Time course of recovery of cytochrome P450 3A function after single doses of grapefruit juice

Clinical Pharmacology and Therapeutics

Volumn 74, Issue 2, 2003, Pages 121-129

  Greenblatt, David J ^a   Von Moltke, Lisa L ^b   Harmatz, Jerold S ^b   Chen, Gengsheng ^b   Weemhoff, James L ^b   Jen, Cheng ^b   Kelley, Charles J ^b   LeDuc, Barbara W ^b   Zinny, Miguel A ^b  

^a TUFTS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

6',7' DIHYDROXYBERGAMOTTIN; BERGAMOTTIN; CYTOCHROME P450 3A; FUROCOUMARIN DERIVATIVE; MIDAZOLAM; PHENACETIN; UNCLASSIFIED DRUG;

ADULT; AREA UNDER THE CURVE; ARTICLE; CLINICAL TRIAL; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; DRUG CLEARANCE; DRUG HALF LIFE; ENZYME ACTIVITY; ENZYME INHIBITION; FEMALE; FOOD DRUG INTERACTION; GRAPEFRUIT JUICE; HUMAN; HUMAN EXPERIMENT; HYDROXYLATION; IN VITRO STUDY; LIVER MICROSOME; MALE; NORMAL HUMAN; PRIORITY JOURNAL; RANDOMIZED CONTROLLED TRIAL;

ADULT; AREA UNDER CURVE; ARYL HYDROCARBON HYDROXYLASES; BEVERAGES; BIOTRANSFORMATION; CHROMATOGRAPHY, GAS; CITRUS PARADISI; CYTOCHROME P-450 CYP3A; FEMALE; HALF-LIFE; HUMANS; HYPNOTICS AND SEDATIVES; ISOENZYMES; KINETICS; LIVER; MALE; MIDAZOLAM; MIDDLE AGED; OXIDOREDUCTASES, N-DEMETHYLATING; PSORALENS; TRIAZOLAM;

EID: 0043128579     PISSN: 00099236     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-9236(03)00118-8     Document Type: Article

References (48)

