Lack of correlation between in vitro and m vivo studies on the effects of tangeretin and tangerine juice on midazolam hydroxylation

Clinical Pharmacology and Therapeutics

Volumn 67, Issue 4, 2000, Pages 382-390

  Backman, Janne T ^a,b   Mäenpää, Jukka ^a,b   Belle, Donna J ^a,b   Wrighton, Steven A ^a,b   Kivistö, Kari T ^a,b   Neuvonen, Pertti J ^a,b  

^a UNIVERSITY OF HELSINKI   (Finland)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 3A4; FLAVONOID; MIDAZOLAM; MIDAZOLAM MALEATE; TANGERETIN;

ADULT; AREA UNDER THE CURVE; ARTICLE; CATALYSIS; CLINICAL TRIAL; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; CORRELATION FUNCTION; DRUG EFFECT; DRUG HYDROXYLATION; DRUG METABOLISM; FEMALE; FOOD DRUG INTERACTION; FRUIT JUICE; HUMAN; IN VITRO STUDY; IN VIVO STUDY; LIVER MICROSOME; MALE; NORMAL HUMAN; PRIORITY JOURNAL; RANDOMIZED CONTROLLED TRIAL;

EID: 0034098176     PISSN: 00099236     EISSN: None     Source Type: Journal    
DOI: 10.1067/mcp.2000.105756     Document Type: Article

References (41)

