Two major grapefruit juice components differ in time to onset of intestinal CYP3A4 inhibition

Journal of Pharmacology and Experimental Therapeutics

Volumn 312, Issue 3, 2005, Pages 1151-1160

  Paine, Mary F ^a,c   Criss, Anne B ^a   Watkins, Paul B ^a,b  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

^c UNIVERSITY OF NORTH CAROLINA HOSPITALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6',7' DIHYDROBERGAMOTTIN; BERGAMOTTIN; CYTOCHROME P450 3A4; FUROCOUMARIN; MIDAZOLAM; TESTOSTERONE; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN CACO 2; CONTROLLED STUDY; DRUG HYDROLYSIS; DRUG INHIBITION; DRUG METABOLISM; ENZYME DEGRADATION; ENZYME INHIBITION; ENZYME SUBSTRATE COMPLEX; FIRST PASS EFFECT; FOOD DRUG INTERACTION; FOOD INTAKE; GRAPEFRUIT JUICE; HUMAN; HUMAN CELL; HYDROXYLATION; INTESTINE CELL; PRIORITY JOURNAL;

CACO-2 CELLS; CATALYSIS; CITRUS PARADISI; CYTOCHROME P-450 ENZYME SYSTEM; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; HUMANS; PSORALENS; TIME FACTORS;

EID: 14344258321     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.104.076836     Document Type: Article

References (32)

