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Research Article

The Human Hepatic Cytochromes P450 Involved in Drug Metabolism

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Pages 1-21 | Published online: 25 Sep 2008

References

  • Nebert D. W., Nelson D. R., Coon M. J., Estabrook R. W., Feyerseisen R., Pujii-Kuriyama Y., Gonzalez F. J., Guengerich F. P., Gunsalus I. C., Johnson E. F., Loper J. C., Sato R., Waterman M. R., Waxman D. J. The P450 superfamily: update on new sequences, gene mapping, and recommended nomenclature. DNA Cell. Biol. 1991; 10: 1
  • Guengerich F. P. Enzymatic oxidation of xeno-biotic chemicals. Biochem. Mol. Biol. 1990; 25: 97
  • Nebert D. W., Jaiswal A. K., Meyer U. A., Gonzalez F. J. Human P-450 genes: evolution, regulation and possible role in carcinogenesis. Biochem. Soc. Trans. 1987; 15: 586
  • Guengerich F. P. Roles of cytochrome P-450 enzymes in chemical carcinogenesis and cancer chemotherapy. Cancer Res. 2946; 48: 1988
  • Ryan D. E., Levin W. Purification and characterization of hepatic microsomal cytochrome P-450. Pharmacol. Ther. 1990; 45: 153
  • Riviere J. L., Cabanne F. Animal and plant cytochrome P-450 systems. Biochimie 1987; 69: 743
  • Sariaslani F. S. Microbial cytochromes P-450 and xenobiotic metabolism. Adv. Appl. Microbiol. 1991; 36: 133
  • Guengerich F. P. Characterization of human microsomal cytochrome P-450 enzymes. Annu. Rev. Pharmacol. Toxicol. 1989; 29: 241
  • Shimada T., Guengerich F. P. Participation of a rat liver cytochrome P-450 induced by pregnenolone 16a-carbonitrile and other compounds in the 4-hydroxylation of mephenytoin. Mol. Pharmacol. 1985; 28: 215
  • Brian W. R., Srivastava P. K., Umbenhauer D. R., Lloyd R. S., Guengerich F. P. Expression of a human liver cytochrome P-450 protein with tolbutamide hydroxylase activity in. Sac-charomyces cerevisiae. Biochemistry 4993; 28: 1989
  • Gonzalez F. J. The molecular biology of cytochrome P450s. Pharmacol. Rev. 1989; 40: 243
  • Nebert D. W. P450 genes: structure, evolution, and regulation. Annu. Rev. Biochem. 1987; 56: 945
  • Smith D. A. Species differences in metabolism and pharmacokinetics: are we close to an understanding?. Drug Metab. Rev. 1991; 23: 355
  • Gonzalez F. J. The molecular biology of cytochrome P450s. Pharmacol. Rev. 1988; 40: 243
  • Jaiswal A. K., Gonzalez F. J., Nebert D. W. Human dioxin-inducible cytochrome P.-450: complementary DNA and amino acid sequence. Science 1985; 228: 80
  • Quattrochi L. C., Pendurthi U. R., Okino S. T., Potenza C., Tukey R. H. Human cytochrome P-450 4 mRNA and gene: part of a multigene family that containsAlu sequences in its mRNA. Proc. Natl. Acad. Sci. U.S.A. 1986; 83: 6731
  • Sogawa K., Fujisawa-Sehara A., Yamane M., Fujii-Kuriyama Y. Localization of regulator elements responsible for drug induction in the rat cytochrome P-450c gene. Proc. Natl. Acad. Sci. U.S.A. 1986; 83: 8044
  • Conney A. H., Gillette J. R., Inscoe J. K., Frams E. R., Posner H. S. Induced synthesis of liver microsomal enzymes which metabolize foreign compounds. Science 1959; 130: 1478
  • Nebert D. W., Jones J. J. Regulation of the mammalian cytochrome P. 450 (CYP1A1) gene. Int. J. Biochem. 1989; 21: 243
  • Whitlock J. P. The regulation of gene expression by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Pharmacol. Rev. 1987; 39: 147
  • Wrighton S. A., Campanile C., Thomas P. E., Maines S. L., Watkins P. B., Parker G., Mendez-Picon G., Haniu M., Shively J., Levin W., Guzelian P. S. Identification of a human liver cytochrome P-450 homologous to the major iso-safrole-inducible cytochrome P-450 in the rat. Mol. Pharmacol. 1986; 29: 405
  • Quattrochi L. C., Tukey R. H. The human cytochrome CyplA2 gene contains regulatory elements responsive to 3-methylcholanthrene. Mol. Pharmacol. 1989; 36: 66
  • Pasanen M., Stenback F., Park S. S., Gelboin H. V., Pelkonen O. Immunohistochemical detection of human placental cytochrome P-450-asso-ciated mono-oxygenase systeminducible by maternal cigarette smoking. Placenta 1988; 9: 267
  • Kawajiri K., Nakachi K., Imai K., Yoshii A., Shinoda N., Watanabe J. Identification of genetically high risk individuals to lung cancer by DNA polymorphisms of the cytochrome P4501A1 gene. FEBS Lett. 1990; 263: 131
