Drug interactions with grapefruit juice

Clinical Pharmacokinetics

Volumn 33, Issue 2, 1997, Pages 103-121

  Ameer, Barbara ^a   Weintraub, Randy A ^b  

^a Independent Pharmacology Consultant   (United States)

^b FMC CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIHISTAMINIC AGENT; AURANTIIN; BENZODIAZEPINE DERIVATIVE; CALCIUM ANTAGONIST; CYCLOSPORIN; CYTOCHROME P450; MIDAZOLAM; TERFENADINE; TRIAZOLAM;

AEROBIC METABOLISM; DRUG BIOAVAILABILITY; DRUG MECHANISM; DRUG METABOLISM; FRUIT JUICE; PRIORITY JOURNAL; REVIEW;

EID: 0030839243     PISSN: 03125963     EISSN: None     Source Type: Journal    
DOI: 10.2165/00003088-199733020-00003     Document Type: Review

References (101)

1. Anderson KE. Influences of diet and nutrition on clinical pharmacokineties. Clin Pharmacokinet 1988; 14: 325-46
2. Melander A. Influence of food on the bioavailability of drugs. Clin Pharmacokinet 1978; 3: 337-51
3. Welling PG. Influence of food und diet on gastrointestinal drug absorption: a review. J Pharmacokinet Biopharm 1977; 5: 291-334
4. Williams L, Hill DP, Davis JA, et al. The influnce of food on the absorption and metabolism of drugs: an update. Eur J Metab Pharmacokinet 1966; 21 (3): 201-11
5. Waller-Sack I, Klotz U. Influence of diet and nutritional status on drug metabolism. Clin Pharmacokinet 1996; 31: 47-64
6. Horowitx RM. The citrus flavonoids. In: Sinclair WB, editor. The orange, its biochemistry and physiology. Riverside ICA): University of California. 1961: 334-72
7. Ameer B, Weintraub RA, Johnson JV, et al. Flavanone absorption after naringin. hesperidin and citrus administration. Clin Pharmacol Ther 1996; 60: 34-40
8. Euhe, Kummert A. The fate of naringin in humans: a key to grapefruit juice-drug interactions'? Clin Pharmacol Ther 1995; 58: 365-73
9. Johnston A, Marsden JT, Hla KK, et al. The effect of vehicle on the oral absorption of cyclosporine. Br J Clin Pharmacol 1986; 21: 331-3
10. Yee GC, Stanley DL, Pessa LJ, et al. Effect of grapefruit juice on blood cyclosporine concentration. Lancet 1994; 345: 955-6
11. Bailey DG, Spence JD, Munoz C, et al. Interaction of citrus juices with felodipine and nifedipine. Lancet 1991; 337: 268-9
12. Bailey DG, Munoz C, Arnold JMO, et al. Grapefruit juice and naringin interaction with nitrendipinc [abstract]. Clin Pharmacol Ther 1992; 51: 156
13. Bailey DG, Arnold JMO, Strong HA, et al. lifted of grapefruit juice and naringin on nisoldipine pharmacokinctics. Clin Pharmacol Ther 1993; 54: 589-94
14. Rashid J, McKinstry C, Renwick AG, et al. Quercetin, an in vitro inhibitor of CYP3A, does not contribute to the interaction between nifedipine and grapefruit juice. Br J Clin Pharmacol 1993: 36: 400-3
15. Edwards DJ, Bellevue FH, Wosler PM. Identification of 6′,7′dihydroxyhergainottin, a cytochrome P450 inhibitor, in grapefruit juice. Drug Metab Dispos 1996; 24 (12): 1287-90
16. McIntosh CA, Mansell RL, Rouseff RL. Distributiun of limonin in the fruit tissues of nine grapefruit cullivars. J Agric Pood Chem 1982; 30: 689-92
17. Rouseff RL. Nomolin, a new bitter component in grapefruit juice. J Agric Food Chem 1982; 30: 504-7
18. Rouseff RL. Differentiating citrus juices using flavanone glycoside concentration profiles. In: Nagy S. Attaway JA, Rhodes ME, editors. Adulteration of fruit juice beverages. New York: Marcel Dekker, 1988: 49-65
19. Rouseff RL, Martin SF, Youlscy CO. Quantitative survey of narirutin, hesperidin. and ncohcspcridin in Citrus. J Agric Food Chem 1987; 35: 1027-30
