Comparison of the rat liver microsomal metabolism of the enantiomers of warfarin and 4′-nitrowarfarin (Acenocoumarol)

References

• Baars L. G. M., Schepers M. T., Hermans J. J. R., Dahlmans H. J. J., Thijssen H. H. W. Enantioselective structure-pharmacokinetic relationships of ring substituted warfarin analogues in the rat. Journal of Pharmacy and Pharmacology 1990; 42: 861–866
   PubMed Web of Science ®Google Scholar
• Banfield C., Rowland M. Stereospecific fluorescence high-performance liquid chromatographic analysis of warfarin and its metabolites in plasma and urine. Journal of Pharmaceutical Sciences 1984; 73: 1392–1396
   PubMed Web of Science ®Google Scholar
• Eichelbaum M. Pharmacokinetic and pharmacodynamic consequences of stereoselective drug metabolism in man. Biochemical Pharmacology 1988; 37: 93–96
   PubMed Web of Science ®Google Scholar
• Fasco M. J., Baker F. D., Fenton J. W. Warfarin—stereochemical aspects of its metabolism by rat liver microsomes. Biochemical Pharmacology 1976; 25: 2153–2162
   PubMedGoogle Scholar
• Fasco M. J., Dymerski P. P., Wos J. D., Kaminsky L. S. A new warfarin metabolite: structure and function. Journal of Medicinal Chemistry 1978; 21: 1054–1059
   PubMed Web of Science ®Google Scholar
• Greenlee W. F., Poland A. An improved assay of 7-ethoxycoumarin O-deethylase activity: induction of hepatic enzyme activity in C57BL/6J and DBA/2J mice by phenobarbital, 3-methylcholanthrene and 2,3,7,8-tetrachlorodibenzo-p-dioxin. Journal of Pharmacology and Experimental Therapeutics 1978; 205: 596–605
   PubMed Web of Science ®Google Scholar
• Guengerich F. P., Dannan G. A., Wright S. T., Martin M. V., Kaminsky L. S. Purification and characterization of microsomal cytochrome P-450s. Xenobiotica 1982; 12: 701–716
   PubMed Web of Science ®Google Scholar
• Heimark L. D., Trager W. F. Stereoselective metabolism of conformational analogues of warfarin by β-napthoflavone-inducible cytochrome P-450. Journal of Medicinal Chemistry 1985; 28: 503–506
   PubMedGoogle Scholar
• Hermans J. J. R., Thijssen H. H. W. The in vitro ketone reduction of warfarin and analogues. Substrate stereoselectivity, product stereoselectivity and species differences. Biochemical Pharmacology 1989; 38: 3365–3370
   PubMed Web of Science ®Google Scholar
• Hoensch H. P., Hutzel H., Kirch W., Ohnhaus E. E. Isolation of human hepatic microsomes and their inhibition by cimetidine and ranitidine. European Journal of Clinical Pharmacology 1985; 29: 199–206
   PubMed Web of Science ®Google Scholar
• Kaminsky L. S. Warfarin as a probe of cytochromes P-450 function. Drug Metabolism Reviews 1989; 20: 479–487
   PubMed Web of Science ®Google Scholar
• Kaminsky L. S., Dunbar D. A., Wang P. P., Beaune P., Larrey D., Guengerich F. P., Schnellemann R. G., Sipes I. G. Human hepatic cytochrome P-450 composition as probed by in vitro microsomal metabolism of warfarin. Drug Metabolism and Disposition 1984; 12: 470–477
   PubMed Web of Science ®Google Scholar
• Kelley J. G., O'Malley K. Clinical pharmacokinetics of oral anticoagulants. Clinical Pharmacokinetics 1979; 4: 1–15
   PubMedGoogle Scholar
• Lewis R. J., Trager W. F., Chan K. K., Breckenridge A., Orme M., Garland M., Schary W. Warfarin. Stereochemical aspects of its metabolism and the interaction with phenylbutazone. Journal of Clinical Investigations 1974; 53: 1607–1617
   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
• Macleod S. M., Renton K. W., Bade N. R. Post mortem characteristics of the hepatic microsomal drug oxidizing enzyme system. Chemical-Biological Interations 1973; 7: 29–37
   PubMed Web of Science ®Google Scholar
• Miners J. O., Smith K. J., Robson R. A., McManus M. E., Veronese M. E., Birkett D. J. Tolbutamide hydroxylation by human liver microsomes. Biochemical Pharmacology 1988; 37: 1137–1144
   PubMed Web of Science ®Google Scholar
