Have a personal or library account? Click to login

How polymorphisms of the cytochrome P450 genes affect ibuprofen and diclofenac metabolism and toxicity / Kako polimorfizmi gena citokroma P450 utječu na metabolizam i toksičnost ibuprofena i diklofenaka

Open Access
|Apr 2016

References

  1. 1. Ma Q, Lu AY. Pharmacogenetics, pharmacogenomics, and individualized medicine. Pharmacol Rev 2011;63:437-59. doi: 10.1124/pr.110.00353310.1124/pr.110.00353321436344
  2. 2. Božina N, Bradamante V, Lovrić M. Genetic polymorphism of metabolic enzymes P450 (CYP) as a susceptibility factor for drug response, toxicity, and cancer risk. Arh Hig Rada Toksikol 2009;60:217-42. doi: 10.2478/10004-1254-60-2009-188510.2478/10004-1254-60-2009-188519581216
  3. 3. Swen JJ, Nijenhuis M, de Boer A, Grandia L, Maitland-van der Zee AH, Mulder H, Rongen GA, van Schaik RH, Schalekamp T, Touw DJ, van der Weide J, Wilffert B, Deneer VH, Guchelaar HJ. Pharmacogenetics: from bench to byte--an update of guidelines. Clin Pharmacol Ther 2011;89:662-73. doi: 10.1038/clpt.2011.3410.1038/clpt.2011.3421412232
  4. 4. Warner TD, Giuliano F, Vojnovic I, Bukasa A, Mitchell JA, Vane JR. Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: a full in vitro analysis. Proc Natl Acad Sci USA 1999;96:7563-8. PMID: 1037745510.1073/pnas.96.13.75632212610377455
  5. 5. Bleumink GS, Feenstra J, Sturkenboom MC, Stricker BH. Nonsteroidal antiinflammatory drugs and heart failure. Drugs 2003;63:525-34. PMID: 1265665110.2165/00003495-200363060-0000112656651
  6. 6. Jinno N, Tagashira M, Tsurui K, Yamada S. Contribution of cytochrome P450 and UDP-glucuronosyltransferase to the metabolism of drugs containing carboxylic acid groups: risk assessment of acylglucuronides using human hepatocytes. Xenobiotica 2014;44:677-86. doi: 10.3109/00498254.2014. 894219
  7. 7. Zhang Y, Han YH, Putluru SP, Matta MK, Kole P, Mandlekar S, Furlong MT, Liu T, Iyer RA, Marathe P, Yang Z, Lai Y, Rodrigues AD. Diclofenac and its acyl glucuronide: determination of in vivo exposure in human subjects and characterization as human drug transporter substrates in vitro. Drug Metab Dispos 2016;44:320-8. doi: 10.1124/ dmd.115.06694410.1124/dmd.115.06694426714763
  8. 8. Kindla J, Müller F, Mieth M, Fromm MF, König J. Influence of non-steroidal anti-inflammatory drugs on organic anion transporting polypeptide (OATP) 1B1- and OATP1B3- mediated drug transport. Drug Metab Dispos 2011;39:1047-53. doi: 10.1124/dmd.110.03762210.1124/dmd.110.03762221389119
  9. 9. Rudy AC, Knight PM, Brater DC, Hall SD. Stereoselective metabolism of ibuprofen in humans: administration of R-, S- and racemic ibuprofen. J Pharmacol Exp Ther 1991;259:1133-9. PMID: 1762067
  10. 10. Woodman TJ, Wood PJ, Thompson AS, Hutchings TJ, Steel GR, Jiao P, Threadgill MD, Lloyd MD. Chiral inversion of 2-arylpropionyl-CoA esters by human α-methylacyl-CoA racemase 1A (P504S): a potential mechanism for the anticancer effects of ibuprofen. Chem Commun (Camb) 2011;47:7332-4. doi: 10.1039/c1cc10763a10.1039/c1cc10763a21614403
  11. 11. Davies NM. Clinical pharmacokinetics of ibuprofen. The first 30 years. Clin Pharmacokinet 1998;34:101-54. doi: 10.2165/00003088-199834020-0000210.2165/00003088-199834020-000029515184
  12. 12. Neunzig I, Göhring A, Drăgan CA, Zapp J, Peters FT, Maurer HH, Bureik M.. Production and NMR analysis of the human ibuprofen metabolite 3-hydroxyibuprofen. J Biotechnol 2012;157:417-20. doi: 10.1016/j.jbiotec.2011.12.01610.1016/j.jbiotec.2011.12.01622226725