1. 1. Thummel KE, Wilkinson GR. In vitro and in vivo drug interactions involving human CYP3A. Annu Rev Pharmacol Toxicol 1998;38:389-430.
2. 2. Fabre G, Rahmani R, Placidi M, Combalbert J, Covo J, Cano JP, et al. Characterization of midazolam metabolism using human hepatic microsomal fractions and hepatocytes in suspension obtained by perfusing whole human livers. Biochem Pharmacol 1988;37:4389-97.
3. 3. Gorski JC, Hall SD, Jones DR, VandenBranden M, Wrighton SA. Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) sub-family. Biochem Pharmacol 1994;47:1643-53.
4. 14C-midazolam in humans following oral dosing. Arzneimittelforschung 1981;31:2220-3.
5. 5. Kronbach T, Mathys D, Umeno M, Gonzalez FJ, Meyer UA. Oxidation of midazolam and triazolam by human liver cytochrome P450IIIA4. Mol Pharmacol 1989;36:89-96.
6. 6. Thummel KE, O'Shea D, Paine MF, Shen DD, Kunze KL, Perkins JD, et al. Oral first-pass elimination of midazolam involves both gastrointestinal and hepatic CYP3A-mediated metabolism. Clin Pharmacol Ther 1996;59:491-502.
7. 7. Wandel C, Böcker R, Böhrer H, Browne A, Rügheimer E, Martin E. Midazolam is metabolized by at least three different cytochrome P450 enzymes. Br J Anaesth 1994; 73:658-61.
8. 3-modified Caco-2 cell monolayers. J Pharmacol Exp Ther 1999;289:1134-42.
9. 9. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, et al. Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res 1999;16:408-14.
10. 10. Takano M, Hasegawa R, Fukuda T, Yumoto R, Nagai J, Murakami T. Interaction with P-glycoprotein and transport of erythromycin, midazolam and ketoconazole in Caco-2 cells. Eur J Pharmacol 1998;358:289-94.
11. 11. Thummel KE, Shen DD, Podoll TD, Kunze KL, Trager WF, Bacchi CE, et al. Use of midazolam as a human cytochrome P450 3A probe; II: characterization of inter-and intraindividual hepatic CYP3A variability after liver transplantation. J Pharmacol Exp Ther 1994;271:557-66.
12. 12. Thummel KE, Shen DD, Podoll TD, Kunze KL, Trager WF, Hartwell PS, et al. Use of midazolam as a human cytochrome P450 3A probe; I: in vitro-in vivo correlations in liver transplant patients. J Pharmacol Exp Ther 1994;271:549-56.
13. 13. Watkins PB. Noninvasive tests of CYP3A enzymes. Pharmacogenetics 1994;4:171-84.
14. 14. Gorski JC, Jones DR, Haehner-Daniels BD, Hamman MA, O'Mara EM Jr, Hall SD. The contribution of intestinal and hepatic CYP3A to the interaction between midazolam and clarithromycin. Clin Pharmacol Ther 1998; 64:133-43.
15. 15. Paine MF, Shen DD, Kunze KL, Perkins JD, Marsh CL, McVicar JP, et al. First-pass metabolism of midazolam by the human intestine. Clin Pharmacol Ther 1996;60:14-24.
16. 16. Backman JT, Olkkola KT, Ojala M, Laaksovirta H, Neuvonen PJ. Concentrations and effects of oral midazolam are greatly reduced in patients treated with carbamazepine or phenytoin. Epilepsia 1996;37:253-7.
17. 17. Backman JT, Kivistö KT, Olkkola KT, Neuvonen PJ. The area under the plasma concentration-time curve for oral midazolam is 400-fold larger during treatment with itraconazole than with rifampicin. Eur J Clin Pharmacol 1998;54:53-8.
18. 18. Olkkola KT, Aranko K, Luurila H, Hiller A, Saarnivaara L, Himberg JJ, et al. A potentially hazardous interaction between erythromycin and midazolam. Clin Pharmacol Ther 1993;53:298-305.
19. 19. Guengerich FP, Shimada T, Yun CH, Yamazaki H, Raney KD, Thier R, et al. Interactions of ingested food, beverage, and tobacco components involving human cytochrome P4501A2, 2A6, 2E1, and 3A4 enzymes. Environ Health Perspect 1994;102(suppl 9):49-53.
20. 20. Yang CS, Brady JF, Hong JY. Dietary effects on cytochromes P450, xenobiotic metabolism, and toxicity. FASEB J 1992;6:737-44.
21. 21. Johnson EF, Schwab GE, Vickery LE. Positive effectors of the binding of an active site-directed amino steroid to rabbit cytochrome P-450 3c. J Biol Chem 1988;263: 17672-7.
22. 22. Kerr BM, Thummel KE, Wurden CJ, Klein SM, Kroetz DL, Gonzalez FJ, et al. Human liver carbamazepine metabolism. Role of CYP3A4 and CYP2C8 in 10,11-epoxide formation. Biochem Pharmacol 1994;47:1969-79.
23. 23. Mäenpää J, Hall SD, Ring BJ, Strom SC, Wrighton SA. Human cytochrome P450 3A (CYP3A) mediated midazolam metabolism: the effect of assay conditions and regio-selective stimulation by alpha-naphthoflavone, terfenadine and testosterone. Pharmacogenetics 1998;8:137-55.
24. 24. Shou M, Grogan J, Mancewicz JA, Krausz KW, Gonzalez FJ, Gelboin HV, et al. Activation of CYP3A4: evidence for the simultaneous binding of two substrates in a cytochrome P450 active site. Biochemistry 1994;33: 6450-5.
25. 25. Siess MH, Leclerc J, Canivenc-Lavier MC, Rat P, Suschetet M. Heterogenous effects of natural flavonoids on monooxygenase activities in human and rat liver microsomes. Toxicol Appl Pharmacol 1995;130:73-8.
26. 26. Ghosal A, Satoh H, Thomas PE, Bush E, Moore D. Inhibition and kinetics of cytochrome P4503A activity in microsomes from rat, human, and cDNA-expressed human cytochrome P450. Drug Metab Dispos 1996;24: 940-7.
27. 27. Lasker JM, Huang MT, Conney AH. In vivo activation of zoxazolamine metabolism by flavone. Science 1982;216: 1419-21.
28. 28. Lasker JM, Huang MT, Conney AH. In vitro and in vivo activation of oxidative drug metabolism by flavonoids. J Pharmacol Exp Ther 1984;229:162-70.
29. 29. Veldhuis MK, Swift LJ, Scott WC. Fully methoxylated flavones in Florida orange juices. J Agric Food Chem 1970;18:590-2.
30. 30. Gaydou EM, Bianchini JP, Randriamiharisoa RP. Orange and mandarin peel oils differentiation using polymethoxylated flavone composition. J Agric Food Chem 1987;35:525-9.
31. 31. Buening MK, Chang RL, Huang MT, Fortner JG, Wood AW, Conney AH. Activation and inhibition of benzo(a)-pyrene and aflatoxin B1 metabolism in human liver microsomes by naturally occurring flavonoids. Cancer Res 1981;41:67-72.
32. 32. Li Y, Wang E, Patten CJ, Chen L, Yang CS. Effects of flavonoids on cytochrome P450-dependent acetaminophen metabolism in rats and human liver microsomes. Drug Metab Dispos 1994;22:566-71.
33. 33. van der Hoeven TA, Coon MJ. Preparation and properties of partially purified cytochrome P-450 and reduced nicotinamide adenine dinucleotide phosphate-cytochrome P-450 reductase from rabbit liver microsomes. J Biol Chem 1974;249:6302-10.
34. 34. Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. Protein measurement with the Polin phenol reagent. J Biol Chem 1951;193:265-75.
35. 35. Wrighton SA, Ring BJ. Inhibition of human CYP3A catalyzed 1′-hydroxy midazolam formation by ketoconazole, nifedipine, erythromycin, cimetidine, and nizatidine. Pharm Res 1994;11:921-4.
36. 36. Ha HR, Rentsch KM, Kneer J, Vonderschmitt DJ. Determination of midazolam and its alpha-hydroxy metabolite in human plasma and urine by high-performance liquid chromatography. Ther Drug Monit 1993;15:338-43.
37. 37. Stone BM. Pencil and paper test: sensitivity to psychotropic drugs. Br J Clin Pharmacol 1984;18(suppl 1):15S-20S.
38. 38. Pelkonen O, Mäenpää J, Taavitsainen P, Rautio A, Raunio H. Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica 1998;28:1203-53.
39. 39. Obermeier MT, White RE, Yang CS. Effects of bioflavonoids on hepatic P450 activities. Xenobiotica 1995;25:575-84.
40. 40. Guengerich FP. Human cytochrome P450 enzymes. In: Ortiz de Montellano PR, editor. Cytochrome P450: structure, mechanism, and biochemistry. New York: Plenum Press; 1995. p. 473-536.
41. 41. Koley AP, Buters JTM, Robinson RC, Markowitz A, Friedman FK. Differential mechanisms of cytochrome P450 inhibition and activation by alpha-naphthoflavone. J Biol Chem 1997;272:3149-52.