Recent Advances: the Cytochrome P450 Enzymes

Nelson DR , Kamataki T , Waxman DJ , Guengerich FP , Estabrook RW , Feyereisen R ,. The P450 superfamily: update on new sequences, gene mapping, accession numbers, early trivial names of enzymes, and nomenclature. DNA Cell Biol 1993;12:1-51.

Krishna D , Klotz U. Extrahepatic metabolism of drugs in humans. Clin Pharmacokinet 1994;26:144-60.

Wrighton SA , Stevens JC . The human hepatic cytochromes P450 involved in drug metabolism. Crit Rev Toxicol 1992;22:1-21.

Guengerich FP . Catalytic selectivity of human cytochrome P450 enzymes: relevance to drug metabolism and toxicity. Toxicol Lett 1994;70:133-8.

Guengerich FP . Characterization of human cytochrome P450 enzymes. FASEBJ 1992;6:745-8.

Murray M. P450 enzymes: inhibition mechanisms, genetic regulation and effects of liver disease. Clin Pharmacokinet 1992;23:132-46.

Halpert JR , Guengerich FP , Bend JR , Correia MA . Selective inhibitors of cytochromes P450. Toxicol Appl Pharmacol 1994;125:163-75.

Birkett DJ , Mackenzie PI , Veronese ME , Miners JO . In vitro approaches can predict human drug metabolism. Trends Pharmacol Sci 1993;14:292-4.

Korzekwa KR , Jones JP . Predicting the cytochrome P450 mediated metabolism of xenobiotics. Pharmacogenetics 1993;3:1-18.

May GD . Genetic differences in drug disposition. J Clin Pharmacol 1994;34:881-97.

Nebert DW , Adesnick M , Coon MJ , Estabrook RW , Gonzalez FJ , Guengerich FP ,. The P450 gene superfamily: recommended nomenclature. DNA 1987;6:1-11.

Shimada T , Yamazaki H , Mimura M , Inui Y , Guengerich FP. Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther 1994;270:414-23.

Chiba K , Kobayashi K , Manabe K , Tani M , Kamataki T. Oxidative metabolism of omeprazole in human liver microsomes: cosegregation with S-mephenytoin 4'-hydroxylation. J Pharmacol Exp Ther 1993;266:52-9.

Campbell ME , Grant DM , Inaba T , Kalow W. Biotransformation of caffeine, paraxanthine, theophylline and theobromine by polycyclic aromatic hydrocarbon inducible cytochromes P450 in human liver microsomes. Drug Metab Dispos 1987;15:237-49.

Kalow W , Tang BK . Use of caffeine metabolic ratios to explore CYPIA2 and xanthine oxidase activities. Clin Pharmacol Ther 1991;50:508-19.

Relling MV , Lin JS , Ayers GD , Evans WE . Racial and gender differences in N-acetyltransferase, xanthine oxidase, and CYP1A2 activities. Clin Pharmacol Ther 1992;52:643-58.

Butler MA , Lang NP , Young JF , Caporaso NE , Vineis P , Hayes RB ,. Determination of CYP1A2 and NAT2 phenotypes in human populations by analysis of caffeine urinary metabolites. Pharmacogenetics 1992;2:116-27.

Fuhr U , Rost KL . Simple and reliable CYP1A2 phenotyping by the paraxanthine/caffeine ratio in plasma and in saliva. Pharmacogenetics 1994;4:109-16.

Teunissen MWE , DeLeede LGJ , Boeijinga JK , Breimer DD . Correlation between antipyrine metabolite formation and theophylline metabolism in humans after simultaneous single-dose administration and at steady state. J Pharmacol Exp Ther 1985;233:770-5.

Kadlubar FF . Biochemical individuality and its implications for drug and carcinogen metabolism: recent insights from acetyltransferase and cytochrome P4501A2 phenotyping and genotyping in humans. Drug Metab Rev 1994;26:37-46.

Kalow W , Tang BK . Caffeine as a metabolic probe: exploration of the enzyme-inducing effects of cigarette smoking. Clin Pharmacol Ther 1991;49:44-8.

Rost KL , Roots I. Accelerated metabolism after omeprazole treatment indicated by urinary metablite ratios: coincidence with plasma clearance and breath test. Clin Pharmacol Ther 1994;55:402-11.

Rest KL , Brosicke H , Brockmoller J , Scheffler M. Helge H , Roots I. Increase of cytochrome P4501A2 activity by omeprazole: evidence by the ¹³C-[N-3-methyl]-caffeine breath test in poor and extensive metabolizers of S-mephenytoin. Clin Pharmacol Ther 1992;52:170-80.

