Cytochrome P450 2C8 and drug metabolism

Current Topics in Medicinal Chemistry

Volumn 13, Issue 18, 2013, Pages 2241-2253

  Lv, Xiaoping ^a   Zhong, Fangfang ^a   Tan, Xiangshi ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

CYP2C8; Disease; Drug metabolism; Inhibitor; Polymorphism

Indexed keywords

ACONITINE; AMFEBUTAMONE; AMIODARONE; AMITRIPTYLINE; ATORVASTATIN; CERIVASTATIN; CISPLATIN; CYTOCHROME P450 2C8; DIAZEPAM; FEBUXOSTAT; FLUOROURACIL; FLUOXETINE; GEMFIBROZIL; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; IMATINIB; KETOPROFEN; LOPERAMIDE; MEVINOLIN; MONTELUKAST; NIFEDIPINE; PACLITAXEL; PIOGLITAZONE; QUERCETIN; RALOXIFENE; REPAGLINIDE; ROSIGLITAZONE; TAMOXIFEN; THIOTEPA; TRIMETHOPRIM; UNINDEXED DRUG;

AEROBIC METABOLISM; ARTICLE; ASTHMA; BLADDER CANCER; BONE NECROSIS; BREAST CANCER; BREAST TUMOR; CRYSTAL STRUCTURE; DEPRESSION; DRUG METABOLISM; DRUG WITHDRAWAL; ENZYME ACTIVITY; GENE FREQUENCY; GENETIC POLYMORPHISM; HEART ARRHYTHMIA; HEART INFARCTION; HUMAN; HYPERCHOLESTEROLEMIA; HYPERLIPIDEMIA; HYPERTENSION; INFLAMMATION; KIDNEY FAILURE; NECK CANCER; NEOPLASM; NEUROTOXICITY; NON INSULIN DEPENDENT DIABETES MELLITUS; OSTEOPOROSIS; OVARY CANCER; PROTEIN EXPRESSION; PROTEIN SECONDARY STRUCTURE; RHABDOMYOLYSIS; SINGLE NUCLEOTIDE POLYMORPHISM; SITE DIRECTED MUTAGENESIS; STRUCTURE ACTIVITY RELATION; URINARY TRACT INFECTION;

ARYL HYDROCARBON HYDROXYLASES; HUMANS; MODELS, MOLECULAR; PHARMACEUTICAL PREPARATIONS;

EID: 84887921294     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/15680266113136660157     Document Type: Article

References (110)

1. Badyal, D. K.; Dadhich, A. P. Cytochrome P450 and drug interactions. Indian J Pharmacol, 2001, 33 (4), 248-259.
2. Nelson, D. R.; Zeldin, D. C.; Hoffman, S. M. G.; Maltais, L. J.; Wain, H. M.; Nebert, D. W. Comparison of cytochrome P450 (CYP) genes from the mouse and human genomes, including nomenclature recommendations for genes, pseudogenes and alternative-splice variants. Pharmacogenetics, 2004, 14 (1), 1-18.
3. Usmani, K. A.; Karoly, E. D.; Hodgson, E.; Rose, R. L. In vitro sulfoxidation of thioether compounds by human cytochrome P450 and flavin-containing monooxygenase isoforms with particular reference to the CYP2C subfamily. Drug Metab. Disposition, 2004, 32 (3), 333-339.
4. Totah, R. A.; Rettie, A. E. Cytochrome P450 2C8: Substrates, inhibitors, pharmacogenetics, and clinical relevance (vol 77, pg 341, 2005). Clin. Pharmacol. Ther, 2005, 78 (2), 153-153.
5. Johnson, D. L.; Lewis, B. C.; Elliot, D. J.; Miners, J. O.; Martin, L. L. Electrochemical characterisation of the human cytochrome P450 CYP2C9. Biochem. Pharmacol, 2005, 69 (10), 1533-1541.
6. Shimada, T.; Yamazaki, H.; Mimura, M.; Inui, Y.; Guengerich, F. P. interindividual variations in human liver cytochrome-P-450 enzymes involved in the oxidation of drugs, carcinogens and toxicchemicals-studies with liver-microsomes of 30 japanese and 30 caucasians. J. Pharmacol. Exp. Ther, 1994, 270 (1), 414-423.
7. Rendic, S.; DiCarlo, F. J. Human cytochrome P450 enzymes: A status report summarizing their reactions, substrates, inducers, and inhibitors. Drug Metab. Rev, 1997, 29 (1-2), 413-580.
8. Schoch, G. A.; Yano, J. K.; Wester, M. R.; Griffin, K. J.; Stout, C. D.; Johnson, E. F. Structure of human microsomal cytochrome P450 2C8. Evidence for a peripheral fatty acid binding site. The Journal of biological chemistry, 2004, 279 (10), 9497-503.
9. Rahman, A.; Korzekwa, K. R.; Grogan, J.; Gonzalez, F. J.; Harris, J. W. selective biotransformation of taxol to 6-alphahydroxytaxol by human cytochrome-P450 2C8. Cancer Res, 1994, 54 (21), 5543-5546.
