Shapes of membrane permeability-lipophilicity curves: Extension of theoretical models with an aqueous pore pathway

European Journal of Pharmaceutical Sciences

Volumn 6, Issue 4, 1998, Pages 321-329

  Camenisch, Gian ^a,b   Folkers, Gerd ^b   Van De Waterbeemd, Han ^a,c  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b ETH ZURICH   (Switzerland)

^c PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

Aqueous pores; Drug absorption models; Lipophilicity; Molecular weight

Indexed keywords

ARTICLE; CONTROLLED STUDY; DIFFUSION; DRUG ADSORPTION; HUMAN; HUMAN CELL; LIPOPHILICITY; MATHEMATICAL MODEL; MEMBRANE PERMEABILITY; MEMBRANE TRANSPORT; MODEL; MOLECULAR WEIGHT; MONOLAYER CULTURE; PARTITION COEFFICIENT; PH; PRIORITY JOURNAL; ALGORITHM; CELL MEMBRANE PERMEABILITY; CHEMISTRY; METABOLISM; PHARMACOKINETICS; PHYSICAL CHEMISTRY; POROSITY; THEORETICAL MODEL;

DRUG; LIPID; WATER;

ALGORITHMS; CELL MEMBRANE PERMEABILITY; CHEMISTRY, PHYSICAL; DIFFUSION; HYDROGEN-ION CONCENTRATION; LIPIDS; MODELS, THEORETICAL; MOLECULAR WEIGHT; PHARMACEUTICAL PREPARATIONS; PHARMACOKINETICS; POROSITY; WATER;

EID: 0032190504     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0928-0987(98)00033-5     Document Type: Article

References (48)

