Food-drug interaction: The case of grapefruit juice

CAB Reviews: Perspectives in Agriculture, Veterinary Science, Nutrition and Natural Resources

Volumn 3, Issue , 2008, Pages

  Uesawa, Yoshihiro ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

CYP3A4; Furanocoumarin; Grapefruit juice; Pharmacokinetic interaction

Indexed keywords

EID: 84891586751     PISSN: None     EISSN: 17498848     Source Type: Journal    
DOI: 10.1079/PAVSNNR20083097     Document Type: Review

References (71)

1. Bailey DG, Spence JD, Edgar B, Bayliff CD, Arnold JM. Ethanol enhances the hemodynamic effects of felodipine. Clinical and Investigative Medicine Médicale Clinique et Expérimentale 1989;12:357-62.
2. Bailey DG, Spence JD, Munoz C, Arnold JM. Interaction of citrus juices with felodipine and nifedipine. Lancet 1991;337:268-9.
3. Josefsson M, Zackrisson AL, Ahlner J. Effect of grapefruit juice on the pharmacokinetics of amlodipine in healthy volunteers. European Journal of Clinical Pharmacology 1996;51:189-93.
4. Hirashima H, Uchida N, Fukuzawa I, Ishigaki S, Uchida E, Yasuhara H. Effect of a single glass of grapefruit juice on the apparent oral bioavailability of the dihydropyridine calcium channel antagonist, azelnidipine, in healthy Japanese volunteers. Japanese Journal of Clinical Pharmacology and Therapeutics 2006;37:127-33.
5. Ohnishi A, Ohtani H, Sawada Y. Major determinant factors of the extent of interaction between grapefruit juice and calcium channel antagonists. British Journal of Clinical Pharmacology 2006;62:196-9.
6. Yajima Y, Iijima H, Yokoyama R. Influence of grapefruit juice on the plasma concentration of efonidipine hydrochloride (Landel). Yakuri To Chiryo 2003;31:579-88.
7. Sugawara K. Optimal use for drugs. The Pharmaceuticals Monthly 1996;38:2591-6.
8. Uno T, Ohkubo T, Sugawara K, Higashiyama A, Motomura S, Ishizaki T. Effects of grapefruit juice on the stereoselective disposition of nicardipine in humans: evidence for dominant presystemic elimination at the gut site. European Journal of Clinical Pharmacology 2000;56:643-9.
9. Fuhr U, Maier-Bruggemann A, Blume H, Muck W, Unger S, Kuhlmann J, et al. Grapefruit juice increases oral nimodipine bioavailability. International Journal of Clinical Pharmacology and Therapeutics 1998;36:126-32.
10. Bailey DG, Arnold JM, Strong HA, Munoz C, Spence JD. Effect of grapefruit juice and naringin on nisoldipine pharmacokinetics. Clinical Pharmacology and Therapeutics 1993;54:589-94.
11. Soons PA, Vogels BA, Roosemalen MC, Schoemaker HC, Uchida E, Edgar B, et al. Grapefruit juice and cimetidine inhibit stereoselective metabolism of nitrendipine in humans. Clinical Pharmacology and Therapeutics 1991;50:394-403.
12. Hashimoto K, Shirafuji T, Sekino H, Matsuoka O, Sekino H, Onnagawa O, et al. Interaction of citrus juices with pranidipine, a new 1,4-dihydropyridine calcium antagonist, in healthy subjects. European Journal of Clinical Pharmacology 1998;54:753-60.
13. Ho PC, Ghose K, Saville D, Wanwimolruk S. Effect of grapefruit juice on pharmacokinetics and pharmacodynamics of verapamil enantiomers in healthy volunteers. European Journal of Clinical Pharmacology 2000;56:693-8.
14. Zaidenstein R, Soback S, Gips M, Avni B, Dishi V, Weissgarten Y, et al. Effect of grapefruit juice on the pharmacokinetics of losartan and its active metabolite E3174 in healthy volunteers. Therapeutic Drug Monitoring 2001;23:369-73.
15. Libersa CC, Brique SA, Motte KB, Caron JF, Guédon-Moreau LM, Humbert L, et al. Dramatic inhibition of amiodarone metabolism induced by grapefruit juice. British Journal of Clinical Pharmacology 2000;49:373-8.