10. Sonnichsen, D. S.; Liu, Q.; Schuetz, E. G.; Schuetz, J. D.; Pappo, A.; Relling, M. V. variability in human cytochrome-p450 paclitaxel metabolism. J. Pharmacol. Exp. Ther, 1995, 275 (2), 566-575.
11. Ohyama, K.; Nakajima, M.; Nakamura, S.; Shimada, N.; Yamazaki, H.; Yokoi, T. A significant role of human cytochrome P4502C8 in amiodarone N-deethylation: An approach to predict the contribution with relative activity factor. Drug Metab. Disposition, 2000, 28 (11), 1303-1310.
12. Yamazaki, H.; Shibata, A.; Suzuki, M.; Nakajima, M.; Shimada, N.; Guengerich, F. P.; Yokoi, T. Oxidation of troglitazone to a quinone-type metabolite catalyzed by cytochrome P-4502C8 and P-450 3A4 in human liver microsomes. Drug Metab. Disposition, 1999, 27 (11), 1260-1266.
13. Kerr, B. M.; Thummel, K. E.; Wurden, C. J.; Klein, S. M.; Kroetz, D. L.; Gonzalez, F. J.; Levy, R. H. human liver carbamazepine metabolism-role of CYP3A4 and CYP2C8 in 10, 11-epoxide formation. Biochem. Pharmacol, 1994, 47 (11), 1969-1979.
14. Dai, D.; Zeldin, D. C.; Blaisdell, J. A.; Chanas, B.; Coulter, S. J.; Ghanayem, B. I.; Goldstein, J. A. Polymorphisms in human CYP2C8 decrease metabolism of the anticancer drug paclitaxel and arachidonic acid. Pharmacogenetics, 2001, 11 (7), 597-607.
15. Stoilov, I.; Akarsu, A. N.; Alozie, I.; Child, A.; Barsoum-Homsy, M.; Turacli, M. E.; Or, M.; Lewis, R. A.; Ozdemir, N.; Brice, G.; Aktan, S. G.; Chevrette, L.; Coca-Prados, M.; Sarfarazi, M. Sequence analysis and homology modeling suggest that primary congenital glaucoma on 2p21 results from mutations disrupting either the hinge region or the conserved core structures of cytochrome P4501B1. Amer J Hum Genet, 1998, 62 (3), 573-584.
16. Plasilova, M.; Stoilov, I.; Sarfarazi, M.; Kadasi, L.; Ferakova, E.; Ferak, V. Identification of a single ancestral CYP1B1 mutation in Slovak Gypsies (Roms) affected with primary congenital glaucoma. J. Med. Genet, 1999, 36 (4), 290-294.
17. Lai, X.-S.; Yang, L.-P.; Li, X.-T.; Liu, J.-P.; Zhou, Z.-W.; Zhou, S.-F. Human CYP2C8: Structure, Substrate Specificity, Inhibitor Selectivity, Inducers and Polymorphisms. Curr. Drug Metab, 2009, 10 (9), 1009-1047.
18. Daily, E. B.; Aquilante, C. L. Cytochrome P450 2C8 pharmacogenetics: a review of clinical studies. Pharmacogenomics, 2009, 10 (9), 1489-1510.
19. Bryson, D.; Lim, P. L.; Lawson, A.; Manjunath, S.; Raner, G. M. Isotopic labeling of the heme cofactor in cytochrome p450 and other heme proteins. BiotL, 2011, 33 (10), 2019-2026.
20. Anzenbacher, P.; Anzenbacherova, E. Cytochromes P450 and metabolism of xenobiotics. Cell. Mol. Life Sci, 2001, 58 (5-6), 737-747.
21. Rittle, J.; Green, M. T. Cytochrome P450 Compound I: Capture, Characterization, and C-H Bond Activation Kinetics. Sci, 2010, 330 (6006), 933-937.
22. Schoch, G. A.; Yano, J. K.; Wester, M. R.; Griffin, K. J.; Stout, C. D.; Johnson, E. F. Structure of human microsomal cytochrome P4502C8-Evidence for a peripheral fatty acid binding site. J. Biol. Chem, 2004, 279 (10), 9497-9503.
23. Williams, P. A.; Cosme, J.; Ward, A.; Angova, H. C.; Vinkovic, D. M.; Jhoti, H. Crystal structure of human cytochrome P4502C9 with bound warfarin. Nature, 2003, 424 (6947), 464-468.
24. Tsao, C. C.; Wester, M. R.; Ghanayem, B.; Coulter, S. J.; Chanas, B.; Johnson, E. F.; Goldstein, J. A. Identification of human CYP2C19 residues that confer S-mephenytoin 4 '-hydroxylation activity to CYP2C9. Biochemistry (Mosc). 2001, 40 (7), 1937-1944.
