Cytochrome P4502C9: An enzyme of major importance in human drug metabolism

British Journal of Clinical Pharmacology

Volumn 45, Issue 6, 1998, Pages 525-538

  Miners, John O ^a   Birkett, Donald J ^a  

^a FLINDERS MEDICAL CENTRE   (Australia)

Author keywords

CYP2C9; Cytochrome P450; Drug interactions; Drug metabolism; Pharmacogenetics

Indexed keywords

AMIODARONE; CARBAMAZEPINE; CYTOCHROME P450; CYTOCHROME P450 2C9; DRUG METABOLIZING ENZYME; FLUCONAZOLE; FLUOXETINE; LOSARTAN; NONSTEROID ANTIINFLAMMATORY AGENT; PHENYLBUTAZONE; PHENYTOIN; RIFAMPICIN; SULFAPHENAZOLE; SULFINPYRAZONE; SULFONAMIDE; TOLBUTAMIDE; TORASEMIDE; UNCLASSIFIED DRUG; WARFARIN;

DRUG METABOLISM; ENZYME ACTIVITY; ENZYME INDUCTION; ENZYME INHIBITION; ENZYME METABOLISM; ENZYME STRUCTURE; ENZYME SUBSTRATE; HUMAN; PHARMACOGENETICS; PRIORITY JOURNAL; PROTEIN EXPRESSION; REVIEW;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ARYL HYDROCARBON HYDROXYLASES; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INDUCTION; ENZYME REPRESSION; HUMANS; PHARMACEUTICAL PREPARATIONS; PHENYTOIN; STEROID 16-ALPHA-HYDROXYLASE; STEROID HYDROXYLASES; SUBSTRATE SPECIFICITY; SULFONAMIDES; TOLBUTAMIDE; WARFARIN;

EID: 0031841377     PISSN: 03065251     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1365-2125.1998.00721.x     Document Type: Review

References (154)

1. Nelson DR, Koymans L, Kamataki T, et al. P450 superfamily: Update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics 1996; 6: 1-42.
2. Wrighton SA, Stevens JC. The human hepatic cytochromes P450 involved in drug metabolism. Crit Rev Toxicol 1992; 22: 1-21.
3. Gonzalez FJ. Human cytochromes P450: Problems and prospects. Trends Pharmacol Sci 1992; 13: 346-352.
4. Cholerton S, Daly AK, Idle JR. The role of individual human cytochromes P450 in drug metabolism and clinical response. Trends Pharmacol Sci 1992; 13: 434-439.
5. Gonzalez FJ. Molecular genetics of the P450 superfamily. Pharmacol Ther 1990; 45: 1-38.
6. Miners JO, Veronese ME, Birkett DJ. In vitro approaches for the prediction of human drug metabolism. Ann Reports Med Chem 1994; 29: 307-316.
7. Birkett DJ, Mackenzie PI, Veronese ME, Miners JO. In vitro approaches can predict human drug metabolism. Trends Pharmacol Sci 1993; 14: 292-294.
8. Ged C, Umbenhauer DR, Bellew TM, et al. Characterization of cDNAs, mRNAs and proteins related to human liver microsomal cytochrome P450 (S)-mephenytoin 4′ -hydroxylase. Biochemistry 1988; 27: 6929-6940.
9. Goldstein JA, de Morais SMF. Biochemistry and molecular biology of the human CYP2C subfamily. Pharmacogenetics 1994; 4: 285-299.
10. Wang P, Beaune P, Kaminsky LS, et al. Purification and characterization of six cytochrome P450 isozymes from human liver microsomes. Biochemistry 1983; 22: 5375-5383.
11. Shimada T, Misono KS, Guengerich FP. Human liver microsomal cytochrome P450 mephenytoin 4′ -hydroxylase, a prototype genetic polymorphism of drug metabolism: Purification and characterization of two similar forms involved in the reaction. J Biol Chem 1986; 261: 909-921.
12. Kimura S, Pastewka J, Gelboin HV, Gonzalez FJ. cDNA and amino acid sequences of two members of the human IIC gene subfamily. Nucleic Acids Res 1987; 15: 10053-10054.
13. Meehan RR, Gosden JR, Rout D, et al. Human cytochrome P450 PB-1: A multigene family involved in mephenytoin and steroid oxidations that maps to chromosome 10. Am J Human Genet 1988; 42: 26-37.