  • Petersen D. D., McKinney C. E., Ikeya K., Smith H. H., Bale A. E., McBride O. W., Nebert D. W. Human CYP1A1 gene: cosegrega-tion of the enzyme inducibility phenotype and an RFLP. Am. J. Hum. Genet. 1991; 48: 720
  • Disterlath L. M., Reilly P. E.B., Martin M. V., Davis G. G., Wilkinson S. G., Guengerich F. P. Purification and characterization of the human liver cytochromes P-450 involved in debrisoquine 4-hydroxylation and phenacetin O-deethylation, two prototypes for genetic polymorphism in oxidative drug metabolism. J. Biol. Chem. 1985; 260: 9057
  • Butler M. A., Iwasaki M., Guengerich F. P., Kadlubar F. F. Human cytochrome P-450PA (P-450IA2), the phenacetin O-deethylase, is primary responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines. Proc. Natl. Acad. Sci. U.S.A. 1989; 86: 7696
  • Guengerich F. P., Turvy C. G. Comparison levels of several human microsomal cytochrome P-450 enzymes and epoxide hydrolase in normal disease states using immunochemical analysis of surgical liver samples. J. Pharmacol. Exp. Ther. 1991; 256: 1189
  • Kalow W., Tang B. K. Caffeine as a metabolite probe: exploration of the enzyme-inducing effect of cigarette smoking. Clin. Pharmacol. Ther. 1991; 49: 44
  • Sesardic D., Boobis A. R., Edwards R. J., Davies D. S. A form of cytochrome P450 in man, orthologous to form d in the rat, catalyses the O-deethylation of phenacetin and is inducible by cigarette smoking. Br. J. Clin. Pharmacol. 1988; 26: 363
  • Boobis A. R., Davies D. S. Human cytochromes P-450. Xenobiotica 1984; 14: 151
  • Vistisen K., Loft S., Poulsen H. E. Cytochrome P450 IA2 activity in man measured by caffeine metabolism: effect of smoking, broccoli, and exercise, in. Biological Reactive Intermediates IV: Molecular and Cellular Effects and Their Impact on Human Health, C Witmer, R. Snyder, D. Jollow, G. Kalf, J. Kocsis, I. Sipes. Plenum Press, New York 1991; vol. 283: 407, s
  • Diaz D., Fabre I., Daujat M., Saint Aubert B., Bories P., Michel H., Maurel P. Omeprazole is an aryl hydrocarbon-like inducer of human hepatic cytochrome P450. Gastroenterology 1990; 99: 737
  • Anderson T., Bergstrand R., Cederberg C., Lagerstrom P. O., Skanberg I. Omeprazole treatment does not affect the metabolism of caffeine. Gastroenterology 1991; 101: 943
  • Michnovicz J. J., Bradlow H. L. Induction of estradiol metabolism by dietary indole-3-carbinol in humans. JNCI 1990; 82: 947
  • Michnovicz J. J., Bradlow H. L. Altered estrogen metabolism and excretion in humans following consumption of indole-3-carbinol. Nutr. Cancer 1991; 16: 59
  • Watkins P. B., Murray S. A., Thomas P. E., Wrighton S. A. Distribution of cytochromes P-450, cytochrome b5, and NADPH-cytochrome P-450 reductase in an entire human liver. Biochem. Pharmacol. 1990; 39: 471
  • Sesardic D., Boobis A. R., Murray B. P., Murray S., Segura J., De La Torre R., Davies D. Furafylline is a potent and selective inhibitor of cytochrome P450IA2 in man. Br. J. Clin. Pharmacol. 1990; 29: 651
  • Ryan D. E., Thomas P. E., Korzeniowski D., Levin W. Separation and characterization of highly purified forms of liver microsomal cytochrome P-450 from rats treated with polychlorinated biphen-yls, phenobarbital, and 3-methylcholanthrene. J. Biol. Chem. 1979; 254: 1365
  • Arlotto M. P., Greenway D. J., Parkinson A. Purification of two isozymes of rat liver microsomal cytochrome P450 with testosterone 7a-hy-droxylation activity. Arch. Biochem. Biophys. 1989; 270: 441
  • Kimura S., Kozak C. A., Gonzalez F. J. Identification of a novel P450 expressed in rat lung: cDNA cloning and sequence, chromosome mapping, and induction by 3-methylcholanthrene. Biochemistry 1989; 28: 3798
  • Lindberg R., Burkhart B., Ichikawa T., Negishi M. The structure and characterization of type I P-450,15α gene as major steroid 15ot-hydroxylase and its comparison with type II P-45015n gene. J. Biol. Chem. 1989; 264: 6465
  • Burkhart B. A., Skow L. C., Negishi M. Two steroid 15a-hydroxylase genes and a homologous gene family in mice. Gene 1990; 87: 205
  • Harada N., Negishi M. Mouse liver testosterone 15a-hydroxylase (cytochrome P-450,15α). J. Biol. Chem. 1984; 259: 1265
  • Negishi M., Lindberg R., Burkhart B., Ichikawa T., Honkakoski P., Lang M. Mouse steroid 15α -hydroxylase gene family: identification of type II P-450,15α as coumarin 7-hydrox-ylase. Biochemistry 1989; 28: 4169
