Bergamottin contribution to the grapefruit juice-felodipine interaction and disposition in humans

Clinical Pharmacology and Therapeutics

Volumn 76, Issue 6, 2004, Pages 607-617

  Goosen, Theunis C ^a   Cillié, Doré ^b   Bailey, David G ^b   Yu, Chongwoo ^b   He, Kan ^b   Hollenberg, Paul F ^b   Woster, Patrick M ^b   Cohen, Lucinda ^b   Williams, J Andrew ^b   Rheeders, Malie ^b   Dijkstra, H Paul ^b  

^a PFIZER

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

BERGAMOTTIN; DRUG METABOLITE; FELODIPINE; FUROCOUMARIN; UNCLASSIFIED DRUG; WATER;

ADULT; AREA UNDER THE CURVE; ARTICLE; BIOAVAILABILITY; CLINICAL TRIAL; CONTROLLED CLINICAL TRIAL; CONTROLLED DRUG RELEASE; CONTROLLED STUDY; CROSSOVER PROCEDURE; DRUG BLOOD LEVEL; FOOD DRUG INTERACTION; GRAPEFRUIT JUICE; HUMAN; INTERMETHOD COMPARISON; MALE; NORMAL HUMAN; PRIORITY JOURNAL; RANDOMIZED CONTROLLED TRIAL;

ADULT; AREA UNDER CURVE; BIOLOGICAL AVAILABILITY; BIOTRANSFORMATION; CALCIUM CHANNEL BLOCKERS; CAPSULES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CITRUS; CROSS-OVER STUDIES; DELAYED-ACTION PREPARATIONS; FELODIPINE; FEMALE; FOOD-DRUG INTERACTIONS; HUMANS; MALE; PSORALENS; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 10044240240     PISSN: 00099236     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.clpt.2004.08.019     Document Type: Article

References (46)