  13. 13. Hamman MA, Thompson GA, Hall SD. Regioselective and stereoselective metabolism of ibuprofen by human Cytochrome P450 2C. Biochem Pharmacol 1997;54:33-41. doi: 10.1016/ S0006-2952(97)00143-310.1016/S0006-2952(97)00143-3
  14. 14. Chang SY, Li W, Traeger SC, Wang B, Cui D, Zhang H, Wen B, Rodrigues AD. Confirmation that Cytochrome P450 2C8 (CYP2C8) plays a minor role in (S)-(+)- and (R)-(-)-ibuprofen hydroxylation in vitro. Drug Metab Dispos 2008;36:2513-22. doi: 10.1124/dmd.108.02297010.1124/dmd.108.022970
  15. 15. Sakaguchi K, Green M, Stock N, Reger TS, Zunic J, King C. Glucuronidation of carboxylic acid containing compounds by UDP-glucuronosyltransferase isoforms. Arch Biochem Biophys. 2004;424(2):219-25. PMID: 15047194.10.1016/j.abb.2004.02.004
  16. 16. Castillo M, Lam YW, Dooley MA, Stahl E, Smith PC. Disposition and covalent binding of ibuprofen and its acyl glucuronide in the elderly. Clin Pharmacol Ther 1995;57:636-44. doi: 10.1016/0009-9236(95)90226-010.1016/0009-9236(95)90226-0
  17. 17. Grillo MP, Lohr MT, Khera S. Interaction of γ-glutamyltrans peptidase with ibuprofen-S-acyl-glutathione in vitro and in vivo in human. Drug Metab Dispos 2013;41:111-21. doi: 10.1124/dmd.112.04864510.1124/dmd.112.048645
  18. 18. Tang W. The metabolism of diclofenac - enzymology and toxicology perspectives. Curr Drug Metab 2003;4:319-29. doi: 10.2174/138920003348939810.2174/1389200033489398
  19. 19. Tang W, Stearns RA, Bandiera SM, Zhang Y, Raab C, Braun MP, Dean DC, Pang J, Leung KH, Doss GA, Strauss JR, Kwei GY, Rushmore TH, Chiu SH, Baillie TA. Studies on Cytochrome P-450-mediated bioactivation of diclofenac in rats and in human hepatocytes: identification of glutathione conjugated metabolites. Drug Metab Dispos 1999;27:365-72. PMID: 10064567
  20. 20. King C, Tang W, Ngui J, Tephly T, Braun M. Characterization of rat and human UDP-glucuronosyltransferases responsible for the in vitro glucuronidation of diclofenac. Toxicol Sci 2001;61:49-53. doi: 10.1093/toxsci/61.1.4910.1093/toxsci/61.1.49
  21. 21. Shipkova M, Armstrong VW, Oellerich M, Wieland E. Acyl glucuronide drug metabolites: toxicological and analytical implications. Ther Drug Monit 2003;25:1-16. PMID: 1254813810.1097/00007691-200302000-00001
  22. 22. Bailey MJ, Dickinson RG. Acyl glucuronide reactivity in perspective: biological consequences. Chem Biol Interact 2003;145:117-37. doi: 10.1016/S0009-2797(03)00020-610.1016/S0009-2797(03)00020-6
  23. 23. Deer TR, Leong MS, Buvanendran A. Comprehensive treatment of chronic pain by medical, interventional, and integrative approaches: the American Academy Of Pain Medicine textbook on patient management. New York (NY): Springer; 201310.1007/978-1-4614-1560-2
  24. 24. King C, Tang W, Ngui J, Tephly T, Braun M. Characterization of rat and human UDP-glucuronosyltransferases responsible for the in vitro glucuronidation of diclofenac. Toxicol Sci 2001;61(1):49-53. PMID: 11294973.10.1093/toxsci/61.1.49
  25. 25. Aithal GP, Ramsay L, Daly AK, Sonchit N, Leathart JB, Alexander G, Kenna JG, Caldwell J, Day CP. Hepatic adducts, circulating antibodies, and cytokine polymorphisms in patients with diclofenac hepatotoxicity. Hepatology 2004;39:1430-40. doi: 10.1002/hep.2020510.1002/hep.20205
  26. 26. Sallustio BC, Sabordo L, Evans AM, Nation RL. Hepatic disposition of electrophilic acyl glucuronide conjugates. Curr Drug Metab 2000;1:163-80. PMID: 1146508110.2174/1389200003339153
