Enantiomer-enantiomer interaction of a uricosuric antihypertensive diuretic (DBCA) in renal tubular secretion and stereoselective inhibition by probenecid in the cynomolgus monkey

References

• Cunningham R. F., Israili Z. H., Dayton P. G. Clinical pharmacokinetics of probenecid. Clinical Pharmacokinetics 1981; 6: 135–151
   PubMed Web of Science ®Google Scholar
• Drayer D. E. Pharmacodynamic and pharmacokinetic differences between drug enantiomers in humans: an overview. Clinical Pharmacology and Therapeutics 1986; 40: 125–133
   PubMed Web of Science ®Google Scholar
• Eichelbaum M., Mikus G., Vogelgesang B. Pharmacokinetics of (+)-, (—)- and (±)- verapamil after intravenous administration. British Journal of Clinical Pharmacology 1984; 17: 453–458
   PubMed Web of Science ®Google Scholar
• Foster R. T., Jamali F. Stereoselective pharmacokinetics of ketoprofen in the rat. Influence of route of administration. Drug Metabolism and Disposition 1988; 16: 623–626
   PubMed Web of Science ®Google Scholar
• Foster R. T., Jamali F., Russeli A. S., Alballa S. R. Pharmacokinetics of ketoprofen enantiomers in young and elderly arthritic patients following single and multiple doses. Journal of Pharmaceutical Sciences 1988; 77: 191–195
   PubMed Web of Science ®Google Scholar
• Giacomini K. M., Nelson W. L., Pershe R. A., Valdivieso L., Turner-Tamiyasu K., Blaschke T. F. In vivo interaction of the enantiomers of disopyramide in human subjects. Journal of Pharmacokinetics and Biopharmaceutics 1986; 14: 335–356
   PubMedGoogle Scholar
• Harada H., Matsushita Y., Yodo Y., Nakamura M., Yonetani Y. Studies on uricosuric diuretics. 1) 6,7-Dichloro-5-sulfamoyl-2,3-dihydrobenzofuran-2-carboxylic acids. Chemical and Pharmaceutical Bulletin 1987a; 35: 3195–3214
   PubMedGoogle Scholar
• Harada H., Matsushita Y., Yodo Y., Nakamura M., Yonetani Y. Studies on uricosuric diuretics. 2) 6,7-Dichloro-4-nitro, 6,7-dichloro-4-sulfamoyl and 6,7-dichloro-4-acyl-2,3-dihydrobenzofuran-2-carboxylic acids. Chemical and Pharmaceutical Bulletin 1987b; 35: 3215–3226
   PubMedGoogle Scholar
• Higaki K., Kadono K., Nakano M. Stereoselective pharmacokinetics of a novel uricosuric antihypertensive diuretic in rats: pharmacokinetic interaction between enantiomers. Journal of Pharmaceutical Sciences 1992a; 81: 935–939
   PubMedGoogle Scholar
• Higaki K., Nakano M. Stereoselective disposition of DBCA, a novel uricosuric antihypertensive diuretic, and itsN-monodemethylated metabolite in a perfused rat liver preparation. Effect of protein binding on the kinetics of DBCA. Drug Metabolism and Disposition 1992b; 20: 350–355
   PubMed Web of Science ®Google Scholar
• Hsyu P.-H., Glacomini K. W. Stereoselective renal clearance of pindolol in humans. Journal of Clinical Investigation 1985; 76: 1720–1726
   PubMed Web of Science ®Google Scholar
• Jamali F., Mehvar R., Pasutto F. M. Enantioselective aspects of drug action and disposition: therapeutic pitfalls. Journal of Pharmaceutical Sciences 1989; 78: 695–715
   PubMed Web of Science ®Google Scholar
• Lee E. J. D., Williams K. M. Chirality. Clinical pharmacokinetic and pharmacodynamic considerations. Clinical Pharmacokinetics 1990; 18: 339–345
   PubMed Web of Science ®Google Scholar
• Lima J. J., Boudoulas H., Shields B. J. Stereoselective pharmacokinetics of diso-pyramide enantiomers in man. Drug Metabolism and Disposition 1985; 13: 572–577
   PubMed Web of Science ®Google Scholar
• Lin J. H., Hsieh J. Y.-K. Enantioselective disposition and protein binding of [(5,6-dichloro-9A-propyl-3-oxo-2,3,9,9A-tetrahydro-1-H-fluoren-7-yl)-oxy] acetic acid, a new cerebral antiedemic agent, in rats. Drug Metabolism and Disposition 1988; 16: 540–545
   PubMedGoogle Scholar
• Morgan T. The use of diuretic drugs and aldosterone antagonists in hypertension. Handbook of Hypertension 1984; 5: 67–91
   Google Scholar
• Nakano M., Kawahara S. High-performance liquid chromatographic method for simultaneous determination of enantiomers of 5-dimethylsulphamoyl-6,7-dichloro-2,3-dihydrobenzofuran-2-carboxylic acid and itsN-monodemethyl metabolite in monkey plasma and urine after chiral derivatization. Journal of Chromatography 1991; 564: 235–241