1. D.G. Bailey, J.D. Spence, C. Munoz, J.M. Arnold Interaction of citrus juices with felodipine and nifedipine Lancet 337 1991 268 269
2. B. Edgar, C.G. Regardh, G. Johnsson, L. Johansson, P. Lundborg, I. Lofberg Felodipine kinetics in healthy men Clin Pharmacol Ther 38 1985 205 211
3. D.G. Bailey, J.M. Arnold, J.D. Spence Grapefruit juice-drug interactions Br J Clin Pharmacol 46 1998 101 110
4. D.G. Bailey, J.R. Bend, J.M. Arnold, L.T. Tran, J.D. Spence Erythromycin-felodipine interaction: magnitude, mechanism, and comparison with grapefruit juice Clin Pharmacol Ther 60 1996 25 33
5. M.P. Ducharme, L.H. Warbasse, D.J. Edwards Disposition of intravenous and oral cyclosporine after administration with grapefruit juice Clin Pharmacol Ther 57 1995 485 491
6. H.H. Kupferschmidt, H.R. Ha, W.H. Ziegler, P.J. Meier, S. Krahenbuhl Interaction between grapefruit juice and midazolam in humans Clin Pharmacol Ther 58 1995 20 28
7. J. Lundahl, C.G. Regardh, B. Edgar, G. Johnsson Effects of grapefruit juice ingestion--pharmacokinetics and haemodynamics of intravenously and orally administered felodipine in healthy men Eur J Clin Pharmacol 52 1997 139 145
8. K.S. Lown, D.G. Bailey, R.J. Fontana, S.K. Janardan, C.H. Adair, L.A. Fortlage Grapefruit juice increases felodipine oral availability in humans by decreasing intestinal CYP3A protein expression J Clin Invest 99 1997 2545 2553
9. M.A. Correia, S.H. Davoll, S.A. Wrighton, P.E. Thomas Degradation of rat liver cytochromes P450 3A after their inactivation by 3,5-dicarbethoxy-2,6- dimethyl-4-ethyl-1,4-dihydropyridine: characterization of the proteolytic system Arch Biochem Biophys 297 1992 228 238
10. H. Takanaga, A. Ohnishi, H. Matsuo, Y. Sawada Inhibition of vinblastine efflux mediated by P-glycoprotein by grapefruit juice components in Caco-2 cells Biol Pharm Bull 21 1998 1062 1066
11. V.A. Eagling, L. Profit, D.J. Back 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 48 1999 543 552
12. A. Ohnishi, H. Matsuo, S. Yamada, H. Takanaga, S. Morimoto, Y. Shoyama 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 130 2000 1369 1377
13. H. Spahn-Langguth, P. Langguth Grapefruit juice enhances intestinal absorption of the P-glycoprotein substrate talinolol Eur J Pharm Sci 12 2001 361 367
14. L. Becquemont, C. Verstuyft, R. Kerb, U. Brinkmann, M. Lebot, P. Jaillon Effect of grapefruit juice on digoxin pharmacokinetics in humans Clin Pharmacol Ther 70 2001 311 316
15. S. Malhotra, D.G. Bailey, M.F. Paine, P.B. Watkins Seville orange juice-felodipine interaction: comparison with dilute grapefruit juice and involvement of furocoumarins Clin Pharmacol Ther 69 2001 14 23
16. G.K. Dresser, D.G. Bailey, S.G. Carruthers Grapefruit juice-felodipine interaction in the elderly Clin Pharmacol Ther 68 2000 28 34
17. D.G. Bailey, J.M. Arnold, H.A. Strong, C. Munoz, J.D. Spence Effect of grapefruit juice and naringin on nisoldipine pharmacokinetics Clin Pharmacol Ther 54 1993 589 594
18. D.G. Bailey, J.M. Arnold, C. Munoz, J.D. Spence Grapefruit juice-felodipine interaction: mechanism, predictability, and effect of naringin Clin Pharmacol Ther 53 1993 637 642
19. T. Rashid, C. McKinstry, A.G. Renwick, M. Dirnhuber, D.G. Waller, C.F. George Quercetin, an in vitro inhibitor of CYP3A, does not contribute to the interaction between nifedipine and grapefruit juice Br J Clin Pharmacol 36 1993 460 463
20. K. Fukuda, L. Guo, N. Ohashi, M. Yoshikawa, Y. Yamazoe Amounts and variation in grapefruit juice of the main components causing grapefruit-drug interaction J Chromatogr B Biomed Sci Appl 741 2000 195 203
21. L.Q. Guo, K. Fukuda, T. Ohta, Y. Yamazoe Role of furanocoumarin derivatives on grapefruit juice-mediated inhibition of human CYP3A activity Drug Metab Dispos 28 2000 766 771
22. K. He, K.R. Iyer, R.N. Hayes, M.W. Sinz, T.F. Woolf, P.F. Hollenberg Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice Chem Res Toxicol 11 1998 252 259
23. W. Tassaneeyakul, L.Q. Guo, K. Fukuda, T. Ohta, Y. Yamazoe Inhibition selectivity of grapefruit juice components on human cytochromes P450 Arch Biochem Biophys 378 2000 356 363
24. T. Ohta, M. Nagahashi, S. Hosoi, S. Tsukamoto Dihydroxybergamottin caproate as a potent and stable CYP3A4 inhibitor Bioorg Med Chem 10 2002 969 973