20. Mansell RL, McIntoshCA, Vest SE. An analysis of the limonin und naringin content of grapefruit juice samples collected from Florida state test houses. J Agric Food Chem 1983; 31: 156-62
21. Herzog P, Monselise SP. Growth and development of grapefruits in two different climatic districts of Israel. Israel J Agric Res 1968; 18: 181-6
22. Albach RF, Redman GH, Cruse RR. Annual and seasonal changes in naringin concentration of ruby red grapefruit juice. J Agric Food Chem 1981 ; 29 (4): 808-11
23. Berhow MA, Vandercouk CE, Biosynthesis of naringen and prunin in detached grapefruit. Phytochem 1989; 28: 1627-30
24. Albach RF, Wutscher HK. Flavanone content of whole grapefruit and juice as influenced by fruit development. J Rio Grande Valley Hort Soc 1988; 41: 89-93
25. Castillo J, Benavente O, del Rio JA. Hesperitin 7-0-glucoside and prunin in Citrus species (C. aurantium and C. paridisi): a study of their quantitative distribution in immature fruits and as immediate precursors of neohesperidin and naringin in C. aurantium. J Agric Food Chem 1993; 41: 1920-4
26. Shaw PE, Calkins CO, McDonald RE, et al. Changes in limonin and naringin levels in grapefruit albedo with maturity and the effects of gibberellic acid on these changes. Phytochemistry 1991; 30: 3215-9
27. Wagner CJ, Wilson CW, Shaw PE. Reduction of grapefruit bitter components in u fluidized B-cyclodextrin polymer bed. J Food Sci 1988; 53(2): 516-8
28. Florida Department of Citrus. Standards for processed citrus products. Chapter 20-64. revised edition August 23, 1993
29. Barthe GA, Jourdan PS, Mclntosh CA, et al. Radioimmunoassay for the quantitative determination of hesperidin and analysis of its distribution in Citrus sinensis. Phytochemistry 1988; 27: 249-54
30. Wilson CW, Wagner CJ, Shaw PE. Reduction of bitter components in grapefruit and navel orange juices with fl-cyclodcxtrin polymers or XAD resins in a fluidized bed process. J Agric Food Chem 1989; 37: 14-8
31. Tsen H-Y, Yu G-K. Limonin and naringin removal from grapefruit juice with naringinase entrapped in cellulose triacetate fibers. J Food Sci 1991; 56 (1): 31-4
32. Braddock RJ, Cadwallader KR. Citrus by-products manufacture for food use. Food Tech 1992; 46: 105-10
33. Kimball DA, Norman SI, Processing effects during commercial debittering of California navel orange juice. J Agric Food Chem 1990; 38: 1396-1400
34. United States Food and Drug Administration, Health and Human Services: 21: code of federal registations 146,132-146,154. Washington, DC: US Government Printing Office, 1995
35. Guengerich FP, Kim DH. In vitro inhibition of dihydropyridine oxidation and aflatoxin BI activation in human liver microsomes by naringenin and other flavonoids. Carcinogen 1990; 11: 2278-9
36. Miniscalco A, Lundahl J, Regirdh CG, et al. Inhibition of dihydropyridine metabolism in rat and human liver microsomes by flavonoids found in grapefruit juice. J Pharmacol Exp Ther 1992; 261: 1195-9
37. Ha HR, Chen J, Leuenhcrger PM, et al. In vitro inhibition of midazolam and quinidine metabolism by flavonoids. Eur J Clin Pharmacol 1995; 48: 367-71
38. Schubert W, Eriksson U, Edgar B, et al. Flavonoids in grapefruit juice inhibit the in vitro hepatic metabolism of 17β-estradiol. Eur J Drug Metab Pharmacokinet 1995; 20: 219-24
39. Jurima-Romet M, Cruwford K, Cyr T, et al. Terfenadine metabolism in human liver: in vitro inhibition by macrolide antibiotics and azoic antifunguls, Drug Metab Dispos 1995; 22: 849-57
40. Fuhr U, Klittich K, Stuib AH. Inhibitory effect of grapefruit juice and the active component naringenin on CYP1A2 dependent metabolism of caffeine in man. Br J Clin Pharmacol 1993; 35: 431-6
