Undesirable effects of citrus juice on the pharmacokinetics of drugs: Focus on recent studies

Drug Safety

Volumn 28, Issue 8, 2005, Pages 677-694

  Saito, Mitsuo ^a   Hirata Koizumi, Mutsuko ^a   Matsumoto, Mariko ^a   Urano, Tsutomu ^a   Hasegawa, Ryuichi ^a  

^a NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIODARONE; ANTIHISTAMINIC AGENT; ATORVASTATIN; CELIPROLOL; CISAPRIDE; CYCLOSPORIN A; CYTOCHROME P450 3A4; DEXTROMETHORPHAN; DIAZEPAM; DIGOXIN; ERYTHROMYCIN; FELODIPINE; FEXOFENADINE; HALOFANTRINE; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; METHYLPREDNISOLONE; MIDAZOLAM; NICARDIPINE; NIFEDIPINE; NIMODIPINE; NISOLDIPINE; NITRENDIPINE; PROGESTERONE; PROPAFENONE; SAQUINAVIR; SCOPOLAMINE; SIMVASTATIN; TERFENADINE; UNINDEXED DRUG; VERAPAMIL;

AREA UNDER THE CURVE; CITRUS FRUIT; CONCENTRATION RESPONSE; DRUG BIOAVAILABILITY; DRUG DISPOSITION; DRUG SAFETY; ENZYME ACTIVITY; ENZYME INHIBITION; FOOD DRUG INTERACTION; HEART VENTRICLE ARRHYTHMIA; HUMAN; HYPERTENSION; INTESTINE CELL; NEPHROTOXICITY; NEUROTOXICITY; ORANGE JUICE; PRIORITY JOURNAL; REVIEW; RHABDOMYOLYSIS; STATISTICAL SIGNIFICANCE; TORSADE DES POINTES;

ANIMALS; BEVERAGES; CITRUS; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; FOOD-DRUG INTERACTIONS; HUMANS; P-GLYCOPROTEINS; PHARMACEUTICAL PREPARATIONS; PHARMACOKINETICS;

EID: 23644436684     PISSN: 01145916     EISSN: None     Source Type: Journal    
DOI: 10.2165/00002018-200528080-00003     Document Type: Review

References (124)

1. Henderson L, Yue QY, Bergquist C, et al. St John's wort (Hypericum perforatum): drug interactions and clinical outcomes. Br J Clin Pharmacol 2002; 54: 349-56
2. Bailey DG, Spence JD, Munoz C, et al. Interaction of citrus juices with felodipine and nifedipine. Lancet 1991; 337: 268-9
3. Bailey DG, Malcolm J, Arnold O, et al. Grapefruit juice-drug interactions. Br J Clin Pharmacol 1998; 46: 101-10
4. Fuhr U. Drug interactions with grapefruit juice: extent, probable mechanism and clinical relevance. Drug Saf 1998; 18: 251-72
5. 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: 2545-53
6. Silverman RB. Mechanism-based enzyme inactivation: chemistry and enzymology. Vol. 1. Boca Raton (FL): CRC Press, 1988: 224
7. Silverman RB. Mechanism-based enzyme inactivation: chemistry and enzymology. Vol. 2. Boca Raton (FL): CRC Press, 1988: 288
8. Chan WK, Nguyen LT, Miller VP, et al. Mechanism-based inactivation of human cytochrome P450 3A4 by grapefruit juice and red wine. Life Sci 1998; 62: PL135-42
9. Guo LQ, Fukuda K, Ohta T, et al. Role of furanocoumarin derivatives on grapefruit juice-mediated inhibition of human CYP3A activity. Drug Metab Dispos 2000; 28: 766-71
10. Bailey DG, Dresser GK, Bend JR. Bergamottin, lime juice, and red wine as inhibitors of cytochrome P450 3A4 activity: comparison with grapefruit juice. Clin Pharmacol Ther 2003; 73: 529-37
11. Schmiedlin Ren P, Edwards DJ, Fitzsimmons ME, et al. Mecha-nisms 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
12. Bailey DG, Dresser GK, Kreeft JH, et al. Grapefruit-felodipine interaction: effect of unprocessed fruit and probable active ingredients. Clin Pharmacol Ther 2000; 68: 468-77
13. Silverman JA. Multidrug-resistance transporters. Pharm Biotechnol 1999; 12: 353-86
14. Rashid TJ, Martin U, Clarke H, et al. Factors affecting the absolute bioavailability of nifedipine. Br J Clin Pharmacol 1995; 40: 51-8
15. Kupferschmidt HH, Fattinger KE, Ha HR, et al. Grapefruit juice enhances the bioavailability of the HIV protease inhibitor saquinavir in man. Br J Clin Pharmacol 1998; 45: 355-9