  • Aida K., Negishi M. Posttranscriptional regulation of coumarin 7-hydroxylase induction by xe-nobiotics in mouse liver: mRNA stabilization by pyr-azole. Biochemistry 1991; 30: 8041
  • Wrighton S. A., Ring B. J., Watkins P. B., VandenBranden M. Identification of a polymorph-ically expressed member of the human cytochrome P-450III family. Mol. Pharmacol. 1989; 36: 97
  • Raunio H., Syngelma T., Pasanen M., Juvonen R., Honkakoski P., Kairaluoma M. A., Sotaniemi E., Lange M. A., Pelkonen O. Immunochemical and catalytical studies on hepatic coumarin 7-hydroxylase in man, rat, and mouse. Biochem. Pharmacol. 1988; 37: 3889
  • Yamano S., Tatsuno J., Gonzalez F. J. The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochemistry 1990; 29: 1322
  • Yun C. H., Shimada T., Guengerich F. P. Purification and characterization of human liver microsomal cytochrome P-450 2A6. Mol. Pharmacol. 1991; 40: 679
  • Wrighton S. A., VandenBranden M., Becker G. W., Black S. D., Thomas P. E. Two monoclonal antibodies recognizing different epitopes on rat cytochrome IIB1 react with human IIE1. Mol. Pharmacol. 1992; 41: 76
  • Wrighton S. A., Thomas P. E., Ryan D. E., Levin W. Purification and characterization of ethanol-inducible human hepatic cytochrome P-450HLJ. Arch. Biochem. Biophys. 1987; 258: 292
  • Waxman D. J., Lapenson D. P., Aoyama T., Gelboin H. V., Gonzalez F. J., Korzekwa K. Steroid hormone hydroxylase specificities of eleven cDNA-expressed human cytochrome P450s. Arch. Biochem. Biophys. 1991; 290: 160
  • Adesnik M., Atchison M. Genes for cytochrome P-450 and their regulation. Crit. Rev. Biochem. 1985; 19: 247
  • Guengerich F. P., Dannan G. A., Wright S. T., Martin M. V., Kaminsky L. S. Purification and characterization of liver microsomal cytochromes P-450: electrophoretic, spectral, catalytic, and immunochemical properties and inducibility of eight isozymes isolated from rats treated with phenobarbital or B-naphthoflavone. Biochemistry 1982; 21: 6019
  • Adams D. J., Seilman S., Amelizad Z., Oesch F., Wolf C. R. Identification of human cytochromes P-450 analogous to forms induced by phenobarbital and 3-methylcholanthrene in the rat. Biochem. J. 1985; 232: 869
  • Fujino T., Park S. S., West D., Gelboin H. V. Phenotyping of cytochromes P-450 in human tissues with monoclonal antibodies. Proc. Natl. Acad. Sci. U.S.A. 1982; 79: 3682
  • Yamano S., Nhamburo P. T., Aoyama T., Meyer U. A., Inaba T., Kalow W., Gelboin H. V., McBride O. W., Gonzalez F. J. cDNA cloning and sequence and cDNA-directed expression of human P450 IIB1: identification of a normal and two variant cDNAs derived from the CYP2B locus on chromosome 19 and differential expression of the IIB mRNAs in human liver. Biochemistry 1989; 28: 7340
  • Miles J. S., Spurr N. K., Gough A. C., Jowett T., McLaren A. W., Brook J. D., Wolf C. R. A novel human cytochrome P450 gene (P450IIB): chromosomal localization and evidence for alternative splicing. Nucleic Acids Res. 1988; 16: 5783
  • Ged C., Umbenhauer D. R., Bellew T. M., Bork R. W., Srivastava P. K., Shinriki N., Lloyd R. S., Guengerich F. P. Characterization of cDNAs, mRNAs, and proteins related to human liver microsomal cytochrome P-450 (S)-mephenytoin 4′-hydroxylase. Biochemistry 1988; 27: 6929
  • Dieter H. H., Miiller-Eberhard U., Johnson E. F. Identification of rabbit microsomal cytochrome P-450 isozyme, form 1, as a hepatic progesterone 21-hydroxylase. Biochem. Biophys. Res. Commun. 1982; 105(2)515
  • Okino S. T., Quattrochi L. C., Pendurthi U. R., McBride O. W., Tukey R. H. Characterization of multiple human cytochrome P-450 1 cDNAs. J. Biol. Chem. 1987; 262: 16072
  • Wrighton S. A., Thomas P. E., Willis P., Maines S. L., Watkins P. B., Levin W., Guzelian P. S. Purification of a human liver cytochrome P-450 immunochemically related to several cytochromes P-450 purified from untreated rats. J. Clin. Invest. 1987; 80: 1017
  • Leo M. A., Lasker J. M., Raucy J. L., Kim C. I., Black M., Lieber C. S. Metabolism of retinal and retinoic acid by human liver cytochrome P450IIC8. Arch. Biochem. Biophys. 1989; 269: 305
  • Romkes M., Faletto M. B., Blaisdell J. A., Raucy J. L., Goldstein J. A. Cloning and expression of complementary DNAs for multiple members of the human cytochrome P450IIC subfamily. Biochemistry 1991; 30: 3247
