Relationship between hepatic cytochrome P450 3A content and activity and the disposition of midazolam administered orally

Drug Metabolism and Disposition

Volumn 26, Issue 2, 1998, Pages 110-114

  Wandel, C ^a   Bocker R H ^b   Bohrer H ^b   Devries, J X ^b   Hofmann, W ^b   Walter, K ^b   Kleingeist, B ^b   Neff, S ^b   Ding, R ^b   Walter Sack, I ^b   Martin, E ^b  

^a VANDERBILT UNIVERSITY   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA HYDROXYMIDAZOLAM; CYTOCHROME P450; INTESTINE ENZYME; MIDAZOLAM; MIDAZOLAM MALEATE;

ARTICLE; DRUG ACTIVITY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DISPOSITION; FEMALE; FIRST PASS EFFECT; HUMAN; HUMAN EXPERIMENT; HUMAN TISSUE; IMMUNOBLOTTING; INTRAVENOUS DRUG ADMINISTRATION; LIVER CLEARANCE; LIVER LEVEL; LIVER MICROSOME; MALE; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL;

ADULT; AGED; ARYL HYDROCARBON HYDROXYLASES; CYTOCHROME P-450 CYP3A; CYTOCHROME P-450 ENZYME SYSTEM; EUROPEAN CONTINENTAL ANCESTRY GROUP; FEMALE; HUMANS; HYDROXYLATION; KINETICS; LIVER NEOPLASMS; MALE; METABOLIC DETOXICATION, DRUG; MICROSOMES, LIVER; MIDAZOLAM; MIDDLE AGED; OXIDOREDUCTASES, N-DEMETHYLATING;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0344222189     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (41)