16. Kupferschmidt HH, Ha HR, Ziegler WH, et al. Interaction between grapefruit juice and midazolam in humans. Clin Pharmacol Ther 1995; 58: 20-8
17. Ducharme MP, Warbasse LH, Edwards DJ. Disposition of intravenous and oral cyclosporine after administration with grapefruit juice. Clin Pharmacol Ther 1995; 57: 485-91
18. Takanaga H, Ohnishi A, Matsuo H, et al. Inhibition of vinblastine efflux mediated by P-glycoprotein by grapefruit juice components in caco-2 cells. Biol Pharm Bull 1998; 21: 1062-6
19. Xu J, Go ML, Lim LY. Modulation of digoxin transport across Caco-2 cell monolayers by citrus fruit juices: lime, lemon, grapefruit, and pummelo. Pharm Res 2003; 20: 169-76
20. Lin JH, Yamazaki M. Role of P-glycoprotein in pharmacokinetics: clinical implications. Clin Pharmacokinet 2003; 42: 59-98
21. Lown KS, Mayo RR, Leichtman AB, et al. Role of intestinal P-glycoprotein (mdr1) in interpatient variation in the oral bioavailability of cyclosporine. Clin Pharmacol Ther 1997; 62: 248-60
22. Edwards DJ, Fitzsimmons ME, Schuetz EG, 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
23. Parker RB, Yates CR, Soberman JE, et al. Effects of grapefruit juice on intestinal P-glycoprotein: evaluation using digoxin in humans. Pharmacotherapy 2003; 23: 979-87
24. Becquemont L, Verstuyft C, Kerb R, et al. Effect of grapefruit juice on digoxin pharmacokinetics in humans. Clin Pharmacol Ther 2001; 70: 311-6
25. Beveridge T, Nuesch E, Ohnhaus EE. Absolute bioavailability of digoxin tablets. Arzneimittel Forschung 1978; 28: 701-3
26. Cohen AF, Kroon R, Schoemaker HC, et al. The bioavailability of digoxin from three oral formulations measured by a specific h.p.l.c. assay. Br J Clin Pharmacol 1993; 35: 136-42
27. Dresser GK, Bailey DG, Leake BF, 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
28. Lilja JJ, Backman JT, Laitila J, et al. Itraconazole increases but grapefruit juice greatly decreases plasma concentrations of celiprolol. Clin Pharmacol Ther 2003; 73: 192-8
29. Dresser GK, Bailey DG. The effects of fruit juices on drug disposition: a new model for drug interactions. Eur J Clin Invest 2003; 33 Suppl. 2: 10-6
30. Clifford CP, Adams DA, Murray S, et al. The cardiac effects of terfenadine after inhibition of its metabolism by grapefruit juice. Eur J Clin Pharmacol 1997; 52: 311-5
31. Ebert U, Oertel R, Kirch W. Influence of grapefruit juice on scopolamine pharmacokinetics and pharmacodynamics in healthy male and female subjects. Int J Clin Pharmacol Ther 2000; 38: 523-31
32. Lilja JJ, Kivisto KT, Backman JT, et al. Grapefruit juice sub-stantially increases plasma concentrations of buspirone. Clin Pharmacol Ther 1998; 64: 655-60
33. Lilja JJ, Kivisto KT, Neuvonen PJ. Grapefruit juice-simvastatin interaction: effect on serum concentrations of simvastatin, simvastatin acid, and HMG-CoA reductase inhibitors. Clin Pharmacol Ther 1998; 64: 477-83
34. Kantola T, Kivisto KT, Neuvonen PJ. Grapefruit juice greatly increases serum concentrations of lovastatin and lovastatin acid. Clin Pharmacol Ther 1998; 63: 397-402
35. Schubert W, Cullberg G, Edgar B, et al. Inhibition of 17 beta-estradiol metabolism by grapefruit juice in ovariectomized women. Maturitas 1994; 20: 155-63
36. Takanaga H, Ohnishi A, Murakami H, 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
37. Fuhr U, Maier Bruggemann A, Blume H, et al. Grapefruit juice increases oral nimodipine bioavailability. Int J Clin Pharmacol Ther 1998; 36: 126-32
38. Soons PA, Vogels BA, Roosemalen MC, et al. Grapefruit juice and cimetidine inhibit stereoselective metabolism of nitrendipine in humans. Clin Pharmacol Ther 1991; 50: 394-403
