Relationship between chemical structure and physicochemical properties of series of bulky organic cations and their hepatic uptake and biliary excretion rates

Journal of Pharmacology and Experimental Therapeutics

Volumn 282, Issue 2, 1997, Pages 715-726

  Proost, Johannes H ^a,b   Roggeveld, Jan ^a,b   Wierda, J Mark K H ^b   Meijer, Dirk K F ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY MEDICAL CENTER GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3ALPHA ACETOXY 17ALPHA BUTYRYLOXY 2BETA PIPERIDINO 5ALPHA ANDROSTAN 16BETA YL) 1 METHYLPIPERIDINIUM BROMIDE; 1 (3ALPHA ACETOXY 17BETA BUTYRYLOXY 2BETA PIPERIDINO 5ALPHA ANDROSTAN 16BETA YL) 1 ALLYLPIPERIDINIUM BROMIDE; 1 (3ALPHA ACETOXY 17BETA BUTYRYLOXY 2BETA PIPERIDINO 5ALPHA ANDROSTAN 16BETA YL) HEXAHYDRO 1 METHYL 1H AZEPINIUM BROMIDE; 2BETA,16BETA DIPIPERIDINO 5ALPHA ANDROSTAN 3ALPHA OL ACETATE DIMETHOBROMIDE; 3 DEACETYLVECURONIUM; CATION; NEUROMUSCULAR BLOCKING AGENT; ORG 20059; ORG 20297; ORG 9273; ORG 9453; ORG 9489; ORG 9955; PANCURONIUM; PIPECURONIUM; RAPACURONIUM BROMIDE; ROCURONIUM; UNCLASSIFIED DRUG; VECURONIUM;

ARTICLE; BILIARY EXCRETION; DRUG ACCUMULATION; DRUG EXCRETION; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG UPTAKE; HUMAN; ISOLATED LIVER; LIPOPHILICITY; NEUROMUSCULAR BLOCKING; NONHUMAN; PARTITION COEFFICIENT; PRIORITY JOURNAL; RAT;

ANIMALS; BILE; BLOOD PROTEINS; CATIONS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; LIVER; MALE; MOLECULAR STRUCTURE; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030877478     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (68)

1. AGOSTON, S., HOUWERTJES, M. C. AND SALT, P. J.: A new method for studying the relationship between hepatic uptake of drugs and their pharmacodynamic effects in anaesthetized cats. Br. J. Pharmacol. 68: 637-643, 1980.
2. BAIRD, W. L. M. AND VIBY-MOGENSEN, J.: Clinical considerations in the rational use of neuromuscular blocking drugs. In Muscle Relaxants, ed. by S. Agoston and W. C. Bowman, pp. 181-197, Elsevier Science Publishers, Amsterdam, 1990.
3. BASS, L. AND KEIDING, S.: Physiologically based models and strategic experiments in hepatic pharmacology. Biochem. Pharmacol. 37: 1425-1431, 1988.
4. BENCINI, A. F., HOUWERTJES, M. C. AND AGOSTON, S.: Effects of hepatic uptake of vecuronium bromide and its putative metabolites on their neuromuscular blocking actions in the cat. Br. J. Anaesth. 57: 789-795, 1985.
5. BENCINI, A. F., MOL, W. E. M., SCAF, A. H. J., ERSTEN, U. W., WOLTERS, K. T. P., AGOSTON, S. AND MEIJER, D. K. F.: Uptake and excretion of vecuronium bromide and pancuronium bromide in the isolated perfused rat liver. Anesthesiology 69: 487-492, 1988.
6. BENCINI, A. F., SCAF, A. H. J., SOHN, Y. J., KERSTEN-KLEEF, U. W. AND AGOSTON, S.: Hepatobiliary disposition of vecuronium bromide in man. Br. J. Anaesth, 58: 988-995, 1986.
7. BOSSUYT, X., MÜLLER, M., HAGENBUCH, B. AND MEIER, P. J.: Polyspecific steroid and drug clearance by an organic anion transporter of mammalian liver. J. Pharmacol. Exp. Ther. 276: 891-896, 1996a.
8. BOUSSUYT, K., MÜLLER, M. AND MEIER, P. J.: Multispecific amphipathic substrate transport by an organic anion transporter of human liver. J. Hepatol. 25: 733-738, 1996b.