25. Schoch, G. A.; Yano, J. K.; Sansen, S.; Dansette, P. M.; Stout, C. D.; Johnson, E. F. Determinants of cytochrome P4502C8 substrate binding-Structures of complexes with montelukast, troglitazone, felodipine, and 9-cis-retinoic acid. J. Biol. Chem, 2008, 283 (25), 17227-17237.
26. Gotoh, O. substrate recognition sites in cytochrome-p450 family-2 (CYP2) proteins inferred from comparative analyses of amino-acid and coding nucleotide-sequences. J. Biol. Chem, 1992, 267 (1), 83-90.
27. Miners, J. O.; Birkett, D. J. Cytochrome P4502C9: an enzyme of major importance in human drug metabolism. Br. J. Clin. Pharmacol, 1998, 45 (6), 525-538.
28. Brehm, J. H.; Mellors, J. W.; Sluis-Cremer, N. Mechanism by which a Glutamine to Leucine Substitution at Residue 509 in the Ribonuclease H Domain of HIV-1 Reverse Transcriptase Confers Zidovudine Resistance. Biochemistry (Mosc). 2008, 47 (52), 14020-14027.
29. Sun, L.; Wang, Z. H.; Ni, F. Y.; Tan, X. S.; Huang, Z. X. The role of Ile476 in the structural stability and substrate binding of human cytochrome P450 2C8. The protein journal, 2010, 29 (1), 32-43.
30. Melet, A.; Marques-Soares, C.; Schoch, G. A.; Macherey, A. C.; Jaouen, M.; Dansette, P. M.; Sari, M. A.; Johnson, E. F.; Mansuy, D. Analysis of human cytochrome P4502C8 substrate specificity using a substrate pharmacophore and site-directed mutants. Biochemistry (Mosc). 2004, 43 (49), 15379-15392.
31. Jiang, H.; Zhong, F.; Sun, L.; Feng, W.; Huang, Z. X.; Tan, X. Structural and functional insights into polymorphic enzymes of cytochrome P450 2C8. Amino Acids, 2011, 40 (4), 1195-204.
32. Hichiya, H.; Tanaka-Kagawa, T.; Soyama, A.; Jinno, H.; Koyano, S.; Katori, N.; Matsushima, E.; Uchiyama, S.; Tokunaga, H.; Kimura, H.; Minami, N.; Katoh, M.; Sugai, K.; Goto, Y.; Tamura, T.; Yamamoto, N.; Ohe, Y.; Kunitoh, H.; Nokihara, H.; Yoshida, T.; Minami, H.; Saijo, N.; Ando, M.; Ozawa, S.; Saito, Y.; Sawada, J. Functional characterization of five novel CYP2C8 variants, G171S, R186X, R186G, K247R, and K383N, found in a Japanese population. Drug Metab. Disposition, 2005, 33 (5), 630-636.
33. Lee, V. H. L.; Sporty, J. L.; Fandy, T. E. Pharmacogenomics of drug transporters: the next drug delivery challenge. Adv. Drug Del. Rev, 2001, 50, S33-S40.
34. Yasar, U.; Bennet, A. M.; Eliasson, E.; Lundgren, S.; Wiman, B.; de Faire, U.; Rane, A. Allelic variants of cytochromes P4502C modify the risk for acute myocardial infarction. Pharmacogenetics, 2003, 13 (12), 715-720.
35. Ishikawa, C.; Ozaki, H.; Nakajima, T.; Ishii, T.; Kanai, S.; Anjo, S.; Shirai, K.; Inoue, I. A frameshift variant of CYP2C8 was identified in a patient who suffered from rhabdomyolysis after administration of cerivastatin. J. Hum. Genet, 2004, 49 (10), 582-585.
36. Soyama, A.; Saito, Y.; Komamura, K.; Ueno, K.; Kamakura, S.; Ozawa, S.; Sawada, J.-i. Five novel single nucleotide polymorphisms in the CYP2C8 gene, one of which induces a frame-shift. Drug Metabolism and Pharmacokinetics, 2002, 17 (4), 374-7.
37. Hanioka, N.; Matsumoto, K.; Saito, Y.; Narimatsu, S. Influence of CYP2C8*13 and CYP2C8*14 Alleles on Amiodarone NDeethylation. Basic Clin. Pharmacol. Toxicol, 2011, 108 (5), 359-362.
38. Yeo, C. W.; Lee, S. J.; Lee, S. S.; Bae, S. K.; Kim, E. Y.; Shon, J. H.; Rhee, B. D.; Shin, J. G. Discovery of a novel allelic variant of CYP2C8, CYP2C8*11, in Asian populations and its clinical effect on the rosiglitazone disposition in vivo. Drug metabolism and disposition: the biological fate of chemicals, 2011, 39 (4), 711-6.
39. Rower, S.; Bienzle, U.; Weise, A.; Lambertz, U.; Forst, T.; Otchwemah, R. N.; Pfutzner, A.; Mockenhaupt, F. P. Short communication: high prevalence of the cytochrome P450 2C8*2 mutation in Northern Ghana. Tropical medicine & international health: TM & IH, 2005, 10 (12), 1271-3.