14. Romkes M, Faletto MB, Blaisdell JA, Raucy JL, Goldstein JA. Cloning and expression of complementary DNAs for multiple members of the human cytochrome P450 IIC subfamily. Biochemistry 1991; 30: 3247-3255.
15. Veronese ME, Doecke CJ, Mackenzie PI, et al. Site-directed mutation studies of human liver cytochrome P450 isoenzymes in the CYP2C subfamily. Biochem J 1993; 289: 533-538.
16. Umbenhauer DR, Martin MV, Lloyd RS, Guengerich FP. Cloning and sequence determination of a complementary DNA related to human liver microsomal cytochrome P450 S-mephenytoin 4′ -hydroxylase. Biochemistry 1987; 26: 1094-1099.
17. Yasumori TS, Kawano K, Nagata M, Shimada Y, Yamazoe Y, Kato R. Nucleotide sequence of a human liver cytochrome P450 related to the male rat specific form. J Biochem (Tokyo) 1987; 102: 1075-1082.
18. Gotoh O. Substrate recognition sites in cytochrome P-450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. J Biol Chem 1992; 267: 83-90.
19. Wong BK, Goldstein J, Spielberg SP, Rushmore TH. Characterisation of an in vitro model for assessing polymorphic metabolism by CYP2C9: Involvement in the mechanism of deficient losartan metabolism. ISSX Proceedings 1996; 10: 236.
20. Haining RF, Jones JP, Koop DR, Trager WF, Rettie AE. Determinants of substrate and inhibitor specificities of human CYP2C9. ISSX Proceedings 1996; 10: 239.
21. Korzekwa K, Jones JP. Predicting the cytochrome P450 mediated metabolism of xenobiotics. Pharmacogenetics 1993; 3: 1-18.
22. Mancy A, Broto P, Dijols S, Dansette PM, Mansuy D. The substrate binding site of human liver cytochrome P4502C9: An approach using designed tienilic acid derivatives and molecular modeling. Biochemistry 1995; 34: 10365-10375.
23. Jones BC, Hawksworth G, Horne VA, et al. Putative active site model for cytochrome P4502C9 (tolbutamide hydroxylase). Drug Metab Dispos 1996; 24: 260-266.
24. Jones JP, He M, Trager WF, Rettie AE. Three dimensional quantitative structure-activity relationship for inhibitors of cytochrome P4502C9. Drug Metab Dispos 1996; 24: 1-6.
25. Shou M, Krausz KW, Gonzalez FJ, Gelboin HV. Metabolic activation of the potent carcinogen dibenzo[a,h]anthracene by cDNA-expressed human cytochromes P450. Arch Biochem Biophys 1996; 238: 201-207.
26. Gautier J-C, Lecoeur S, Cosme J, et al. Contribution of human cytochrome P450 to benzo[a]pyrene and benzo[a]pyrene-7, 8-dihydrodiol metabolism, as predicted from heterologous expression in yeast. Pharmacogenetics 1996; 6: 489-499.
27. Miners JO, Smith KJ, Robson RA, McManus ME, Veronese ME, Birkett DJ. Tolbutamide hydroxylation by human liver microsomes: Kinetic characterisation and relationship to other cytochrome P450 dependent xenobiotic oxidations. Biochem Pharmacol 1988; 37: 1137-1144.
28. Back DJ, Tjia JF, Karbwang J, Colberg J. In vitro inhibition studies of tolbutamide hydroxylase activity of human liver microsomes by azoles, sulphonamides and quinolones. Br J Clin Pharmacol 1988; 25: 23-29.
29. Veronese ME, Mackenzie PI, Doecke CJ, McManus ME, Miners JO, Birkett DJ. Tolbutamide and phenytoin hydroxylations by cDNA-expressed human liver cytochrome P4502C9. Biochem Biophys Res Commun 1991; 175: 1112-1118.
30. Miners JO, Birkett DJ. The use of tolbutamide as a substrate probe for human hepatic cytochrome P4502C9. Methods Enzymol 1996; 272: 139-145.
31. Baldwin SJ, Bloomer JC, Smith GJ, Ayrton AD, Clarke SE, Chenery RJ. Ketoconazole and sulphaphenazole as the respective selective inhibitors of P4503A and 2C9. Xenobiotica 1995; 25: 261-270.
32. Veronese ME, Miners JO, Randles D, Birkett DJ. Validation of the tolbutamide metabolic ratio for population screening with use of sulphaphenazole to produce model phenotypic poor metabolisers. Clin Pharmacol Ther 1990; 47: 403-411.
