Phenacetin O-deethylation by human liver microsomes: Kinetics and propranolol inhibition

References

• Bax N. D. S., Lennard M. S., Shaw L., Tucker G. T., Woods H. F. Covalent binding of propranolol to human liver microsomes: Biochemical and metabolic studies. British Journal of Pharmacology 1986; 89: 709P
   Google Scholar
• Boobis A. R., Brodie M. J., Kahn G. C., Fletcher D. R., Saunders J. H., Davies D. S. Monooxygenase activity of.human liver in microsomal fractions of needle biopsy specimens. British Journal of Clinical Pharmacology 1980; 9: 11–19
   PubMed Web of Science ®Google Scholar
• Boobis A. R., Kahn G. C., Whyte C., Brodie M. J., Davies D. S. Biphasic O-deethylation of phenacetin and 7-ethoxycoumarin by human and rat liver microsomal fractions. Biochemical Pharmacology 1981; 30: 2451–2456
   PubMed Web of Science ®Google Scholar
• Büch H., Gerhards W., Karachristianidis G., Pfleger K., Rummel W. Hemmung der durch Phenacetin und p-Phenetidin verursachten Methämoglobin-Bildung durch Barbiturate. Biochemical Pharmacology 1967; 16: 1575–1583
   PubMed Web of Science ®Google Scholar
• Convey A. H., Pantuck E. J., Hsaio K. -C., Garland W. A., Anderson K. E., Alvares A. P., Kappas A. Enhanced phenacetin metabolism in human subjects fed charcoal-broiled beef. Clinical Pharmacology and Thetapeutics 1976; 20: 633–642
   Google Scholar
• Devonshire H. W., Kong I., Cooper M., Sloan T. P., Idle J. R., Smith R. L. The contribution of genetically determined oxidation status to inter-individual variation in phenacetin disposition. British Journal of Clinical Pharmacology 1983; 16: 157–166
   PubMed Web of Science ®Google Scholar
• Distlerath L. M., Reiliy P. E. B., Martin M. V., Wilkinson G. R., Guengerich F. P. Immunochemical characterization of the human liver cytochrome P-450 involved in Debrisoquine 4-hydroxylation. Microsomes and Drug Oxidations, A. R. Boobis, J. Caldwell, F. de Matteis, C. R. Elcombe. Taylor & Francis, London 1985a; 380–389
   Google Scholar
• Distlerath L. M., Reiliy P. E. B., Martin M. V., Davis G. G., Wilkinson G. R., Guengekich 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. Journal of Biological Chemistry 1985b; 260: 9057–9067
   PubMed Web of Science ®Google Scholar
• Duggleby R. G. Regression analysis of nonlinear Arrhenius, plots: an empirical model and a computer program. Computers in Biology and Medicine 1984; 14: 447–455
   PubMed Web of Science ®Google Scholar
• Ellis K. J., Duggleby R. G. What happens wtien data are fitted to the wrong equation?. Biochemical Journal 1978; 171: 513–517
   PubMed Web of Science ®Google Scholar
• Estabrook R. W., Peterson J., Baron J., Hildebrandt A. The spectrophotometric measurement of turbid suspensions of cytochromes associated with drug metabolism. Methods in Pharmacology, C. F. Chignell. Appleton-Century-Crofts, New York 1972; Volume 2: 303–350
   Google Scholar
• Guengerich F. P. Microsomal enzymes involved in toxicology—analysis and separation. Principles and Methods of Toxicology, A. Wallace Hayes. Raven Press, New York 1982; 609–634
   Google Scholar
• Guengerich F. P., Müller-Enoch D., Blair I. A. Oxidation of quinidine by human liver cytochrome P-450. Molecular Pharmacology 1986; 30: 287–295
   PubMed Web of Science ®Google Scholar
• Hall S. D., Guengerich F. P., Branch R. A., Wilkinson G. R. Characterization and inhibition of mephenytoin 4-hydroxylase activity in human liver microsomes. Journal of Pharmacology and Experimental Therapeutics 1987; 240: 216–222
   PubMed Web of Science ®Google Scholar
• Inaba T., Jurima M., Mahon W. A., Kalow W. In vitro inhibition studies of two isozymes of human liver cytochrome P-450, Mephenytoin p-hydroxylase and sparteine monooxygenase. Drug Metabolism and Disposition 1985; 13: 443–448
   PubMed Web of Science ®Google Scholar
• Jurima M., Inaba T., Kalow W. Mephenytoin metabolism in vitro by human liver. Drug Metabolism and Disposition 1985; 13: 151–155
   PubMed Web of Science ®Google Scholar