41. Lee YS, Lorenzo BJ, Koufis T, et al. Grapefruit juice and its fluvonoids inhibit 11β-hydroxysleroid dehydrogenuse. Clin Pharmacol Ther 1996; 59: 62-71
42. Obermeier MT, White RE, Yang CS. Effects of bioflavonoids on hepatic P450 activities. Xenobiotica 1995; 25: 575-84
43. Fusco MJ, Silkworth JB, Dunbar DA, et al. Rat smull intestinal cytochromes P450 probed by warfarin metabolism. Molecular Pharmacol 1993; 43: 226-33
44. Lown KS, Kolars JC, Thummel KE, et al. Interpatient heterogeneity in expression of CYP3A4 and CYP3A5 in small bowel. Luck of prediction by the erythromycin breath test. Drug Meubl Dispos 1994; 22: 947-55
45. Lampen A, Uwe C, Guengerich FP, et al. Metabolism of the immunosuppressunl tacrolimus in the small intestine: cytochrome P450, drug interactions, and interindividual variability, Drug Metab Dispos 1995; 23: 1315-24
46. Vernet A, Siess MH. Comparison of the effects of various flavonoids on ethoxycoumarin deethylase activity of rat intestinal and hepatic microsomes. Food Chem Toxicol 1986; 24: 857-61
47. Balogh A, Weber A, Klinger G. Can grapefruit juice influence the bioavailability of ethinylestradiol? [abstract]. Eur J Clin Pharmacol 1994; 47: A93
48. Ducharme MP, Provenzano R, Dehoorne-Smith M, et al. Trough concentrations of cyclosporin following administration with grapefruit juice. Br J Clin Pharmacol 1993; 36: 457-9
49. Herlitz H, Edgar B, Hedner T, et al. Grapefruit juice: a possible source of variability in blood concentrations of cyclosporinc A [letter]. Nephrol Dial Transplant 1993; 8: 375
50. Hollander AAMJ, van Rooij J, Lentjcs EGWM, et al. The effect of grapefruit juice on cyclosporine and prednisone metabolism in transplant patients. Clin Pharmacol Ther 1995; 57: 318-24
51. Proppe DG, Hoch OD, McLean AJ, et al. Influence of chronic ingestion of grapefruit juice on steady-state blood concentrations of cyclosporine A in renul transplant patients with stable graft function [letter]. Br J Clin Pharmacol 1995; 39: 337-8
52. Proppe DG, Visser K, Bartels R, et al. Grupefruit juice selectively modifies cyclosporin A metabolite patterns in renal transplant patients [abstract]. Clin Pharmacol Ther 1996; 59: 138
53. Schubert W, Cullberg G, Fidgar B, et al. Inhibition of 17β-estradiol metaibolism by grapefruit juice in ovariectomized women. Maturitas 1995; 20: 155-63
54. Edgar B, Builey D, Bergstrand R, et al. Acute effects of drinking grapefruit juice on the pharmaeokineties and dynamics of l'elodipine: its potential clinical relevance. Eur J Clin Phurmucol 1992; 42: 313-7
55. Bailey DG, Arnold JMO, Munoz C, et al. Grapefruit juice-felodipine inicraction: mechanism, predictability and effect of naringen. Clin Pharmacol Ther 1993; 53: 637-42
56. Lundahl J, Regardh CCI. Edgar B, et al. Relationship between time of intake of grapefruit juice and its effect on pharmacokinetics and pharmacodynamicss of felodipine in healthy subjects. Eur J Clin Pharmacol 1995; 49: 61-7
57. Benton RE, Honig PK, Zumuni K, et al. Grapefruit juice alters lertenadine pharmacokinetics. resulting in prolongation of repolarization on the electrocardiogram. Clin Pharmacol Ther 1996; 59: 383-8
58. Honig PK, Wortham DC, Luzurev A, et al. Grapefruit juice alters the systemic bioavailability and cardiac repolarization of icrfenadine in poor metabolizers of terfenadine. J Clin Pharmacol 1996; 36: 345-51
59. Fuhr U, Harder S, Lopez-Rojas P, et al. Increase of verapamil concentrations in steady stale by coadministration of grapefruit juice [abstract]. Arch Pharmacol 1994; 349 Suppl.: R134