33. Back DJ, Tjia J, Ohnhaus EE, Park BK. Selective inhibition of drug oxidation after simultaneous administration of two probe drugs, antipyrine and tolbutamide. Eur J Clin Pharmacol 1998; 34: 157-163.
34. Pond SM, Birkett DJ, Wade DN. Mechanisms of inhibition of tolbutamide metabolism: phenylbutazone, oxyphenbutazone, sulphaphenazole. Clin Pharmacol Ther 1977; 22: 573-579.
35. Thomas RC, Ikeda GJ. The metabolic fate of tolbutamide in man and in the rat. J Med Chem 1966; 9: 507-510.
36. Nelson E, O'Reilly I. Kinetics of carboxytolbutamide excretion following tolbutamide and carboxytolbutamide administration. J Pharmacol Exp Ther 1961; 132: 103-109.
37. Doecke CJ, Veronese ME, Pond SM, et al. Relationship between phenytoin and tolbutamide hydroxylations in human liver microsomes. Br J Clin Pharmacol 1991; 31: 125-130.
38. Miners JO, Rees DLP, Valente L, Veronese ME, Birkett DJ. Human hepatic cytochrome P4502C9 catalyzes the rate-limiting pathway of torsemide metabolism. J Pharmacol Exp Ther 1995; 272: 1076-1081.
39. Relling MV, Aoyama T, Gonzalez FJ, Meyer UA. Tolbutamide and mephenytoin hydroxylation by human cytochromes P450 in the CYP2C subfamily. J Pharmacol Exp Ther 1990; 252: 442-447.
40. Tassaneeyakul W. PhD Thesis, Flinders University of South Australia 1994.
41. Dickinson RG, Hooper WD, Patterson M, Eadìe MJ, Maguire B. Extent of urinary excretion of p-hydroxyphenytoin in healthy subjects given phenytoin. Ther Drug Monit 1985; 7: 283-289.
42. Molholm-Hansen J, Kampmann JP, Siersbaek-Nielsen K, et al. The effect of different sulphonamides on phenytoin metabolism in man. Acta Med Scand 1979; suppl 624: 106-110.
43. Hall SD, Hamman MA, Rettie AE, et al. Relationships between the levels of cytochrome P4502C9 and its prototypic catalytic activities in human liver microsomes. Drug Metab Dispos 1994; 22: 975-978.
44. Tassaneeyakul W, Veronese ME, Birkett DJ, et al. Co-regulation of phenytoin and tolbutamide metabolism in humans. Br J Clin Pharmacol 1992; 34: 494-498.
45. Toon S, Low LK, Gibaldi M, et at. The warfarin-sulfinpyrazole interaction: stereochemical considerations. Clin Pharmacol Ther 1986; 39: 15-24.
46. Rettie AE, Korzekwa KR, Kunze KL, Lawrence RF, Eddy AC, Aoyama T, Gelboin HV, Gonzalez FJ, Trager WF. Hydroxylation of warfarin by human cDNA-expressed cytochrome P450: A role for P4502C9 in the etiology of (S)-warfarin drug interactions. Chem Res Toxicol 1992; 5: 54-59.
47. Kunze KL, Wienkers LC, Thummel KF, Trager WF. Warfarin-fluconazole I. Inhibition of human cytochrome P450 dependent metabolism of warfarin by fluconazole: in vitro studies. Drug Metab Dispos 1996; 24: 414-421.
48. Hamman MA, Thompson GA, Hall SD. Regioselective and stereoselective metabolism of ibuprofen by human cytochrome P4502C. Biochem Pharmacol 1997; 54: 33-41.
49. Tracy TS, Rosenbluth BW, Wrighton SA, Gonzalez FJ, Korzekwa KR. Role of cytochrome P4502C9 and an allelic variant in the 4′ -hydroxylation of (R)- and (S)-flurbiprofen. Biochem Pharmacol 1995; 49: 1269-1275.
50. Miners JO, Coulter S, Tukey RH, Veronese ME, Birkett DJ. Cytochromes P450 1A2 and 2C9 are responsible for the human hepatic O-demethylation of (R)- and (S)-naproxen. Biochem Pharmacol 1996; 51: 1003-1008.
51. 14C]naproxen O-demethylase activity in human liver microsomes. Evidence for the involvement of cytochrome P4501A2 and P4502C9/10. Drug Metab Dispos 1996; 24: 126-136.
