The effects of fruit juices on drug disposition: A new model for drug interactions

European Journal of Clinical Investigation, Supplement

Volumn 33, Issue 2, 2003, Pages 10-16

  Dresser, G K ^a,b   Bailey, D G ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

^b LONDON HEALTH SCIENCES CENTRE   (Canada)

Author keywords

Cytochrome P450; Drug interactions; Fruit juice; Grapefruit juice; Organic anion transporting polypeptides; P glycoprotein

Indexed keywords

6',7' DIHYDROXYBERGAMOTTIN; ANTIASTHMATIC AGENT; ANTICOAGULANT AGENT; ANTIINFECTIVE AGENT; ANTIINFLAMMATORY AGENT; ANTILIPEMIC AGENT; ARTEMETHER; BENDAZOL; BERGAMOTTIN; CARDIOVASCULAR AGENT; CENTRAL NERVOUS SYSTEM AGENTS; CYCLOSPORIN; CYTOCHROME P450 3A4; DIGOXIN; ERYTHROMYCIN; ESTROGEN; FELODIPINE; FEXOFENADINE; FUROCOUMARIN DERIVATIVE; GASTROINTESTINAL AGENT; GLYCOPROTEIN P; HALOFANTRINE; HISTAMINE H1 RECEPTOR ANTAGONIST; IMMUNOSUPPRESSIVE AGENT; ORGANIC ANION TRANSPORTER; ORGANIC ANION TRANSPORTER INHIBITOR; PRAZIQUANTEL; PROTEIN INHIBITOR; SAQUINAVIR; UNCLASSIFIED DRUG; UNINDEXED DRUG; 6,7 DIHYDROXYBERGAMOTTIN; CYTOCHROME P450;

COMPETITIVE INHIBITION; CONFERENCE PAPER; DRUG BIOAVAILABILITY; DRUG DISPOSITION; DRUG MECHANISM; DRUG POTENCY; DRUG POTENTIATION; DRUG UPTAKE; FIRST PASS EFFECT; FOOD DRUG INTERACTION; GRAPEFRUIT JUICE; HUMAN; IN VITRO STUDY; IN VIVO STUDY; PRIORITY JOURNAL; PROTEIN FUNCTION; AREA UNDER THE CURVE; DRUG ABSORPTION; DRUG METABOLISM; DRUG TRANSPORT; INTESTINE ABSORPTION; REVIEW;

EID: 0242469224     PISSN: 0960135X     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1365-2362.33.s2.2.x     Document Type: Conference Paper

References (57)