40. Soyama, A.; Saito, Y.; Hanioka, N.; Murayama, N.; Nakajima, O.; Katori, N.; Ishida, S.; Sai, K.; Ozawa, S.; Sawada, J. Nonsynonymous single nucleotide alterations found in the CYP2C8 gene result in reduced in vitro paclitaxel metabolism. Biol. Pharm. Bull, 2001, 24 (12), 1427-1430.
41. Bahadur, N.; Leathart, J. B. S.; Mutch, E.; Steimel-Crespi, D.; Dunn, S. A.; Gilissen, R.; Van Houdt, J.; Hendrickx, J.; Mannens, G.; Bohets, H.; Williams, F. M.; Armstrong, M.; Crespi, C. L.; Daly, A. K. CYP2C8 polymorphisms in Caucasians and their relationship with paclitaxel 6 alphahydroxylase activity in human liver microsomes. Biochem. Pharmacol, 2002, 64 (11), 1579-1589.
42. Hanioka, N.; Matsumoto, K.; Saito, Y.; Narimatsu, S. Functional Characterization of CYP2C8. 13 and CYP2C8. 14: Catalytic Activities toward Paclitaxel. Basic Clin. Pharmacol. Toxicol, 2010, 107 (1), 565-569.
43. Jiang, H.; Sun, L.; Huang, Z.; Tan, X. Structural and functional insights into CYP2C8. 3: A genetic polymorph of cytochrome P450 2C8. Science China Chemistry, 2010, 53 (10), 2200-2207.
44. Kudzi, W.; Dodoo, A. N.; Mills, J. J. Characterisation of CYP2C8, CYP2C9 and CYP2C19 polymorphisms in a Ghanaian population. BMC medical genetics, 2009, 10, 124.
45. Parikh, S.; Ouedraogo, J. B.; Goldstein, J. A.; Rosenthal, P. J.; Kroetz, D. L. Amodiaquine metabolism is impaired by common polymorphisms in CYP2C8: implications for malaria treatment in Africa. Clin. Pharmacol. Ther, 2007, 82 (2), 197-203.
46. Muthiah, Y. D.; Lee, W. L.; Teh, L. K.; Ong, C. E.; Salleh, M. Z.; Ismail, R. A simple multiplex PCR method for the concurrent detection of three CYP2C8 variants. Clinica chimica acta; international journal of clinical chemistry, 2004, 349 (1-2), 191-8.
47. Naraharisetti, S. B.; Lin, Y. S.; Rieder, M. J.; Marciante, K. D.; Psaty, B. M.; Thummel, K. E.; Totah, R. A. Human liver expression of CYP2C8: gender, age, and genotype effects. Drug metabolism and disposition: the biological fate of chemicals, 2010, 38 (6), 889-93.
48. Niemi, M.; Leathart, J. B.; Neuvorten, A.; Backman, J. T.; Daly, A. K.; Neuvonen, P. J. Polymorphism in C Upsilon P2C8 is associated with reduced plasma concentrations of repaglinide. Clin. Pharmacol. Ther, 2003, 74 (4), 380-387.
49. Pedersen, R. S.; Brasch-Andersen, C.; Sim, S. C.; Bergmann, T. K.; Halling, J.; Petersen, M. S.; Weihe, P.; Edvardsen, H.; Kristensen, V. N.; Brosen, K.; Ingelman-Sundberg, M. Linkage disequilibrium between the CYP2C19*17 allele and wildtype CYP2C8 and CYP2C9 alleles: identification of CYP2C haplotypes in healthy Nordic populations. Eur. J. Clin. Pharmacol, 2010, 66 (12), 1199-205.
50. Tomalik-Scharte, D.; Fuhr, U.; Hellmich, M.; Frank, D.; Doroshyenko, O.; Jetter, A.; Stingl, J. C. Effect of the CYP2C8 genotype on the pharmacokinetics and pharmacodynamics of repaglinide. Drug metabolism and disposition: the biological fate of chemicals, 2011, 39 (5), 927-32.
51. Leskela, S.; Jara, C.; Leandro-Garcia, L. J.; Martinez, A.; Garcia-Donas, J.; Hernando, S.; Hurtado, A.; Vicario, J. C.; Montero-Conde, C.; Landa, I.; Lopez-Jimenez, E.; Cascon, A.; Milne, R. L.; Robledo, M.; Rodriguez-Antona, C. Polymorphisms in cytochromes P450 2C8 and 3A5 are associated with paclitaxel neurotoxicity. The pharmacogenomics journal, 2011, 11 (2), 121-9.
52. Rowbotham, S. E.; Boddy, A. V.; Redfern, C. P.; Veal, G. J.; Daly, A. K. Relevance of nonsynonymous CYP2C8 polymorphisms to 13-cis retinoic acid and paclitaxel hydroxylation. Drug metabolism and disposition: the biological fate of chemicals, 2010, 38 (8), 1261-6.