52. Miners JO, Mackenzie PI. Drug glucuronidation in humans. Pharmacol Ther 1991; 51: 347-369.
53. TB (CYP2C): A major monooxygenase catalyzing diclofenac 4′ -hydroxylation in human liver. Life Sci 1993; 52: 29-34.
54. Bonnabry P, Leemann T, Dayer P. Role of human liver microsomal CYP2C9 in the biotransformation of lornoxicam. Eur J Clin Pharmacol 1996; 49: 305-308.
55. Zhao J, Leemann T, Dayer P. In vitro oxidation of oxicam NSAIDs by a human liver cytochrome P450. Life Sci 1992; 51: 575-581.
56. Bonnabry P, Leemann T, Dayer P. Biotransformation by hepatic P450TB (CYP2C) controls mefenamic acid elimination. Clin Pharmacol Ther 1994; 55: 139.
57. Bort R, Ponsoda E, Carrasco E, Gomez-Lechon MJ, Castell JV. Metabolism of aceclofenac in humans. Drug Metab Dispos 1996; 24: 834-841.
58. Neugebauer G, Bessenfelder E, von Mollendorff E. Pharmacokinetics and metabolism of torsemide in man. Arzneim.-Forsch 1988; 38: 164-166.
59. Lopez Garcia MP, Dansette PM, Valadon P, et al. Human liver cytochromes P450 expressed in yeast as tools for reactive metabolite formation studies. Oxidative activation of tienilic acid by cytochromes P450 2C9 and 2C10. Eur J Biochem 1993; 213: 223-232.
60. Dansette PM, Amar C, Valadon P, Pons C, Beaune PH, Mansuy D. Hydroxylation and formation of electrophilic metabolites of tienilic acid and its isomer by human liver microsomes. Catalysis by a cytochrome P450 IIC different from that responsible for mephenytoin hydroxylation. Biochem Pharmacol 1991; 41: 553-560.
61. Lecouer S, Andre C, Beune PH. Tienilic-induced autoimmune hepatitis: Anti-liver and -kidney microsomal type 2 autoantibodies recognise a three-site conformational epitope on cytochrome P4502C9. Mol Pharmacol 1996; 50: 326-333.
62. Ghahramani P, Ellis SW, Lennard MS, Ramsay LE, Tucker GT. Cytochromes P450 mediating the N-demethylation of amitriptyline. Br J Clin Pharmacol 1997; 43: 137-144.
63. von Moltke LL, Greenblatt DJ, Duan SX, Schmider J, Harmatz JS, Shader RI. Human cytochromes mediating N-demethylation of fluoxetine in vitro. Clin Pharmacol Ther 1997; 61: 177.
64. Stearns RA, Chakravarty PK, Chen R, Chui S-HL. Biotransformation of losartan to its active carboxylic metabolite in human liver microsomes. Role of cytochrome P450 2C and 3A subfamily members. Drug Metab Dispos 1995; 23: 207-215.
65. Kumar GN, Dubberke E, Rodrigues AD, Roberts E, Dennisen JF. Identification of cytochromes P450 involved in the human liver microsomal metabolism of the thromboxane A2 inhibitor seratrodast (ABT-001). Drug Metab Dispos 1997; 25: 110-115.
66. Bornheim LM, Lasker JM, Raucy JL. Human hepatic microsomal metabolism of Δ1-tetrahydrocannabinol. Drug Metab Dispos 1992; 20: 241-246.
67. Weaver RJ, Dickins M, Burke MD. Cytochrome P4502C9 is responsible for hydroxylation of the naphthoquinone antimalarial drug 58C80 in human liver. Biochem Pharmacol 1993; 46: 1183-1197.
68. Weaver RT, Dickins M, Burke MD. Hydroxylation of the antimalarial drug 58C80 by CYP2C9 in human liver microsomes: Comparison with mephenytoin and tolbutamide hydroxylations. Biochem Pharmacol 1995; 49: 997-1004.
69. Jones CR, Guengerich FP, Rice JM, Lubet RA. Induction of various cytochromes CYP2B, CYP2C and CYP3A by phenobarbitone in non-human primates. Pharmacogenetics 1992; 2: 160-172.
70. Serlin MJ, Breckinridge AM. Drug interactions with warfarin. Drugs 1983; 25: 610-620.
71. Nation RL, Evans AM, Milne RW. Pharmacokinetic drug interactions with phenytoin. Clin Pharmacokinet 1990; 18: 37-60.
72. Oda Y. Yoshida N, Nishi S, et al. Effect of high dose barbiturate therapy on phenytoin pharmacokinetics. Clin Pharmacol Ther 1992; 51: 187.