1. Adson, A., Raub, T.J., Burton, P.S., Barsuhn, C.L., Hilgers, A.R., Audus, K.L., Ho, N.F.H., 1994. Quantitative approaches to delineate paracellular diffusion in cultured epithilial cell monolayers. J. Pharm. Sci. 83, 1529-1536.
2. Adson, A., Burton, P.S., Raub, Th.J., Barsuhn, C.L., Audus, K.L., Ho, N.F.H., 1995. Passive diffusion of weak organic electrolytes across Caco-2 cell monolayers: Uncoupling the contributions of hydrodynamic, transcellular, and paracellular barriers. J. Pharm. Sci. 84, 1197-1204.
3. Austel, V., Kutter, E., 1983. Absorption, distribution, and metabolism of drugs. In: Topliss, J.G. (Ed.), Quantitative Structure-Activity Relationships of Drugs. Academic Press, London, pp. 437-496.
4. Burton, P.S., Conradi, R.A., Ho, N.F.H., Hilgers, A.R., Borchardt, R.T., 1996. How structural features influence the biomembrane permeability of peptides. J. Pharm. Sci. 85, 1336-1340.
5. Camenisch, G., 1996. Drug transport across membranes: Structure-property correlations in the prediction of passive membrane permeation. Ph.D. Thesis, ETH Zürich, Switzerland.
6. Camenisch, G., Folkers, G., Van de Waterbeemd, H., 1996. Review of theoretical passive drug absorption models: Historical background, recent developments and limitations. Pharm. Acta Helv. 71, 309-327.
7. Camenisch, G., Alsenz, J., Van de Waterbeemd, H., Folkers, G. (in press) Estimation of permeability by passive diffusion through Caco-2 cell monolayers using the drugs' lipophilicity and molecular weight. Eur. J. Pharm. Sci.
8. Chan, O.H., Stewart, B.H., 1996. Physicochemical and drug-delivery considerations for oral drug bioavailability. Drug Discov. Today 1, 461-473.
9. Collander, R., 1950. The distribution of organic compounds between iso-butanol and water. Acta Chem. Scand. 4, 1085-1098.
10. Collander, R., 1951. The partition of organic compounds between higher alcohols and water. Acta Chem. Scand. 5, 774-780.
11. Dearden, J.C. (1990) Molecular structure and drug transport. In: Hansch, C., Sammes, P.G., Taylor, J.B., Ramsden, C.R. (Eds.), Comprehensive Medicinal Chemistry, vol. 4. Pergamon Press, New York, pp. 375-411.
12. De Haan, F.H.N., 1985. The Role of Drug Transport in QSAR. Ph.D. Thesis, University of Leiden, The Netherlands.
13. De Haan, F.H.N., Jansen, A.C.A., 1985. Rationally designed model with general applicability for absorption by passive diffusion. In: Seydel, J.K. (Ed.), QSAR and Strategies in the Design of Bioactive Compounds. VCH, Weinheim, pp. 198-204.
14. Flynn, G.L., Yalkowsky, S.H., Roseman, T.J., 1974. Mass transport phenomena and models: Theoretical concepts. J. Pharm. Sci. 63, 479-509.
15. Garrigues, T.M., Pérez-Varona, A.T., Climent, E., Bermejo, M.V., Martin-Villodre, A., Plá-Delfina, J.M., 1990. Gastric absorption of acidic xenobiotics in the rat: Biophysical interpretation of an apparently atypical behaviour. Int. J. Pharm. 64, 127-138.
16. Hansch, C., 1969. A quantitative approach to biochemical structure-activity relationships. Accounts Chem. Res. 2, 232-239.
17. Ho, N.F.H., Higuchi, W.I., 1971. Quantitative interpretation of in vivo buccal absorption of n-alkanoic acids by the physical model approach. J. Pharm. Sci. 60, 537-541.
18. Ho, N.F.H., Park, J.Y., Morozowich, W., Higuchi, W.I., 1977. Physical model approach to the design of drugs with improved intestinal absorption. In: Roche, E.B. (Ed.), Design of Biopharmaceutical Properties through Prodrugs and Analogs. APhA/APS, Washington, DC, pp. 136-227.
19. Ho, N.F.H., Park, J.Y., Ni, P.F. and Higuchi, W.I., 1983. Advancing quantitative and mechanistic approaches in interfacing gastrointestinal drug absorption studies in animals and man. In: Crouthamel, W.G., Sarapu, A. (Eds.), Animal Models for Oral Drug Delivery in Man: In Situ and In Vivo Approaches. APhA/APS, Washington, DC, pp. 27-106.
20. Ho, N.F.H., Burton, P.S., Conradi, R.A., Barsuhn, C.L., 1995. A biophysical model of passive and polarized active transport processes in Caco-2 cells: Approaches to uncoupling apical and basolateral membrane events in the intact cell. J. Pharm. Sci. 84, 21-27.
21. Kakemi, K., Arita, T., Hori, R., Konishi, R., 1967. Absorption and excretion of drugs: XXX. Absorption of barbituric acid derivates from rat stomach. Chem. Pharm. Bull. 17, 1534-1539.
22. Kubinyi, H., 1976. Quantitative structure-activity relationships: IV Non-linear dependence of biological activity on hydrophobic character: A new model. Arzneim. Forsch. (Drug Res.) 26, 1991-1997.
23. Kubinyi, H., 1979. Lipophilicity and drug activity. Progr. Drug Res. 23, 97-198.