9. BOXENBAUM, H. G., RIEGELMAN, S. AND ELASHOFF, R. M.: Statistical estimation in pharmacokinetics. J. Pharmacokinet. Biopharm. 2: 123-148, 1974.
10. BUSCH, A. E., QUESTER, S., ULZHEIMER, J. C., WALDEGGER, S., GORBOULEV, V., ARNDT, P., LANG, F. AND KOEPSELL, H.: Electrogenic properties and substrate specificity of the polyspecific rat cation transporter rOCT1. J. Biol. Chem. 271: 32698-32604, 1996.
11. COLBURN W. A., BRAZZELL, R. K. AND BEKERSKY, I.: Organ perfusion studies. J. Pharm. Sci. 72: 970, 1983.
12. D'ARGENIO, D. Z. AND SCHUMITZKY, A.: A program package for simulation and parameter estimation in pharmacokinetic systems. Comp. Prog. Biomed. 9: 115-134, 1979.
13. DRAPER, N. R. AND SMITH, H.: Applied Regression Analysis, pp. 44-85, John Wiley & Sons, New York, 1981.
14. DUVALDESTIN, P. AND HENZEL, D.: Binding of tubocurarine, fazadinium, pancuronium and Org NC 45 to serum proteins in normal man and in patients with cirrhosis. Br. J. Anaesth. 54: 513-516, 1982.
15. FEITSMA, K. G., DRENTH, B. F. H., DE ZEEUW, R. A., OOSTING, R. AND MEIJER, D. K, F.: Unequal disposition of enantiomers of the organic cation oxyphenonium in the rat isolated perfused liver. J. Pharm. Pharmacol. 41: 27-31, 1989.
16. FOLDES, F. F. AND DEERY, A.: Protein binding of atracurium and other shortacting neuromuscular blocking agents and their interaction with human cholinesterases. Br. J. Anaesth. 55: 31S-34S, 1983.
17. GODFREY, K. R. AND CHAPMAN, M. J.: The problem of model indistinguishability in pharmacokinetics. J. Pharmacokinet. Biopharm. 17: 229-267, 1989.
18. GODFREY, K. R., CHAPMAN, M. J. AND VAJDA, S.: Identifiability and indistinguishability of nonlinear pharmacokinetic models. J. Pharmacokinet. Biopharm. 22: 229-251, 1994.
19. GRÜNDEMANN, D., GORBOULEV, V., GAMBARYAN, S., VEYHL, M. AND KOEPSELL, H.: Drug excretion mediated by a new prototype of polyspecific transporter. Nature 372: 549-552, 1994.
20. JACQUEZ, J. A.: Identifiability: The first step in parameter estimation. FASEB Fed. Proc. 46: 2477-2480, 1987.
21. KARTENBECK, J., KEUSCHNER, U., MAYER, R. AND KEPPLER, D.: Absense of the canalicular isoform of the MRP gene-encoded conjugate export pump from the hepatocytes in Dubin-Johnson syndrome. Hepatology 23: 1061-1066, 1996.
22. KLEEF, U. W., PROOST, J. H., ROGGEVELD, J. AND WIERDA, J. M. K. H.: Determination of rocuronium and its putative metabolites in body fluids and tissue homogenates. J. Chromatogr. 621: 65-76, 1993.
23. LAVY, U. I., HESPE, W. AND MEIJER, D. K. F.: Uptake and excretion of the quaternary ammonium compound deptropine methoiodide in the isolated perfused rat liver. Naunyn-Schmiedebergs Arch. Pharmacol. 275: 183-192, 1872.
24. MEIJER, D. K. F., Bos, E. S. AND VAN DER LAAN, K. J.: Hepatic transport of mono- and bisquaternary ammonium compounds. Eur. J. Pharmacol. 11: 371-377, 1970.
25. MEIJER D. K. F., ARENDS, J. W. AND WEITERING, J. G.: The cardiac glycoside sensitive step in the hepatic transport of the bisquaternary ammonium compound, hexafluorenium. Eur. J. Pharmacol. 15: 245-251, 1971.