  • Shimada T., Misono K. S., Guengerich F. P. Human liver microsomal cytochrome P-450 mephenytoin 4-hydroxylase, a prototype of genetic polymorphism in oxidative drug metabolism. J. Biol. Chem. 1986; 261: 909
  • Yasumori T., Murayama N., Yamazoe Y., Abe A., Nogi Y., Fukasawa T., andKato R. Expression of a human P-450IIC gene in yeast cells using galactose-inducible expression system. Mol. Pharmacol. 1989; 35: 443
  • Relling M. V., Aoyama T., Gonzalez F. J., Meyer U. A. Tolbutamide and mephenytoin hy-droxylation by human cytochrome P450s in the CYP2C subfamily. J. Pharm. Exp. Ther. 1989; 252: 442
  • Srivastava P. K., Yun C. H., Beaune P. H., Ged C., Guengerich F. P. Separation of human liver microsomal tolbutamide hydroxylase and (S)-mephenytoin 4′-hydroxylase cytochrome P-450 enzymes. Mol. Pharmacol. 1991; 40: 69
  • Back D. J., Tjia J. F., Karbwang J., Colbert J. In vitro inhibition studies of tolbutamide hydroxylase activity of human liver microsomes by azoles, suphonamides and quinolines. Br. J. Clin. Pharmacol. 1988; 26: 23
  • Miners J. O., Smith K. J., Robson R. A., McManus M. E., Veronese M. E., Birkett D. J. Tolbutamide hydroxylation by human liver microsomes. Biochem. Pharmacol. 1988; 37: 1137
  • Homberg J. C., Andre C., Abuaf N. A new anti-liver-kidney microsome antibody (anti-LKM2) in tienilic acid-induced hepatitis. Clin. Exp. Immunol. 1984; 55: 561
  • Beaune P., Dansette P. M., Mansuy D., Kiffel L., Finck M., Amar C., Leroux J. P., Homberg J. C. Human anti-endoplasmic reticulum autoantibodies appearing in a drug-induced hepatitis are directed against a human liver cytochrome P-450 that hydroxylates the drug. Proc. Natl. Acad. Sci. U.S.A. 1987; 84: 551
  • Meier U. T., Meyer U. A. Genetic polymorphism of human cytochrome P-450 (S)-mephen-ytoin 4-hydroxylase. Studies with human autoantibodies suggest a functionally altered cytochrome P-450 isozyme as cause of the genetic deficiency. Biochemistry 1987; 26: 8466
  • Kalow W. Genetics of drug transformation. Clin. Biochem. 1986; 19: 76
  • Guengerich F. P. Polymorphism of cytochrome P-450 in humans. TiPS 1989; 10: 107
  • Relling M. V. Polymorphic drug metabolism. Clin. Pharm. 1989; 8: 852
  • Meyer U. A., Zanger U. M., Grant D., Blum M. Genetic polymorphisms of drug metabolism. Adv. Drug Res. 1990; 19: 198
  • Helsby N. A., Ward S. A., Howells R. E., Breckenridge A. M. In vitro metabolism of the biguanide antimalarials in human liver microsomes: evidence for a role of the mephenytoin hydroxylase (P450 MP) enzyme. Br. J. Clin. Pharmacol. 1990; 30: 287
  • Wedlund P. J., Sweetman B. J., Wilkinson G. R., Branch R. A. Pharmacogenetic association between the formation of 4-hydroxyme-phenytoin and a new metabolite of S-mephenytoin in man. Drug Metab. Dispos. 1987; 15: 277
  • Zhou H. H., Anthony L. B., Wood A. J.J., Wilkinson G. R. Induction of polymorphic 4′-hydroxylation of S-mephenytoin by rifampicin. Br. J. Clin. Pharmacol 1990; 30: 471
  • Jurima M., Inaba T., Kalow W. Mephenytoin hydroxylase activity in human liver: inhibition by steroids. Drug Metab. Dispos. 1985; 13: 746
  • Mahgoub A., Dring L. G., Idle J. R., Lancaster R., Smith R. L. Polymorphic hydroxylation of debrisoquine in man. Lancet 1977; 2: 584
  • Evans D. P., Mahgoub A., Sloan T. P., Idle J. R., Smith R. L. A family and population study of the genetic polymorphism of debrisoquine oxidation in a white British population. J. Med. Genet. 1980; 17: 102
  • Nakamura K., Goto F., Ray W. A., McAllister C. B., Jacqz E. Interethnic differences in genetic polymorphism of debrisoquine and mephenytoin hydroxylation between Japanese and Caucasian populations. Clin. Pharmacol. Ther. 1987; 38: 402
  • Larrey D., Disterlath L. M., Dannan G. A., Wilkinson G. R., Guengerich F. P. Purification and characterization of the rat microsomal cytochrome P-450 involved in the 4-hydroxylation of debrisoquine, a prototype for genetic variation in oxidative drug metabolism. Biochemistry 1984; 23: 2787
  • Disterlath L. M., Guengerich F. P. Characterization of a human liver cytochrome P-450 involved in the oxidation of debrisoquine and other drugs by using antibodies raised to the analogous rat enzyme. Proc. Natl. Acad. Sci. U.S.A. 1984; 81: 7348
  • Zanger U. M., Vilbois F., Hardwick J., Meyer U. A. Absence of hepatic cytochrome P450bufl causes genetically deficient debrisoquine oxidation in man. Biochemistry 1988; 27: 5447