39. Fingerova H, Oborna I, Petrova P, et al. Does grapefruit juice increase the bioavailability of orally administered sex steroids? [in Czech]. Ceska Gynekol 2003; 68: 117-21
40. Charbit B, Becquemont L, Lepere B, et al. Pharmacokinetic and pharmacodynamic interaction between grapefruit juice and halofantrine. Clin Pharmacol Ther 2002; 72: 514-23
41. Di Marco MP, Edwards DJ, Wainer IW, et al. The effect of grapefruit juice and seville orange juice on the pharmacokinetcs of dextromethorphan: the role of gut CYP3A and P-glyco-protein. Life Sci 2002; 71: 1149-60
42. Lilja JJ, Kivisto KT, Neuvonen PJ. Grapefruit juice increases serum concentrations of atorvastatin and has no effect on pravastatin. Clin Pharmacol Ther 1999; 66: 118-27
43. Edgar B, Bailey D, Bergstrand R, et al. Acute effects of drinking grapefruit juice on the pharmacokinetics and dynamics of felodipine and its potential clinical relevance. Eur J Clin Pharmacol 1992; 42: 313-7
44. Munoz CE, Ito S, Bend JR, et al. Propafenone interaction with CYP3A4 inhibitors in man [abstract]. Clin Pharmacol Ther 1997; 61: 154
45. Uno T, Ohkubo T, Sugawara K, et al. Effects of grapefruit juice on the stereoselective disposition of nicardipine in humans: evidence for dominant presystemic elimination at the gut site. Eur J Clin Pharmacol 2000; 56: 643-9
46. Veronese ML, Gillen LP, Burke JP, et al. Exposure-dependent inhibition of intestinal and hepatic CYP3A4 in vivo by grapefruit juice. J Clin Pharmacol 2003; 43: 831-9
47. Fuhr U, Muller Peltzer H, Kern R, et al. Effects of grapefruit juice and smoking on verapamil concentrations in steady state. Eur J Clin Pharmacol 2002; 58: 45-53
48. Kanazawa S, Ohkubo T, Sugawara K. The effects of grapefruit juice on the pharmacokinetics of erythromycin. Eur J Clin Pharmacol 2001; 56: 799-803
49. Desta Z, Kivisto KT, Lilja JJ, et al. Stereoselective pharmacokinetics of cisapride in healthy volunteers and the effect of repeated administration of grapefruit juice. Br J Clin Pharmacol 2001; 52: 399-407
50. Weber A, Jager R, Borner A, et al. Can grapefruit juice influ ence ethinylestradiol bioavailability? Contraception 1996; 53: 41-7
51. Sigusch H, Hippius M, Henschel L, et al. Influence of grapefruit juice on the pharmacokinetics of a slow release nifedipine formulation. Pharmazie 1994; 49: 522-4
52. Lilja JJ, Kivisto KT, Backman JT, et al. Effect of grapefruit juice dose on grapefruit juice-triazolam interaction: repeated consumption prolongs triazolam half-life. Eur J Clin Pharmacol 2000; 56: 411-5
53. Hollander AA, van Rooij J, Lentjes GW, et al. The effect of grapefruit juice on cyclosporine and prednisone metabolism in transplant patients [abstract]. Clin Pharmacol Ther 1995; 57: 318-24
54. Libersa CC, Brique SA, Motte KB, et al. Dramatic inhibition of amiodarone metabolism induced by grapefruit juice. Br J Clin Pharmacol 2000; 49: 373-8
55. Garg SK, Kumar N, Bhargava VK, et al. Effect of grapefruit juice on carbamazepine bioavailability in patients with epilepsy. Clin Pharmacol Ther 1998; 64: 286-8
56. Ozdemir M, Aktan Y, Boydag BS, et al. Interaction between grapefruit juice and diazepam in humans. Eur J Drug Metab Pharmacokinet 1998; 23: 55-9
57. Castro N, Jung H, Medina R, et al. Interaction between grapefruit juice and praziquantel in humans. Antimicrob Agents Chemother 2002; 46: 1614-6
58. Varis T, Kivisto KT, Neuvonen PJ. Grapefruit juice can increase the plasma concentrations of oral methylprednisolone. Eur J Clin Pharmacol 2000; 56: 489-93
59. Fuhr U, Klittich K, Staib AH. Inhibitory effect of grapefruit juice and its bitter principal, naringenin, on CYP1A2 dependent metabolism of caffeine in man. Br J Clin Pharmacol 1993; 35: 431-6