73. Goldberg MR, Lo MW, Deutsch PJ, Wilson SE, McWilliams EJ, McCrea JB. Phenobarbital minimally alters plasma concentrations of losartan and its active metabolite E-3174. Clin Pharmacol Ther 1996; 59: 268-274.
74. Baciewicz AM. Carbamazepine drug interactions. Therapeutic Drug Monit 1986; 8: 305-317.
75. Iber FL. Drug metabolism in heavy consumers of ethyl alcohol. Clin Pharmacol Ther 1977; 22: 735-742.
76. Kater RMH, Roggm G, Tobon F, Zieve P, Iber FL. Increased rate of clearance of drugs from the circulation of alcoholics. Am J Med Sci 1969; 258: 35-39.
77. Sandor P, Sellers EM, Dumbrell M, Khouw V. Effect of short- and long-term alcohol use on phenytoin kinetics in chronic alcoholics. Clin Pharmacol Ther 1981; 30: 390-397.
78. Heimark LD, Gibaldi M, Trager WF, O'Reilly RA, Goulart DA. The mechanism of the warfarin-rifampin drug interaction in humans. Clin Pharmacol Ther 1987; 42: 388-394.
79. Zilly W, Breimer DD, Richter E. Induction of drug metabolism in man after rifampicin treatment measured by increased hexobarbital and tolbutamide clearance. Eur J Clin Pharmacol 1975; 9: 219-227.
80. Kay L, Kampmann JP, Svendsen TL, et al. Influence of rifampicin and isoniazid on the kinetics of phenytoin. Br J Clin Pharmacol 1985; 20: 323-326.
81. Williamson KM, Patterson JH, Pieper JA, McQueen RH, Adams KF. Effects of erythromycin or rifampin on steady state losartan kinetics in healthy volunteers. Clin Pharmacol Ther 1997; 61: 202.
82. Nolan PE, Marcus FI, Hoyer GL, Bliss M, Gear K. Pharmacokinetic interaction between intravenous phenytoin and annodarone in healthy volunteers. Clin Pharmacol Ther 1989; 46: 43-50.
83. O'Reilly RA, Trager WF, Rettie AE, Goulart DA. Interaction of amiodarone with racaemic warfarin and its separated enantiomorphs in humans. Clin Pharmacol Ther 1987; 42: 290-294.
84. Heimark ED, Wienkers E, Kunze K, et al. The mechanism of the interaction between amiodarone and warfarin in humans. Clin Pharmacol Ther 1992; 51: 398-407.
85. Skovsted L, Kristensen M, Hansen JM, Siersbaek-Nielsen K. The effect of different oral anticoagulants on diphenylhydration and tolbutamide metabolism. Acta Med Scand 1976; 199: 513-515.
86. Serlin MJ, Mossnian S, Sibeon RG, et al. Cimetidine: Interaction with oral anticoagulants in man. Lancet 1979; ii: 317-319.
87. Toon S, Hopkins KJ, Garstang FM, Rowland M. Comparative effects of ramtidine and cimetidine on the pharmacokinetics and pharmacodynamics of warfarin in man. Eur J Clin Pharmacol 1987; 32: 165-172.
88. Niopas I, Toon S, Rowland M. Further insight into the stereoselective interaction between warfarin and cimetidine in man. Br J Clin Pharmacol 1991; 32: 508-511.
89. Hargreaves JA, Jezequel S, Houston JB. Effect of azole antifungals on human microsomal metabolism of diclofenac and midazolam. Br J Clin Pharmacol 1994; 38: 175P.
90. Kazierad DJ, Martin DE, Tenero D, et al. Fluconazole significantly alters the pharmacokinetics of losartan but not eprosartan. Clin Pharmacol Ther 1997; 61: 203.
91. Blum RA, Wilton JH, Hilligoss DM, et al. Effect of fluconazole on the disposition of phenytoin. Clin Pharmacol Ther 1991; 49: 420-425.
92. Lazar JD, Wilner KD. Drug interactions with fluconazole. Rev Infec Dis 1990; 12 (Suppl 3): S327-S333.
93. Black DJ, Kunze KL, Wienkers EC, et al. Warfarin-fluconazole II. A metabolically based drug interaction. Drug Metab Dispos 1996; 24: 422-428.