24. Leahy, D.E., Lynch, J., Taylor, D.C., 1989. Mechanisms of absorption of small molecules. In: Prescott, L.F., Nimmo, W.S. (Eds.), Novel Drug Delivery and its Therapeutic Application. John Wiley & Sons, New York, pp. 33-44.
25. Lee, A.J., King, J.R., Barrett, D.A., 1997. Percutaneous absorption: a multiple pathway model. J. Control. Release 45, 141-151.
26. Lennernäs, H., 1995. Does fluid flow across the intestinal mucosa affect quantitative oral drug absorption? Is it time for a reevaluation?. Pharm. Res. 12, 1573-1582.
27. Leo, A., Hansch, C., Elkins, D., 1971. Partition coefficients and their uses. Chem. Rev. 71, 525-616.
28. Lieb, W.R., Stein, W.D., 1971. The molecular basis of simple diffusion within biological membranes. Curr. Top. Membr. Transp. 2, 1-39.
29. Lovering, E.G., Black, D.B., 1974. Diffusion layer effects on permeation of phenylbutazone through polydimethylsiloxane. J. Pharm. Sci. 63, 1399-1402.
30. Ong, S., Liu, H., Pidgeon, Ch., 1996. Immobilized-artificial-membrane chromatography: measurements of membrane partition coefficient and predicting drug membrane permeability. J. Chromatogr. A 728, 113-128.
31. Pauletti, G.M., Okumu, F.W., Vander Velde, D.G., Borchardt, R.T., 1996. The effect of charge and conformational flexibility on the pathway of permeation of model hexapeptides across Caco-2 cell monolayers in unperturbed and perturbed states. Pharm Res. (Suppl.) 13, S235.
32. Plá-Delfina, J., Moreno, J., 1981. Intestinal absorption-partition relationships: A tentative functional nonlinear model. J. Pharmacokinet. Biopharm. 9, 191-215.
33. Pliska,Y, Testa, B., Van de Waterbeemd, H. (Eds.), 1996. Lipophilicity in Drug Action and Toxicology. VCH, Weinheim.
34. Raub, T.J., Barsuhn, C.L., Williams, L.R., Deckers, D.E., Sawada, G.A., Ho, N.F.H., 1993. Use of a biophysical-kinetic model to understand the roles of protein binding and membrane partitioning on passive diffusion of highly lipophilic molecules across cellular barriers. J. Drug Target. 1, 269-286.
35. Reymond, F., Steyaert, G., Carrupt, P.A., Testa, B., Girault, H.H., 1996. Mechanism of transfer of a basic drug across the water/1,2-dichlorethane interface: The case of quinidine. Helv. Chim. Acta 79, 101-117.
36. Scheuplein, R.J., 1966. Analysis of permeability data for the case of parallel diffusion pathway. Biophys. J. 6, 1-17.
37. Shore, P.A., Brodie, B.B., Hogben, C.A.M., 1957. The gastric secretions of drugs: A pH partition hypothesis. J. Pharm. Exp. Ther. 119, 361-369.
38. Stehle, R.G., Higuchi, W.I., 1972. In vitro model for transport of solutes in three-phase system I: Theoretical principles. J. Pharm. Sci. 61, 1922-1930.
39. Van de Waterbeemd, H., Jansen, A., 1981. Transport in QSAR V: Application of the interfacial drug tranfer model. Pharm. Weekbl. Sci. Ed. 3, 587-594.
40. Van de Waterbeemd, H., Van Boeckel, S., Jansen, A.C.A., Gerritsma, K., 1980. Transport in QSAR II: Rate-equilibrium relationships and the interfacial transfer of drugs. Eur. J. Med. Chem. 3, 279-282.
41. Van de Waterbeemd, H., Van Boeckel, C., De Sevaux, R., Jansen, A., Gerritsma, K., 1981. Transport in QSAR IV: The interfacial transfer model. Relationships between partition coefficients and rate constants of drug partitioning. Pharm. Weekbl. Sci. Ed. 3, 224-237.
42. Van de Waterbeemd, H., Camenisch, G., Folkers, G., Raevsky, O.A., 1996. Estimation of Caco-2 cell permeability using calculated molecular descriptors. Quant. Struct. Act. Relat. 15, 480-490.
43. Van de Waterbeemd, H., Kansy, M., Wagner, B., Fischer, H., 1996b. Lipophilicity measurement by reversed-phase high performance liquid chromatography (RP-HPLC). In: Pliska, V, Testa, B., Van de Waterbeemd, H. (Eds.), Lipophilicity in Drug Action and Toxicology. VCH, Weinheim, pp. 73-87.
44. Wacher, V.J., Salphati, L., Benet, L.Z., 1996. Active secretion and enterocytic drug metabolism barriers to drug absorption. Adv. Drug Deliv. Rev. 20, 99-112.
45. Wagner, J.G., Sedman, A.J., 1973. Quantitation of rate of gastrointestinal and buccal absorption of acidic and basic drugs based on extraction theory. J. Pharmacokinet. Biopharm. 1, 23-50.
46. Walter, A., Gutknecht, J., 1986. Permeability of small nonelectrolytes through lipid bilayer membranes. J. Membr. Biol. 90, 207-217.
47. Xiang, T.X., Anderson, B.D., 1994. The relationship between permeant size and permeability in lipid bilayer membranes. J. Membr. Biol. 140, 111-122.
48. Yalkowsky, S.H., Slunick, T.G., Flynn, G.L., 1974. Effects of alkyl chain length on biological activity: Alkyl p-aminobenzoate-induced narcosis in goldfish. J. Pharm. Sci. 63, 691-695.