25. P. Schmiedlin-Ren, D.J. Edwards, M.E. Fitzsimmons, K. He, K.S. Lown, P.M. Woster Mechanisms of enhanced oral availability of CYP3A4 substrates by grapefruit constituents Decreased enterocyte CYP3A4 concentration and mechanism-based inactivation by furanocoumarins Drug Metab Dispos 25 1997 1228 1233
26. D.J. Greenblatt, L.L. von Moltke, J.S. Harmatz, G. Chen, J.L. Weemhoff, C. Jen Time course of recovery of cytochrome P450 3A function after single doses of grapefruit juice Clin Pharmacol Ther 74 2003 121 129
27. D.J. Edwards, F.H. Bellevue III, P.M. Woster Identification of 6',7'-dihydroxybergamottin, a cytochrome P450 inhibitor, in grapefruit juice Drug Metab Dispos 24 1996 1287 1290
28. L.Q. Guo, M. Taniguchi, Y.Q. Xiao, K. Baba, T. Ohta, Y. Yamazoe Inhibitory effect of natural furanocoumarins on human microsomal cytochrome P450 3A activity Jpn J Pharmacol 82 2000 122 129
29. D.G. Bailey, J.H. Kreeft, C. Munoz, D.J. Freeman, J.R. Bend Grapefruit juice-felodipine interaction: effect of naringin and 6′,7′- dihydroxybergamottin in humans Clin Pharmacol Ther 64 1998 248 256
30. S.M. Kakar, M.F. Paine, P.W. Stewart, P.B. Watkins 6′7′- Dihydroxybergamottin contributes to the grapefruit juice effect Clin Pharmacol Ther 75 2004 569 579
31. E.J. Wang, C.N. Casciano, R.P. Clement, W.W. Johnson Inhibition of P-glycoprotein transport function by grapefruit juice psoralen Pharm Res 18 2001 432 438
32. K. Fukuda, T. Ohta, Y. Oshima, N. Ohashi, M. Yoshikawa, Y. Yamazoe Specific CYP3A4 inhibitors in grapefruit juice: furocoumarin dimers as components of drug interaction Pharmacogenetics 7 1997 391 396
33. D.G. Bailey, G.K. Dresser, J.R. Bend Bergamottin, lime juice, and red wine as inhibitors of cytochrome P450 3A4 activity: comparison with grapefruit juice Clin Pharmacol Ther 73 2003 529 537
34. J. Sahi, E.L. Reyner, J.N. Bauman, K. Gueneva-Boucheva, J.E. Burleigh, V.H. Thomas The effect of bergamottin on diazepam plasma levels and P450 enzymes in beagle dogs Drug Metab Dispos 30 2002 135 140
35. T.C. Goosen, J. Van Rooyen, E. Erasmus, H.C. Potgieter Cyclosporine pharmacokinetics following co-administration with grapefruit juice, bergamottin or vitamin E TPGS in rats [abstract] Pharmacologist 44 2002 A172
36. K. Mohri, Y. Uesawa Effects of furanocoumarin derivatives in grapefruit juice on nifedipine pharmacokinetics in rats Pharm Res 18 2001 177 182
37. M. Ahnoff Determination of felodipine in plasma by capillary gas chromatography with electron capture detection J Pharm Biomed Anal 2 1984 519 526
38. D.G. Bailey, G.K. Dresser, J.H. Kreeft, C. Munoz, D.J. Freeman, J.R. Bend Grapefruit-felodipine interaction: effect of unprocessed fruit and probable active ingredients Clin Pharmacol Ther 68 2000 468 477
39. M.F. Paine, W. Widmer, H.L. Hart, S.S. Brown, B.F. Thomas, S.N. Pusek A furanocoumarin-free grapefruit juice does not alter the oral pharmacokinetics of felodipine [abstract] Drug Metab Rev 35 Suppl 2 2003 67
40. T. Ohta, T. Maruyama, M. Nagahashi, Y. Miyamoto, S. Hosoi, F. Kiuchi Paradisin C: a new CYP3A4 inhibitor from grapefruit juice Tetrahedron 58 2002 6631 6635
41. P.C. Ho, D.J. Saville, S. Wanwimolruk Inhibition of human CYP3A4 activity by grapefruit flavonoids, furanocoumarins and related compounds J Pharm Pharm Sci 4 2001 217 227
42. A.B. Criss, M.F. Paine, P.B. Watkins The two major furocoumarins in grapefruit juice have distinct absorption and protein binding characteristics [abstract] Drug Metab Rev 34 Suppl 1 2002 169
43. C.L. Cummins, W. Jacobsen, L.Z. Benet Unmasking the dynamic interplay between intestinal P-glycoprotein and CYP3A4 J Pharmacol Exp Ther 300 2002 1036 1045
44. L.L. Koenigs, W.F. Trager Mechanism-based inactivation of cytochrome P450 2B1 by 8-methoxypsoralen and several other furanocoumarins Biochemistry 37 1998 13184 13193
45. S.A. Wrighton, E.G. Schuetz, K.E. Thummel, D.D. Shen, K.R. Korzekwa, P.B. Watkins The human CYP3A subfamily: practical considerations Drug Metab Rev 32 2000 339 361
46. B.S. Mayhew, D.R. Jones, S.D. Hall An in vitro model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation Drug Metab Dispos 28 2000 1031 1037