharmacol Exp Ther 271:557-566.
36. Thummel KE and Wilkinson GR (1998) In Vitro and in vivo drug interactions involving human CYP3A. Annu Rev Pharmacol Toxicol 38:389-430.
37. Ueng Y-F, Kuwabara T, Chun Y-J and Guengerich FP (1997) Cooperativity in oxidations catalyzed by cytochrome P450 3A4. Biochemistry 36:370-381.
38. Watkíns PB, Wrighton SA, Schuetz EG, and Guzelian PS (1987) Identification of glucocorticoid-inducible cytochromes P450 in the intestinal mucosa of rats and man. J Clin Invest 80:1029-1036.
39. Williams PEO, Muirhead GJ, Madigan MJ, Mitchell AM and Shaw T (1992) Disposition and bioavailability of the HIV-proteinase inhibitor, Ro 31-8959, after single doses in healthy volunteers. Br J Clin Pharmacol 34:155P-156P.
40. Wrighton SA, Brian WR, Sari M-A, Iwasaki M, Guengerich FP, Raucy JL, Molowa DT and VandenBraden M (1990) Studies on the expression and metabolic capabilities of human liver cytochrome P450IIIA5 (HLp3). Mol Pharmacol 38:207-213.
41. Yamazaki H, Ueng Y-F, Shimada T and Guengerich FP (1995) Roles of divalent metal ions in oxidations catalyzed by recombinant cytochrome P450 3A4 and replacement of NADPH-cytochrome P450 reductase with other flavoproteins, ferredoxin, and oxygen surrogates. Biochemistry 34:8380-8389.