60. Vanukoski J, Mattila MJ, Seppala T. Grapefruit juice does not enhance the effects of midazolam and triazolum in man. Eur J Clin Pharmacol 1996; 50: 501-8
61. Sigusch H, Henschel L, Kraul H, et al. Lack of effect of grapefruit juice on diltiazem bioavailability in normal subjects. Pharmime 1994; 49: 675-9
62. Kupferschmidt HHT, Ha HR. Ziegler WH, et al. Interaction between grapefruit juice and midazilam in humans. Clin Pharmacol Ther 1995; 58: 20-8
63. Bailey DG, Bend JR, Arnold JMO, et al. Erythromycin-felodipine interaction: magnitude, mechanism and comparison with grapefruit juice. Clin Pharmacol Ther 1996; 60: 25-33
64. Merkel U, Sigusch H, Hoffmann A. Grapefruit juice inhibits 7-hydroxylationofcoumarin in healthy volunteers. Eur J Clin Pharmacol 1994; 46: 175-7 65.
65. Fuhr U, Maier A, Keller A, et al. Lacking effect of grapefruit juice on theophylline pharmacokineties. Int J Clin Pharmacol 1995; 33: 311-4
66. Ameer B, Weintrauh RA, Rouseff RL. Citrus flavanone determination by HPLC [abstract]. J Clin Pharmacol 1996; 36: 852
67. Edgar B, Bailey DG, Bergstrand R, et al. Formulation dependent interaction between felodipinc and grapefruit juice (abstract). Clin Pharmacol Ther 1990; 47: 181
68. Thummel KE, O'Shea D, Paine MF, et al. Oral first-pass elimination of midazolam involves both gastrointestinal and hepatic CYP3A-mediated metabolism. Clin Pharmacol Ther 1996; 59: 491-502
69. Hukkinen SK, Varhe A, Olkkolu KT, et al. Plasma concentrations of triazolam are increased by concomitant ingestion of grapefruit juice. Clin Pharmacol Ther 1995; 58: 127-31
70. Ducharme MP, Warhasse LH, Edwards DJ. Disposition of intravenous and oral cyclosporine after administration with grapefruit juice. Clin Pharmacol Ther 1995; 57: 485-91
71. Bailey DO, Arnold JMO, Bend JR, et al. Grapefruit juice-felodipine interaction: reproducibility and characterisation with the extended release drug formulation. Br J Clin Pharmacol 1995; 40: 135-40
72. Soons PA, Vogels BAPM, Roosemalen MCM, et al. Grapefruit juice and cimetidine inhibit slereoselective metabolism of nitrendipine in humans. Clin Pharmacol Ther 1991: 50: 394-403
73. Rashid TJ, Martin U, Clarke H, et al. Factors affecting the absolute bioavailability of nifedipine, Br J Clin Pharmacol 1995; 40; 51-8
74. Josefsson M, Zackrisson A-L, Ahlner J. Effect of grapefruit juice on the pharmucokinetics of amlodipine in healthy volunteers. Eur J Clin Pharmacol 1996; 51: 189-93
75. Fuhr U, Maier A, Blume H, et al. Grapefruit juice increases oral nimodipine bioavailability [abstract]. Eur J Clin Pharmacol 1994; 47: A100
76. Uno T, Ohkuho T, Sugawara K, et al. Effect of grapefruit juice on the disposition of nicardipine after intravenous and oral doses [abstract]. Clin Pharmacol Ther 1997; 61: 209
77. Ingersoll B. FDA proposes to force Soldant: off the market. Wall Street J 1997 Jan 14: Sect, B: 1 (col.3-6)-11 (col.6)
78. Van Rooij J, van der Meer FJM, Schoemaker HC, et al. Comparison of the effect of grapefruit juice and cimetidine on pharmacokinetics and anticoagulant effect of a single dose of acenocoarnarol [proceedings abstract]. Br J Clin Pharmacol 1993; 35: 548P
79. Maish WA, Hampton EM, Whitselt TL, et al. Influence of grapefruit juice on caffeine pharmacokinetics and pharmacodynamics. Pharmacothcrapy 1996; 16 (6): 1046-52
80. Spatzenegger M, Jaeger W. Clinical importance of hepatic cytochrome P450 in drug metabolism. Drug Metab Rev 1995; 27: 397-417