16. Kupferschmidt HH, Fattinger KE, Ha HR, Follath F, Krähenbühl S. Grapefruit juice enhances the bioavailability of the HIV protease inhibitor saquinavir in man. British Journal of Clinical Pharmacology 1998;45:355-9.
17. van Agtmael MA, Gupta V, van der Graaf CA, van Boxtel CJ. The effect of grapefruit juice on the time-dependent decline of artemether plasma levels in healthy subjects. Clinical Pharmacology and Therapeutics 1999;66:408-14.
18. van Agtmael MA, Gupta V, van der Wösten TH, Rutten JP, van Boxtel CJ. Grapefruit juice increases the bioavailability of artemether. European Journal of Clinical Pharmacology 1999;55:405-10.
19. Nagy J, Schipper HG, Koopmans RP, Butter JJ, Van Boxtel CJ, Kager PA. Effect of grapefruit juice or cimetidine coadministration on albendazole bioavailability. American Journal of Tropical Medicine and Hygiene 2002;66:260-3.
20. Christensen H, Asberg A, Holmboe AB, Berg KJ. Coadministration of grapefruit juice increases systemic exposure of diltiazem in healthy volunteers. European Journal of Clinical Pharmacology 2002;58:515-20.
21. Kupferschmidt HH, Ha HR, Ziegler WH, Meier PJ, Krähenbühl S. Interaction between grapefruit juice and midazolam in humans. Clinical Pharmacology and Therapeutics 1995;58:20-8.
22. Hukkinen SK, Varhe A, Olkkola KT, Neuvonen PJ. Plasma concentrations of triazolam are increased by concomitant ingestion of grapefruit juice. Clinical Pharmacology and Therapeutics 1995;58:127-31.
23. Garg SK, Kumar N, Bhargava VK, Prabhakar SK. Effect of grapefruit juice on carbamazepine bioavailability in patients with epilepsy. Clinical Pharmacology and Therapeutics 1998;64:286-8.
24. Lilja JJ, Kivisto KT, Backman JT, Lamberg TS, Neuvonen PJ. Grapefruit juice substantially increases plasma concentrations of buspirone. Clinical Pharmacology and Therapeutics 1998;64:655-60.
25. Lee AJ, Chan WK, Harralson AF, Buffum J, Bui BC. The effects of grapefruit juice on sertraline metabolism: an in vitro and in vivo study. Clinical Therapeutics 1999;21:1890-9.
26. Kivisto KT, Lilja JJ, Backman JT, Neuvonen PJ. Repeated consumption of grapefruit juice considerably increases plasma concentrations of cisapride. Clinical Pharmacology and Therapeutics 1999;66:448-53.
27. Rau SE, Bend JR, Arnold MO, Tran LT, Spence JD, Bailey DG. Grapefruit juice-terfenadine single-dose interaction: magnitude, mechanism, and relevance. Clinical Pharmacology and Therapeutics 1997;61:401-9.
28. Lilja JJ, Kivisto KT, Neuvonen PJ. Grapefruit juice-simvastatin interaction: effect on serum concentrations of simvastatin, simvastatin acid, and HMG-CoA reductase inhibitors. Clinical Pharmacology and Therapeutics 1998;64:477-83.
29. Yee GC, Stanley DL, Pessa LJ, Dalla Costa T, Beltz SE, Ruiz J, et al. Effect of grapefruit juice on blood cyclosporin concentration. Lancet 1995;345:955-6.
30. Obach RS, Zhang QY, Dunbar D, Kaminsky LS. Metabolic characterization of the major human small intestinal cytochrome p450s. Drug Metabolism and Disposition 2001;29:347-52.
31. 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 Metabolism and Disposition 1997;25:1228-33.
32. 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. Journal of Clinical Investigation 1997;99:2545-53.
33. He K, Iyer KR, Hayes RN, Sinz MW, Woolf TF, Hollenberg PF. Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice. Chemical Research in Toxicology 1998;11:252-9.