53. Ishikawa, C.; Ozaki, H.; Nakajima, T.; Ishii, T.; Kanai, S.; Anjo, S.; Shirai, K.; Inoue, I. A frameshift variant of CYP2C8 was identified in a patient who suffered from rhabdomyolysis after administration of cerivastatin. J. Hum. Genet, 2004, 49 (10), 582-5.
54. Kaspera, R.; Naraharisetti, S. B.; Tamraz, B.; Sahele, T.; Cheesman, M. J.; Kwok, P. Y.; Marciante, K.; Heckbert, S. R.; Psaty, B. M.; Totah, R. A. Cerivastatin in vitro metabolism by CYP2C8 variants found in patients experiencing rhabdomyolysis. Pharmacogenetics and genomics, 2010, 20 (10), 619-29.
55. Kaspera, R.; Naraharisetti, S. B.; Evangelista, E. A.; Marciante, K. D.; Psaty, B. M.; Totah, R. A. Drug metabolism by CYP2C8. 3 is determined by substrate dependent interactions with cytochrome P450 reductase and cytochrome b5. Biochem. Pharmacol, 2011, 82 (6), 681-691.
56. Lopez-Rodriguez, R.; Novalbos, J.; Gallego-Sandin, S.; Roman-Martinez, M.; Torrado, J.; Gisbert, J. P.; Abad-Santos, F. Influence of CYP2C8 and CYP2C9 polymorphisms on pharmacokinetic and pharmacodynamic parameters of racemic and enantiomeric forms of ibuprofen in healthy volunteers. Pharmacological research: the official journal of the Italian Pharmacological Society, 2008, 58 (1), 77-84.
57. 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 drugdrug interactions. Xenobiotica; the fate of foreign compounds in biological systems, 2010, 40 (7), 467-75.
58. Nakajima, M.; Fujiki, Y.; Noda, K.; Ohtsuka, H.; Ohkuni, H.; Kyo, S.; Inoue, M.; Kuroiwa, Y.; Yokoi, T. Genetic polymorphisms of CYP2C8 in Japanese population. Drug metabolism and disposition: the biological fate of chemicals, 2003, 31 (6), 687-90.
59. Klose, T. S.; Blaisdell, J. A.; Goldstein, J. A. Gene structure of CYP2C8 and extrahepatic distribution of the human CYP2Cs. J. Biochem. Mol. Toxicol, 1999, 13 (6), 289-295.
60. Agundez, J. A. G.; Garcia-Martin, E.; Martinez, 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 Opinion on Drug Metabolism & Toxicology, 2009, 5 (6), 607-620.
61. Wang, L.-L.; Li, Y.; Zhou, S.-F. A Bioinformatics Approach for the Phenotype Prediction of Nonsynonymous Single Nucleotide Polymorphisms in Human Cytochromes P450. Drug Metab. Disposition, 2009, 37 (5), 977-991.
62. Gil, J. P.; Gil Berglund, E. CYP2C8 and antimalaria drug efficacy. Pharmacogenomics, 2007, 8 (2), 187-98.
63. Chang, C. C.; Lin, P. C.; Lin, C. H.; Yeh, K. T.; Hung, H. Y.; Chang, J. G. Rapid identification of CYP2C8 polymorphisms by high resolution melting analysis. Clin. Chim. Acta, 2012, 413 (1-2), 298-302.
64. Solus, J. F.; Arietta, B. J.; Harris, J. R.; Sexton, D. P.; Steward, J. Q.; McMunn, C.; Ihrie, P.; Mehall, J. M.; Edwards, T. L.; Dawson, E. P. Genetic variation in eleven phase I drug metabolism genes in an ethnically diverse population. Pharmacogenomics, 2004, 5 (7), 895-931.
65. Dorado, P.; Cavaco, I.; Caceres, M. C.; Piedade, R.; Ribeiro, V.; Llerena, A. Relationship between CYP2C8 genotypes and diclofenac 5-hydroxylation in healthy Spanish volunteers. Eur. J. Clin. Pharmacol, 2008, 64 (10), 967-70.
66. Jernstrom, H.; Bageman, E.; Rose, C.; Jonsson, P. E.; Ingvar, C. CYP2C8 and CYP2C9 polymorphisms in relation to tumour characteristics and early breast cancer related events among 652 breast cancer patients. Br. J. Cancer, 2009, 101 (11), 1817-23.
67. Garcia-Martin, E.; Martinez, C.; Tabares, B.; Frias, J.; Agundez, J. A. Interindividual variability in ibuprofen pharmacokinetics is related to interaction of cytochrome P450 2C8 and 2C9 amino acid polymorphisms. Clin. Pharmacol. Ther, 2004, 76 (2), 119-27.
68. Rodenburg, E. M.; Visser, L. E.; Danser, A. H.; Hofman, A.; van Noord, C.; Witteman, J. C.; Uitterlinden, A. G.; Stricker, B. H. Genetic variance in CYP2C8 and increased risk of myocardial infarction. Pharmacogenetics and genomics, 2010, 20 (7), 426-34.