1. Backman JT, Olkkola KT, Aranko K, Himberg JJ and Neuvonen PJ (1994) Dose of midazolam should be reduced during diltiazem and verapamil treatments. Br J Clin Pharmacol 37:221-225.
2. Backman JT, Olkkola KT and Neuvonen PJ (1996) Rifampin drastically reduces plasma concentrations and effects of oral midazolam. Clin Pharmacol Ther 59:7-13.
3. Baker MT, Chadam MV and Ronnenberg WC Jr (1993) Inhibitory effects of propofol on cytochrome P450 activities in rat hepatic microsomes. Anesth Analg 76:817-821.
4. Baker MT, Olson MJ, Wang Y, Ronnenberg WC Jr, Johnson JT and Brady AN (1995) Isoflurane-chlorodifluoroethene interaction in human liver microsomes: role of cytochrome P450 2B6 in potentiation of haloethene metabolism. Drug Metab Dispos 23:60-64.
5. Baker MT and Ronnenberg WC Jr (1992) Acute stimulation of trifluoroethene defluorination and cytochrome P450 inactivation in the rat by exposure to isoflurane. Toxicol Appl Pharmacol 114:25-30.
6. Böcker R and Guengerich FP (1986) Oxidation of 4-aryl- and 4-alkyl-substituted 2,6-dimethyl-3,5-bis(alkoxycarbonyl)-1,4-dihydropyridines by human liver microsomes and immunochemical evidence for the involvement of a form of cytochrome P-450. J Med Chem 29:1596-1603.
7. Burke MD, Thompson S, Weaver RJ, Wolf CR and Mayer RT (1994) Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochem Pharmacol 48:923-936.
8. Chen TL, Ueng TH, Chen SH, Lee PH, Fan SZ and Liu CC (1995a) Human cytochrome P450 mono-oxygenase system is suppressed by propofol. Br J Anaesth 74:558-562.
9. Chen TL, Wang MJ, Huang CH, Liu CC and Ueng TH (1995b) Difference between in vivo and in vitro effects of propofol on defluorination and metabolic activities of hamster hepatic cytochrome P450-dependent mono-oxygenases. Br J Anaesth 75:462-466.
10. Combalbert J, Fabre I and Fahre G (1988) Metabolism of cyclosporine A: purification and identification of the rifampicin-inducible human liver cytochrome P-450 (cyclosporine A oxidase) as a product of the P450IIIA gene subfamily. Drug Metab Dispos 17:197-207.
11. Fabre G, Rahmani R, Placidi M, Combalbert J, Covo J, Cano JP, Coulange C, Ducros M and Rampal M (1988) Characterization of midazolam metabolism using human hepatic microsomal fractions and hepatocytes in suspension obtained by perfusing whole human livers. Biochem Pharmacol 37:4389-4397.
12. Fee JPH, Collier PS, Howard PJ and Dundee JW (1987) Cimetidine and ranitidine increase midazolam bioavailability. Clin Pharmacol Ther 41:80-84.
13. Feierman DE (1996) Identification of cytochrome P450 3A1/2 as the major P450 isoform responsible for the metabolism of fentanyl by rat liver microsomes. Anesth Analg 82:936-941.
14. Ghosal A, Satoh H, Thomas PE, Bush E and Moore D (1996) Inhibition and kinetics of cytochrome P4503A activity in microsomes from rat human, and cDNA-expressed human cytochrome P450. Drug Metab Dispos 24:940-947.
15. Gorski JC, Hall SD, Jones DR, VandenBranden M and Wrighton S (1994) Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) subfamily. Biochem Pharmacol 47:1643-1653.
16. Guengerich FP and Böcker RH (1988) Cytochrome P-450-catalyzed dehydrogenation of 1,4-dihydropyridines. J Biol Chem 263:8168-8175.
17. Guengerich FP and Turvey CG (1991) Comparisons of levels of several human microsomal cytochrome P-450 enzymes and epoxide hydrolase in normal and disease states using immunochemical analysis of surgical liver samples. J Pharmacol Exp Ther 256:1189-1194.
18. Hiller A, Olkkola KT, Isohanni P and Saarnivaara L (1990) Unconsciousness associated with midazolam and erythromycin. Br J Anaesth 65:826-828.
19. Kharasch ED and Thummel KE (1993) Identification of cytochrome P450 2E1 as the predominant enzyme catalyzing human liver microsomal defluorination of sevoflurane, isoflurane, and methoxyflurane Anesthesiology 79:795-807.
20. Kolars JC, Schmiedlin-Ren P, Schuetz JD, Fang C and Watkins PB (1992) Identification of rifampin-inducible P450IIIA4 (CYP3A4) in human small bowel enterocytes. J Clin Invest 90:1871-1878.
21. Koopmans R, Dingemanse J, Danhof M, Horsten GPM and van Boxtel CJ (1988) Pharmacokinetic-pharmacodynamic modeling of midazolam effects on the human central nervous system. Clin Pharmacol Ther 44:14-22.