1. Bailey DG, Spence JD, Edgar B, Bayliff CD, Arnold JM. Ethanol enhances the hemodynamic effects of felodipine. Clin Invest Med 1989;12:357-62.
2. Kane GC, Lipsky JJ. Drug-grapefruit juice interactions. Mayo Clin Proc 2000;75:933-42.
3. Ameer B, Weintraub RA. Drug interactions with grapefruit juice. Clin Pharmacokinet 1997;33:103-21.
4. Greenblatt DJ, Patki KC, von Moltke LL, Shader RI. Drug interactions with grapefruit juice: an update. J Clin Psychopharmacol 2001;21:357-9.
5. Bailey DG, Malcom J, Arnold O, Spence JD. Grapefruit juice - drug interactions. Br J Clin Pharmacol 1998;46:101-10.
6. Fuhr U. Drug interactions with grapefruit juice. Extent, probable mechanism and clinical relevance. Drug Saf 1998;18:251-72.
7. Edwards DJ, Bellevue FH III, Woster PM. Identification of 6′, 7′-dihydroxybergamottin, a cytochrome P450 inhibitor, in grapefruit juice. Drug Metab Dispos 1996;24:1287-90.
8. Bailey DG, Dresser GK, Kreeft JH, Munoz C, Freeman DJ, Bend JR. Grapefruit-felodipine interaction: effect of unprocessed fruit and probable active ingredients. Clin Pharmacol Ther 2000;68:468-77.
9. Fukuda K, Guo L, Ohashi N, Yoshikawa M, Yamazoe Y. Amounts and variation in grapefruit juice of the main components causing grapefruit-drug interaction. J Chromatogr B Biomed Sci Appl 2000;741:195-203.
10. Guo LQ, Fukuda K, Ohta T, Yamazoe Y. Role of furanocoumarin derivatives on grapefruit juice-mediated inhibition of human CYP3A activity. Drug Metab Dispos 2000;28:766-71.
11. Ohnishi A, Matsuo H, Yamada S, Takanaga H, Morimoto S, Shoyama Y, et al. Effect of furanocoumarin derivatives in grapefruit juice on the uptake of vinblastine by Caco-2 cells and on the activity of cytochrome P450 3A4. Br J Pharmacol 2000;130:1369-77.
12. Lown KS, Bailey DG, Fontana RJ, Janardan SK, Adair CH, Fortlage LA, et al. Grapefruit juice increases felodipine oral availability in humans by decreasing intestinal CYP3A protein expression. J Clin Invest 1997;99:2545-53.
13. Bailey DG, Kreeft JH, Munoz C, Freeman DJ, Bend JR. Grapefruit juice-felodipine interaction: effect of naringin and 6′, 7′-dihydroxybergamottin in humans. Clin Pharmacol Ther 1998;64:248-56.
14. Edwards DJ, Fitzsimmons ME, Schuetz EG, Yasuda K, Ducharme MP, Warbasse LH, et al. 6′,7′-Dihydroxybergamottin in grapefruit juice and Seville orange juice: effects on cyclosporine disposition, enterocyte CYP3A4, and P-glycoprotein. Clin Pharmacol Ther 1999;65:237-44.
15. Schmiedlin-Ren P, Edwards DJ, Fitzsimmons ME, He K, Lown KS, Woster PM, et al. Mechanisms of enhanced oral availability of CYP3A4 substrates by grapefruit constituents. Decreased enterocyte CYP3A4 concentration and mechanism-based inactivation by furanocoumarins. Drug Metab Dispos 1997;25:1228-33.
16. Tassaneeyakul W, Guo LQ, Fukuda K, Ohta T, Yamazoe Y. Inhibition selectivity of grapefruit juice components on human cytochromes P450. Arch Biochem Biophys 2000;378:356-63.
17. Guo LQ, Taniguchi M, Xiao YQ, Baba K, Ohta T, Yamazoe Y. Inhibitory effect of natural furanocoumarins on human microsomal cytochrome P450 3A activity. Jpn J Pharmacol 2000;82:122-9.
18. Fukuda K, Ohta T, Oshima Y, Ohashi N, Yoshikawa M, Yamazoe Y. Specific CYP3A4 inhibitors in grapefruit juice: furocoumarin dimers as components of drug interaction. Pharmacogenetics 1997;7:391-6.
19. He K, Iyer KR, Hayes RN, Sinz MW, Woolf TF, Hollenberg PF. Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice. Chem Res Toxicol 1998;11:252-9.
20. Venkatakrishnan K, von Moltke LL, Greenblatt DJ. Effects of the antifungal agents on oxidative drug metabolism: clinical relevance. Clin Pharmacokinet 2000;38:111-80.
21. Greenblatt DJ, von Moltke LL, Harmatz JS, Durol ALB, Daily JP, Graf JA, et al. Differential impairment of triazolam and zolpidem clearance by ritonavir. J Acquir Immune Defic Syndr 2000;24:129-36.
22. Lilja JJ, Kivistö KT, Backman JT, Neuvonen PJ. Effect of grapefruit juice dose on grapefruit juice-triazolam interaction: repeated consumption prolongs triazolam half-life. Eur J Clin Pharmacol 2000;56:411-5.
23. Lilja JJ, Kivistö KT, Neuvonen PJ. Duration of effect of grapefruit juice on the pharmacokinetics of the CYP3A4 substrate simvastatin. Clin Pharmacol Ther 2000;68:384-90.
24. Takanaga H, Ohnishi A, Murakami H, Matsuo H, Higuchi S, Urae A, et al. Relationship between time after intake of grapefruit juice and the effect on pharmacokinetics and pharmacodynamics of nisoldipine in healthy subjects. Clin Pharmacol Ther 2000;67:201-14.
25. Takanaga H, Ohnishi A, Matsuo H, Murakami H, Sata H, Kuroda K, et al. Pharmacokinetic analysis of felodipine-grapefruit juice interaction based on an irreversible enzyme inhibition model. Br J Clin Pharmacol 2000;49:49-58.