69. Haschke-Becher, E.; Kirchheiner, J.; Trummer, O.; Gruenbacher, G.; Kainz, A.; Boehm, B. O.; Maerz, W.; Renner, W. Impact of CYP2C8 and 2C9 polymorphisms on coronary artery disease and myocardial infarction in the LURIC cohort. Pharmacogenomics, 2010, 11 (10), 1359-1365.
70. Teh, L. K.; Zahri, M. K.; Zakaria, Z. A.; Ismail, R.; Salleh, M. Z. Mutational analysis of CYP2C8 in hypertensive patients using denaturing high performance liquid chromatography. J. Clin. Phar. Ther, 2010, 35 (6), 723-8.
71. Dreisbach, A. W.; Japa, S.; Sigel, A.; Parenti, M. B.; Hess, A. E.; Srinouanprachanh, S. L.; Rettie, A. E.; Kim, H.; Farin, F. M.; Hamm, L. L.; Lertora, J. J. The Prevalence of CYP2C8, 2C9, 2J2, and soluble epoxide hydrolase polymorphisms in African Americans with hypertension. Am. J. Hypertens, 2005, 18 (10), 1276-81.
72. Lee, C. R.; North, K. E.; Bray, M. S.; Couper, D. J.; Heiss, G.; Zeldin, D. C. CYP2J2 and CYP2C8 polymorphisms and coronary heart disease risk: the Atherosclerosis Risk in Communities (ARIC) study. Pharmacogenetics and genomics, 2007, 17 (5), 349-358.
73. Durrmeyer, X.; Hovhannisyan, S.; Medard, Y.; Jacqz-Aigrain, E.; Decobert, F.; Barre, J.; Alberti, C.; Aujard, Y.; Danan, C.; Baud, O. Are cytochrome P450 CYP2C8 and CYP2C9 polymorphisms associated with ibuprofen response in very preterm infants? PLoS ONE, 2010, 5 (8), e12329.
74. Blanco, G.; Martinez, C.; Ladero, J. M.; Garcia-Martin, E.; Taxonera, C.; Gamito, F. G.; Diaz-Rubio, M.; Agundez, J. A. G. Interaction of CYP2C8 and CYP2C9 genotypes modifies the risk for nonsteroidal anti-inflammatory drugs-related acute gastrointestinal bleeding. Pharmacogenetics and genomics, 2008, 18 (1), 37-43.
75. Smith, H. E.; Jones, J. P., 3rd; Kalhorn, T. F.; Farin, F. M.; Stapleton, P. L.; Davis, C. L.; Perkins, J. D.; Blough, D. K.; Hebert, M. F.; Thummel, K. E.; Totah, R. A. Role of cytochrome P450 2C8 and 2J2 genotypes in calcineurin inhibitor-induced chronic kidney disease. Pharmacogenetics and genomics, 2008, 18 (11), 943-53.
76. Sarasquete, M. E.; Garcia-Sanz, R.; Marin, L.; Alcoceba, M.; Chillon, M. C.; Balanzategui, A.; Santamaria, C.; Rosinol, L.; de la Rubia, J.; Hernandez, M. T.; Garcia-Navarro, I.; Lahuerta, J. J.; Gonzalez, M.; San Miguel, J. F. Bisphosphonate-related osteonecrosis of the jaw is associated with polymorphisms of the cytochrome P450 CYP2C8 in multiple myeloma: a genome-wide single nucleotide polymorphism analysis. Blood, 2008, 112 (7), 2709-12.
77. Martinez, C.; Garcia-Martin, E.; Alonso-Navarro, H.; Jimenez-Jimenez, F. J.; Benito-Leon, J.; Garcia-Ferrer, I.; Vazquez-Torres, P.; Puertas, I.; Zurdo, J. M.; Lopez-Alburquerque, T.; Agundez, J. A. G. Changes at the CYP2C locus and disruption of CYP2C8/9 linkage disequilibrium in patients with essential tremor. Neuromolecular Med, 2007, 9 (2), 195-204.
78. Honkalammi, J.; Niemi, M.; Neuvonen, P. J.; Backman, J. T. Mechanism-based inactivation of CYP2C8 by gemfibrozil occurs rapidly in humans. Clin. Pharmacol. Ther, 2011, 89 (4), 579-86.
79. Tornio, A.; Neuvonen, P. J.; Backman, J. T. The CYP2C8 inhibitor gemfibrozil does not increase the plasma concentrations of zopiclone. Eur. J. Clin. Pharmacol, 2006, 62 (8), 645-51.
80. Wang, A.; Yu, B. N.; Luo, C. H.; Tan, Z. R.; Zhou, G.; Wang, L. S.; Zhang, W.; Li, Z.; Liu, J.; Zhou, H. H. Ile118Val genetic polymorphism of CYP3A4 and its effects on lipid-lowering efficacy of simvastatin in Chinese hyperlipidemic patients. Eur. J. Clin. Pharmacol, 2005, 60 (12), 843-848.