22. Krainev A, Shimizu T, Hiroya K and Hatamo M (1992) Effect of mutations as Lys250, Arg251, and Lys253 of cytochrome P450 1A2 on the catalytic activities and the bindings of bifunctional axial ligands. Arch Biochem Biophys 298:198-203.
23. Kronbach T, Fischer V and Meyer UA (1988) Cyclosporine metabolism in human liver: identification of a cytochrome P-450III gene family as the major cyclosporine-metabolizing enzyme explains interactions of cyclosporine with other drugs. Clin Pharmacol Ther 43:630-635.
24. Kronbach T, Mathys D, Umeno M, Gonzalez FJ and Meyer UA (1989) Oxidation of midazolam and triazolam by human liver cytochrome P450IIIA4. Mol Pharmacol 36:89-96.
25. Kupferschmidt HHT, Ha HR, Ziegler WH, Meier PJ and Kraehenbuehl S (1995) Interaction between grapefruit juice and midazolam in humans. Clin Pharmacol Ther 58:20-28.
26. Loch JM, Potter J and Bachmann KA (1995) The influence of anesthetic agents on rat hepatic cytochromes P450 in vivo. Pharmacology 50:146-153.
27. Lowry OH, Rosebrough NJ, Farr AL and Randall RJ (1951) Protein measurement with the Polin phenol reagent. J Biol Chem 193:265-275.
28. McKinnon RA, Burgess WM, de la Hall P, Roberts-Thomson SJ, Gonzalez FJ and McManus ME (1995) Characterization of CYP 3A gene subfamily expression in human gastrointestinal tissues. Gut 36:259-267.
29. Olkkola KT, Ahonen J and Neuvonen PJ (1996) The effect of the systemic antimycotics, itraconazole and fluconazole, on the pharmacokinetics and pharmacodynamics of intravenous and oral midazolam. Anesth Analg 82:511-516.
30. Olkkola KT, Backman JT and Neuvonen PJ (1994) Midazolam should be avoided in patients receiving the systemic antimycotics ketoconazole or itraconazole. Clin Pharmacol Ther 55:481-485.
31. Omura T and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. J Biol Chem 239:2370-2378.
32. Paine MF, Shen DD, Kunze KL, Perkins JD, Marsh CL, McVicar JP, Barr DM, Gillies BS and Thummel KE (1996) First-pass metabolism of midazolam by the human intestine. Clin Pharmacol Ther 60:14-24.
33. Persson MP, Nilsson A and Hartvig P (1988) Relation of sedation and amnesia to plasma concentrations of midazolam in surgical patients. Clin Pharmacol Ther 43:324-331.
34. Sadeque AJM, Fisher MB, Korzekwa KR, Gonzalez FJ and Renie AE (1997) Human CYP2C9 and CYP2A6 mediate formation of the hepatotoxin 4-ene valproic acid. J Pharmacol Exp Ther, 283:698-703.
35. Schuetz EG, Wrighton SA, Barwick JL and Guzelian PS (1984) Induction of cytochrome P-450 by glucocorticoids in rat liver. I. Evidence that glucocorticoids and pregnenolone 16α-carbonitrile regulate de novo synthesis of a common form of cytochrome P-450 in cultures of adult rat hepatocytes and in the liver in vivo. J Biol Chem 259:1999-2006.
36. Tateishi T, Krivoruk Y, Ueng YF, Wood AJJ, Guengerich FP and Wood M (1996) Identification of human liver cytochrome P-450 3A4 as the enzyme responsible for fentanyl and sufentanil N-dealkylation. Anesth Analg 82:167-172.
37. Thummel KE, O'Shea D, Paine MF, Shen DD, Kunze KL, Perkins JD and Wilkinson GR (1996) Oral first-pass elimination of midazolam involves both gastrointestinal and hepatic CYP3A-mediated metabolism. Clin Pharmacol Ther 59:491-502.
38. Thummel KE, Shen DD, Podoll TD, Kunze KL, Trager WF, Hartwell PS, Raisys VA, Marsh CL, McVicar JP, Barr DM, Perkins JD and Carithers RL Jr (1994) Use of midazolam as a human cytochrome P450 3A probe. I. In vitro-in vivo correlations in liver transplant patients. J Pharmacol Exp Ther 271:549-556.
39. van der Hoeven TA, Haugen DA and Coon MJ (1974) Cytochrome P-450 purified to apparent homogeneity from phenobarbital-induced rabbit liver microsomes: catalytic activity and other properties. Biochem Biophys Res Commun 60:569-575.
40. Wandel C, Böcker R, Böhrer H, Browne A, Rühgheimer E and Martin E (1993) Midazolam is metabolized by at least three different cytochrome P450 enzymes. Br J Anaesth 73:658-661.
41. Watkins PB, Wrighton SA, Maurel P, Schuetz EG, Mendez-Picon G, Parker GA and Guzelian PS (1985) Identification of an inducible form of cytochrome P-450 in human liver. Proc Natl Acad Sci USA 82:6310-6314.