26. MEIJER, D. K. F.: The mechanisms for hepatic uptake and biliary excretion of organic cations. In Intestinal Permeation, ed. by M. Kramer and F. Lauterbach, pp. 196-207, Excerptia Medica, Amsterdam, 1976.
27. MEIJER, D. K. F., MOL, W. E. M., MÜLLER, M. AND KURZ, G.: Mechanisms for hepato-biliary transport of cationic drugs studied with the intact organ and on the membrane level. In Hepatic Transport in Organic Substances, ed. by E. Petzinger, R. K. H. Kinne and H. Sies, pp. 344-367, Springer-Verlag, Berlin/Heidelberg, 1989.
28. MEIJER, D. K. F., MOL, W. E. M., MÜLLER, M. AND KURZ, G.: Carrier-mediated transport in the hepatic distribution and elimination of drugs, with special reference to the category of organic cations. J. Pharmacokinet. Biopharm. 18: 35-70, 1990.
29. MEIJER, D. K. F., MOL, W. E. M., MÜLLER, M., STEEN, H. AND KURZ, G.: Carrier-mediated transport in the hepatic distribution and elimination of organic cations. In Hepatic metabolism and disposition of endo- and xenobiotics, ed. by K. W. Bock, S. Matern, W. Gerok and R. Schmid, pp. 259-270, Kluwer Academic Publishers, Dordrecht/Boston/London, 1991.
30. MEIJER, D. K. F. AND WEITERING, J. G.: Curare-like agents: relation between lipid solubility and transport into bile in perfused liver. Eur. J. Pharmacol. 10: 283-289, 1970.
31. MOL, W. E. M., FOKKEMA, G. N., WEERT, B. AND MEIJER, D. K. F.: Mechanisms for the hepatic uptake of organic cations: Studies with the muscle relaxant vecuronium in isolated rat hepatocytes. J. Pharmacol. Exp. Ther. 244: 268-275, 1988.
32. MOL, W. E. M. AND MEIJER, D. K. F.: Hepatic transport mechanisms for bivalent organic cations: Subcellular distribution and hepato-biliary concentration gradients of some steroidal muscle relaxants. Biochem. Pharmacol. 39: 383-390, 1990.
33. MOL, W. E. M., ROMBOUT, F. PAANAKKER, J. E., OOSTING, R., SCAF, A. H. J. AND MEIJER, D. K. F.: Pharmacokinetics of steroidal muscle relaxants in isolated perfused rat liver. Biochem. Pharmacol. 44: 1453-1459, 1992.
34. MOSELEY, R. H. AND VAN DYKE, R. W.: Organic cation transport by rat liver lysosomes. Am. J. Physiol. 268 (Gastrointest. Liver Physiol. 31): G480-G486, 1995.
35. NEEF, C. AND MEIJER, D. K. F.: Structure-pharmacokinetics relationship of Quaternary ammonium compounds: Correlation of physicochemical and pharmacokinetic parameters. Naunyn-Schmiedebergs Arch. Pharmacol. 328: 111-118, 1984
36. NELDER, J. A. AND MEAD, R.: A simplex method for function minimization. Comput. J. 7: 308-313, 1965.
37. NOY, N. AND ZAKIM, D.: Physical-chemical basis for the uptake of organic compounds by cells. In Hepatic Transport and Bile Secretion: Physiology and Pathophysiology, ed. by N. Tavoloni and P. D. Berk, pp. 313-335, Raven Press, New York, 1993.
38. OUDE ELFERINK, R. P. J., MEIJER, D. K. F., KUIPERS, F., JANSEN, P. L. M., GROEN, A. K. AND GROOTHUIS, G. M. M.: Hepatobiliary secretion of organic compounds; molecular mechanisms of membrane transport. Biochim. Biophys. Acta 1241: 215-268, 1995.
39. PAANAKKER, J. E., THIO, J. S. L. M., VAN DE WILDENBERG, H. M. AND KASPERSEN, F. M.: Assay of vecuronium in plasma using solid-phase extraction, HPLC and post-column ion-pair extraction with fluorimetric detection. J. Chromatogr. 421: 327-335, 1987.