60. van Agtmael MA, Gupta V, van der Graaf CA, et al. The effect of grapefruit juice on the time-dependent decline of artemether plasma levels in healthy subjects. Clin Pharmacol Ther 1999; 66: 408-14
61. Lee AJ, Chan WK, Harralson AF, et al. The effects of grapefruit juice on sertraline metabolism: an in vitro and in vivo study. Clin Ther 1999; 21: 1890-9
62. Ho PC, Chalcroft SC, Coville PF, et al. Grapefruit juice has no effect on quinine pharmacokinetics. Eur J Clin Pharmacol 1999; 55: 393-8
63. Josefsson M, Zackrisson AL, Ahlner J. Effect of grapefruit juice on the pharmacokinetics of amlodipine in healthy volunteers. Eur J Clin Pharmacol 1996; 51: 189-93
64. Vincent J, Harris SI, Foulds G, et al. Lack of effect of grapefruit juice on the pharmacokinetics and pharmacodynamics of amlodipine. Br J Clin Pharmacol 2000; 50: 455-63
65. Yasui N, Kondo T, Furukori H, et al. Effects of repeated ingestion of grapefruit juice on the single and multiple oral-dose pharmacokinetics and pharmacodynamics of alprazolam. Psychopharmacology (Berl) 2000; 150: 185-90
66. Min DI, Ku YM, Geraets DR, et al. Effect of grapefruit juice on the pharmacokinetics and pharmacodynamics of quinidine in healthy volunteers. J Clin Pharmacol 1996; 36: 469-76
67. Penzak SR, Acosta EP, Turner M, et al. Effect of Seville orange juice and grapefruit juice on indinavir pharmacokinetics. J Clin Pharmacol 2002; 42: 1165-70
68. Shelton MJ, Wynn HE, Hewitt RG, et al. Effects of grapefruit juice on pharmacokinetic exposure to indinavir in HIV-positive subjects. J Clin Pharmacol 2001; 41: 435-42
69. Cheng KL, Nafziger AN, Peloquin CA, et al. Effect of grapefruit juice on clarithromycin pharmacokinetics. Antimicrob Agents Chemother 1998; 42: 927-9
70. Vandel P, Regina W, Reix I, et al. Grapefruit juice as a contraindication? An approach in psychiatry [in French]. Encephale 1999; 25: 67-71
71. Yasui N, Kondo T, Suzuki A, et al. Lack of significant pharmacokinetic interaction between haloperidol and grape-fruit juice. Int Clin Psychopharmacol 1999; 14: 113-8
72. Tassaneeyakul W, Vannaprasaht S, Yamazoe Y. Formation of omeprazole sulphone but not 5-hydroxyomeprazole is inhibited by grapefruit juice. Br J Clin Pharmacol 2000; 49: 139-44
73. Christensen H, Asberg A, Holmboe AB, et al. Coadministration of grapefruit juice increases systemic exposure of diltiazem in healthy volunteers. Eur J Clin Pharmacol 2002; 58: 515-20
74. Sigusch H, Henschel L, Kraul H, et al. Lack of effect of grapefruit juice on diltiazem bioavailability in normal subjects. Pharmazie 1994; 49: 675-9
75. Jetter A, Kinzig Schippers M, Walchner Bonjean M, et al. Effects of grapefruit juice on the pharmacokinetics of sildenafil. Clin Pharmacol Ther 2002; 71: 21-9
76. Zaidenstein R, Soback S, Gips M, et al. Effect of grapefruit juice on the pharmacokinetics of losartan and its active metabolite E3174 in healthy volunteers. Ther Drug Monit 2001; 23: 369-73
77. Lane HY, Jann MW, Chang YC, et al. Repeated ingestion of grapefruit juice does not alter clozapine's steady-state plasma levels, effectiveness, and tolerability. J Clin Psychiatry 2001; 62: 812-7
78. Vandel S, Netillard C, Perault MC, et al. Plasma levels of clozapine and desmethylclozapine are unaffected by concomitant ingestion of grapefruit juice. Eur J Clin Pharmacol 2000; 56: 347-8
79. 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 acenocoumarol [abstract]. Br J Clin Pharmacol 1993; 35: 548
80. Kumar N, Garg SK, Prabhakar S. Lack of pharmacokinetic interaction between grapefruit juice and phenytoin in healthy male volunteers and epileptic patients. Methods Find Exp Clin Pharmacol 1999; 21: 629-32