81. Jaakkola, T.; Backman, J. T.; Neuvonen, M.; Niemi, M.; Neuvonen, P. J. Montelukast and zafirlukast do not affect the pharmacokinetics of the CYP2C8 substrate pioglitazone. Eur. J. Clin. Pharmacol, 2006, 62 (7), 503-9.
82. Yang, T. J.; Shou, M.; Korzekwa, K. R.; Gonzalez, F. J.; Gelboin, H. V.; Yang, S. K. Role of cDNA-expressed human cytochromes P450 in the metabolism of diazepam. Biochem. Pharmacol, 1998, 55 (6), 889-896.
83. Naik, H.; Wu, J. T.; Palmer, R.; McLean, L. The Effects of Febuxostat on the Pharmacokinetic Parameters of Rosiglitazone, A CYP2C8 Substrate. Br. J. Clin. Pharmacol, 2012.
84. Turpeinen, M.; Tolonen, A.; Chesne, C.; Guillouzo, A.; Uusitalo, J.; Pelkonen, O. Functional expression, inhibition and induction of CYP enzymes in HepaRG cells. Toxicology in vitro: an international journal published in association with BIBRA, 2009, 23 (4), 748-53.
85. Dravid, P. V.; Frye, R. F. Determination of N-desethylamodiaquine by hydrophilic interaction liquid chromatography with tandem mass spectrometry: application to in vitro drug metabolism studies. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 2008, 863 (1), 129-34.
86. Muschler, E.; Lal, J.; Jetter, A.; Rattay, A.; Zanger, U.; Zadoyan, G.; Fuhr, U.; Kirchheiner, J. The Role of Human CYP2C8 and CYP2C9 Variants in Pioglitazone Metabolism In vitro. Basic Clin. Pharmacol. Toxicol, 2009, 105 (6), 374-379.
87. Bidstrup, T. B.; Bjornsdottir, I.; Sidelmann, U. G.; Thomsen, M. S.; Hansen, K. T. CYP2C8 and CYP3A4 are the principal enzymes involved in the human in vitro biotransformation of the insulin secretagogue repaglinide. Br. J. Clin. Pharmacol, 2003, 56 (3), 305-314.
88. Niemi, M.; Backman, J. T.; Neuvonen, P. J. Effects of trimethoprim and rifampin on the pharmacokinetics of the cytochrome P450 2C8 substrate rosiglitazone. Clin. Pharmacol. Ther, 2004, 76 (3), 239-49.
89. Glowka, F.; Karazniewicz-Lada, M.; Grzeskowiak, E.; Rogozinska, D.; Romanowski, W. Clinical pharmacokinetics of ketoprofen enantiomers in wild type of Cyp 2c8 and Cyp 2c9 patients with rheumatoid arthritis. Eur. J. Drug Metab. Pharmacokinet, 2011.
90. Nebot, N.; Crettol, S.; d'Esposito, F.; Tattam, B.; Hibbs, D. E.; Murray, M. Participation of CYP2C8 and CYP3A4 in the Ndemethylation of imatinib in human hepatic microsomes. Br. J. Pharmacol, 2010, 161 (5), 1059-69.
91. Prakash, C.; Wang, W.; O'Connell, T.; Johnson, K. A. CYP2C8-and CYP3A-mediated C-demethylation of (3-{[(4-tertbutylbenzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenoxy)-ac etic acid (CP-533, 536), an EP2 receptor-selective prostaglandin E2 agonist: characterization of metabolites by high-resolution liquid chromatography-tandem mass spectrometry and liquid chromatography/mass spectrometry-nuclear magnetic resonance. Drug metabolism and disposition: the biological fate of chemicals, 2008, 36 (10), 2093-103.
92. Tang, L.; Ye, L.; Lv, C.; Zheng, Z.; Gong, Y.; Liu, Z. Involvement of CYP3A4/5 and CYP2D6 in the metabolism of aconitine using human liver microsomes and recombinant CYP450 enzymes. Toxicol. Lett, 2011, 202 (1), 47-54.
93. Salminen, K. A.; Meyer, A.; Jerabkova, L.; Korhonen, L. E.; Rahnasto, M.; Juvonen, R. O.; Imming, P.; Raunio, H. Inhibition of human drug metabolizing cytochrome P450 enzymes by plant isoquinoline alkaloids. Phytomedicine: international journal of phytotherapy and phytopharmacology, 2011, 18 (6), 533-8.
94. Peiró, A. M.; Novalbos, J.; Zapater, P.; Moreu, R.; López-Rodríguez, R.; Rodríguez, V.; Abad-Santos, F.; Horga, J. F. Pharmacogenetic relevance of the CYP2C9*3 allele in a tenoxicam bioequivalence study performed on Spaniards. Pharmacol. Res, 2009, 59 (1), 62-68.
