Drug interaction potential of toremifene and N-desmethyltoremifene with multiple cytochrome P450 isoforms

Xenobiotica

Volumn 41, Issue 10, 2011, Pages 851-862

  Kim, Juhyun ^a   Peraire, Concepcion ^b   Solà, Josep ^b   Johanning, Karla M ^c   Dalton, James T ^a   Veverka, Karen A ^a  

^a GTx Inc   (United States)

^b IPSEN   (France)

^c Life Technologies   (United States)

Author keywords

drug drug interaction; enzyme induction; enzyme inhibition; hepatocytes; liver microsomes; Metabolism; pharmacokinetics

Indexed keywords

3 METHYLCHOLANTHRENE; AMFEBUTAMONE; CHLORZOXAZONE; COUMARIN; CYTOCHROME P450; CYTOCHROME P450 1A2; CYTOCHROME P450 2A6; CYTOCHROME P450 2B6; CYTOCHROME P450 2C19; CYTOCHROME P450 2C8; CYTOCHROME P450 2C9; CYTOCHROME P450 2D6; CYTOCHROME P450 2E1; CYTOCHROME P450 3A4; DEXTROMETHORPHAN; DICLOFENAC; DRUG METABOLITE; MEPHENYTOIN; MIDAZOLAM; N DESMETHYLTOREMIFENE; PACLITAXEL; PHENACETIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; RIFAMPICIN; TESTOSTERONE; TOREMIFENE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ADULT; ARTICLE; COMPETITIVE INHIBITION; DRUG CYTOTOXICITY; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME INDUCTION; ENZYME INHIBITION; FEMALE; GENE EXPRESSION; HUMAN; HUMAN CELL; HUMAN TISSUE; INHIBITION KINETICS; LIVER CELL; LIVER MICROSOME; MALE;

CELLS, CULTURED; CYTOCHROME P-450 ENZYME SYSTEM; DRUG INTERACTIONS; HEPATOCYTES; HUMANS; MICROSOMES, LIVER; TAMOXIFEN; TOREMIFENE;

EID: 80052878600     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.3109/00498254.2011.590546     Document Type: Article

References (41)