Andersson T , Miners JO , Veronese ME , Tassaneeyakul Wi , Tassaneeyakul WO , Meyer UA ,. Identification of human liver cytochrome P450 isoforms mediating omeprazole metabolism. Br J Clin Pharmacol 1993;36:521-30.

Fuhr U , Strobl G , Manaut F , Anders EM , Sorgel F , Lopez-de Brinas E ,. Quinolone antibacterial agents: relationship between structure and in vitro inhibition of the human cytochrome P450 isoform CYP1A2. Mol Pharmacol 1993;43:191-9.

Fuhr U , Anders EM , Mahr G , Sorgel F , Staib AH . Inhibitory potency of quinolone antibacterial agents against cytochrome P4501A2 activity in vivo and in vitro. Antimicrob Agents Chemother 1992;36:942-8.

Gonzalez FJ , Meyer UA . Molecular genetics of the debrisoquin-sparteine polymorphism. Clin Pharmacol Ther 1991;50:233-8.

Saxena R , Shaw GL , Relling MV , Frame JN , Moir DT , Evans WE ,. Identification of a new variant CYP2D6 allele with a single base deletion in exon 3 and its association with the poor metabolizer phenotype. Human Mol Genetics 1994;3:923-6.

Dahl ML , Johansson I , Palmertz MP , Ingelman-Sundberg M , Sjoqvist F. Analysis of the CYP2D6 gene in relation to debrisoquin and desipramine hydroxylation in a Swedish population. Clin Pharmacol Ther 1992;51:12-7.

Evans WE , Relling MV , Rahman A , McLeod HL , Scott EP , Lin JS . Genetic basis for a lower prevalence of deficient CYP2D6 oxidative drug metabolism phenotypes in black Americans. J Clin Invest 1993;91:2150-4.

Agundez JAG , Martinez C , Ledesma MC , Ladona MG , Ladero JM , Benitez J. Genetic basis for differences in debrisoquine polymorphism between a Spanish and other white populations. Clin Pharmacol Ther 1994;55:412-7.

Relling MV , Cherrie J , Schell MJ , Petras WP , Meyer UA , Evans WE . Lower prevalence of the debrisoquin oxidative poor metabolizer phenotype in American blacks versus whites. Clin Pharmacol Ther 1991;50:308-13.

Bertilsson L , Lou YQ , Du YL , Liu Y , Kuang TY , Liao XM ,. Pronounced differences between native Chinese and Swedish populations in the polymorphic hydroxylations of debrisoquin and S-mephenytoin. Clin Pharmacol Ther 1992;51:388-97.

Koymans L , Vermeulen NPE , van Acker SABE , te Koppele JM , Heykants JJP , Lavrijsen K ,. A predictive model for substrates of cytochrome P450-debrisoquine (2D6). Chem Res Toxicol 1992;5:211-9.

Inaba T , Jurima M , Mahon WA , Kalow W. In vitro inhibition studies of two isozymes of human liver cytochrome P-450: mephenytoin p-hydroxylase and sparteine monooxygenase. Drug Metab Dispos 1985;13:443-8.

Young D , Midha KK , Fossler MJ , Hawas EM , Hubbard JW , McKay G ,. Effect of quinidine on the interconversion kinetics between haloperidol and reduced haloperidol in humans: implications for the involvement of cytochrome P450IID6. Eur J Clin Pharmacol 1993;44:433-8.

Wedlund PJ , Aslanian WS , McAllister CB , Wilkinson GR , Branch RA . Mephenytoin hydroxylation deficiency in Caucasians: frequency of a new oxidative drug metabolism polymorphism. Clin Pharmacol Ther 1984;36:773-80.

Sohn DR , Kusaka M , Ishizaki T , Shin SG , Jang IJ , Shin SG ,. Incidence of S-mephenytoin hydroxylation deficiency in a Korean population and the interphenotypic differences in diazepam pharmacokinetics. Clin Pharmacol Ther 1992;52:160-9.

Goldstein JA , Faletto MB , Romkes-Sparks M , Sullivan T , Kitareewan S , Raucy JL ,. Evidence that CYP2C19 is the major (S)-mephenytoin 4'-hydroxylase in humans. Biochemistry 1994;33:1743-52.

Wrighton SA , Stevens JC , Becker GW , VandenBranden M. Isolation and characterization of human liver cytochrome P4502C19: correlation between 2C19 and S-mephenytoin 4'-hydroxylation. Arch Biochem Biophys 1993;306:240-5.

De Morais SMF , Wilkinson GR , Blaisdell J , Nakamura K , Meyer UA , Goldstein JA . The major genetic defect responsible for the polymorphism of S-mephenytoin metabolism in humans. J Biol Chem 1994;269:15419-22.