81. Fukazawa I, Uchida N, Uchida E, et al. Effects of grapefruit juice on pharmacokinetics of atorvastatin and pravastatin in Japanese. Br J Clin Pharmacol 2004; 57: 448-55
82. Banfield C, Gupta S, Marino M, et al. Grapefruit juice reduces the oral bioavailability of fexofenadine but not desloratadine. Clin Pharmacokinet 2002; 41: 311-8
83. Penzak SR, Gubbins PO, Gurley BJ, et al. Grapefruit juice decreases the systemic availability of itraconazole capsules in healthy volunteers. Ther Drug Monit 1999; 21: 304-9
84. Demarles D, Gillotin C, Bonaventure Paci S, et al. Single-dose pharmacokinetics of amprenavir coadministered with grape-fruit juice. Antimicrob Agents Chemother 2002; 46: 1589-90
85. Reif S, Nicolson MC, Bisset D, et al. Effect of grapefruit juice intake on etoposide bioavailability. Eur J Clin Pharmacol 2002; 58: 491-4
86. Gupta MC, Garg SK, Badyal D, et al. Effect of grapefruit juice on the pharmacokinetics of theophylline in healthy male volunteers. Methods Find Exp Clin Pharmacol 1999; 21: 679-82
87. 14C-buspirone HC1 after intravenous and oral dosing in man [abstract]. Clin Pharmacol Ther 1985; 37: 210
88. Kivisto KT, Lamberg TS, Neuvonen PJ. Interactions of buspirone with itraconazole and rifampicin: effects on the pharmacokinetics of the active 1-(2-pyrimidinyl)-piperazine metabolite of buspirone. Pharmacol Toxicol 1999; 84: 94-7
89. Bailey DG. Grapefruit juice-drug interaction issues. In: Boullata J, Armeni V, editors. Handbook of drug-nutrient interactions. Totawa (NJ): The Humana Press, 2004: 175-194
90. Rogers JD, Zhao J, Liu L, 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
91. Willner K. Excretion and decomposition of 3-methoxy-N methylmorphinan and its demethylated derivatives in man [in German]. Arzneimittel Forschung 1963; 13: 26-9
92. Talajic M, DeRoode MR, Nattel S. Comparative electrophysiologic effects of intravenous amiodarone and desethylami odarone in dogs: evidence for clinically relevant activity of the metabolite. Circulation 1987; 75: 265-71
93. Zhou L, Chen BP, Kluger J, et al. Effects of amiodarone and its active metabolite desethylamiodarone on the ventricular defibrillation threshold. J Am Coll Cardiol 1998; 31: 1672-8
94. Ku YM, Min DI, Flanigan M. Effect of grapefruit juice on the pharmacokinetics of microemulsion cyclosporine and its metabolite in healthy volunteers: does the formulation difference matter? J Clin Pharmacol 1998; 38: 959-65
95. Brunner LJ, Pai KS, Munar MY, et al. Effect of grapefruit juice on cyclosporin A pharmacokinetics in pediatric renal trans-plant patients. Pediatr Transplant 2000; 4: 313-21
96. Hermann M, Asberg A, Reubsaet JL, et al. Intake of grapefruit juice alters the metabolic pattern of cyclosporin A in renal transplant recipients. Int J Clin Pharmacol Ther 2002; 40: 451-6
97. Venkatakrishnan K, von Moltke LL, Greenblatt DJ. Effects of the antifungal agents on oxidative drug metabolism: clinical relevance. Clin Pharmacokinet 2000; 38: 111-80
98. Kaukonen KM, Olkkola KT, Neuvonen PJ. Fluconazole but not itraconazole decreases the metabolism of losartan to E-3174. Eur J Clin Pharmacol 1998; 53: 445-9
99. Lippert C, Ling J, Brown P, et al. Mass balance and pharmacokinetics of MDL 16455A in healthy male volunteers [abstract]. Pharm Res 1995; 12: S390
100. Gubbins PO, McConnell SA, Gurley BJ, et al. Influence of grapefruit juice on the systemic availability of itraconazole oral solution in healthy adult volunteers. Pharmacotherapy 2004; 24: 460-7
101. Dresser GK, Bailey DG, Carruthers SG. Grapefruit juice: felodipine interaction in the elderly. Clin Pharmacol Ther 2000; 68: 28-34