1. Haynes RB, Sackett DL, Gibson ES, Taylor DW, Hackett BC, Roberts RS et al. Improvement of medication compliance in uncontrolled hypertension. Lancet 1976;1:1265-8.
2. Thummel KE, Wilkinson GR. In vitro and in vivo drug interactions involving human CYP3A. Annu Rev Pharmacol Toxicol 1998;38:389-430.
3. Bailey DG, Spence JD, Munoz C, Arnold JM. Interaction of citrus juices with felodipine and nifedipine. Lancet 1991;337:268-9.
4. Ameer B, Weintraub RA. Drug interactions with grapefruit juice. Clin Pharmacokinet 1997;33:103-21.
5. Bailey DG, Arnold JM, Spence JD. Grapefruit juice and drugs. How significant is the interaction? Clin Pharmacokinet 1994;26:91-8.
6. Bailey DG, Malcolm J, Arnold O, Spence JD. Grapefruit juice-drug interactions. Br J Clin Pharmacol 1998;46:101-10.
7. Fuhr U. Drug interactions with grapefruit juice. Extent, probable mechanism and clinical relevance. Drug Saf 1998;18:251-72.
8. Edgar B, Hoffmann KJ, Lundborg P, Regardh CG, Ronn O, Weidolf L. Absorption, distribution and elimination of felodipine in man. Drugs 1985;29 (Suppl. 2):9-15.
9. Blychert E, Edgar B, Elmfeldt D, Hedner T. A population study of the pharmacokinetics of felodipine. Br J Clin Pharmacol 1991;31:15-24.
10. Guengerich FP, Brian WR, Iwasaki M, Sari MA, Baarnhielm C, Berntsson P. Oxidation of dihydropyridine calcium channel blockers and analogues by human liver cytochrome P-450 IIIA4. J Med Chem 1991;34:1838-44.
11. Guengerich FP. Cytochrome P-450 3A4: regulation and role in drug metabolism. Annu Rev Pharmacol Toxicol 1999;39:1-17.
12. Kolars JC, Schmiedlin-Ren P, Schuetz JD, Fang C, Watkins PB. Identification of rifampin-inducible P450IIIA4 (CYP3A4) in human small bowel enterocytes. J Clin Invest 1992;90:1871-8.
13. Lown KS, Kolars JC, Thummel KE, Barnett JL, Kunze KL, Wrighton SA et al. Interpatient heterogeneity in expression of CYP3A4 and CYP3A5 in small bowel. Lack of prediction by the erythromycin breath test [published erratum appears in Drug Metab Dispos 1995;23: following table of contents]. Drug Metab Dispos 1994;22:947-55.
14. Dresser GK, Spence JD, Bailey DG. Pharmacokinetic-pharmacodynamic consequences and clinical relevance of cytochrome P450 3A4 inhibition. Clin Pharmacokinet 2000;38:41-57.
15. Lundahl J, Regardh CG, Edgar B, Johnsson G. Effects of grapefruit juice ingestion - pharmacokinetics and haemodynamics of intravenously and orally administered felodipine in healthy men. Eur J Clin Pharmacol 1997;52:139-45.
16. 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.
17. 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.
18. Buening MK, Chang RL, Huang MT, Fortner JG, Wood AW, Conney AH. Activation and inhibition of benzo (a) pyrene and aflatoxin B1 metabolism in human liver microsomes by naturally occurring flavonoids. Cancer Res 1981;41:67-72.
19. Guengerich FP, Kim DH. In vitro inhibition of dihydropyridine oxidation and aflatoxin B1 activation in human liver microsomes by naringenin and other flavonoids. Carcinogenesis 1990;11:2275-9.
20. Miniscalco A, Lundahl J, Regardh CG, Edgar B, Eriksson UG. Inhibition of dihydropyridine metabolism in rat and human liver microsomes by flavonoids found in grapefruit juice. J Pharmacol Exp Ther 1992;261:1195-9.
21. Bailey DG, Arnold JM, Munoz C, Spence JD. Grapefruit juice - felodipine interaction, mechanism, predictability, and effect of naringin. Clin Pharmacol Ther 1993;53:637-42.
22. Bailey DG, Arnold JM, Strong HA, Munoz C, Spence JD. Effect of grapefruit juice and naringin on nisoldipine pharmacokinetics. Clin Pharmacol Ther 1993;54:589-94.
23. 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.
24. 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.
25. 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.
26. 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.
27. 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.
28. Malhotra S, Bailey DG, Paine MF, Watkins PB. Seville orange juice-felodipine interaction: comparison with dilute grapefruit juice and involvement of furocoumarins. Clin Pharmacol Ther 2001;69:14-23.
29. 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.
30. Lown KS, Mayo RR, Leichtman AB, Hsiao HL, Turgeon DK, Schmiedlin-Ren P et al. Role of intestinal P-glycoprotein (mdr1) in interpatient variation in the oral bioavailability of cyclosporine. Clin Pharmacol Ther 1997;62:248-60.
31. Kim RB. Drugs as P-glycoprotein substrates, inhibitors, and inducers. Drug Metab Rev 2002;34:47-54.
32. Cordon-Cardo C, O'Brien JP, Boccia J, Casals D, Bertino JR, Melamed MR. Expression of the multidrug resistance gene product (P-glycoprotein) in human normal and tumor tissues. J Histochem Cytochem 1990;38:1277-87.