81. Kolurs JC, Lowns KS, Schmiedlin-Ren P, et al. CYP3A geneexpression in human gut epithelium. Pharmacogenetics 1994: 4: 247-59
82. Kolars JC, Schmiedlin-Ren P, Sehnetz JD, et al. Identification of rifampin-inducible P450IIIA4 (CYP3A4) in human small howel enterocytes. J Clin Invest 1992; 90: 1871-8
83. Kivistö KT, Bookjan G, Fromm MF, et al. Expression of CYP3A4, CYP3A5 and CYP3A7 in human duodenal tissue. Br J Clin Pharmacol 1996; 42: 387-9
84. Bonkovsky HL, Kauri H-P, Marti LI, et al. Cytochrome P450 of small intestinal epithelial cells. Gastroenterology 1985; 88: 458-67
85. Krishna DR, Klotz U. Extrahepatic metabolism of drugs in humans. Clin Pharmacokinet 1994; 26: 144-60
86. Lown KS, Thummel KE, Benedict PE, et al. The erythromycin breath test predicts the clearance of midazolam, Clin Pharmacol Ther 1995; 57: 16-24
87. Pichard L, Gillet G, Fahre I, et al. Identification of the rabbit and human cytochromes P-450IIIA as the major enzymes involved in the N-demethylation ot'diltiazem. Drug Metah Dispos 1990; 18: 711-9
88. Sesardic D, Boohis AR, Edwards RJ, et al. A form of cytochrome P450 in man, orthologous to form d in the rat, catalyzes the O-deethylation of phenacetin and is inducible by cigarette smoking. Br J Clin Pharmacol 1988; 26: 363-72
89. Paine MF, Shen DR, Kunze KL, et al. First-pass metabolism of midazolam by the human intestine. Clin Pharmacol Ther 1996; 60; 14-24
90. Wu C-Y, Benet LZ, Hebert MF, et al. Differentiation of absorption and first-pass gut and hepatic metabolism in humans: studies with cyclosporine. Clin Pharmacol Ther 1995; 58: 492-7
91. Lown KS, Bailey DG, Fontana RJ, et al. Grapefruit juice increases felodipine oral availability in humans by decreasing intestinal CYP3A protein expression. J Clin Invest 1997;99: 2245-53
92. Wucher VJ, Wu C-Y, Berief LZ. Overlapping substrate specificities and tissue distribution of cytochrome P450 3A und P-glycoprotein: implications for drug delivery und activity in cancer chemotherapy. Mol Carcinog 1995; 13: 129-34
93. Willie RT, Lown KS, Huszczo UR, et al. Short term effect of medications on CYP3A and P-glycoprotein expression in human intestinal mucosa [abstract].Gastroenterology 1997; 112 Suppl.: A419
94. Kivistö KT, Kroemer HK, Eichelbaum M. The role of human cytochrome P450 enzymes in the metabolism of anticancer agents: implication for drug interactions. Br J Clin Pharmacol 1995; 40: 523-30
95. Inaba T, Ncbert DW, Burchell B, et al. Pharmacogenetics in clinical pharmacology and toxicology: a tribute to Werner Kalow. Can J Physiol Pharmacol 1995; 73: 331-8
96. Honig PK, Smith JE, Wortham DC, et al. Population variability in the pharmacokinetics of terfenadine: the case for a pseudopolymorphism with clinical implications. Drug Metab Drug Interact 1994; 11: 161-8
97. Hunt CM, Westerkam WR, Stave CM. Effect of age and gender on the activity of human hepatic CYP3A. Biochem Pharmacol 1992; 44: 275-83
98. Vincent J, Foulds G, Dngolo LC, et al. Grapefruit juice dees not alter the pharmaeokinetics of amlodipine in man [abstract]. Clin Pharmacol Thor 1997; 11: 233
99. Burggraaf J, Schoemakcr R, Cohen AF. The effect of grapefruit juice (GF) on the pharmacokinetics (PK) and pharmacodynumics (PD) of nifedipine administered in two different formulations [abstract]. Clin Pharmucol Ther 1997; 61: 232
100. Ncoral® soft gelatin capsules and oral solution for microemulsiun. product labeling. East Hanover (NJ): Sandoz Pharmaceuticals Corporation, 1995
101. Bailey DG, Arnold JMO, Spence JD. Grapefruit juice and drugs. how significant is the interaction? Clin Pharmacokinet 1994; 26: 91-8