Advances in predicting of drug-drug interaction in vivo by using cytochrome P450 mechanism-based inhibition data in vitro

Abstract

Abstract: In the last decade, the approaches for the invitro inhibition assessment of the potentials of drug-drug interaction in vivo have received process. DDIs remain an important issue in clinical practice and the development of new drugs.Mechanism-based inactivation is gaining more attention among in vitro study. This review would describe methods in identifying mechanism-based inactivation, and introduce predictive models and parameters in the field.

Key words: drug-drug interaction, irreversible inhibition, mechanism-based inactivation, cytochrome P450, in vitro-in vivo extrapolation

CLC Number:

R968

CAO Shan, ZHOU Hong-hao. Advances in predicting of drug-drug interaction in vivo by using cytochrome P450 mechanism-based inhibition data in vitro[J]. Chinese Journal of Clinical Pharmacology and Therapeutics, 2008, 13(3): 241-248.

References

[1] Ripp SL, Mills JB, Fahmi OA, et al.Use of immortalized human hepatocytes to predict the magnitude of clinical drug-drug interactions caused by CYP3A4 induction[J]. Drug Metab Dispos, 2006,34(10):1742-1748.
[2] Bera AK, Polovnikova LS, Roestamadji J, et al.Mechanism-based inactivation of benzoylformate decarboxylase, a thiamin diphosphate-dependent enzyme[J].J Am Chem Soc, 2007, 129(14):4120-4121.
[3] Ito K, Brown HS, Houston JB.Database analyses for the prediction of in vivo drug-drug interactions from in vitro data[J].Br J Clin Pharmacol, 2004, 57(4):473-486.
[4] Ito K, Ogihara K, Kanamitsu S, et al.Prediction of the in vivo interaction between midazolam and macrolides based on in vitro studies using human liver microsomes[J].Drug Metab Dispos, 2003,31(7):945-954.
[5] Obach RS, Walsky RL, Venkatakrishnan K, et al.The utility of in vitro cytochrome P450 inhibition data in the prediction of drug-drug interactions[J].J Pharmacol Exp Ther, 2006,316(1):336-348.
[6] Massey V, Edmondson D.On the mechanism of inactivation of xanthine oxidase by cyanide[J].J Biol Chem, 1970, 245(24):6595-6598.
[7] Rando RR.Mechanism-based enzyme inactivators[J]. Pharmacol Rev, 1984,36(2):111-142.
[8] Kent UM, Juschyshyn MI, Hollenberg PF.Mechanismbased inactivators as probes of cytochrome P450 structure and function[J].Curr Drug Metab, 2001, 2(3):215-243.
[9] Bertelsen KM, Venkatakrishnan K, Von Moltke LL, et al.Apparent mechanism-based inhibition of human CYP2D6 in vitro by paroxetine:comparison with fluoxetine and quinidine[J].Drug Metab Dispos, 2003,31(3): 289-293.
[10] Harleton E, Webster M, Bumpus NN, et al.Metabolism of N, N', N”-triethylenethiophosphoramide by CYP2B1 and CYP2B6 results in the inactivation of both isoforms by two distinct mechanisms[J].J Pharmacol Exp Ther, 2004,310(3):1011-1019.
[11] Heydari A, Yeo KR, Lennard MS, et al.Mechanismbased inactivation of CYP2D6 by methylenedioxymethamphetamine[J].Drug Metab Dispos, 2004,32(11):1213-1217.
[12] Iwata H, Tezuka Y, Kadota S, et al.Mechanism-based inactivation of human liver microsomal CYP3A4 by rutaecarpine and limonin from Evodia fruit extract[J].Drug Metab Pharmacokinet, 2005, 20(1):34-45.
[13] Lin HL, Kent UM, Hollenberg PF.The grapefruit juice effect is not limited to cytochrome P450 (P450) 3A4:evidence for bergamottin-dependent inactivation, heme destruction, and covalent binding to protein in P450s 2B6 and 3A5[J].J Pharmacol Exp Ther, 2005,313(1):154-164.
