Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro

Journal of Pharmacology and Experimental Therapeutics

Volumn 311, Issue 3, 2004, Pages 996-1007

  Polasek, Thomas M ^a   Elliot, David J ^a   Lewis, Benjamin C ^a   Miners, John O ^a  

^a FLINDERS UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AMIODARONE; AZITHROMYCIN; CLARITHROMYCIN; CYTOCHROME P450 2C8; CYTOCHROME P450 3A4; DESIPRAMINE; DILTIAZEM; ERYTHROMYCIN; FELODIPINE; FLUOXETINE; GLUTATHIONE; INDINAVIR; ISONIAZID; KETOCONAZOLE; MACROLIDE; MIBEFRADIL; MONOAMINE OXIDASE INHIBITOR; NICARDIPINE; NORCLOMIPRAMINE; NORTRIPTYLINE; PACLITAXEL; PHENELZINE; ROXITHROMYCIN; SELEGILINE; SUPEROXIDE DISMUTASE; TAMOXIFEN; TRANYLCYPROMINE; TRICYCLIC ANTIDEPRESSANT AGENT; TROLEANDOMYCIN; VERAPAMIL;

ARTICLE; COMPLEX FORMATION; DRUG CLEARANCE; DRUG EFFECT; DRUG INACTIVATION; DRUG INHIBITION; DRUG MECHANISM; HUMAN; HUMAN TISSUE; HYDROXYLATION; IN VITRO STUDY; LIVER MICROSOME; METABOLIC CLEARANCE RATE; PRIORITY JOURNAL; STOICHIOMETRY; ULTRAFILTRATION;

ALGORITHMS; ANTIDEPRESSIVE AGENTS, TRICYCLIC; ANTINEOPLASTIC AGENTS, PHYTOGENIC; ARYL HYDROCARBON HYDROXYLASES; CARBON MONOXIDE; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; GENE EXPRESSION REGULATION; HUMANS; HYDROXYLATION; MICROSOMES, LIVER; MONOAMINE OXIDASE INHIBITORS; PACLITAXEL; PLASMIDS; RECEPTORS, G-PROTEIN-COUPLED; RECEPTORS, NEUROPEPTIDE; RECOMBINANT PROTEINS; SPECTROPHOTOMETRY, ULTRAVIOLET; SULFONAMIDES; TESTOSTERONE; ULTRAFILTRATION;

EID: 10044257558     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.104.071803     Document Type: Article

References (40)