1. Anttila M, Valavaara R, Kivinen S, Mäenpää J. (1990).Pharmacokinetics of toremifene. J Steroid Biochem 36:249-252. (Pubitemid 20222782)
2. Berthou F, Dreano Y, Belloc C, Kangas L, Gautier JC, Beaune P. (1994).Involvement of cytochrome P450 3A enzyme family in the major metabolic pathways of toremifene in human liver microsomes. Biochem Pharmacol 47:1883-1895. (Pubitemid 24172859)
3. Bjornsson TD, Callaghan JT, Einolf HJ, Fischer V, Gan L, Grimm S, Kao J, King SP, Miwa G, Ni L, Kumar G, McLeod J, Obach RS, Roberts S, Roe A, Shah A, Snikeris F, Sullivan JT, Tweedie D, Vega JM, Walsh J, Wrighton SA; Pharmaceutical Research and Manufacturers of America (PhRMA) Drug Metabolism/Clinical Pharmacology Technical Working Group; FDA Center for Drug Evaluation and Research (CDER).(2003).The conduct of in vitro and in vivo drug-drug interaction studies: a Pharmaceutical Research and Manufacturers of America (PhRMA) perspective. Drug Metab Dispos 31:815-832. (Pubitemid 36759050)
4. Coller JK, Krebsfaenger N, Klein K, Endrizzi K, Wolbold R, Lang T, Nüssler A, Neuhaus P, Zanger UM, Eichelbaum M, Mürdter TE. (2002).The influence of CYP2B6, CYP2C9 and CYP2D6 genotypes on the formation of the potent antioestrogen Z-4-hydroxytamoxifen in human liver. Br J Clin Pharmacol 54:157-167. (Pubitemid 35024939)
5. Crewe HK, Ellis SW, Lennard MS, Tucker GT. (1997).Variable contribution of cytochromes P450 2D6, 2C9 and 3A4 to the 4-hydroxylation of tamoxifen by human liver microsomes. Biochem Pharmacol 53:171-178. (Pubitemid 27013472)
6. Dehal SS, Kupfer D. (1997).CYP2D6 catalès tamoxifen 4-hydroxylation in human liver. Cancer Res 57:3402-3406. (Pubitemid 27355484)
7. Desai PB, Nallani SC, Sane RS, Moore LB, Goodwin BJ, Buckley DJ, Buckley AR. (2002).Induction of cytochrome P450 3A4 in primary human hepatocytes and activation of the human pregnane X receptor by tamoxifen and 4-hydroxytamoxifen. Drug Metab Dispos 30:608-612. (Pubitemid 34456986)
8. Desta Z, Ward BA, Soukhova NV, Flockhart DA. (2004).Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther 310:1062-1075. (Pubitemid 39108928)
9. FDA. (2006). Drug interaction studies-study design, data analysis, and implications for dosing and labeling. Department of Health and Human Services Food and Drug Administration; Center for Drug Evaluation and Research (CDER) (Ed.) (pp. 35).
10. Freedland SJ, Eastham J, Shore N. (2009).Androgen deprivation therapy and estrogen deficiency induced adverse effects in the treatment of prostate cancer. Prostate Cancer Prostatic Dis 12:333-338.
11. Guengerich FP. (1999).Cytochrome P-450 3A4: regulation and role in drug metabolism. Annu Rev Pharmacol Toxicol 39:1-17. (Pubitemid 29222549)
12. Hariparsad N, Nallani SC, Sane RS, Buckley DJ, Buckley AR, Desai PB. (2004).Induction of CYP3A4 by efavirenz in primary human hepatocytes: comparison with rifampin and phenobarbital. J Clin Pharmacol 44:1273-1281. (Pubitemid 39391486)
13. Kivistö KT, Villikka K, Nyman L, Anttila M, Neuvonen PJ. (1998).Tamoxifen and toremifene concentrations in plasma are greatly decreased by rifampin. Clin Pharmacol Ther 64:648-654. (Pubitemid 29011384)
14. LeCluyse EL, Alexandre E, Hamilton GA, Viollon-Abadie C, Coon DJ, Jolley S, Richert L. (2005).Isolation and culture of primary human hepatocytes. Methods Mol Biol 290:207-229.
15. Livak KJ, Schmittgen TD. (2001).Analysis of relative gene expression data using real-time quantitative PCR and the 2(-Delta Delta C(T)) Method. Methods 25:402-408. (Pubitemid 34164012)
16. Madan A, Graham RA, Carroll KM, Mudra DR, Burton LA, Krueger LA, Downey AD, Czerwinski M, Forster J, Ribadeneira MD, Gan LS, LeCluyse EL, Zech K, Robertson P Jr, Koch P, Antonian L, Wagner G, Yu L, Parkinson A. (2003).Effects of prototypical microsomal enzyme inducers on cytochrome P450 expression in cultured human hepatocytes. Drug Metab Dispos 31:421-431. (Pubitemid 36378519)
17. Mäenpää JU, Ala-Fossi SL. (1997).Toremifene in postmenopausal breast cancer. Efficacy, safety and cost. Drugs Aging 11:261-270. (Pubitemid 27464758)
18. Mayhew BS, Jones DR, 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. (Pubitemid 30660356)
19. Meunier V, Bourrié M, Julian B, Marti E, Guillou F, Berger Y, Fabre G. (2000).Expression and induction of CYP1A1/1A2, CYP2A6 and CYP3A4 in primary cultures of human hepatocytes: a 10-year follow-up. Xenobiotica 30:589-607. (Pubitemid 30449569)