  • Gonzalez F. J., Vibois F., Hardwick J. P., McBride O. W., Nebert D. W., Gelboin H. V., Meyer U. A. Human debrisoquine 4-hydroxylase (P450IID1): cDNA and deduced amino acid sequence and assignment of CYP2D locus to chromosome 22. Genomics 1988; 2: 174
  • Gonzalez F. J., Skoda R., Kimura S., Umeno M., Zanger U. M., Nebert D. W., Gelboin H. V., Hardwick J. P., Meyer U. A. Characterization of the common genetic defect in humans deficient in debrisoquine metabolism. Nature 1988; 331: 442
  • Kagimoto M., Heim M., Kagimoto K., Zeugin T., Meyer U. A. Multiple mutations of the human cytochrome P450IID6 gene (CYP2D6) in poor metabolizers of debrisoquine: study of the functional significance of individual mutations by expression of chimeric genes. J. Biol. Chem. 1990; 265: 17209
  • Broly F., Gaedigk A., Heim M., Eichelbaum M., Morike K., Meyer U. A. Debrisoquine/ sparteine hydroxylation genotype and phenotype: analysis of common mutations and alleles of CYP2D6 in a European population. DNA Cell Biol. 1991; 10: 545
  • Lindberg R. L.P., Negishi M. Alteration of mouse cytochrome P450coh substrate specificity by mutation of a single amino acid sequence. Nature 1989; 339: 6226
  • Kronbach T., Larabee T. M., Johnson E. F. Hybrid cytochromes P-450 identify a substrate binding domain in P-450IIC5 and P-450IIC4. Proc. Natl. Acad. Sci. U.S.A. 1989; 86: 8262
  • Skoda R. C., Gonzalez F. J., Demierre A., Meyer U. A. Two mutant alleles of the human cytochrome P-450dbl gene (P4502D1) associated with genetically deficient metabolism of debrisoquine and other drugs. Proc. Natl. Acad. Sci. U.S.A. 1988; 85: 5240
  • Meyer U. A. Genetic polymorphisms of drug metabolism. Fund. Clin. Pharmacol. 1990; 4: 595
  • Heim M., Meyer U. A. Genotyping of poor metabolizers of debrisoquine by allele-specific PCR amplification. Lancet 1990; 336: 529
  • Balant L. P., Gundert-Remy U., Boobis A. R., van Bahr C. Relevance of genetic polymorphism in drug metabolism in the development of new drugs. Eur. J. Clin. Pharmacol. 1989; 36: 551
  • Brosen K., Gram L. F. Clinical significance of the sparteine/debrisoquine oxidation polymorphism. Eur. J. Clin. Pharmacol. 1989; 36: 537
  • Dahlstrom B., Paalzow L. Pharmacokinetics and analgesia of codeine and its metabolite morphine, in. Opiates and Endogenous Opioid Peptides, H. W. Kos-terlitz. North Holland, Amsterdam 1976; 395
  • Desmeules J., Dayer P., Gascon M. P., Magistris M. Impact of genetic and environmental factors in codeine analgesia [Abstr.]. Clin. Pharmacol. Ther. 1989; 45: 122
  • Dayer P., Desmeules J., Leeman T., Striberni R. Bioactivation of the narcotic drug codeine in human liver is mediated by the polymorphic monooxygenase catalyzing debrisoquine 4-hydrox-ylation (cytochrome P-450dbl/bufl). Biochem. Bio-phys. Res. Commun. 1988; 152: 411
  • Yue Q. Y., Svenson J. O., Aim C., Sjoqvist F., Sawe J. Codeine O-demethylation co-segregates with polymorphic debrisoquine hydroxylation. Br. J. Clin. Pharmacol. 1989; 28: 639
  • Mortimer O., Person K., Landona M. G., Spalding D., Zanger U. M., Meyer U. A., Rane A. Polymorphic formation of morphine from codeine in poor and extensive metabolizers of dextromethorphan: relationship to the presence of im-munoidentified cytochrome P-450IID1. Clin. Pharmacol. Ther. 1990; 47: 27
  • Sindrup S. H., Brosen K., Bjerring P., Arendt-Nielsen L., Larsen U., Angelo H. R., Gram L. Codeine increases pain thresholds to copper vapor laser stimuli in extensive but not poor metabolizers of sparteine. Clin. Pharmacol. Ther. 1990; 48: 686
  • Barbeau A., Roy M., Paris S., Cloutier T., Plasse L., Poirier J. The ecogenetics of Parkinson's disease: 4-hydroxylation of debrisoquine. Lancet 1985; 1213
  • Baer A. N., McAllister C. B., Wilkinson G. R., Woosley R. I., Pincus T. Altered distribution of debrisoquine oxidation phenotypes in patients with systemic lupus erythematosus. Arthritis Rheum. 1986; 29: 137
  • Ayesh R., Idle J. R., Ritchie J. C., Crothers M. J., Hetzel M. R. Metabolic oxidation phenotypes as markers for susceptibility to lung cancer. Nature 1984; 312: 169
  • Caporaso N., Hayes R. B., Dosemeci M., Hoover R., Ayesh R., Hetzel M., Idle J. R. Lung cancer risk, occupational exposure, and the debrisoquine metabolic phenotype. Cancer Res. 1989; 49: 3675