40. PAULUSMA, C. C., BOSMA, P. J., ZAMAN, G. J. R., BAKKER, C. T. M., OTTER, M., SCHEFFER, G. L., SCHEPER, R. J., BORST, P. AND OUDE ELFERINK, R. P. J.: Congenital jaundice in rats with a mutation in a multidrug resistance-associated protein gene. Science 271: 1126-1128, 1996.
41. PECK, C. C., BARR, W. H. BENET, L. Z., COLLINS, J., DESJARDINS, R. E., FURST, D. E., HARTER, J. G., LEVY, G., LUDDEN, T., RODMAN, J. H. SANTHANAN, L., SCHENTAG, J. J., SHAH, V. P., SHEINER, L. B., SKELLY, J. P., STANSKY, D. R. TEMPLE, R. J., VISWANATHAN, C. T., WEISSINGER, J. AND YACOBI, A.: Opportunities for integration of pharmacokinetics, pharmacodyinamics, and toxicokinetics in rational drug development. Clin. Pharmacol. Ther. 51: 465-473, 1992.
42. PRESS, W. H., FLANNERY, B. P., TEUKOLSKY, S. A. AND VETTERLING, W. T.: Numerical Recipes, Cambridge University Press, Cambridge, 1986.
43. PROOST, J. H., NIJSSEN, H. M. J., STRATING, C. B., MEIJER, D. K. F. AND GROOTHUIS, G. M. M.: Pharmacokinetic modeling of the sinusoidal efflux of anionic ligands from the isolated perfused rat liver: The influence of albumin. J. Pharmacokinet. Biopharm. 21: 375-394, 1993.
44. PROOST, J. H., WIERDA, J. M. K. H. AND MEIJER, D. K. F.: Structure-pharmacokinetic and pharmacodynamic relationships of steroidal neuromuscular blocking agents. In Muscle Relaxants: Physiologic and Pharmacologic Aspects, ed. by K. Fukushima and R. Ochiai, pp. 205-212, Springer-Verlag, Tokyo, 1995.
45. PROOST, J. H., WIERDA, J. M. K. H. AND MEIJER, D. K. F.: An extended pharmacokinetic/pharmacodynamic (PK/PD) model describing quantitatively the influence of plasma protein binding, tissue binding, and receptor binding on the potency and time course of action of drugs. J. Pharmacokinet. Biopharm. 24: 45-77, 1996.
46. REKKER, R. F.: Hydrophobic aspects of binding, In Biological Activity and Chemical Structure, ed. by J. A. Keverling Buisman, pp. 107-130, Elsevier Scientific Publishing Company, Amsterdam, 1977.
47. SANDKER, G. W., WEERT, B., OLINGA, P. WOLTERS, H., SLOOFF, M. J. H., MEIJER, D. K. F. AND GROOTHUIS, G. M. M.: Characterization of transport in isolated human hepatocytes: A study with the bile acid tauocholic acid, the uncharged ouabain and the organic cations vecuronium and rocuronium. Biochem. Pharmacol. 47: 2193-2200, 1994.
48. SAVARESE, J. J., LIEN, C. A., BELMONT, M. R., MAEHR, R. B. AND WASTILA, W. B.: Future goals of the benzylisoquinolinium ester program. In Muscle Relaxants: Physiological and Pharmacological Aspects, ed. by K. Fukushima and R. Ochiai, pp. 335-341, Springer-Verlag, Tokyo, 1995.
49. SCHANKER, L. S.: Hepatic transport of organic cations. In The Biliary System, ed. by W. Taylor, pp. 469-480, Blackwell, Oxford, 1965.
50. SEYDEL, J. K. AND SCHAPER, K. J.: Quantitative structure-pharmacokinetic relationships and drug design. Pharmacol. Ther. 15: 131-182, 1982.
51. SHEINER, L. B. AND BEAL, S. L.: A note on confidence intervals with extended least squares parameter estimates. J. Pharmacokinet. Biopharm. 15: 93-98, 1987.
52. STEEN, H.: Mechanisms for the hepatic disposition of cationic drugs: Molecular aspects of membrane transport in the hepatocyte, pp. 125-132. Thesis, University of Groningen, 1992.
53. STEEN, H., MARING, J. G. AND MEIJER, D. K. F.: Differential effects of metabolic inhibitors on cellular and mitochondrial uptake of organic cations in rat liver. Biochem. Pharmacol. 45: 809-818, 1993.