De Morais SMF , Wilkinson GR , Blaisdell J , Meyer UA , Nakamura K , Goldstein JA . Identification of a new genetic defect responsible for the polymorphism of S-mephenytoin metabolism in Oriental populations (abstract 47). Proceedings of the 6th North American ISSX Meeting, Raleigh, NC, October 23–27, 1994.

Relling MV , Aoyama T , Gonzalez FJ , Meyer UA . Tolbutamide and mephenytoin hydroxylation by human cytochrome P450s in the CYP2C subfamily. J Pharmacol Exp Ther 1990;252:442-7.

Tassaneeyakul W , Veronese M , Birkett DJ , Doecke C , McManus M , Sansom L ,. Co-regulation of phenytoin and tolbutamide metabolism in humans. Br J Clin Pharmacol 1992;34:494-8.

Rettie AE , Korzekwa KR , Kunze KL , Lawrence RF , Eddy AC , Aoyama T ,. 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;5:54-9.

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;34:75-8.

Watkins PB , Wrighton SA , Schuetz EG , Molowa DT , Guzelian PS . Identification of glucocorticoid-inducible cytochromes P-450 in the intestinal mucosa of rats and man. J Clin Invest 1987;80:1029-36.

Wrighton SA , Brian WR , Sari MA , Iwasaki M , Guengerich FP , Raucy JL ,. Studies on the expression and metabolic capabilities of human liver cytochrome P450JJIA5 (Hlp3). Mol Pharmacol 1990;38:207-13.

Kolars JC , Lown KS , Schmiedlin-Ren P , Ghosh M , Fang C , Wrighton SA ,. CYP3A gene expression in human gut epithelium. Pharmacogenetics 1994;4:247-59.

Gorski JC , Jones DR , Wrighton SA , Hall SA . Characterization of dextromethorphan N-demethylation by human liver microsomes. Biochem Pharmacol 1994;48:173-82.

Watkins PB . Noninvasive tests of CYP3A enzymes. Pharmacogenetics 1994;4:171-84.

Thummel KE , Shen DD , Podoll TD , Kunze KL , Trager WF , Hartwell PS ,. Use of midazolam as a human cytochrome P450 3A probe: I. In vitro-in vivo correlations in liver transplant patients. J Pharmacol Exp Ther 1994;271:549-56.

Watkins PB , Turgeon K , Saenger P , Lown KS , Kolars JC , Hamilton T ,. Comparison of urinary 6-β-cortisol and the erythromycin breath test as measures of hepatic P450IIIA (CYP3A) activity. Clin Pharmacol Ther 1992;52:265-73.

Kinirons MT , O'Shea D , Downing TE , Fitzwilliam AT , Jollenbeck L , Groopman JD ,. Absence of correlations among three putative in vivo probes of human cytochrome P4503A activity in young healthy men. Clin Pharmacol Ther 1993;54:621-9.

May DG , Porter J , Wilkinson GR , Branch RA . Frequency distribution of dapsone N-hydroxylase, a putative probe for P4503A4 activity, in a white population. Clin Pharmacol Ther 1994;55:492-500.

Ducharme J , Abdullah S , Fried K , Wainer IW . Dextromethorphan as an in vivo probe for CYP3A4 activity (abstract 240). Proceedings of the 6th North American ISSX meeting. Raleigh, NC, October 23–27, 1994.

Hebert MF , Roberts JP , Prueksaritanont T , Benet LZ . Bioavailability of cyclosporine with concomitant rifampin administration is markedly less than predicted by hepatic enzyme induction. Clin Pharmacol Ther 1992;52:453-7.

First MR , Schroeder TJ , Michael A , Hariharan S , Weiskittel P , Alexander JW . Safety and efficacy of long-term cyclosporine-ketoconazole administration and preliminary results of a randomized trial. Transplant Proc 1993;25:591-4.

Dahl ML , Bertillson L. Genetically variable metabolism of antidepressants and neuroleptic drugs in man. Pharmacogenetics 1993;3:61-70.

Smith CAD , Gough AC , Leigh PN , Summers BA , Harding AE , Maranganore DM ,. Debrisoquine hydroxylase gene plymorphism and susceptibility to Parkinson's disease. Lancet 1992;339:1375-7.

Roots I , Brockmoller J , Drakoulis N , Kerb R. Mutant alleles of cytochrome P450HD6 in lung cancer (abstract). Clin Pharmacol Ther 1992;51:181.

Fleming CM , Persad R , Kaisary A , Smith P , Adedoyin A , Porter J ,. Low activity of dapsone N-hydroxylation as a susceptibility risk factor in aggressive bladder cancer. Pharmacogenetics 1994;4:199-207.

Honig PK , Wortham DC , Zamani K , Conner DP , Mullin JC , Cantilena LR . Terfenadine-ketoconazole interaction: pharmacokinetic and electrocardiographic consequences. JAMA 1993;269:1513-8.