[14] Lu P, Schrag ML, Slaughter DE, et al.Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor[J].Drug Metab Dispos, 2003,31(11):1352-1360.
[15] Luo G, Lin J, Fiske WD, et al.Concurrent induction and mechanism-based inactivation of CYP3A4 by an L-valinamide derivative[J].Drug Metab Dispos, 2003,31(9): 1170-1175.
[16] Margolis JM, Obach RS.Impact of nonspecific binding to microsomes and phospholipid on the inhibition of cytochrome P4502D6:implications for relating in vitro inhibition data to in vivo drug interactions[J].Drug Metab Dispos, 2003,31(5):606-611.
[17] O' Donnell JP, Dalvie DK, Kalgutkar AS, et al.Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen[J]. Drug Metab Dispos, 2003,31(11):1369-1377.
[18] Peng JZ, Remmel RP, Sawchuk RJ.Inhibition of murine cytochrome P4501A by tacrine:in vitro studies[J].Drug Metab Dispos, 2004,32(8):805-812.
[19] Polasek TM, Elliot DJ, Lewis BC, et al.Mechanismbased inactivation of human cytochrome P4502C8 by drugs in vitro[J].J Pharmacol Exp Ther, 2004,311(3):996-1007.
[20] Obach RS, Walsky RL, Venkatakrishnan K.Mechanismbased inactivation of human cytochrome p450 enzymes and the prediction of drug-drug interactions[J].Drug Metab Dispos, 2007,35(2):246-255.
[21] Debrunner PG, Dexter AF, Schulz CE, et al.Mossbauer and electron paramagnetic resonance studies of chloroperoxidase following mechanism-based inactivation with allylbenzene[ J].Proc Natl Acad Sci USA, 1996, 93(23): 12791-12798.
[22] Ernest CS 2nd, Hall SD, Jones DR.Mechanism-based inactivation of CYP3A by HIV protease inhibitors[J].J Pharmacol Exp Ther, 2005,312(2):583-591.
[23] Galetin A, Burt H, Gibbons L, et al.Prediction of timedependent CYP3A4 drug-drug interactions:impact of enzyme degradation, parallel elimination pathways, and intestinal inhibition[J].Drug Metab Dispos, 2006,34(1):166-175.
[24] Ito K, Hallifax D, Obach RS, et al.Impact of parallel pathways of drug elimination and multiple cytochrome P450 involvement on drug-drug interactions:CYP2D6 paradigm[J].Drug Metab Dispos, 2005,33(6):837-844.
[25] Khan KK, He YQ, Correia MA, et al.Differential oxidation of mifepristone by cytochromes P450 3A4 and 3A5: selective inactivation of P450 3A4[J].Drug Metab Dispos, 2002,30(9):985-990.
[26] Polasek TM, Elliot DJ, Somogyi AA, et al.An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid[J].Br J Clin Pharmacol, 2006, 61(5):570-584.
[27] Polasek TM, Miners JO.Time-dependent inhibition of human drug metabolizing cytochromes P450 by tricy clic antidepressants[ J].Br J Clin Pharmacol, 2008, 65(1):87-97.
[28] Richter T, Murdter TE, Heinkele G, et al.Potent mechanism-based inhibition of human CYP2B6 by clopidogrel and ticlopidine[J].J Pharmacol Exp Ther, 2004,308(1):189-197.
[29] Correia MA.Hepatic cytochrome P450 degradation: mechanistic diversity of the cellular sanitation brigade[J]. Drug Metab Rev, 2003,35(2 3):107-143.
[30] Kanamitsu SI, Ito K, Okuda H, et al.Prediction of in vivo drug-drug interactions based on mechanism-based inhibition from in vitro data:inhibition of 5-fluorouracil metabolism by (E)-5-(2-Bromovinyl) uracil[J].Drug Metab Dispos, 2000, 28(4):467-474.
[31] Yoo HH, LeeMW, Kim YC, et al.Mechanism-based inactivation of cytochrome P450 2A6 by decursinol angelate isolated from Angelica Gigas[J].Drug Metab Dispos, 2007,35(10):1759-1765.