54. STEEN, H., MEREMA, M. AND MEIJER, D. K. F.: A multispecific uptake system for taurocholate, cardiac glycosides and cationic drugs in the liver. Biochem. Pharmacol. 44: 2323-2331, 1992.
55. TOMLINSON, E.: Chromatographic hydrophobic parameters in correlation analysis of structure-activity relationships. J. Chromatogr. 113: 1-45, 1975.
56. VAN DER SLUIJS, P. AND MEIJER, D. K. F.: Binding of drugs with a quaternary ammonium group to alpha-1 acid glycoprotein and asialo alpha-1 acid glycoprotein. J. Pharmacol. Exp. Ther. 234: 703-707, 1985.
57. VAN DYKE, R. W., FABER, E. D. AND MEIJER, D. K. F.: Sequestration of organic cations by acidified hepatic endocytic vesicles and implications for biliary excretion. J. Pharmacol. Exp. Ther. 261: 1-11, 1992.
58. VENG PEDERSEN, P.: Curve fitting and modeling in pharmacokinetics and some practical experiences with NONLIN and a new program FUNFIT. J. Pharmacokinet. Biopharm. 5: 513-531, 1977.
59. WEIBEL, E. R., STÄUBLI, W., GNÄGI, H. R. AND HESS, F. A.: Correlated morphometric and biochemical studies on the liver cell. I. Morphometric model, stereologic methods and normal morphometric data for rat liver. J. Cell Biol. 42: 68-91, 1969.
60. WEITERING, J. G., MULDER, G. J., MEIJER, D. K. F., LAMMERS, W., VEENHUIS, M. AND WENDELAAR BONGA, S. E.: On the localization of d-tubocurarine in rat liver lysosomes in vivo by electron microscopy and subcellular fractionation. Naunyn-Schmiedebergs Arch. Pharmacol. 289: 251-256, 1975
61. WEITERING, J. G., LAMMERS, W., MEIJER, D. K. F. AND MULDER, G. J.: Localization of d-tubocurarine in rat liver lysosomes: Lysosomal uptake, biliary excretion and displacement by quinacrine in vivo. Naunyn-Schmiedebergs Arch. Pharmacol. 299: 277-281, 1977.
62. WIERDA, J. M. K. H., PROOST, J. H., MUIR, A. W. AND MARSHALL, R. J.: Design of drugs for rapid onset. Anaesth, Pharmacol. Rev. 1: 57-68, 1993.
63. WIERDA, J. M. K. H. AND PROOST, J. H.: (Pre-)clinical development of new aminosteroidal nondepolarizing neuromuscular blocking agents. In The Development of Aminosteroidal Neuromuscular Blocking Agents, ed. by P. Denissen, pp. 43-82, Interface, Turnhout, Belgium, 1992.
64. WIERDA, J. M. K. H. AND PROOST, J. H.: Structure-onset relations of steroidal neuromuscular blocking agents. In Muscle Relaxants: Physiologic and Pharmacologic Aspects, ed. K. Fukushima and R. Ochiai, pp. 163-166, Springer-Verlag, Tokyo, 1995a.
65. WIERDA, J. M. K. H. AND PROOST, J. H.: Structure-pharmacodynamic-pharmacokinetic relationships of steroidal neuromuscular blocking agens Eur. J. Anaesthesiol. 12 (Suppl. 11): 45-54, 1995b.
66. WIERDA, J. M. K. H. AND PROOST, J. H.: Molecular design of steroidal muscle relaxants. In Proceedings of the 24th Central European Congress on Anesthesiology, Volume of the Refresher, Main Lectures, Symposia, ed. by W. K. Ilias, A. Hammerle, W. List, W. Mauritz, N. Mutz, V. Schalk and M. Zimpfer pp. 543-548, Monduzzi Editore, Bologna, 1995c.
67. WILKINSON, G. R.: Clearance approaches in pharmacology. Pharmacol. Rev. 39: 1-47, 1987.
68. WINKLER, K, KEIDING, S. AND TYGSTRUP, N.: Clearance as a quantitative measure of liver function. In The liver: Quantitative Aspects of Structure and Function, ed. by G. Paumgartner and R. Preisig, pp. 144-155, Karger, Basel, 1973.