94. Kunze KL, Trager WF. Warfarin-fluconazole III. A rational approach to management of a metabolically based drug interaction. Drug Metab Dispos 1996; 24: 429-435.
95. O'Reilly RA, Goulart DA, Kunze KL, et al. Mechanisms of the stereoselective interaction between miconazole and racemic warfarin in human subjects. Clin Pharmacol Ther 1992; 51: 656-667.
96. Back DJ, Stevenson P, Tjia JF. Comparative effects of two antimycotic agents, ketoconazole and terbinafine, on the metabolism of tolbutamide, ethinyloestradiol, cyclosporin and ethoxycoumarin by human liver microsomes. Br J Clin Pharmacol 1989; 28: 166-170.
97. McCrea JB, Lo MW, Furtek CI, et al. Ketoconazole does not affect the systemic conversion of losartan to E-3174. Clin Pharmacol Ther 1996; 59: 169.
98. Touchette MA, Chandrasekar PH, Milad MA, Edwards DJ. Contrasting effects of fluconazole and ketoconazole on phenytoin and testosterone disposition in man. Br J Clin Pharmacol 1992; 34: 75-78.
99. Transon C, Leeman R, Dayer P. In vitro comparative inhibition profiles of major drug metabolising cytochrome P450 isozymes (CYP2C9, CYP2D6, CYP3A4) by HMG-CoA reductase inhibitors. Eur J Clin Pharmacol 1996; 50: 209-215.
100. TB (CYP2C9) by (±)-fluvastatin. Clin Pharmacol Ther 1995; 58: 412-417.
101. Lewis RJ, Trager WF, Chan KE, et al. Warfarin - Stereochemical aspects of its metabolism and the interaction with phenylbutazone. J Clin Invest 1974; 53: 1607-1617.
102. Miners JO, Foenander T, Wanwimolruk S, Gallus AS, Birkett DJ. The effect of sulphinpyrazone on oxidative drug metabolism in man: Inhibition of tolbutamide elimination. Eur J Clin Pharmacol 1982; 22: 321-326.
103. Miners JO, Foenander T, Wanwimolruk S, Gallus AS, Birkett DJ. Interaction of sulphinpyrazone with warfarin. Eur J Clin Pharmacol 1982; 22: 327-331.
104. He M, Kunze KL, Trager WF. Inhibition of S-warfarin metabolism by sulfinpyrazone and its metabolites. Drug Metab Dispos 1995; 23: 659-663.
105. Christensen LK, Hansen JM, Kristensen M. Sulphaphenazole-induced hypoglycaemic attacks in tolbutamide-treated diabetics. Lancet 1963; 2: 1298-1301.
106. Hansen JM, Kampmann JP, Siersbaek-Nielsen K, et al. The effect of different sulfonamides on phenytoin metabolism in man. Acta Med Scand 1979; 24 (Suppl 6): 106-110.
107. Wing LMH, Miners JO. Cotrimoxazole as an inhibitor of oxidative drug metabolism: Effects of trimethoprim and sulphamethoxazole separately and combined on tolbutamide disposition. Br J Clin Pharmacol 1985; 20: 482-485.
108. Lumholtz B, Siersbaek-Nielsen K, Skovsted L, Kampmann J, Molholm-Hansen J. Sulfamethizole-induced inhibition of diphenylhydratoin, tolbutamide and warfarin metabolism. Clin Pharmacol Ther 1975; 17: 731-734.
109. Suttle AB, Vargo DL, Wilkinson LA, Birmingham BK, Lasseter K. Effect of zafirlukast on the pharmacokinetics of R- and S-warfarin in healthy men. Clin Pharmacol Ther 1997; 61: 186.
110. Miners JO, Wing LMH, Lillywhite KJ, Smith KJ. Failure of therapeutic doses of β-adrenoreceptor antagonists to alter the disposition of tolbutamide and lignocaine. Br J Clin Pharmacol 1984; 18: 853-860.
111. Robson RA, Miners JO, White-head AG, Birkett DJ. Specificity of the inhibitory effect of dextropropoxyphene on oxidative drug metabolism: Lack of effect on theophylline and tolbutamide disposition. Br J Clin Pharmacol 1987; 23: 772-776.
112. Abernethy DR, Kaminsky LS, Dickinson TH. Selective inhibition of warfarin metabolism by diltiazem in humans. 1991; 257: 411-416.