  27. 27. Lagas JS, Sparidans RW, Wagenaar E, Beijnen JH, Schinkel AH. Hepatic clearance of reactive glucuronide metabolites of diclofenac in the mouse is dependent on multiple ATP-binding cassette efflux transporters. Mol Pharmacol 2010;77:687-94. doi: 10.1124/mol.109.06236410.1124/mol.109.062364
  28. 28. Nies AT, Keppler D. The apical conjugate efflux pump ABCC2 (MRP2). Pflugers Arch 2007;453:643-59. doi: 10.1007/ s00424-006-0109-y10.1007/s00424-006-0109-y
  29. 29. Johansson I, Ingelman-Sundberg M. Genetic polymorphism and toxicology - with emphasis on Cytochrome p450. Toxicol Sci 2011;120:1-13. doi: 10.1093/toxsci/kfq37410.1093/toxsci/kfq374
  30. 30. Sim SC, Kacevska M, Ingelman-Sundberg M. Pharmaco genomics of drug-metabolizing enzymes: a recent update on clinical implications and endogenous effects. Pharmaco genomics J 2013;13:1-11. doi: 10.1038/tpj.2012.4510.1038/tpj.2012.45
  31. 31. Zhang D, Surapaneni S, editors. ADME-enabling technologies in drug design and development. Hoboken (NJ): Wiley; 2012.10.1002/9781118180778
  32. 32. Agúndez JA, García-Martín E, Martínez C. Genetically based impairment in CYP2C8- and CYP2C9-dependent NSAID metabolism as a risk factor for gastrointestinal bleeding: is a combination of pharmacogenomics and metabolomics required to improve personalized medicine? Expert Opin Drug Metab Toxicol 2009;5:607-20. doi: 10.1517/1742525090 2970998
  33. 33. Totah RA, Rettie AE. Cytochrome P450 2C8: substrates, inhibitors, pharmacogenetics, and clinical relevance. Clin Pharmacol Ther 2005;77:341-52. doi: 10.1016/j. clpt.2004.12.267
  34. 34. Klose TS, Blaisdell JA, Goldstein JA. Gene structure of CYP2C8 and extrahepatic distribution of the human CYP2Cs. J Biochem Mol Toxicol 1999;13:289-95. PMID: 1048741510.1002/(SICI)1099-0461(1999)13:6<;289::AID-JBT1>3.0.CO;2-N
  35. 35. The Human Cytochrome P450 (CYP) Allele Nomenclature Database [displayed 20 October 2015]. Available at http:// www.cypalleles.ki.se/
  36. 36. Daily EB, Aquilante CL. Cytochrome P450 2C8 pharmacogenetics: a review of clinical studies. Pharmacogenomics 2009;10:1489-510. doi: 10.2217/pgs.09. 82
  37. 37. Gao Y, Liu D, Wang H, Zhu J, Chen C. Functional characterization of five CYP2C8 variants and prediction of CYP2C8 genotype-dependent effects on in vitro and in vivo drug-drug interactions. Xenobiotica 2010;40:467-75. doi: 10.3109/00498254.2010.48716310.3109/00498254.2010.487163
  38. 38. Paganotti GM, Gramolelli S, Tabacchi F, Russo G, Modiano D, Coluzzi M, Romano R. Distribution of human CYP2C8*2 allele in three different African populations. Malar J 2012;11:125. doi: 10.1186/1475-2875-11-12510.1186/1475-2875-11-125335323322531455
  39. 39. Daly AK, Aithal GP, Leathart JB, Swainsbury RA, Dang TS, Day CP. Genetic susceptibility to diclofenac-induced hepatotoxicity: contribution of UGT2B7, CYP2C8, and ABCC2 genotypes. Gastroenterology 2007;132:272-81. doi: 10.1053/j.gastro.2006.11.02310.1053/j.gastro.2006.11.02317241877
  40. 40. Wu X, Zuo J, Guo T, Yuan L. CYP2C8 polymorphism frequencies among Han, Uighur, Hui, and Mongolian Chinese populations. Genet Test Mol Biomarkers 2013;17:104-8. doi: 10.1089/gtmb.2012.025610.1089/gtmb.2012.025623336573
  41. 41. Speed WC, Kang SP, Tuck DP, Harris LN, Kidd KK. Global variation in CYP2C8-CYP2C9 functional haplotypes. Pharmacogenomics J 2009;9:283-90. doi: 10.1038/tpj.2009.1010.1038/tpj.2009.10278240519381162