1. Bensoussan C, Delaforge M, and Mansuy D (1995) Particular ability of cytochromes P450 3A to form inhibitory P450-iron-metabolite complexes upon metabolic oxidation of amino drugs. Biochem Pharmacol 49:591-602.
2. Bertelsen KM, Venkatrishnan K, von Moltke LL, Obach RS, and Greenblatt DJ (2003) Apparent mechanism-based inhibition of human CYP2D6 in vitro by paroxetine: comparison with fluoxetine and quinidine. Drug Metab Dispos 31:289-293.
3. Bidstrup TB, Bjornsdottir I, Sidelmann UG, Thomsen MS, and Hansen KT (2003) CYP2C8 and CYP3A4 are the principal enzymes involved in the human in vitro biotransformation of the insulin secretagogue repaglinide. Br J Clin Pharmacol 56:305-314.
4. Boye SL, Kerdpin O, Elliot DJ, Miners JO, Kelly L, McKinnon RA, Bhasker CR, Yoovathaworn K, and Birkett DJ (2004) Optimizing bacterial expression of catalytically active human cytochromes P450: comparison of CYP2C8 and CYP2C9. Xenobiotica 34:49-60.
5. Cresteil T, Monsarrat B, Dubois J, Sonnier M, Alvinerie P, and Gueritte F (2002) Regioselective metabolism of taxoids by human CYP3A4 and 2C8: structure-activity relationship. Drug Metab Dispos 30:438-445.
6. Desta Z, Wu GM, Morocho AM, and Flockhart DA (2002) The gastroprokinetic and antiemetic drug metoclopramide is a substrate and inhibitor of cytochrome P450 2D6. Drug Metab Dispos 30:336-343.
7. Foti RS and Fisher MB (2003) Characterisation of cytochrome P450 3A4 and 3A5 levels in a human liver microsome bank using midazolam and paclitaxel metabolic activity and immunoquantitation (Abstract). Drug Metab Rev 35:34.
8. Ha-Duong NT, Dijols S, Macherey AC, Goldstein JA, Dansette PM, and Mansuy D (2001) Ticlopidine as a selective mechanism-based inhibitor of human cytochrome P450 2C19. Biochemistry 40:12112-12122.
9. Harris JW, Rahman A, Kim BR, Guengerich FP, and Collins JM (1994) Metabolism of taxol by human hepatic microsomes and liver slices: participation of cytochrome P450 3A4 and an unknown P450 enzyme. Cancer Res 54:4026-4035.
10. Ito K, Ogihara K, Kanamitsu S, and Itoh T (2003) Prediction of the in vivo interaction between midazolam and macrolides based on in vitro studies using human liver microsomes. Drug Metab Dispos 31:945-954.
11. Kerdpin O, Elliot DJ, Boye SL, Birkett DJ, Yoovathaworn K, and Miners JO (2004) Differential contribution of active site residues in substrate recognition sites 1 and 5 to cytochrome P450 2C8 substrate- and regio-selectivity. Biochemistry 43:7834-7842.
12. Koudriakova T, Iatsimirskaia E, Utkin I, Gangl E, Vouros P, Storozhuk E, Orza D, Marinina J, and Gerber N (1998) Metabolism of the human immunodeficiency virus protease inhibitors indinavir and ritonavir by human intestinal microsomes and expressed cytochrome P4503A4/3A5: mechanism-based inactivation of cytochrome P4503A by ritonavir. Drug Metab Dispos 26:552-561.
13. Larrey D, Tinel M, Letteron P, Geneve J, Descatoire V, and Pessayre D (1986) Formation of an inactive cytochrome P-450Fe(II)-metabolite complex after administration of amiodarone in rats, mice and hamsters. Biochem Pharmacol 35:2213-2220.
14. Lin HL, Kent UM, and Hollenberg PF (2002) Mechanism-based inactivation of cytochrome P450 3A4 by 17 alpha-ethynylestradiol: evidence for heme destruction and covalent binding to protein. J Pharmacol Exp Ther 301:160-167.
15. Lin JH and Lu AY (1998) Inhibition and induction of cytochrome P450 and the clinical implications. Clin Pharmacokinet 35:361-390.
16. Lowry OH, Rosenbrough NJ, Farr L, and Randall RJ (1951) Protein measurement with the folin phenol reagent. J Biol Chem 193:265-267.
17. Lu P, Schrag ML, Slaughter DE, Raab CE, Shou M, and Rodrigues AD (2003) Mechanism-based inhibition of human liver microsomal cytochrome P4501A2 by zileuton, a 5-lipoxygenase inhibitor. Drug Metab Dispos 31:1352-1360.
18. Ma B, Prueksaritanont T, and Lin JH (2000) Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos 28:125-130.
19. Mayhew BS, Jones DR, and Hall SD (2000) An in vitro model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation. Drug Metab Dispos 28:1031-1037.