102. Bailey DG, Dresser GK. Interactions between grapefruit juice and cardiovascular drugs. Am J Cardiovasc Drugs 2004; 4: 281-97
103. Lilja JJ, Juntti-Patinen L, Neuvonen PJ. Orange juice substantially reduces the bioavailability of the beta-adrenergic-blocking agent celiprolol. Clin Pharmacol Ther 2004; 75: 184-90
104. Malhotra S, Bailey DG, Paine MF, et al. Seville orange juice-felodipine interaction: comparison with dilute grapefruit juice and involvement of furocoumarins. Clin Pharmacol Ther 2001; 69: 14-23
105. Backman JT, Maenpaa J, Belle DJ, et al. Lack of correlation between in vitro and in vivo studies on the effects of tangeretin and tangerine juice on midazolam hydroxylation. Clin Pharmacol Ther 2000; 67: 382-90
106. Silverman JA, Thorgeirsson SS. Regulation and function of the multidrug resistance genes in liver. Prog Liver Dis 1995; 13: 101-23
107. Cvetkovic M, Leake B, Fromm MF, et al. OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos 1999; 27: 866-71
108. Kim RB. Organic anion-transporting polypeptide (OATP) trans porter family and drug disposition. Eur J Clin Invest 2003; 33 Suppl. 2: 1-5
109. Ranganna S, Govindarajan VS, Ramana KV. Citrus fruits: varieties, chemistry, technology, and quality evaluation. Part II: chemistry, technology, and quality evaluation. A. Chemistry. Crit Rev Food Sci Nutr 1983; 18: 313-86
110. Bailey DG, Arnold JM, Spence JD. Grapefruit juice and drugs: how significant is the interaction? Clin Pharmacokinet 1994; 26: 91-8
111. Kuhnau J. The flavonoids: a class of semi-essential food components: their role in human nutrition. World Rev Nutr Diet 1976; 24: 117-91
112. Cheng KJ, Krishnamurty HG, Jones GA, et al. Identification of products produced by the anaerobic degradation of naringin by Butyrivibrio sp. C3. Can J Microbiol 1971; 17: 129-31
113. Fuhr U, Kummert AL. The fate of naringin in humans: a key to grapefruit juice-drug interactions? Clin Pharmacol Ther 1995; 58: 365-73
114. Bailey DG, Arnold JM, Munoz C, et al. Grapefruit juice: felodipine interaction. Mechanism, predictability, and effect of naringin. Clin Pharmacol Ther 1993; 53: 637-42
115. Bailey DG, Arnold JM, Strong HA, et al. Effect of grapefruit juice and naringin on nisoldipine pharmacokinetics. Clin Pharmacol Ther 1993; 54: 589-94
116. Bailey DG, Munoz C, Arnold JMO, et al. Grapefruit juice and naringin interaction with nitrendipine [abstract]. Clin Pharmacol Ther 1992; 51: 156
117. Bailey DG, Kreeft JH, Munoz C, et al. Grapefruit juice-felodipine interaction: effect of naringin and 6',7'-dihydrox-ybergamottin in humans. Clin Pharmacol Ther 1998; 64: 248-56
118. Kakar SM, Paine MF, Stewart PW, et al. 6'7'-Dihydroxybergamottin contributes to the grapefruit juice effect. Clin Pharmacol Ther 2004; 75: 569-79
119. Ohnishi A, Matsuo H, Yamada S, et al. Effect of fura-nocoumarin 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
120. Tassaneeyakul W, Guo LQ, Fukuda K, et al. Inhibition selectivi ty of grapefruit juice components on human cytochromes P450. Arch Biochem Biophys 2000; 378: 356-63
121. 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
122. Ikegawa T, Ushigome F, Koyabu N, et al. Inhibition of P-glycoprotein by orange juice components, polymethox-yflavones in adriamycin-resistant human myelogenous leukemia (K562/ADM) cells. Cancer Lett 2000; 160: 21-8
123. Takanaga H, Ohnishi A, Yamada S, 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
124. Manthey JA, Grohmann K. Phenols in citrus peel byproducts: concentrations of hydroxycinnamates and polymethoxylated flavones in citrus peel molasses. J Agric Food Chem 2001; 49: 3268-73