20. Morello KC, Wurz GT, DeGregorio MW. (2003).Pharmacokinetics of selective estrogen receptor modulators. Clin Pharmacokinet 42:361-372. (Pubitemid 36433876)
21. Nallani SC, Goodwin B, Buckley AR, Buckley DJ, Desai PB. (2004).Differences in the induction of cytochrome P450 3A4 by taxane anticancer drugs, docetaxel and paclitaxel, assessed employing primary human hepatocytes. Cancer Chemother Pharmacol 54:219-229. (Pubitemid 39141738)
22. Ogilvie BW, Zhang D, Li W, Rodrigues AD, Gipson AE, Holsapple J, Toren P, Parkinson A. (2006).Glucuronidation converts gemfibrozil to a potent, metabolism-dependent inhibitor of CYP2C8: implications for drug-drug interactions. Drug Metab Dispos 34:191-197. (Pubitemid 43042661)
23. Pascussi JM, Gerbal-Chaloin S, Drocourt L, Maurel P, Vilarem MJ. (2003).The expression of CYP2B6, CYP2C9 and CYP3A4 genes: a tangle of networks of nuclear and steroid receptors. Biochim Biophys Acta 1619:243-253. (Pubitemid 36163419)
24. Pearce RE, McIntyre CJ, Madan A, Sanzgiri U, Draper AJ, Bullock PL, Cook DC, Burton LA, Latham J, Nevins C, Parkinson A. (1996).Effects of freezing, thawing, and storing human liver microsomes on cytochrome P450 activity. Arch Biochem Biophys 331:145-169. (Pubitemid 26256063)
25. Rendic S. (2002).Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev 34:83-448. (Pubitemid 34311090)
26. Rodrigues DA. (2008).Drug-drug interactions (2nd edn. Vol. 179).New York, NY: Informa Healthcare USA, Inc.
27. Saylor PJ, Keating NL, Smith MR. (2009).Prostate cancer survivorship: prevention and treatment of the adverse effects of androgen deprivation therapy. J Gen Intern Med 24 Suppl 2:S389-S394.
28. Segel IH. (1975).Enzyme kinetics: behaviour and analysis of rapid equilibrium and steady-state enzyme systems. New York, NY: John Wiley & Sons, Inc.
29. Sharifi N, Gulley JL, Dahut WL. (2005).Androgen deprivation therapy for prostate cancer. JAMA 294:238-244. (Pubitemid 41043794)
30. Silverman RB. (1995).Mechanism-based enzyme inactivators. Meth Enzymol 249:240-283.
31. Sipilä H, Näntö V, Kangas L, Anttila M, Halme T. (1988).Binding of toremifene to human serum proteins. Pharmacol Toxicol 63:62-64.
32. Smith MR, Morton RA, Barnette KG, Sieber PR, Malkowicz SB, Rodriguez D, Hancock ML, Steiner MS. (2010).Toremifene to reduce fracture risk in men receiving androgen deprivation therapy for prostate cancer. J Urol 184:1316-1321.
33. Stearns V, Johnson MD, Rae JM, Morocho A, Novielli A, Bhargava P, Hayes DF, Desta Z, Flockhart DA. (2003).Active tamoxifen metabolite plasma concentrations after coadministration of tamoxifen and the selective serotonin reuptake inhibitor paroxetine. J Natl Cancer Inst 95:1758-1764. (Pubitemid 38008898)
34. Sutton D, Butler AM, Nadin L, Murray M. (1997).Role of CYP3A4 in human hepatic diltiazem N-demethylation: inhibition of CYP3A4 activity by oxidized diltiazem metabolites. J Pharmacol Exp Ther 282:294-300. (Pubitemid 27425554)
35. Taras TL, Wurz GT, Linares GR, DeGregorio MW. (2000).Clinical pharmacokinetics of toremifene. Clin Pharmacokinet 39:327-334.
36. Tucker GT, Houston JB, Huang SM. (2001).Optimizing drug development: strategies to assess drug metabolism/transporter interaction potential-toward a consensus. Pharm Res 18:1071-1080. (Pubitemid 32900389)
37. Tyson C, Green C. (1987).In the isolated hepatocyte: use in toxicology and xenobiotic biotransformation. New York, NY: Academic Press.
38. Vrzal R, Stejskalova L, Monostory K, Maurel P, Bachleda P, Pavek P, Dvorak Z. (2009).Dexamethasone controls aryl hydrocarbon receptor (AhR)-mediated CYP1A1 and CYP1A2 expression and activity in primary cultures of human hepatocytes. Chem Biol Interact 179:288-296.
39. Wang H, LeCluyse EL. (2003).Role of orphan nuclear receptors in the regulation of drug-metabolising enzymes. Clin Pharmacokinet 42:1331-1357. (Pubitemid 38045840)
40. Yamazaki H, Shimada T. (1998).Comparative studies of in vitro inhibition of cytochrome P450 3A4-dependent testosterone 6beta-hydroxylation by roxithromycin and its metabolites, troleandomycin, and erythromycin. Drug Metab Dispos 26:1053-1057. (Pubitemid 28516578)
41. Zhao XJ, Jones DR, Wang YH, Grimm SW, Hall SD. (2002).Reversible and irreversible inhibition of CYP3A enzymes by tamoxifen and metabolites. Xenobiotica 32:863-878. (Pubitemid 35155521)