95. Doehmer, J.; Weiss, G.; McGregor, G. P.; Appel, K. Assessment of a dry extract from milk thistle (Silybum marianum) for interference with human liver cytochrome-P450 activities. Toxicology in vitro: an international journal published in association with BIBRA, 2011, 25 (1), 21-7.
96. Filppula, A. M.; Laitila, J.; Neuvonen, P. J.; Backman, J. T. Reevaluation of the microsomal metabolism of montelukast: major contribution by CYP2C8 at clinically relevant concentrations. Drug metabolism and disposition: the biological fate of chemicals, 2011, 39 (5), 904-11.
97. Baer, B. R.; DeLisle, R. K.; Allen, A. Benzylic Oxidation of Gemfibrozil-1-O-beta-Glucuronide by P450 2C8 Leads to Heme Alkylation and Irreversible Inhibition. Chem. Res. Toxicol, 2009, 22 (7), 1298-1309.
98. Tornio, A.; Niemi, M.; Neuvonen, P. J.; Backman, J. T. Trimethoprim and the CYP2C8*3 allele have opposite effects on the pharmacokinetics of pioglitazone. Drug metabolism and disposition: the biological fate of chemicals, 2008, 36 (1), 73-80.
99. Doehmer, J.; Tewes, B.; Klein, K. U.; Gritzko, K.; Muschick, H.; Mengs, U. Assessment of drug-drug interaction for silymarin. Toxicology in vitro: an international journal published in association with BIBRA, 2008, 22 (3), 610-7.
100. Tornio, A.; Pasanen, M. K.; Laitila, J.; Neuvonen, P.; Backman, J. T. Comparison of 3-hydroxy-3-methylglutaryl coenzyme A (HMGCoA) reductase inhibitors (statins) as inhibitors of cytochrome P4502C8. Basic Clin. Pharmacol. Toxicol, 2005, 97 (2), 104-108.
101. Niemi, M.; Kajosaari, L. I.; Neuvonen, M.; Backman, J. T.; Neuvonen, P. J. The CYP2C8 inhibitor trimethoprim increases the plasma concentrations of repaglinide in healthy subjects. Br. J. Clin. Pharmacol, 2004, 57 (4), 441-7.
102. Backman, J. T.; Honkalammi, J.; Neuvonen, M.; Kurkinen, K. J.; Tornio, A.; Niemi, M.; Neuvonen, P. J. CYP2C8 activity recovers within 96 hours after gemfibrozil dosing: estimation of CYP2C8 half-life using repaglinide as an in vivo probe. Drug metabolism and disposition: the biological fate of chemicals, 2009, 37 (12), 2359-66.
103. Zhang, W.; Dutschman, G. E.; Li, X.; Cheng, Y.-C. Quantitation of paclitaxel and its two major metabolites using a liquid chromatography-electrospray ionization tandem mass spectrometry. J. Chromatogr. B, 2011, 879 (22), 2018-2022.
104. Alexander, M. S.; Kiser, M. M.; Culley, T.; Kern, J. R.; Dolan, J. W.; McChesney, J. D.; Zygmunt, J.; Bannister, S. J. Measurement of paclitaxel in biological matrices: high-throughput liquid chromatographic-tandem mass spectrometric quantification of paclitaxel and metabolites in human and dog plasma. Journal of Chromatography B-Analytical Technologies in the Biomedical and Life Sciences, 2003, 785 (2), 253-261.
105. Lau, T. K.; Leachman, D. R.; Lufschanowski, R. Severe rhabdomyolysis associated with the cerivastatin-gemfibrozil combination therapy-Report of a case. Tex. Heart Inst. J, 2001, 28 (2), 142-145.
106. Lucas, R. A.; Weathersby, B. B.; Rocco, V. K.; Pepper, J. M.; Butler, K. L. Rhabdomyolysis associated with cerivastatin: Six cases within 3 months at one hospital. Pharmacotherapy, 2002, 22 (6), 771-774.
107. Karonen, T.; Neuvonen, P. J.; Backman, J. T. The CYP2C8 inhibitor gemfibrozil does not affect the pharmacokinetics of zafirlukast. Eur. J. Clin. Pharmacol, 2011, 67 (2), 151-5.
108. Kim, K. A.; Park, P. W.; Kim, K. R.; Park, J. Y. Effect of multiple doses of montelukast on the pharmacokinetics of rosiglitazone, a CYP2C8 substrate, in humans. Br. J. Clin. Pharmacol, 2007, 63 (3), 339-45.
109. Amlani, S.; Nadarajah, T.; McIvor, R. A. Montelukast for the treatment of asthma in the adult population. Expert opinion on pharmacotherapy, 2011, 12 (13), 2119-28.
110. Karonen, T.; Filppula, A.; Laitila, J.; Niemi, M.; Neuvonen, P. J.; Backman, J. T. Gemfibrozil markedly increases the plasma concentrations of montelukast: a previously unrecognized role for CYP2C8 in the metabolism of montelukast. Clin. Pharmacol. Ther, 2010, 88 (2), 223-30.