• Pohl L. H., Bales R., Trager W. F. Warfarin: stereochemical aspects of its metabolism in vivo in the rat. Research Communications of Chemical and Pathological Pharmacology 1976; 15: 233–255
   PubMedGoogle Scholar
• Pohl L. R., Porter W. R., Trager W. F. Stereochemical biotransformation of warfarin as a probe of the homogeneity and mechanism of microsomal hydroxylases. Biochemical Pharmacology 1977; 26: 115–120
   PubMedGoogle Scholar
• Powell M. L., Pope B., Elmer G. W., Trager W. F. Biliary excretion of warfarin metabolites and their metabolism by rat gut flora. Life Sciences 1977; 20: 171–178
   PubMed Web of Science ®Google Scholar
• Rane A., Wilkinson G. R., Shand D. G. Prediction of hepatic extraction ratio from in vitro measurement of intrinsic clearance. Journal of Pharmacology and Experimental Therapeutics 1977; 200: 420–424
   PubMed Web of Science ®Google Scholar
• Rendic S., Kajfez F., Ruf H.-H. Characterization of cimetidine, ranitidine, and related structures' interaction with cytochrome P-450. Drug Metabolism and Disposition 1983; 11: 137–142
   PubMed Web of Science ®Google Scholar
• Rettie A. E., Eddy C., Heimark L. D., Gibaldi M., Trager W. F. Characteristics of warfarin hydroxylation by human liver microsomes. Drug Metabolism and Disposition 1989; 17: 265–270
   PubMedGoogle Scholar
• Rutten A. J. J. L., Flake H. E., Catsburg J. F., Topp R., Blaauboer B. J., Holsteijn I., Doorn L., Leeuwen F. R. X. Interlaboratory comparison of total cytochrome P-450 and protein determinations in rat liver microsomes. Archives of Toxicology 1987; 61: 27–35
   PubMed Web of Science ®Google Scholar
• Sachs L. Angewandte Statistik6th edn. Springer-Verlag, Berlin 1984; 381–426
   Google Scholar
• Testa B. Substrate and product stereoselectivity in monooxygenase-mediated drug activation and inactivation. Biochemical Pharmacology 1988; 37: 85–92
   PubMed Web of Science ®Google Scholar
• Thijssen H. H. W., Baars L. G. M. The biliary excretion of acenocoumarol in the rat: stereochemical aspects. Journal of Pharmaceutical Pharmacology 1987; 39: 655–657
   PubMedGoogle Scholar
• Thijssen H. H. W., Baars L. G. M., Drittij-Reijnders M. J. Stereoselective aspects in the pharmacokinetics and pharmacodynamics of acenocoumarol and its amino and acetamido derivatives in the rat. Drug Metabolism and Disposition 1985; 13: 593–597
   PubMedGoogle Scholar
• Thijssen H. H. W., Jansen G. M. J., Baars L. G. M. Lack of effect of cimetidine on pharmacodynamics and kinetics of single oral doses of R- and S-acenocoumarol. European Journal of Pharmacology 1986; 30: 619–623
   Google Scholar
• Trager W. F., Lewis R. J., Garland W. A. Mass spectral analysis in the identification of human metabolites of warfarin. Journal of Medicinal Chemistry 1970; 13: 1196–1204
   PubMed Web of Science ®Google Scholar
• Valente E. J., Trager W. F. Anomalous chiroptical properties of warfarin and phenprocoumon. Journal of Medicinal Chemistry 1978; 21: 141–143
   PubMedGoogle Scholar
• West B. D., Preis S., Schroeder C. H., Link K. P. Studies on the 4-hydroxycoumarins. XVII. The resolution and absolute configuration of warfarin. Biochemical Pharmacology 1961; 83: 2676–2679
   Google Scholar
• Wheeler C., Trager W. F., Porter W. R. Stereochemical aspects of the metabolism of phenprocoumon in rat liver microsomes. Biochemical Pharmacology 1981; 30: 1785–1790
   PubMedGoogle Scholar
• Williams K., Lee E. Importance of drug enantiomers in clinical pharmacology. Drugs 1985; 30: 333–354
   PubMed Web of Science ®Google Scholar
• Yacobi A., Levy G. Pharmacokinetics of the warfarin enantiomers in rats. Journal of Pharmacokinetics and Biopharmaceutics 1974; 2: 239–255
   PubMedGoogle Scholar
• Yacobi A., Levy G. Protein binding of warfarin enantiomers in serum of humans and rats. Journal of Pharmacokinetics and Biopharmaceutics 1977; 5: 123–131
   PubMedGoogle Scholar