113. Toon S, Hopkins KJ, Garstang FM, Aarons L, Sedman A, Rowland M. Enoxacin-warfarin interaction: Pharmacokinetic and stereochemical aspects. Clin Pharmacol Ther 1987; 42: 33-41.
114. Milne RW, Coulthard K, Nation RL, Penna AC, Roberts G, Sansom LN. Lack of effect of erythromycin on the pharmacokinetics of single oral doses of phenytoin. Br J Clin Pharmacol 1988; 26: 330-333.
115. Jensen JC, Gugler R. Interaction between metronidazole and drugs eliminated by oxidative metabolism. Clin Pharmacol Ther 1985; 37: 407-410.
116. Maya JF, Callaghan JT, Bergstrom RF, Cerimele BJ, Kassahun K, Nyhart EH. Olanzapine and warfarin drug interaction. Clin Pharmacol Ther 1997; 61: 182.
117. Andersson T, Lagerstrom P-O, Unge P. A study of the interaction between omeprazole and phenytoin in epileptic patients. Ther Drug Monit 1990; 12: 329-333.
118. Surfin T, Balmer K, Bostrom H, Eriksson S, Hoglund P, Paulsen O. Stereoselective interaction of omeprazole with warfarin in healthy men. Ther Drug Monit 1989; 11: 176-184.
119. Scott J, Poffenbarger PL. Pharmacogenetics of tolbutamide metabolism in humans. Diabetes 1979; 28: 41-51.
120. Back DJ, Orme ML'E. Genetic factors influencing the metabolism of tolbutamide. Pharmacol Ther 1989; 44: 147-155.
121. Miners JO, Wing LMH, Birkett DJ. Normal metabolism of debnsoquine and theophylline in a slow tolbutamide metaboliser. Aust NZ J Med 1985; 15: 348-349.
122. Sullivan-Klose TH, Ghanayem BI, Bell DA, et al. The role of the CYP2C9-Leu (359) allelic variant in the tolbutamide polymorphism. Pharmacogenetics 1996; 6: 341-349.
123. Page MA, Boutagy JS, Shenfield GM. A screening test for slow metabolisers of tolbutamide. Br J Clin Pharmacol 1991; 31: 649-654.
124. Veronese ME, Miners JO, Rees DLP, Birkett DJ. Tolbutamide hydroxylation in humans: Lack of biomodality in 106 healthy subjects. Phamacogenetics 1993; 3: 86-93.
125. Vermeij P, Ferrari MD, Buruma JS. Veenema H, deWolff FA. Inheritance of poor phenytoin parahydroxylation capacity in a Dutch family. Clin Pharmacol Ther 1988; 44: 588-593.
126. Inaba T. Phenytoin: Pharmacogenetic polymorphism of 4′-hydroxylation. Pharmacol Ther 1990; 46: 341-347.
127. Spielberg S, McCrea J, Cribb A, et al. A mutation in CYP2C9 is responsible for decreased metabolism of losartan. Clin Pharmacol Ther 1996; 59: 215.
128. Bhasker CR, Miners JO, Coulter S, Birkett DJ. Allelic and functional variability of cytochrome P4502C9. Pharmacogenetics 1997; 7: 51-58.
129. Stubbins MJ, Harries LW, Smith G, Tarbit MH, Wolf CR. Genetic analysis of the human cytochrome P4502C9 locus. Pharmacogenetics 1996; 6: 429-439.
130. Inoue K, Yamazaki H, Imiya K, Akasaka S, Guengerich FP, Shimada T. Relationship between CYP 2C9 and 2C19 genotypes and tolbutamide methylhydroxylation and S-mephenyotin 4′ -hydroxylation activities in livers of Japanese and Caucasian populations. Pharmacogenetics 1997; 7: 103-113.
131. Wang S-L, Huang J-D, Lai M-D, Tsai J-J. Detection of CYP2C9 polymorphism based on the polymerase chain reaction in Chinese. Pharmacogenetics 1995; 5: 37-42.
132. Nasu K, Kubota T, Ishizaki T. Genetic analysis of CYP2C9 polymorphism in a Japanese population. Pharmacogenetics 1997; 7: 405-409.
133. Haining RL, Hunter AP, Veronese ME, Trager WF, Rettic AE. Allelic variants of human cytochrome P4502C9: Baculovirus-mediated expression, purification, structural characterization, substrate stereoselectivity, and prochiral selectivity of the wild-type and 1359L mutant forms. Arch Biochem Biophys 1996; 333: 447-458.