   PubMedGoogle Scholar
• Nakano M., Kawahara S. Stereoselective renal tubular secretion of a new uricosuric diuretic, 6,7-dichloro-5-(N,N-dimethylsulfamoyl)-2,3-dihydro-2-benzofurancarboxylic acid (S-8666), in cynomolgus monkeys. Drug Metabolism and Disposition 1992; 20: 179–185
   PubMedGoogle Scholar
• Nakamura M., Kawabata T., Itoh T., Miyata K., Harada H. Stereoselective saluretic effect and localization of renal tubular secretion of enantiomers of S-8666, a novel uricosuric antihypertensive diuretic. Drug Development Research 1990; 19: 23–36
   Google Scholar
• Nakamura M., Shimizu T., Miyata K., Kawabata T., Harada H. Diuretic effects of a novel uricosuric antihypertensive S-8666 in rats, mice, monkey, and dogs: comparison with furosemide and trichlormethiazide. Drug Development Research 1988; 12: 41–51
   Google Scholar
• Notterman D. A., Drayer D. E., Metakis L., Reidenberg M. M. Stereoselective renal tubular secretion of quinidine and quinine. Clinical Pharmacology and Therapeutics 1986; 40: 511–517
   PubMed Web of Science ®Google Scholar
• Ofori-Adjei D., Ericsson O., Lindstrom B., Hermansson J., Adjepon-Yamoah K., Sjöq-Vist F. Enantioselective analysis of chloroquine and desethylchloroquine after oral administration of racemic chloroquine. Therapeutic Drug Monitoring 1986; 8: 457–461
   PubMed Web of Science ®Google Scholar
• Paxton J. W. Interaction of probenecid with the protein binding of methotrexate. Pharmacology 1984; 28: 86–89
   PubMedGoogle Scholar
• Sjöholm I., Ekman B., Kober A., Ljungstedt-Påhiman I., Seiving B., Sjödin T. Binding of drugs to human serum albumin: XI. The specificity of three binding sites as studied with albumin immobilized in microparticles. Molecular Pharmacology 1979; 16: 767–777
   PubMed Web of Science ®Google Scholar
• Somogyi A. A., Bochner F., Sallustio B. C. Stereoselective inhibition of pindolol renal clearance by cimetidine in humans. Clinical Pharmacology and Therapeutics 1992; 51: 379–387
   PubMed Web of Science ®Google Scholar
• Spahn H., Spahn I., Benet L. Z. Probenecid-induced changes in the clearance of carprofen enantiomers: a preliminary study. Clinical Pharmacology and Therapeutics 1989; 45: 500–505
   PubMed Web of Science ®Google Scholar
• Stoeckel K., Trueb V., Dubach U. C., McNamara P. J. Effect of probenecid on the elimination and protein binding of ceftriaxone. European Journal of Clinical Pharmacology 1988; 34: 151–156
   PubMedGoogle Scholar
• Takahashi H., Ogata H., Shimizu M., Hashimoto K., Masuhara K., Kashiwada K., Someya K. Comparative pharmacokinetics of unbound disopyramide enantiomers following oral administration of racemic disopyramide in humans. Journal of Pharmaceutical Sciences 1991; 80: 709–711
   PubMedGoogle Scholar
• Tocco D. J., De Luna F. A., Duncan A. E. W., Hsieh J. H., Lin J. H. Interspecies differences in stereoselective protein binding and clearance of MK-571. Drug Metabolism and Disposition 1990; 18: 388–392
   PubMed Web of Science ®Google Scholar
• Tucker G. T., Lennard M. S. Enantiomer specific pharmacokinetics. Pharmacology and Therapeutics 1990; 45: 309–329
   PubMed Web of Science ®Google Scholar
• Vangiessen G. J., Kaiser D. G. GLC Determination of ibuprofen [dl-2-(p-isobutylphenyl)propionic acid] enantiomers in biological specimens. Journal of Pharmaceutical Sciences 1975; 64: 798–801
   PubMedGoogle Scholar
• Yamaoka Y., Tanigawara Y., Nakagawa T., Uno T. A pharmacokinetic analysis program (MULTI) for microcomputer. Journal of Pharmacobio-Dynamics 1981; 4: 879–885
   PubMedGoogle Scholar
• Yonetani Y., Iwaki K., Shinosaki T., Kawase-Hanafusa A., Harada H., Van Es A. A. A new uricosuric diuretic, S-8666, in rats and chimpanzees. Japanese Journal of Pharmacology 1987a; 43: 389–398
   PubMedGoogle Scholar
• Yonetani Y., Iwaki K., Ishii M., Harada H. A new diuretic that does not reduce renal handling of uric acid in rats, S-8666. Japanese Journal of Pharmacology 1987b; 43: 399–405
   PubMedGoogle Scholar