Oxidation of celecoxib by polymorphic cytochrome P450 2C9 and alcohol dehydrogenase

British Journal of Clinical Pharmacology

Volumn 54, Issue 4, 2002, Pages 423-429

  Sandberg, Mia ^a   Yasar, Ümit ^a   Strömberg, Patrik ^b   Höög, Jan Olov ^b   Eliasson, Erik ^a  

^a KAROLINSKA UNIVERSITY HOSPITAL   (Sweden)

^b KAROLINSKA INSTITUTE   (Sweden)

Author keywords

Adverse drug reactions; Alcohol dehydrogenase; COX 2 inhibitors; Cytochrome P450; Drug metabolism; Genetic polymorphism

Indexed keywords

ALCOHOL DEHYDROGENASE; CARBOXYCELECOXIB; CELECOXIB; CYTOCHROME P450 2C9; DRUG METABOLITE; HYDROXYCELECOXIB; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DNA VECTOR; DRUG HYDROXYLATION; DRUG METABOLISM; DRUG OXIDATION; ENZYME ACTIVITY; ENZYME POLYMORPHISM; GENETIC VARIABILITY; GENOTYPE; HUMAN; HUMAN CELL; HUMAN TISSUE; LIVER CYTOSOL; LIVER MICROSOME; NONHUMAN; PRIORITY JOURNAL; YEAST;

ALCOHOL DEHYDROGENASE; ANALYSIS OF VARIANCE; ARYL HYDROCARBON HYDROXYLASES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOOXYGENASE INHIBITORS; HUMANS; HYDROXYLATION; MICROSOMES, LIVER; OXIDATION-REDUCTION; POLYMORPHISM, GENETIC; PYRAZOLES; SULFONAMIDES;

EID: 0036431725     PISSN: 03065251     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1365-2125.2002.01660.x     Document Type: Article

References (25)

1. Vane JR, Warner TD. Nomenclature for COX-2 inhibitors. Lancet 2000; 356: 1373-1374.
2. Brooks PM, Day RO. COX-2 inhibitors. Med J Aust 2000; 173: 433-436.
3. Davies NM, McLachlan AJ, Day RO, Williams KM. Clinical pharmacokinetics and pharmacodynamics of celecoxib: A selective cyclo-oxygenase-2 inhibitor. Clin Pharmacokinet 2000; 38: 225-242.
4. Paulson SK, Hribar JD, Liu NW, et al. Metabolism and excretion of [(14) C]celecoxib in healthy male volunteers. Drug Metab Dispos 2000; 28: 308-314.
5. Tang C, Shou M, Mei Q, Rushmore TH, Rodrigues AD. Major role of human liver microsomal cytochrome P450 2C9 (CYP2C9) in the oxidative metabolism of celecoxib, a novel cyclooxygenase-II inhibitor. J Pharmacol Exp Ther 2000; 293: 453-459.
6. Miners JO, Birkett DJ. Cytochrome P4502C9: An enzyme of major importance in human drug metabolism. Br J Clin Pharmacol 1998; 45: 525-538.
7. Yasar Ü, Eliasson E, Dahl ML, et al. Validation of methods for CYP2C9 genotyping: Frequencies of mutant alleles in a Swedish population [published erratum appears in Biochem Biophys Res Commun 1999; 258 (April): 227]. Biochem Biophys Res Commun 1999; 254: 628-631.
8. Takanashi K, Tainaka H, Kobayashi K, et al. CYP2C9 Ile359 and Leu359 variants: Enzyme kinetic study with seven substrates. Pharmacogenetics 2000; 10: 95-104.
9. Yasar Ü, Tybring G, Hidestrand M, et al. The role of CYP2C9 polymorphism in losartan oxidation. Drug Metab Dispos 2001; 29: 1051-1056.
10. Odani A, Hashimoto Y, Otsuki Y, et al. Genetic polymorphism of the CYP2C subfamily and its effect on the pharmacokinetics of phenytoin in Japanese patients with epilepsy. Clin Pharmacol Ther 1997; 62: 287-292.
11. Aithal GP, Day CP, Kesteven PJ, Daly AK. Association of polymorphisms in the cytochrome P450 CYP2C9 with warfarin dose requirement and risk of bleeding complications. Lancet 1999; 353: 717-719.
12. Rettie AE, Haining RL, Bajpai M, Levy RH. A common genetic basis for idiosyncratic toxicity of warfarin and phenytoin. Epilepsy Res 1999; 35: 253-255.
13. von Bahr C, Groth CG, Jansson H, et al. Drug metabolism in human liver in vitro: Establishment of a human liver bank. Clin Pharmacol Ther 1980; 27: 711-725.
14. Strömberg P, Svensson S, Hedberg JJ, Nordling E, Höög J-O. Identification and characterisation of two allelic forms of human alcohol dehydrogenase 2. Cell Mol Life Sci 2002; 59: 552-559.
15. Duester G, Felder M, Holmes R, Höög J-O, Parés X. Recommended nomenclature for the vertebrate alcohol dehydrogenase gene family. Biochem Pharmacol 1999; 58: 389-395.
16. Hedberg JJ, Strömberg P, Höög J-O. An attempt to transform class characteristics within the alcohol dehydrogenase family. FEBS Lett 1998; 436: 67-70.
17. Werner U, Werner D, Pahl A, et al. Investigation of the pharmacokinetics of celecoxib by liquid chromatography-mass spectrometry. Biomed Chromatogr 2002; 16: 56-60.
18. Bloomer JC, Baldwin SJ, Smith GJ, et al. Characterisation of the cytochrome P450 enzymes involved in the in vitro metabolism of granisetron. Br J Clin Pharmacol 1994; 38: 557-566.
19. Newton DJ, Wang RW, Lu AY. Cytochrome P450 inhibitors. Evaluation of specificities in thein vitrometabolism of therapeutic agents by human liver microsomes. Drug Metab Dispos 1995; 23: 154-158.
20. Yamazaki H, Shimada T. Comparative studies ofin vitro inhibition of cytochrome P450 3A4- dependent testosterone 6beta-hydroxylation by roxithromycin and its metabolites, troleandomycin, and erythromycin. Drug Metab Dispos 1998; 26: 1053-1057.
21. Tang C, Shou M, Rushmore TH, et al. In vitro metabolism of celecoxib, a cyclooxygenase-2 inhibitor, by allelic variant forms of human liver microsomal cytochrome P450 2C9: Correlation with CYP2C9 genotype and in vivo pharmacokinetics. Pharmacogenetics 2001; 11: 223-235.
22. Edenberg HJ, Bosron WF. In Alcohol Dehydrogenases Comprehensive Toxicology, Vol. 3 ed. Guengerich FP. Pergamon Press, New York: 1997; 119-131.
23. Jörnvall H, Höög J-H, Persson B, Parés X. Pharmacogenetics of the Alcohol Dehydrogenase System. Pharmacology 2000; 61: 184-191.
24. Eisses KT. Differences in teratogenic and toxic properties of alcohol dehydrogenase inhibitors pyrazole and 4-methylpyrazole in Drosophila melanogaster. I. ADH allozymes in variable genetic backgrounds. Teratog Carcinog Mutagen 1995; 15: 1-10.
25. Penning TD, Talley JJ, Bertenshaw SR, et al. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib). J Med Chem 1997; 40: 1347-1365.