1. Bailey DG, Arnold JMO, and Spence JD (1998a) Grapefruit juice-drug interactions. Br J Clin Pharmacol 46:101-110.
2. Bailey DG, Dresser GK, and Bend JR (2003) Bergamottin, lime juice and red wine as inhibitors of cytochrome P450 3A4 activity: comparison with grapefruit juice. Clin Pharmacol Ther 73:529-537.
3. Bailey DG, Dresser GK, Kreeft JH, Munoz C, Freeman DJ, and Bend JR (2000) Grapefruit - felodipine interaction: effect of unprocessed fruit and probable active ingredients. Clin Pharmacol Ther 68:468-477.
4. Bailey DG, Kreeft JH, Munoz C, Freeman DJ, and Bend JR (1998b) Grapefruit juice-felodipine interaction: effect of naringin and 6′,7′- dihydroxybergamottin in humans. Clin Pharmacol Ther 64:248-256.
5. Doherty MM and Charman WN (2002) The mucosa of the small intestine: how clinically relevant as an organ of drug metabolism? Clin Pharmacokinet 41:235-253.
6. Dundee JW, Halliday NJ, Harper KW, and Brogden RN (1984) Midazolam. A review of its pharmacological properties and therapeutic use. Drugs 28:519-543.
7. Edwards DJ, Fitzsimmons ME, Schuetz EG, Yasuda K, Ducharme MP, Warbasse LH, Woster PM, Schuetz JD, and Watkins P (1999) 6′,7′- Dihydroxybergamottin in grapefruit juice and Seville orange juice: effects on cyclosporine disposition, enterocyte CYP3A4 and P-glycoprotein. Clin Pharmacol Ther 65:237-244.
8. Fisher JM, Wrighton SA, Calamia JC, Shen DD, Kunze KL, and Thummel KE (1999a) Midazolam metabolism by modified Caco-2 monolayers: effects of extracellular protein binding. J Pharmacol Exp Ther 289:1143-1150.
9. 3-modified Caco-2 cell monolayers. J Pharmacol Exp Ther 289:1134-1142.
10. Fukuda K, Guo L, Ohashi N, Yoshikawa M, and Yamazoe Y (2000) Amounts and variation in grapefruit juice of the main components causing grapefruit-drug interaction. J Chromatog B Biomed Sci Appl 741:195-203.
11. Fukuda K, Ohta T, Oshima Y, Ohashi N, Yoshikawa M, and Yamazoe Y (1997) Specific CYP3A4 inhibitors in grapefruit juice: furocoumarin dimers as components of drug interaction. Pharmacogenetics 7:391-396.
12. Galetin A, Clarke SE, and Houston JB (2003) Multisite kinetic analysis of interactions between prototypical CYP3A4 subgroup substrates: midazolam, testosterone and nifedipine. Drug Metab Dispos 31:1108-1116.
13. Gibbs MA, Baillie MT, Shen DD, Kunze KL, and Thummel KE (2000) Persistent inhibition of CYP3A4 by ketoconazole in modified Caco-2 cells. Pharm Res (NY) 17:299-305.
14. Guo LQ, Fukuda K, Ohta T, and Yamazoe Y (2000) Role of furanocoumarin derivatives on grapefruit juice-mediated inhibition of human CYP3A activity. Drug Metab Dispos 28:766-771.
15. He K, Iyer KR, Hayes RN, Sinz MW, Woolf TF, and Hollenberg PF (1998) Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice. Chem Res Toxicol 11:252-259.
16. Hochman JH, Chiba M, Nishime J, Yamazaki M, and Lin JH (2000) Influence of P-glycoprotein on the transport and metabolism of indinavir in Caco-2 cells expressing cytochrome P-450 3A4. J Pharmacol Exp Ther 292:310-318.
17. Huang SM and Lesko LJ (2004) Drug-drug, drug-dietary supplement and drug-citrus fruit and other food interactions: what have we learned? J Clin Pharmacol 44:559-569.
18. Kakar SM, Paine MF, Stewart PW, and Watkins PB (2004) 6′7′-Dihydroxybergamottin contributes to the grapefruit juice effect. Clin Pharmacol Ther 75:569-579.
19. Kenworthy KE, Bloomer JC, Clarke SE, and Houston JB (1999) CYP3A4 drug interactions: correlation of 10 in vitro probe substrates. Br J Clin Pharmacol 48:716-727.
20. Lown KS, Bailey DG, Fontana RJ, Janardan SK, Adair CH, Fortlage LA, Brown MB, Guo W, and Watkins PB (1997) Grapefruit juice increases felodipine oral availability in humans by decreasing intestinal CYP3A protein expression [see comments]. J Clin Investig 99:2545-2553.
21. Lowry OH, Rosebrough NJ, Farr AL, and Randall RJ (1951) Protein measurement with the folin phenol reagent. J Biol Chem 193:265-275.
22. Mouly SJ, Paine MF, and Watkins PB (2004) Contributions of CYP3A4, P-glycoprotein and serum protein binding to the intestinal first-pass extraction of saquinavir. J Pharmacol Exp Ther 308:941-948.
23. Paine MF, Criss AB, and Watkins PB (2004) Two major grapefruit juice components differ in intestinal CYP3A4 inhibition kinetic and binding properties. Drug Metab Dispos 32:1146-1153.
24. Paine MF, Khalighi M, Fisher JM, Shen DD, Kunze KL, Marsh CL, Perkins JD, and Thummel KE (1997) Characterization of interintestinal and intraintestinal variations in human CYP3A-dependent metabolism. J Pharmacol Exp Ther 283:1552-1562.
25. Paine MF, Leung LY, Lim HK, Liao K, Oganesian A, Zhang MY, Thummel KE, and Watkins PB (2002) Identification of a novel route of extraction of sirolimus in human small intestine: roles of metabolism and secretion. J Pharmacol Exp Ther 301:174-186.
26. Pfrunder A, Gutmann H, Beglinger C, and Drewe J (2003) Gene expression of CYP3A4, ABC-transporters (MDR1 and MRP1-MRP5) and hPXR in three different human colon carcinoma cell lines. J Pharm Pharmacol 55:59-66.
27. Schmiedlin-Ren P, Edwards DJ, Fitzsimmons ME, He K, Lown KS, Woster PM, Rahman A, Thummel KE, Fisher JM, Hollenberg PF, et al. (1997a) Mechanisms of enhanced oral availability of CYP3A4 substrates by grapefruit constituents. Decreased enterocyte CYP3A4 concentration and mechanism-based inactivation by furanocoumarins. Drug Metab Dispos 25:1228-1233.
28. 3. Mol Pharmacol 51:741-754.
29. Schrag ML and Wienkers LC (2001) Covalent alteration of the CYP3A4 active site: evidence for multiple substrate binding domains. Arch Biochem Biophys 391:49-55.
30. Tassaneeyakul W, Guo LQ, Fukuda K, Ohta T, and Yamazoe Y (2000) Inhibition selectivity of grapefruit juice components on human cytochromes P450. Arch Biochem Biophys 378:356-363.
31. Thummel KE and Wilkinson GR (1998) In vitro and in vivo drug interactions involving human CYP3A. Annu Rev Pharmacol Toxicol 38:389-430.
32. Wen YH, Sahi J, Urda E, Kulkarni S, Rose K, Zheng X, Sinclair JF, Cai H, Strom SC, and Kostrubsky VE (2002) Effects of bergamottin on human and monkey drug-metabolizing enzymes in primary cultured hepatocytes. Drug Metab Dispos 30:977-984.