  • Law M. R., Hetzel M. R., Idle M. R. Debrisoquine metabolism and genetic predisposition to cancer. Br. J. Cancer 1989; 59: 686
  • Harris C. C. Interindividual variation among humans in carcinogen metabolism, DNA adduct formation and DNA repair. Carcinogenesis 1527; 11: 1990
  • Speirs C. J., Murray S., Davies D. S., Biola Mabadeje A. F., Boobis A. R. Debrisoquine oxidation phenotype and susceptibility to lung cancer. Br. J. Clin. Pharmacol. 1990; 29: 101
  • Sugimura H., Caporaso N. E., Shaw G. L., Modali R. V., Gonzalez F. J., Hoover R. N., Resau J. H., Trump B. F., Weston A., Harris C. C. Human debrisoquine hydroxylase gene polymorphisms in cancer patients and controls. Carcinogenesis 1990; 11: 1527
  • Zanger U. M., Hauri H. P., Loeper J., Homberg J. C., Meyer U. A. Antibodies against human cytochrome P-450dbl in autoimmune hepatitis type II. Proc. Natl. Acad. Sci. U.S.A. 1988; 85: 8256
  • Manns M. P., Johnson E. F., Griffin K. J., Tan E. M., Sullivan K. F. Major antigen of liver kidney microsomal autoantibodies in idiopathic autoimmune hepatitis is cytochrome P450dbl. J. Clin. Invest. 1989; 83: 1066
  • Leeman T., Dayer P., Meyer U. A. Single-dose quinidine treatment inhibits metoprolol oxidation in extensive metabolizers. Eur. J. Clin. Pharmacol. 1986; 29: 739
  • Yang C. S., Yoo J. S.H., Ishizaki H., Hong J. Cytochrome P450IIE1: roles in nitrosa-mine metabolism and mechanisms of regulation. Drug Metab. Rev. 1990; 22: 147
  • Ryan D. E., Ramanathan L., Iida S., Thomas P. E., Haniu M., Shively J. E., Lieber C. S., Levin W. Characterization of a major form of rat hepatic microsomal cytochrome P-450 induced by isoniazid. J. Biol. Chem. 1985; 260: 6385
  • Patten C. J., Ning S. M., Lu A. Y.H., Yang C. S. Acetone-inducible cytochrome P-450: purification, catalytic activity, and interaction with cytochrome b5. Arch. Biochem. Biophys. 1986; 251: 629
  • Wrighton S. A., Thomas P. E., Molowa D. T., Haniu M., Shively J. E., Maines S. L., Watkins P. B., Parker G., Mendez-Picon G., Levin W., Guzelian P. S. Characterization of ethanol-inducible human liver N-nitrosodimethylamine de-methylase. Biochemistry 1986; 25: 6731
  • Lasker J. M., Raucy J., Kubota S., Bloswick B. P., Black M., Lieber C. S. Purification and characterization of human liver cytochrome P-450-ALC. Biochem. Biophys. Res. Commun. 1987; 148: 232
  • Ekstrom G., von Bahr C., Ingelman-Sundberg M. Human liver microsomal cytochrome P-450IIE1. Immunological evaluation of its contribution to microsomal ethanol oxidation, carbon tetrachloride reduction and NADPH oxidase activity. Biochem. Pharmacol 1989; 38: 689
  • Raucy J. L., Lasker J. M., Lieber C. S., Black M. Acetaminophen activation by human liver cytochromes P450IIE1 and P450IA2. Arch. Biochem. Biophys. 1989; 271: 270
  • Guengerich F. P., Kim D. H., Iwasaki M. Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chem. Res. Toxicol. 1991; 4: 168
  • Peter R., Bocker R., Beaune P. H., Iwasaki M., Guengerich F. P., Yang C. S. Hydrox-ylation of chlorzoxazone as a specific probe for human liver cytochrome P-450HE1. Chem. Res. Toxicol. 1990; 3: 566
  • Tinel M., Belghiti J., Descatoire V., Amouyal G., Letteron P., Geneve J., Larrey D., Pessayre D. Inactivation of human liver cytochrome P-450 by the drug methoxsalen and other psoralen derivatives. Biochem. Pharmacol. 1987; 36: 951
  • Thomas P. E., Bandiera S., Maines S. L., Ryan D. E., Levin W. Regulation of cytochrome P-450j, a high-affinity N-nitrosodimethylamine de-methylase, in rat hepatic microsomes. Biochemistry 1987; 26: 2280
  • Song B. J., Gelboin H. V., Park S. S., Yang C. S., Gonzalez F. J. Complementary DNA and protein sequences of ethanol-inducible rat and human cytochrome P-450s. J. Biol. Chem. 1986; 261: 16689
  • Perrot N., Nalpas B., Yang C. S., Beaune P. H. Modulation of cytochrome P450 isozymes in human liver, by ethanol and drug intake. Eur. J. Clin. Invest. 1989; 19: 549
  • Porter T. D., Khani S. C., Coon M. J. Induction and tissue-specific expression of rabbit cytochrome P450IIE1 and IIE2 genes. Mol. Pharmacol. 1989; 36: 61
  • Peng H. M., Porter T. D., Ding X., Coon M. J. Differences in the developmental expression of rabbit cytochromes P-450 2E1 and 2E2. Mol. Pharmacol. 1991; 40: 58