33. Cordon-Cardo C, O'Brien JP, Casals D, Rittman-Grauer L, Biedler JL, Melamed MR et al. Multidrug-resistance gene (P-glycoprotein) is expressed by endothelial cells at blood-brain barrier sites. Proc Natl Acad Sci 1989;86:695-8.
34. MacFarland A, Abramovich DR, Ewen SW, Pearson CK. Stage-specific distribution of P-glycoprotein in first-trimester and full-term human placenta. Histochem J 1994;26:417-23.
35. Shapiro AB, Fox K, Lam P, Ling V. Stimulation of P-glycoprotein-mediated drug transport by prazosin and progesterone. Evidence for a third drug-binding site. Eur J Biochem 1999;259:841-50.
36. Shapiro AB, Ling V. Positively cooperative sites for drug transport by P-glycoprotein with distinct drug specificities. Eur J Biochem 1997;250:130-7.
37. Soldner A, Christians U, Susanto M, Wacher VJ, Silverman JA, Benet LZ. Grapefruit juice activates P-glycoprotein-mediated drug transport. Pharm Res 1999;16:478-85.
38. Dresser GK, Bailey DG, Leake BF, Schwarz UI, Dawson PA, Freeman DJ et al. Fruit juices inhibit organic anion transporting polypeptide-mediated drug uptake to decrease the oral availability of fexofenadine. Clin Pharmacol Ther 2002;71:11-20.
39. Eagling VA, Profit L, Back DJ. Inhibition of the CYP3A4-mediated metabolism and P-glycoprotein-mediated transport of the HIV-1 protease inhibitor saquinavir by grapefruit juice components. Br J Clin Pharmacol 1999;48:543-52.
40. Ikegawa T, Ushigome F, Koyabu N, Morimoto S, Shoyama Y, Naito M et al. Inhibition of P-glycoprotein by orange juice components, polymethoxyflavones in adriamycin-resistant human myelogenous leukemia (K562/ADM) cells. Cancer Lett 2000;160:21-8.
41. Mitsunaga Y, Takanaga H, Matsuo H, Naito M, Tsuruo T, Ohtani H et al. Effect of bioflavonoids on vincristine transport across blood-brain barrier. Eur J Pharmacol 2000;395:193-201.
42. 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.
43. Takanaga H, Ohnishi A, Matsuo H, Sawada Y. Inhibition of vinblastine efflux mediated by P-glycoprotein by grapefruit juice components in caco-2 cells. Biol Pharm Bull 1998;21:1062-6.
44. Takanaga H, Ohnishi A, Yamada S, Matsuo H, Morimoto S, Shoyama Y et al. Polymethoxylated flavones in orange juice are inhibitors of P-glycoprotein but not cytochrome P450 3A4. J Pharmacol Exp Ther 2000;293:230-6.
45. Wacher VJ, Wu CY, Benet LZ. Overlapping substrate specificities and tissue distribution of cytochrome P4503A and P-glycoprotein: implications for drug delivery and activity in cancer chemotherapy. Mol Carcinog 1995;13:129-34.
46. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ et al. Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res 1999;16:408-14.
47. Mayer U, Wagenaar E, Beijnen JH, Smit JW, Meijer DK, van Asperen J et al. Substantial excretion of digoxin via the intestinal mucosa and prevention of long-term digoxin accumulation in the brain by the mdr 1a P-glycoprotein. Br J Pharmacol 1996;119:1038-44.
48. Cavet ME, West M, Simmons NL. Transport and epithelial secretion of the cardiac glycoside, digoxin, by human intestinal epithelial (Caco-2) cells. Br J Pharmacol 1996;118:1389-96.
49. Becquemont L, Verstuyft C, Kerb R, Brinkmann U, Lebot M, Jaillon P et al. Effect of grapefruit juice on digoxin pharmacokinetics in humans. Clin Pharmacol Ther 2001;70:311-6.
50. Mooradian AD. Digitalis. An update of clinical pharmacokinetics, therapeutic monitoring techniques and treatment recommendations. Clin Pharmacokinet 1988;15:165-79.
51. Lippert C, Ling J, Brown P, Burmaster S, Eller M, Cheng L et al. Mass balance and pharmacokinetics of MDL 16455A in healthy male volunteers. Pharm Res 1995;12:S390 (abstract).
52. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB. OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos 1999;27:866-71.
53. Walters HC, Craddock AL, Fusegawa H, Willingham MC, Dawson PA. Expression, transport properties, and chromosomal location of organic anion transporter subtype 3. Am J Physiol-Gastrointestinal Liver Physiol 2000;279:G1188-G1200.
54. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F et al. Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology 2001;120:525-33.
55. Konig J, Cui Y, Nies AT, Keppler D. A novel human organic anion transporting polypeptide localized to the basolateral hepatocyte membrane. Am J Physiol-Gastrointestinal Liver Physiol 2000;278:G156-G164.
56. Reichel C, Gao B, Van Montfoort J, Cattori V, Rahner C, Hagenbuch B et al. Localization and function of the organic anion-transporting polypeptide Oatp2 in rat liver. Gastroenterology 1999;117:688-95.
57. Kullak-Ublick GA, Hagenbuch B, Stieger B, Schteingart CD, Hofmann AF, Wolkoff AW et al. Molecular and functional characterization of an organic anion transporting polypeptide cloned from human liver. Gastroenterology 1995;109:1274-82.