20. Muakkassah SF, Bidlack WR, and Yang WC (1981) Mechanism of the inhibitory action of isoniazid on microsomal drug metabolism. Biochem Pharmacol 30:1651-1658.
21. Muakkassah SF and Yang WC (1981) Mechanism of the inhibitory action of phenelzine on microsomal drug metabolism. J Pharmacol Exp Ther 219:147-155.
22. O'Donnell JP, Dalvie DK, Kalgutkar AS, and Obach RS (2003) Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen. Drug Metab Dispos 31:1369-1377.
23. Ohyama K, Nakajima M, Nakamura S, Shimada N, Yamazaki H, and Yokoi T (2000a) A significant role of human cytochrome P450 2C8 in amiodarone N-deethylation: an approach to predict the contribution with relative activity factor. Drug Metab Dispos 28:1303-1310.
24. Ohyama K, Nakajima M, Suzuki M, Shimada N, Yamazaki H, and Yokoi T (2000b) Inhibitory effects of amiodarone and its N-deethylated metabolite on human cytochrome P450 activities: prediction of in vivo drug interactions. Br J Clin Pharmacol 49:244-253.
25. Omura T and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. J Biol Chem 239:2379-2385.
26. Ong CE, Coulter S, Birkett DJ, Bhasker CR, and Miners JO (2000) The xenobiotic inhibitor profile of cytochrome P4502C8. Br J Clin Pharmacol 50:573-580.
27. Palamanda JR, Casciano CN, Norton LA, Clement RP, Favreau LV, Lin C, and Nomeir AA (2001) Mechanism-based inactivation of CYP2D6 by 5-fluoro-2-[4- [(2phenyl-1H-imidazol-5-yl)methyl]-1-piperazinyl]pyrimidine. Drug Metab Dispos 29:863-867.
28. Projean D, Baune B, Farinotti R, Flinois JP, Beaune P, Taburet AM, and Ducharme J (2003) In vitro metabolism of chloroquine: identification of CYP2C8, CYP3A4 and CYP2D6 as the main isoforms catalyzing N-desethylchloroquine formation. Drug Metab Dispos 31:748-754.
29. Racha JK, Rettie AE, and Kunze KL (1998) Mechanism-based inactivation of human cytochrome P450 1A2 by furafylline: detection of a 1:1 adduct to protein and evidence for the formation of a novel imidazomethide intermediate. Biochemistry 37:7407-7419.
30. Richardson TH, Jung F, Griffin KJ, Wester M, Raucy JL, Kemper B, Bornheim LM, Hassett C, Omiecinski CJ, and Johnson EF (1995) Universal approach to the expression of human and rabbit cytochrome P450s of the 2c subfamily in Escherichia coli. Arch Biochem Biophys 323:87-96.
31. Richter T, Murdter TE, Heinkele G, Pleiss J, Tatzel S, Schwab M, Eichelbaum M, and Zanger UM (2004) Potent mechanism-based inhibition of human CYP2B6 by clopidogrel and ticlopidine. J Pharmacol Exp Ther 308:189-197.
32. Silverman RB (1988) Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology, CRC Press LLC, Boca Raton, FL.
33. Taavitsainen P, Anttila M, Nyman L, Karnani H, Salonen JS, and Pelkonen O (2000) Selegiline metabolism and cytochrome P450 enzymes: in vitro study in human liver microsomes. Pharmacol Toxicol 86:215-221.
34. Taavitsainen P, Juvonen R, and Pelkonen O (2001) In vitro inhibition of cytochrome P450 enzymes in human liver microsomes by a potent CYP2A6 inhibitor, trans-2-phenylcyclopropylamine (tranylcypromine) and its nonamine analog, cyclopropylbenzene. Drug Metab Dispos 29:217-222.
35. Tinel M, Belghiti J, Descatoire V, Amouyal G, Letteron P, Geneve J, Larrey D, and Pessayre D (1987) Inactivation of human liver cytochrome P-450 by the drug methoxsalen and other psoralen derivatives. Biochem Pharmacol 36:951-955.
36. Wang JS and DeVane CL (2003) Involvement of CYP3A4, CYP2C8 and CYP2D6 in the metabolism of (R)- and (S)-methadone in vitro. Drug Metab Dispos 31:742-747.
37. Wang Y, Jones DR, and Hall SD (2004) Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos 32:259-266.
38. Wen X, Wang JS, Neuvonen PJ, and Backman JT (2002) Isoniazid is a mechanism-based inhibitor of cytochrome P450 1A2, 2A6, 2C19 and 3A4 isoforms in human liver microsomes. Eur J Clin Pharmacol 57:799-804.
39. Yasukochi Y and Masters BS (1976) Some properties of a detergent-solubilized NADPH-cytochrome c(cytochrome P-450) reductase purified by biospecific affinity chromatography. J Biol Chem 251:5337-5344.
40. Zhao XJ, Jones DR, Wang YH, Grimm SW, and Hall SD (2002) Reversible and irreversible inhibition of CYP3A enzymes by tamoxifen and metabolites. Xenobiotica 32:863-878.