  • Watkins P. B. Role of cytochromes P450 in drug metabolism and hepatotoxicity. Semin. Liv. Dis. 1990; 10: 235
  • Hardwick J. P., Gonzalez F. J., Kasper C. B. Cloning of DNA complementary to cytochrome P-450 induced by pregnenolone-16a-carbon-itrile. J. Biol. Chem. 1983; 258: 10182
  • Gonzalez F. J., Song B. J., Hardwick J. P. Pregnenolone 16a-carbonitrile-inducible P-450 gene family: gene conversion and differential regulation. Mol. Cell. Biol 1986; 6: 2969
  • Hostetler K. A., Wrighton S. A., Kremers P., Guzelian P. S. Immunochemical evidence for multiple steroid-inducible hepatic cytochromes P-450 in the rat. Biochemistry 1987; 245: 27
  • Graves P. E., Kaminsky L. S., Halpert J. Evidence for functional and structural multiplicity of pregnenolone-16a-carbonitrile-inducible cytochrome P-450 isozymes in rat liver microsomes. Biochemistry 1987; 26: 3887
  • Halpert J. R. Multiplicity of steroid-inducible cytochromes P-450 in rat liver microsomes. Arch. Biochem. Biophys. 1988; 263: 59
  • Wrighton S. A., Maurel P., Schuetz E. G., Watkins P. B., Young B., Guzelian P. S. Identification of the cytochrome P-450 induced by macrolide antibiotics in rat liver as the glucocorticoid responsive cytochrome P-450p. Biochemistry 1985; 24: 2171
  • Sonderfan A. J., Arlotto M. P., Dutton D. R., McMillen S. K., Parkinson A. Regulation of testosterone hydroxylation by rat liver microsomal cytochrome P-450. Arch. Biochem. Biophys. 1987; 255: 27
  • Wang P. P., Beaune P., Kaminsky L. S., Dannan G. A., Kadlubar F. F., Larrey D., Guengerich F. P. Purification and characterization of six cytochrome P-450 isozymes from human liver microsomes. Biochemistry 1983; 22: 5375
  • Watkins P. B., Wrighton S. A., Maurel P., Schuetz E. G., Mendez-Picon G., Parker G. A., Guzelian P. S. Identification of an inducible form of cytochrome P-450 in human liver. Proc. Natl. Acad. Sci. U.S.A. 1985; 82: 6310
  • Guengerich F. P., Martin M. V., Beaune P. H., Kremers P., Wolff T., Waxman D. J. Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism. J. Biol. Chem. 1986; 262: 5051
  • Beaune P., Kremers P., Letawa-Goujon F., Gielen J. E. Monoclonal antibodies against human liver cytochrome P-450. Biochem. Pharmacol. 1985; 34: 3547
  • Molowa D. T., Schuetz E. G., Wrighton S. A., Watkins P. B., Kremers P., Mendez-Picon G., Parker G. A., Guzelian P. S. Complete cDNA sequence of a cytochrome P-450 inducible by glucocorticoids in human liver. Proc. Natl. Acad. Sci. U.S.A. 1986; 83: 5311
  • Beaune P. H., Umbenhauer D. R., Bork R. W., Lloyd R. S., Guengerich F. P. Isolation and sequence determination of a cDNA clone related to human cytochrome P-450 nifedipine oxidase. Proc. Natl. Acad. Sci. U.S.A. 1986; 83: 8064
  • Gonzalez F. J., Schmid B. J., Umeno M., McBride O. W., Hardwick J. P., Meyer U. A., Gelboin H. V., Idle J. R. Human P450PCN1: sequence, chromosome localization, and direct evidence through cDNA expression that P450PCN1 is nifedipine oxidase. DNA 1988; 7: 79
  • Bork R. W., Muto T., Beaune P. H., Srivastava P. K., Lloyd R. S., Guengerich F. P. Characterization of mRNA species related to human liver cytochrome P-450 nifedipine oxidase and the regulation of catalytic activity. J. Biol. Chem. 1989; 264: 910
  • Waxman D. J., Attisano C., Guengerich F. P., Lapenson D. P. Human liver microsomal steroid metabolism: identification of the major microsomal steroid hormone 66-hydroxylase cytochrome P-450 enzyme. Arch. Biochem. Biophys. 1988; 263: 424
  • Kitada M., Kamataki T., Itahashio K., Rikihisa T., Kanakubo Y. P-450 HFLa, a form of cytochrome P-450 purified from human fetal livers, is the 16ot-hydroxylase of dehydroepiandrosterone 3-sulfate. J. Biol. Chem. 1987; 262: 13534
  • Bocker R. H., Guengerich F. P. Oxidation of 4-aryl- and 4-alkyl-substituted 2,6-dimethyl-3,5, bis(alkoxycarbonyl)-l, 4-dihydropyridines by human liver microsomes and immunochemical evidence for the involvement of a form of cytochrome P-450. J. Med. Chem. 1986; 29: 1596
  • Kronbach T., Fischer V., Meyer U. A. Cyclosporine metabolism in human liver: identification of a cytochrome P-450III gene family as the major cyclosporine-metabolizing enzyme explains interactions of cyclosporin with other drugs. Clin. Pharmacol. Ther. 1988; 43: 630