34. Lin HL, Kent UM, Hollenberg PF. The grapefruit juice effect is not limited to cytochrome P450 (P450) 3A4: evidence for bergamottin-dependent inactivation, heme destruction, and covalent binding to protein in P450s 2B6 and 3A5. Journal of Pharmacology and Experimental Therapeutics 2005;313:154-64.
35. 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. Clinical Pharmacology and Therapeutics 2000;67:201-14.
36. Arias IM, Gatmaitan Z, Mazzanti R, Shu H, Kumamoto Y. Structure and function of P-glycoprotein in the normal liver and intestine. Princess Takamatsu Symposia 1990;21:229-39.
37. Wacher VJ, Wu CY, Benet LZ. Overlapping substrate specificities and tissue distribution of cytochrome P450 3A and P-glycoprotein: implications for drug delivery and activity in cancer chemotherapy. Molecular Carcinogenesis 1995;13:129-34.
38. Zhang Y, Guo X, Lin ET, Benet LZ. Overlapping substrate specificities of cytochrome P450 3A and P-glycoprotein for a novel cysteine protease inhibitor. Drug Metabolism and Disposition 1998;26:360-6.
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. British Journal of Clinical Pharmacology 1999;48:543-52.
40. Parker RB, Yates CR, Soberman JE, Laizure SC. Effects of grapefruit juice on intestinal P-glycoprotein: evaluation using digoxin in humans. Pharmacotherapy 2003;23:979-87.
41. Wangensteen H, Molden E, Christensen H, Malterud KE. Identification of epoxybergamottin as a CYP3A4 inhibitor in grapefruit peel. European Journal of Clinical Pharmacology 2003;58:663-8.
42. Fukuda K, Guo L, Ohashi N, Yoshikawa M, Yamazoe Y. Amounts and variation in grapefruit juice of the main components causing grapefruit-drug interaction. Journal of Chromatography B, Biomedical Sciences and Applications 2000;741:195-203.
43. Guo LQ, Taniguchi M, Xiao YQ, Baba K, Ohta T, Yamazoe Y. Inhibitory effect of natural furanocoumarins on human microsomal cytochrome P450 3A activity. Japanese Journal of Pharmacology 2000;82:122-9.
44. Mohri K, Uesawa Y. Effects of furanocoumarin derivatives in grapefruit juice on nifedipine pharmacokinetics in rats. Pharmaceutical Research 2001;18:177-82.
45. Kane GC, Lipsky JJ. Drug-grapefruit juice interactions. Mayo Clinic Proceedings Mayo Clinic 2000;75:933-42.
46. 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.
47. Bailey DG, Dresser GK, Leake BF, Kim RB. Naringin is a major and selective clinical inhibitor of organic aniontransporting polypeptide 1A2 (OATP1A2) in grapefruit juice. Clinical Pharmacology and Therapeutics 2007;81:495-502.
48. Lane HY, Jann MW, Chang YC, Chiu CC, Huang MC, Lee SH, et al. Repeated ingestion of grapefruit juice does not alter clozapine's steady-state plasma levels, effectiveness, and tolerability. Journal of Clinical Psychiatry 2001;62:812-7.
49. Uesawa Y, Mohri K. Relationship between lipophilicities of 1,4-dihydropyridine derivatives and pharmacokinetic interaction strengths with grapefruit juice. Yakugaku Zasshi Journal of the Pharmaceutical Society of Japan 2008;128:117-22.
50. Goosen TC, Cillié D, Bailey DG, Yu C, He K, Hollenberg PF, et al. Bergamottin contribution to the grapefruit juice-felodipine interaction and disposition in humans. Clinical Pharmacology and Therapeutics 2004;76:607-17.
51. Uesawa Y, Mohri K. Drug interaction potentials among different brands of grapefruit juice. Die Pharmazie 2008;63:144-6.
52. De Castro WV, Mertens-Talcott S, Rubner A, Butterweck V, Derendorf H. Variation of flavonoids and furanocoumarins in grapefruit juices: a potential source of variability in grapefruit juice-drug interaction studies. Journal of Agricultural and Food Chemistry 2006;54:249-55.