  42. 42. López-Rodríguez R, Novalbos J, Gallego-Sandín S, Román- Martínez M, Torrado J, Gisbert JP, Abad-Santos F. Influence of CYP2C8 and CYP2C9 polymorphisms on pharmacokinetic and pharmacodynamic parameters of racemic and enantiomeric forms of ibuprofen in healthy volunteers. Pharmacol Res 2008;58:77-84. doi: 10.1016/j.phrs.2008.07.00410.1016/j.phrs.2008.07.00418694831
  43. 43. Martínez C, García-Martín E, Blanco G, Gamito FJ, Ladero JM, Agúndez JA. The effect of the Cytochrome P450 CYP2C8 polymorphism on the disposition of (R)-ibuprofen enantiomer in healthy subjects. Br J Clin Pharmacol 2005;59:62-9. doi: 10.1111/j.1365-2125.2004.02183.x10.1111/j.1365-2125.2004.02183.x188495915606441
  44. 44. Garcia-Martin E, Martínez C, Tabarés B, Frías J, Agúndez JA. Interindividual variability in ibuprofen pharmacokinetics is related to interaction of Cytochrome P450 2C8 and 2C9 amino acid polymorphisms. Clin Pharmacol Ther 2004;76:119-27. doi: 10.1016/j.clpt.2004.04.00610.1016/j.clpt.2004.04.00615289789
  45. 45. McGreavey LE, Turner F, Smith G, Boylan K, Timothy Bishop D, Forman D, Roland Wolf C, Barrett JH; Colorectal Cancer Study Group. No evidence that polymorphisms in CYP2C8, CYP2C9, UGT1A6, PPARdelta and PPARgamma act as modifiers of the protective effect of regular NSAID use on the risk of colorectal carcinoma. Pharmacogenet Genomics 2005;15:713-21. PMID: 1614179710.1097/01.fpc.0000174786.85238.6316141797
  46. 46. Dorado P, Cavaco I, Cáceres MC, Piedade R, Ribeiro V, Llerena A. Relationship between CYP2C8 genotypes and diclofenac 5-hydroxylation in healthy Spanish volunteers. Eur J Clin Pharmacol 2008;64:967-70. doi: 10.1007/s00228-008-0508-410.1007/s00228-008-0508-418548238
  47. 47. Benzon H, Raja SN, Fishman SE, Liu S, Cohen SP eds. Essentials of Pain Medicine. 3rd ed. Elsevier Health Sciences;
  48. 2011.
  49. 48. Aithal GP, Day CP. Nonsteroidal anti-inflammatory druginduced hepatotoxicity. Clin Liver Dis 2007;11:563-75. doi: 10.1016/j.cld.2007.06.00410.1016/j.cld.2007.06.00417723920
  50. 49. O’Connor N, Dargan PI, Jones AL. Hepatocellular damage from non-steroidal anti-inflammatory drugs. QJM 2003;96:787-91. PMID: 14566034 10.1093/qjmed/hcg13814566034
  51. 50. Aithal GP, Day CP, Leathart JB, Daly AK. Relationship of polymorphism in CYP2C9 to genetic susceptibility to diclofenac-induced hepatitis. Pharmacogenetics 2000;10:511-8. PMID: 1097560510.1097/00008571-200008000-0000410975605
  52. 51. CYP2C9 allele nomenclature [displayed 20 October 2015]. Available at http://www.cypalleles.ki.se/cyp2c9.htm
  53. 52. Kirchheiner J, Meineke I, Freytag G, Meisel C, Roots I, Brockmöller J. Enantiospecific effects of cytochrome P450 2C9 amino acid variants on ibuprofenpharmacokinetics and on the inhibition of cyclooxygenases 1 and 2. Clin Pharmacol Ther 2002;72:62-75. doi: 10.1067/mcp.2002.12572610.1067/mcp.2002.12572612152005
  54. 53. Karaźniewicz-Łada M, Luczak M, Główka F. Pharmacokinetic studies of enantiomers of ibuprofen and its chiral metabolites in humans with different variants of genes coding CYP2C8 and CYP2C9 isoenzymes. Xenobiotica 2009;39:476-85. doi: 10.1080/0049825090286270510.1080/0049825090286270519480553
  55. 54. Poon G. Ibuprofen lysine (NeoProfen) for the treatment of patent ductus arteriosus. Proc (Bayl Univ Med Cent) 2007;20(1):83-5.10.1080/08998280.2007.11928244176954117256050
  56. 55. Durrmeyer X, Hovhannisyan S, Médard Y, Jacqz-Aigrain E, Decobert F, Barre J, Alberti C, Aujard Y, Danan C, Baud O.