134. Steward DJ, Haining RL, Henne KR, et al. Genetic association between sensitivity to warfarin and expression of CYP2C9*3. Pharmacogenetics 1997; 7: 361-367.
135. Kaminsky LS, deMorais S, Faletto MB, Dunbar DA, Goldstein JA. Correlation of human cytochrome P4502C substrate specificities with primary structure: Warfarin as a probe. Mol Pharmacol 1993; 43: 234-239.
136. Rettie AE, Wienkers LC, Gonzalez FJ, Trager WF, Korzekwa KR. Impaired (S)-warfarin metabolism catalysed by the R144C allelic variant of CYP2C9. Pharmacogenetics 1994; 4: 39-42.
137. Crespi CR, Miller VP. The R144C change in the CYP2C9*2 allele alters interaction of the cytochrome P450 with NADPH: cytochrome P450 oxidoreductase. Pharmacogenetics 1997; 7: 203-210.
138. Furuya H, Fernandez-Salguero P, Gregory W, et al. Genetic polymorphism of CYP2C9 and its effect on warfarin maintenance dose requirement in patients undergoing anticoagulation therapy. Pharmacogenetics 1995; 5: 389-392.
139. London SJ, Sullivan-Klose T, Daly AK, Idle JR. Lung cancer risk in relation to the CYP2C9 genetic polymorphism among Caucasians in Los Angeles County. Pharmacogenetics 1997; 7: 401-404.
140. Furuya H, Meyer UA, Gelboin HV, Gonzalez FJ. Polymerase chain reaction directed identification, cloning and quantitation of CYP2C18 mRNA. Mol Pharmacol 1991; 40: 375-382.
141. deMorais SMF, Schweiki H, Blaisdell J, Goldstein JA. Gene structure and upstream regulatory regions of human CYP2C9 and CYP2C18. Biochem Biophys Res Commun 1993; 194: 194-201.
142. Ibeanu GC, Goldstein JA. Transcriptional regulation of human CYP2C genes: Functional comparison of CYP2C9 and CYP2C18 promoter regions. Biochemistry 1995; 34: 8028-8036.
143. Shimada T, Yamazaki H, Mimura M, et al. Characterisation of microsomal cytochrome P450 enzymes involved in the oxidation of xenobiotic chemicals in human fetal livers and adult lungs. Drug Metab Dispos 1996; 24: 515-522.
144. Hakkola J, Pasanen M, Hukkanen J, et al. Expression of xenobiotic-metabolising cytochrome P450 forms in human full-term placenta. Biochem Pharmacol 1996; 51: 403-411.
145. Hakkola J, Pasanen M, Purkunen R, et al. Expression of xenobiotic metabolising cytochrome P450 forms in human adult and fetal liver. Biochem Pharmacol 1994; 48: 59-64.
146. Ratanasavanh D, Beaune P, Morel F, Flinois J-P, Guengerich FP, Guillouzo A. Intralobular distribution and quantitation of cytochrome P450 enzymes in human liver as a function of age. Hepatology 1991; 13: 1142-1151.
147. Morrow JI, Richens A. Disposition of anticonvulsants in children. Clin Pharmacokinet 1989; 17(Suppl 1): 89-104.
148. Loi C-M, Vestal RE. Drug metabolism in the elderly. Pharmacol Ther 1988; 36: 131-149.
149. Horn JR, Wittkowsky AK, Linenberger M. Greenberg D, Meade DM, Lam A. Effect of age on disposition of warfarin enantiomers. Clin Pharmacol Ther 1997; 61: 175.
150. Harris RZ, Benet LZ, Schwartz JB. Gender effects in pharmacokinetics and pharmacodynamics. Drugs 1995; 50: 222-239.
151. Chan E, Ti TY, Lee HS. Population pharmacokinetics of phenytoin in Singapore Chinese. Eur J Clin Pharmacol 1990; 39: 177-181.
152. Grasela TH, Sheiner LB, Rambeck B, et al. Steady-state pharmacokinetics of phenytoin from routinely collected patient data. Clin Pharmacokinet 1983; 8: 355-364.
153. James AH, Britt RP, Raskino CL, Thompson SG. Factors affecting the maintenance doses of warfarin. J Clin Pathol 1992; 45: 704-706.
154. Chen L, Yasumori T, Yamazoe Y, Kato R. Hepatic microsomal tolbutamide hydroxylation in Japanese: In vitro evidence for rapid and slow metabolisers. Pharmacogenetics 1993; 3: 77-85.