• Kahn G. C., Boobis A. R., Brodie M. J., Toverud E. -L., Murray S., Davies D. S. Phenacetin O-deethylase: an activity of a cytochrome P-450 showing genetic linkage with that catalysing the 4-hydroxylation of debrisoquine?. British Journal of Clinical Pharmacology 1985; 20: 67–76
   PubMed Web of Science ®Google Scholar
• Kalow W. The genetic defect of mephenytoin hydroxylation. Xenobiotica 1986; 16: 379–389
   PubMed Web of Science ®Google Scholar
• Kremers P., Beaune P., Cresteil T., De Grave J., Columelli S., Leroux J. -P., Geilen J. E. Cytochrome P-450 monooxygenase activities in human and rat liver microsomes. European Journal of Biochemistry 1981; 118: 599–606
   PubMedGoogle Scholar
• Larrey D., Distlerath L. M., Dannan G. A., Wilkinson G. R., Guengerich F. P. Purification and characterization of the rat liver microsomal cytochrome P-450 involved in the 4-hydroxylation of debrisoquine, a prototype for genetic variation in oxidative drug metabolism. Biochemistry 1984; 23: 2787–2795
   PubMed Web of Science ®Google Scholar
• Lennard M. S., Tucker G. T., Silas J. H., Woods H. F. Debrisoquine polymorphism and the metabolism and action of metoprolol, timolol, propranolol and atenolol. Xenobiotica 1986; 16: 435–447
   PubMed Web of Science ®Google Scholar
• Lowry O. H., Rosebrough N. J., Farr A. L., Randall R. J. Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry 1951; 193: 265–275
   PubMed Web of Science ®Google Scholar
• Nash T. The colorimetric estimation of formaldehyde by means of the Hantzsch reaction. Biochemical Journal 1953; 55: 416–421
   PubMed Web of Science ®Google Scholar
• Otton S. V., Inaba T., Kalow W. Competitive inhibition of sparteine oxidation in human liver by β-adrenoceptor antagonists and other cardiovascular drugs. Life Sciences 1984; 34: 73–80
   PubMed Web of Science ®Google Scholar
• Pantuck E. J., Hsaio K. -C., Loub W. D., Wattenberg L. W., Kuntzman R., Conney A. H. Stimulatory effect of vegetables on intestinal drug metabolism in the rat. Journal of Pharmacology and Experimental Therapeutics 1976; 198: 278–283
   PubMed Web of Science ®Google Scholar
• Phillips A. H., Langdon R. G. Hepatic triphosphopyridine nucleotide-cytochrome c reductase: isolation, characterization, and kinetic studies. Journal of Biological Chemistry 1962; 237: 2652–2660
   PubMed Web of Science ®Google Scholar
• Reilly P. E. B., Winzor D. J. Adverse drug interactions with cimetidine: competitive inhibition of monooxygenase-dependent N-demethylation of morphine. Biochemical Pharmacology 1984; 33: 1151–1153
   PubMed Web of Science ®Google Scholar
• Sloan T. P., Mahgoub A., Lancaster R., Idle J. R., Smith R. L. Polymorphism of carbon oxidation of drugs and clinical implications. British Medical Journal 1978; 2: 655–657
   PubMed Web of Science ®Google Scholar
• Souhaili-El Amri H., Batt A. M., Siest G. Comparison of cytochrome P-450 content and activities in liver microsomes of seven animal species, including man. Xenobiotica 1986; 16: 351–358
   PubMed Web of Science ®Google Scholar
• Thomas B. H., Coldwell B. B., Zeitz W., Solomonraj G. Effect of aspirin, caffeine, and codeineonthe metabolismof phenacetin and acetaminophen. Clinical Pharmacology and Therapeutics 1972; 13: 906–910
   PubMed Web of Science ®Google Scholar
• von Bahr C., Birgersson C., Morgan E. T., Eriksson Ö, Göramsson M., Spina E., Woodhouse K. Oxidation of tricyclic antidepressant drugs, debrisoquineand 7-ethoxyresorufin, by human liver preparations. Xenobioiica 1986; 16: 391–400
   PubMed Web of Science ®Google Scholar
• Wang P. P., Beaine 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: 5375–5383
   PubMed Web of Science ®Google Scholar
• Wolff T., Distlerath L. M., Worthington M. T., Groopman J. D., Mammons G. J., Kadlubar F. F., Provgh R. A., Martin M. V., Guengerich F. P. Substrate specificity of human liver cytochrome P-450 debrisoquine 4-hydroxylase probed using immunochemical inhibition and chemical modeling. Cancer Research 1985; 45: 2116–2122
   PubMed Web of Science ®Google Scholar