  • Imaoka S., Enomoto K., Oda Y., Asada A., Fujimori M., Shimada T., Fujita S., Guengerich F. P., Funae Y. Lidocaine metabolism by human cytochrome P-450s purified from hepatic microsomes: comparison of those with rat hepatic cytochrome P-450s. J. Pharm. Exp. Ther. 1990; 255: 1385
  • Ramsdell H. S., Parkinson A., Eddy A. C., Eaton D. L. Bioactivation of aflatoxin B, by human liver microsomes: role of cytochrome P450 IIIA enzymes. Toxicol. Appl. Pharmacol. 1991; 108: 436
  • Guengerich F. P., Miiller-Enoch D., Blair I. A. Oxidation of quinidine by human liver cytochrome P-450. Mol. Pharmacol. 1986; 30: 287
  • Guengerich F. P. Oxidation of 17a-ethynylestra-diol by human liver cytochrome P-450. Mol. Pharmacol. 1988; 33: 500
  • Kronbach T., Mathys D., Umeno M., Gonzalez F. J., Meyer U. A. Oxidation of midazolam and triazolam by human liver cytochrome P450IIIA4. Mol. Pharmacol. 1989; 36: 89
  • Miranda C. L., Reed R. L., Guengerich F. P., Buhler D. R. Role of cytochrome P450IIIA4 in the metabolism of the pyrrolizidine alkaloid se-necionine in human liver. Carcinogenesis 1991; 12: 515
  • Wang R. A., Kari P. H., Lu A. Y.H., Thomas P. E., Guengerich F. P., Vyas K. P. Biotransformation of lovastatin. IV. Identification of cytochrome P450 3A proteins as the major enzymes responsible for the oxidative metabolism of lovastatin in rat and human liver microsomes. Arch. Biochem. Biophys. 1991; 290: 355
  • Guengerich F. P. Mechanism-based inactivation of human liver microsomal cytochrome P-450 IIIA4 by gestodene. Chem. Res. Toxicol. 1990; 3: 363
  • Watkins P. B., Murray S. A., Winkelman L. G., Heuman D. M., Wrighton S. A., Guzelian P. S. Erythromycin breath test as an assay of glucocorticoid-inducible liver cytochromes P-450. J. Clin. Invest. 1989; 83: 688
  • Saenger P., Forster E., Kream J. 6b˜-Hy-droxycortisol: a noninvasive indicator of enzyme induction. J. Clin. Endocrinol. Metab. 1981; 52: 381
  • Oellerich M., Burdelski M., Lautz H. U., Schulz M., Schmidt F. W., Herrmann H. Lidocaine metabolite formation as a measure of liver function in patients with cirrhosis. Ther. Drug Monit. 1990; 12: 219
  • Wrighton S. A., Brian W. R., Sari M. A., Iwasaki M., Guengerich F. P., Raucy J. L., Molowa D. T., VandenBranden M. Studies on the expression and metabolic capabilities of human liver cytochrome P450IIIA5 (HLp3). Mol. Pharmacol. 1990; 38: 207
  • Aoyama T., Yamano S., Waxman D. J., Lapenson D. P., Meyer U. A., Fischer V., Tyndale R., Inaba T., Kalow W., Gelboin H. V., Gonzalez F. J. Cytochrome P-450 hPCN3, a novel cytochrome P-450 IIIA gene product that is differentially expressed in adult human liver. J. Biol. Chem. 1989; 264: 10388
  • Schuetz J. D., Molowa D. T., Guzelian P. S. Characterization of a cDNA encoding a new member of the glucocorticoid-responsive cytochromes P450 in human liver. Arch. Biochem. Biophys. 1989; 274: 355
  • Rane A., Sjoqvist F., Orrenius S. Drugs and fetal metabolism. Clin. Pharmacol. Ther. 1973; 14: 666
  • Cresteil T., Beaune P., Kremers P., Flinois J. P., Leroux J. P. Drug-metabolizing enzymes in human foetal liver: partial resolution of multiple cytochromes P-450. Pediatr. Pharmacol. 1982; 2: 199
  • Wrighton S. A., Molowa D. T., Guzelian P. S. Identification of a cytochrome P-450 in human fetal liver related to glucorcorticoid-inducible cytochrome P-450HLp in the adult. Biochem. Pharmacol. 1988; 37: 3053
  • Wrighton S. A., VandenBranden M. Isolation and characterization of human fetal liver cytochrome P450HLp2: a third member of the P450III gene family. Arch. Biochem. Biophys. 1989; 268: 144
  • Kitada M., Kamataki T., Itahashi K., Rikihisa T., Kato R., Kanakurbo Y. Purification and properties of cytochrome P-450 from homogenates of human fetal livers. Arch. Biochem. Biophys. 1985; 241: 275
  • Hulla J. E., Juchau M. R. Occurrence and inducibility of cytochrome P450IIIA in maternal and fetal rats during prenatal development. Biochemistry 1989; 28: 4871
  • Kitada M., Taneda M., Itahashi K., Kamataki T. Four forms of cytochrome P-450 in human fetal liver: purification and their capacity to activate promutagens.y. Cancer Res. 1991; 82: 426
  • Eberhart D. C., Gemzik B., Halvorson M. R., Parkinson A. Species differences in the toxicity and cytochrome P450 IIIA-dependent metabolism of digitoxin. Mol. Pharmacol. 1991; 40: 859
  • Wrighton S. A., Stevens J. C., unpublished observations

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