Permeation characteristics of a hydrophilic basic compound across a bio-mimetic artificial membrane

International Journal of Pharmaceutics

Volumn 275, Issue 1-2, 2004, Pages 271-278

  Sugano, Kiyohiko ^a   Nabuchi, Yoshiaki ^a   Machida, Minoru ^a   Asoh, Yoshinori ^a  

^a CHUGAI PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Hydrophilic basic compound; Permeability; Phospholipid; Physicochemical properties

Indexed keywords

ALKADIENE; BIOMIMETIC MATERIAL; CATION; CHLORPROMAZINE DERIVATIVE; CHOLESTEROL; KETOPROFEN; PHOSPHATIDYLCHOLINE; PHOSPHATIDYLETHANOLAMINE; PHOSPHATIDYLINOSITOL; PHOSPHATIDYLSERINE; PINDOLOL; QUATERNARY AMMONIUM DERIVATIVE; TIMOLOL MALEATE;

ARTICLE; ARTIFICIAL MEMBRANE; ASSAY; DIFFUSION; DRUG PENETRATION; DRUG SCREENING; FILTER; LIPID COMPOSITION; MATHEMATICAL COMPUTING; MOLECULAR MECHANICS; PH; PRIORITY JOURNAL;

CHEMISTRY, PHARMACEUTICAL; CHEMISTRY, PHYSICAL; CHLORPROMAZINE; HYDROGEN-ION CONCENTRATION; KINETICS; MEMBRANES, ARTIFICIAL; OINTMENT BASES; PERMEABILITY; PHARMACEUTICAL PREPARATIONS; PHOSPHOLIPIDS; QUATERNARY AMMONIUM COMPOUNDS;

EID: 1842638319     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2004.02.010     Document Type: Article

References (29)

1. Avdeef A. Physicochemical profiling (solubility, permeability and charge state). Curr. Top. Med. Chem. 1:2001;277-351.
2. Avdeef, A., 2003. Absorption and Drug Development. Wiley-Interscience, New York.
3. Barton, P., Fessey, R., Wood, M., 2002. Investigation of the physicochemical parameters of the parallel artificial membrane permeability assay (PAMPA) and their optimization for drug discovery. PAMPA 2002 Symposium, San Francisco.
4. Di L., Kerns E.H., Fan K., McConnell O.J., Carter G.T. High throughput artificial membrane permeability assay for blood-brain barrier. Eur. J. Med. Chem. 38:2003;223-232.
5. Hallen B., Sundwall A., Sandquist S. Ion pair formation and gastrointestinal absorption of emepronium. Acta Pharm. Toxicol. 57:1985;271-278.
6. Huang C.L., Mir G.M., Yeh J.Z. Distribution, excretion, and metabolism of 14C-labeled quaternary ammonium salt of perphenazine in rats. J. Pharm. Sci. 59:1970;976-979.
7. Hogben C.A.M., Tacco D.J., Brodie B.B., Schanker L.S. On the mechanism of intestinal absorption of drugs. J. Pharmacol. Exp. Ther. 269:1959;275-282.
8. Kansy M., Senner F., Gubernator K. Physicochemical high throughput screening: parallel artificial membrane permeation assay in the description of passive absorption processes. J. Med. Chem. 41:1998;1007-1010.
9. Kerns E.H. High throughput physicochemical profiling for drug discovery. J. Pharm. Sci. 90:2001;1838-1858.
10. Kitagawa S., Sato K., Sato S., Sasaki M. Absorption of methochlorpromazine in rat small intestinal everted sac. Biol. Pharm. Bull. 19:1996;998-1000.
11. Lipka G., Op den Kamp J.A., Hauser H. Lipid asymmetry in rabbit small intestinal brush border membrane as probed by an intrinsic phospholipid exchange protein. Biochemistry. 30:1991;11828-11836.
12. Maxwell J.D., Watson W.C., Watt J.K., Ferguson A. Radiotelemetering studies of jejunal pH before and after vagotomy and pyloroplasty. Gut. 9:1968;612-616.
13. Neubert R. Ion pair transport across membrane. Pharm. Res. 6:1989;743-747.
14. Ozaki S., DeWald D.B., Shope J.C., Chen J., Prestwich G.D. Intracellular delivery of phosphoinositides and inositol phosphates using polyamine carriers. Proc. Natl. Acad. Sci. U.S.A. 97:2000;11286-11291.
15. Proulx P. Structure-function relationships in intestinal brush border membranes. Biochem. Biophys. Acta. 1071:1991;255-271.
16. flux-optimized design (pOD-PAMPA). Eur. J. Pharm. Sci. 20:2003;393-402.
17. Saitoh H., Kawai S., Miyazaki K., Arita T. Transport characteristics of propantheline across rat intestinal brush border membrane. J. Pharm. Pharmacol. 40:1988;176-180.
18. Saitoh H., Noujoh A., Chiba Y., Iseki K., Miyazaki K., Arita T. Correlation between structures of organic cations and their binding behaviours to brush border membrane isolated from rat small intestine. J. Pharm. Pharmacol. 42:1990;308-313.
19. Sugano K., Hamada H., Machida M., Ushio H. High throughput prediction of oral absorption: improvement of the composition of the lipid solution used in parallel artificial membrane permeation assay. J. Biomol. Screen. 6:2001a;189-196.
20. Sugano K., Hamada H., Machida M., Ushio H., Saitoh K., Terada K. Optimized conditions of bio-mimetic artificial membrane permeation assay. Int. J. Pharm. 228:2001b;181-188.
21. Sugano K., Takata N., Machida M., Saitoh K., Terada K. Prediction of passive intestinal absorption using bio-mimetic artificial membrane permeation assay and the paracellular pathway model. Int. J. Pharm. 241:2002;241-251.
22. Sugano K., Nabuchi Y., Machida M., Aso Y. Prediction of human intestinal permeability using artificial membrane permeability. Int. J. Pharm. 257:2003;245-251.
23. Takács-Novák K., Szasz G. Ion-pair partition of quarternary ammonium drugs: the influence of counter ions of different lipophilicity, size, and flexibility. Pharm. Res. 16:1999;1633-1638.
24. Thompson M., Lennox R.B., McClelland R.A. Structure and electrochemical properties of microfilteration filter-lipid membrane systems. Anal. Chem. 54:1982;76-81.
25. Tsuji A., Tamai I. Carrier-mediated intestinal transport of drugs. Pharm. Res. 13:1996;963-977.
26. Veber D.F., Johnson S.R., Cheng H.-Y., Smith B.R., Ward K.W., Kopple K.D. Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem. 45:2002;2615-2623.
27. Walter A., Gutknecht J. Monocarboxylic acid permeation through lipid bilayer membranes. J. Membr. Biol. 77:1984;255-264.
28. Wohnsland F., Faller B. High-throughput permeability pH profile and high-throughput alkane/water log P with artificial membranes. J. Med. Chem. 44:2001;923-930.
29. Zhu C., Jiang L., Chen T.M., Hwang K.K. A comparative study of artificial membrane permeability assay for high throughput profiling of drug absorption potential. Eur. J. Med. Chem. 37:2002;399-407.