  57. Are cytochrome P450 CYP2C8 and CYP2C9 polymorphisms associated with ibuprofen response in very preterm infants? PLoS One 2010;5(8):e12329. doi: 10.1371/journal. pone.0012329 56.
  58. 56. Zi J, Liu D, Ma P, Huang H, Zhu J, Wei D, Yang J, Chen C. Effects of CYP2C9*3 and CYP2C9*13 on diclofenac metabolism and inhibition-based drug-drug interactions. Drug Metab Pharmacokinet 2010;25:343-50. doi: 10.2133/dmpk. DMPK-10-RG-009
  59. 57. Yasar U, Eliasson E, Forslund-Bergengren C, Tybring G, Gadd M, Sjöqvist F, Dahl ML The role of CYP2C9 genotype in the metabolism of diclofenac in vivo and in vitro. Eur J Clin Pharmacol 2001;57:729-35. doi: 10.1007/s00228-001-0376-710.1007/s00228-001-0376-711829203
  60. 58. Pilotto A, Seripa D, Franceschi M, Scarcelli C, Colaizzo D, Grandone E, Niro V, Andriulli A, Leandro G, Di Mario F, Dallapiccola B. Genetic susceptibility to nonsteroidal antiinflammatory drug-related gastroduodenal bleeding: role of Cytochrome P450 2C9 polymorphisms. Gastroenterology 2007;133:465-71. doi: 10.1053/j.gastro.2007.05.02510.1053/j.gastro.2007.05.02517681167
  61. 59. Ishihara M, Ohmiya N, Nakamura M, Funasaka K, Miyahara R, Ohno E, Kawashima H, Itoh A, Hirooka Y, Watanabe O, Ando T, Goto H. Risk factors of symptomatic NSAID-induced small intestinal injury and diaphragm disease. Aliment Pharmacol Ther 2014;40:538-47. doi: 10.1111/apt.1285810.1111/apt.1285825041257
  62. 60. Node K, Huo Y, Ruan X, Yang B, Spiecker M, Ley K, Zeldin DC, Liao JK.Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids. Science 1999;285 (5431):1276-9. PMID: 10455056;10.1126/science.285.5431.1276272002710455056
  63. 61. Bellien J, Joannides R. Epoxyeicosatrienoic acid pathway in human health and diseases. J Cardiovasc Pharmacol 2013;61(3):188-96. doi: 10.1097/FJC.0b013e318273b00710.1097/FJC.0b013e318273b00723011468
  64. 62. Fleming I, Michaelis UR, Bredenkötter D, Fisslthaler B, Dehghani F, Brandes RP, Busse R. Endothelium-derived hyperpolarizing factor synthase (Cytochrome P450 2C9) is a functionally significant source of reactive oxygen species in coronary arteries. Circ Res 2001;88(1):44-51. PMID: 11139472.10.1161/01.RES.88.1.44
  65. 63. Stamer UM, Zhang L, Stuber F. Personalized therapy in pain management: where do we stand? Pharmacogenomics 2010;11:843-64. doi: 10.2217/pgs.10.47 10.2217/pgs.10.4720504256
DOI: https://doi.org/10.1515/aiht-2016-67-2754 | Journal eISSN: 1848-6312 | Journal ISSN: 0004-1254
Language: English, Croatian, Slovenian
Page range: 1 - 8
Submitted on: Dec 1, 2015
Accepted on: Mar 1, 2016
Published on: Apr 15, 2016
Published by: Institute for Medical Research and Occupational Health
In partnership with: Paradigm Publishing Services
Publication frequency: 4 times per year

© 2016 Valon Krasniqi, Aleksandar Dimovski, Iva Klarica Domjanović, Ivan Bilić, Nada Božina, published by Institute for Medical Research and Occupational Health
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.