53. Uesawa Y, Abe M, Mohri K. White and colored grapefruit juice produce similar pharmacokinetic interactions. Die Pharmazie 2008;63:598-600.
54. de Castro WV, Mertens-Talcott S, Derendorf H, Butterweck V. Effect of grapefruit juice, naringin, naringenin, and bergamottin on the intestinal carrier-mediated transport of talinolol in rats. Journal of Agricultural and Food Chemistry 2008;56:4840-5.
55. 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. Drug Metabolism and Disposition 1994;22:947-55.
56. Simon JC, Pfieger D, Schöpf E. Recent advances in phototherapy. European Journal of Dermatology 2000;10:642-5.
57. Morlière P, Hüppe G, Averbeck D, Young AR, Santus R, Dubertret L. In vitro photostability and photosensitizing properties of bergamot oil. Effects of a cinnamate sunscreen. Journal of Photochemistry and Photobiology B, Biology 1990;7:199-208.
58. Abou Elzahab M. Photooxygenation of some potentially skin- photosensitizing hydroxyfurocoumarins. Part 2: xanthotoxol and bergaptol. Die Pharmazie 1993;48:144-5.
59. Uesawa Y, Mohri K. UV-irradiated grapefruit juice loses pharmacokinetic interaction with nifedipine in rats. Biological & Pharmaceutical Bulletin 2006;29:1286-9.
60. Uesawa Y, Mohri K. The use of heat treatment to eliminate drug interactions due to grapefruit juice. Biological and Pharmaceutical Bulletin 2006;29:2274-8.
61. Paine MF, Widmer WW, Hart HL, Pusek SN, Beavers KL, Criss AB, et al. A furanocoumarin-free grapefruit juice establishes furanocoumarins as the mediators of the grapefruit juice-felodipine interaction. American Journal of Clinical Nutrition 2006;83:1097-105.
62. 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. Clinical Pharmacology and Therapeutics 2002;71:11-20.
63. Lilja JJ, Backman JT, Laitila J, Luurila H, Neuvonen PJ. Itraconazole increases but grapefruit juice greatly decreases plasma concentrations of celiprolol. Clinical Pharmacology and Therapeutics 2003;73:192-8.
64. Lilja JJ, Juntti-Patinen L, Neuvonen PJ. Orange juice substantially reduces the bioavailability of the beta-adrenergicblocking agent celiprolol. Clinical Pharmacology and Therapeutics 2004;75:184-90.
65. Lilja JJ, Raaska K, Neuvonen PJ. Effects of orange juice on the pharmacokinetics of atenolol. European Journal of Clinical Pharmacology 2005;61:337-40.
66. Lilja JJ, Raaska K, Neuvonen PJ. Effects of grapefruit juice on the pharmacokinetics of acebutolol. British Journal of Clinical Pharmacology 2005;60:659-63.
67. Schwarz UI, Seemann D, Oertel R, Miehlke S, Kuhlisch E, Fromm MF, et al. Grapefruit juice ingestion significantly reduces talinolol bioavailability. Clinical Pharmacology and Therapeutics 2005;77:291-301.
68. Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I. Functional characterization of pH-sensitive organic anion transporting polypeptide OATP-B in human. Journal of Pharmacology and Experimental Therapeutics 2004;308:438-45.
69. Dresser GK, Kim RB, Bailey DG. Effect of grapefruit juice volume on the reduction of fexofenadine bioavailability: possible role of organic anion transporting polypeptides. Clinical Pharmacology and Therapeutics 2005;77:170-7.
70. Uesawa Y, Mohri K. Hesperidin in orange juice reduces the absorption of celiprolol in rats. Biopharmaceutics and Drug Disposition 2008;29:185-8.
71. Spahn-Langguth H, Langguth P. Grapefruit juice enhances intestinal absorption of the P-glycoprotein substrate talinolol. European Journal of Pharmaceutical Sciences 2001;12:361-7.