26. Lundahl J, Regardh CG, Edgar B, Johnsson G. Relationship between time of intake of grapefruit juice and its effect on pharmacokinetics and pharmacodynamics of felodipine in healthy subjects. Eur J Clin Pharmacol 1995;49:61-7.
27. Streetman DS, Bertino JS Jr, Nafziger AN. Phenotyping of drug-metabolizing enzymes in adults: a review of in-vivo cytochrome P450 phenotyping probes. Pharmacogenetics 2000;10:187-216.
28. Kronbach T, Mathys D, Umeno M, Gonzalez FJ, Meyer UA. Oxidation of midazolam and triazolam by human liver cytochrome P450IIIA4. Mol Pharmacol 1989;36:89-96.
29. Gorski JC, Hall SD, Jones DR, VandenBranden M, Wrighton SA. Regioselective biotransformation of midazolam of members of the human cytochrome P450 3A (CYP3A) subfamily. Biochem Pharmacol 1994;47:1643-53.
30. Ghosal A, Satoh H, Thomas P, Bush E, Moore D. Inhibition and kinetics of cytochrome P4503A activity in microsomes from rat, human, and cDNA-expressed human cytochrome P450. Drug Metab Dispos 1996;24:940-7.
31. Perloff MD, von Moltke LL, Court MH, Kotegawa T, Shader RI, Greenblatt DJ. Midazolam and triazolam biotransformation in mouse and human liver microsomes: relative contribution of CYP3A and CYP2C9 isoforms. J Pharmacol Exp Ther 2000;292:618-28.
32. von Moltke LL, Greenblatt DJ, Schmider J, Duan SX, Wright CE, Harmatz JS, et al. Midazolam hydroxylation by human liver microsomes in vitro: inhibition by fluoxetine, norfluoxetine, and by azole antifungal agents. J Clin Pharmacol 1996;36:783-91.
33. Tsunoda SM, Velez RL, von Moltke LL, Greenblatt DJ. Differentiation of intestinal and hepatic cytochrome P450 3A activity with use of midazolam as an in vivo probe: effect of ketoconazole. Clin Pharmacol Ther 1999;66:461-71.
34. Thummel KE, O'Shea D, Paine MF, Shen DD, Kunze KL, Perkins JD, et al. Oral first-pass elimination of midazolam involves both gastrointestinal and hepatic CYP3A-mediated metabolism. Clin Pharmacol Ther 1996;59:491-502.
35. Gorski JC, Jones DR, Haehner-Daniels BD, Hamman MA, O'Mara EM, Hall SD. The contribution of intestinal and hepatic CYP3A to the interaction between midazolam and clarithromycin. Clin Pharmacol Ther 1998;64:133-43.
36. Rogers JD, Zhao J, Liu L, Amin RD, Gagliano KD, Porras AG, et al. Grapefruit juice has minimal effects on plasma concentrations of lovastatin-derived 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors. Clin Pharmacol Ther 1999;66:358-66.
37. Kupferschmidt HHT, Ha HR, Ziegler WH, Meier PJ, Krähenbühl S. Interaction between grapefruit juice and midazolam in humans. Clin Pharmacol Ther 1995;58:20-8.
38. Andersen V, Pedersen N, Larsen NE, Sonne J, Larsen S. Intestinal first pass metabolism of midazolam in liver cirrhosis - effect of grapefruit juice. Br J Clin Pharmacol 2002;54:120-4.
39. Arendt RM, Greenblatt DJ, Garland WA. Quantitation by gas chromatography of the 1- and 4-hydroxy metabolites of midazolam in human plasma. Pharmacology 1984;29:158-64.
40. Bellevue FH, Woster PM, Edwards DJ, He K, Hollenberg PF. Synthesis and biological evaluation of 6′,7′-dihydroxybergamottin (6,7-DHB), a naturally occurring inhibitor of cytochrome P450 3A4. Bioorg Med Chem Lett 1997;7:2593-8.
41. von Moltke LL, Greenblatt DJ, Harmatz JS, Duan SX, Harrel LM, Cotreau-Bibbo MM, et al. Triazolam biotransformation by human liver microsomes in vitro: effects of metabolic inhibitors, and clinical confirmation of a predicted interaction with ketoconazole. J Pharmacol Exp Ther 1996;276:370-9.
42. Kotegawa T, Laurijssens BE, von Moltke LL, Cotreau MM, Perloff MD, Venkatakrishnan K, et al. In vitro, pharmacokinetic, and pharmacodynamic interactions of ketoconazole and midazolam in the rat. J Pharmacol Exp Ther 2002;302:1228-37.
43. von Moltke LL, Durol ALB, Duan SX, Greenblatt DJ. Potent mechanism-based inhibition of human CYP3A in vitro by amprenavir and ritonavir: comparison with ketoconazole. Eur J Clin Pharmacol 2000;56:259-61.
44. Bertelsen KM, Venkatakrishnan K, von Moltke LL, Obach RS, Greenblatt DJ. Apparent mechanism-based inhibition of human CYP2D6 in vitro by paroxetine: comparison with fluoxetine and quinidine. Drug Metab Dispos 2003;31:289-93.
45. von Moltke LL, Greenblatt DJ, Grassi JM, Granda BW, Duan SX, Fogelman SM, et al. Protease inhibitors as inhibitors of human cytochromes P450: high risk associated with ritonavir. J Clin Pharmacol 1998;38:106-11.
46. Greenblatt DJ, Abernethy DR, Locniskar A, Harmatz JS, Limjuco RA, Shader RI. Effect of age, gender, and obesity on midazolam kinetics. Anesthesiology 1984;61:27-35.
47. Venkatakrishnan K, von Moltke LL, Greenblatt DJ. Human drug metabolism and the cytochromes P450: application and relevance of in vitro models. J Clin Pharmacol 2001;41:1149-79.
48. Silverman R. Mechanism-based enzyme inactivators. Methods Enzymol 1995;249:240-83.