Prediction of blood-brain barrier permeation using quantum chemically derived information

Journal of Computer-Aided Molecular Design

Volumn 17, Issue 7, 2003, Pages 415-443

  Hutter, Michael C ^a,b  

^a MAX PLANCK INSTITUTE OF BIOPHYSICS   (Germany)

^b SAARLAND UNIVERSITY   (Germany)

Author keywords

Blood brain partition coefficient; Brain penetration; Drug transport; Hydrogen bonding; QSPR; Semi empirical calculations; Structure activity relationship

Indexed keywords

ALKALINITY; BLOOD; HYDROGEN BONDS; INFORMATION USE; IONIZATION POTENTIAL; PRINCIPAL COMPONENT ANALYSIS; QUALITY CONTROL; QUANTUM CHEMISTRY; REGRESSION ANALYSIS;

BLOOD-BRAIN BARRIER; BLOOD-BRAIN PARTITION COEFFICIENT; BRAIN PENETRATION; DESCRIPTORS; DRUG TRANSPORT; MULTIPLE REGRESSION ANALYSIS; PARTITION COEFFICIENT; QSPR; SEMI-EMPIRICAL CALCULATION; STRUCTURE-ACTIVITY RELATIONSHIPS;

BRAIN;

ACETYLSALICYLIC ACID; ASTEMIZOLE; CARBIDOPA; CAREBASTINE; CETIRIZINE; CIPROFLOXACIN; DIFLOXACIN; DIPHENHYDRAMINE; DOPAMINE; DOXYLAMINE; EBASTINE; ENOXACIN; FEXOFENADINE; FLEROXACIN; FUNCTIONAL GROUP; HALOPERIDOL; LEVODOPA; LOMEFLOXACIN; LOPERAMIDE; LORATADINE; MEFLOQUINE; NORDAZEPAM; NORFLOXACIN; OFLOXACIN; PEFLOXACIN; PERPHENAZINE; RUFLOXACIN; SPARFLOXACIN; TERFENADINE; UNINDEXED DRUG;

ALKALINITY; BINDING AFFINITY; BLOOD BRAIN BARRIER; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; CORRELATION ANALYSIS; COVALENT BOND; DRUG DESIGN; DRUG STRUCTURE; ELECTRIC POTENTIAL; HYDROGEN BOND; IONIZATION; MULTIPLE REGRESSION; PREDICTION; PRIORITY JOURNAL; QUANTUM CHEMISTRY; REVIEW; STRUCTURE ACTIVITY RELATION; SURFACE PROPERTY;

EID: 0344703614     PISSN: 0920654X     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1027359714663     Document Type: Review

References (53)

1. Hansch, C., Bjorkroth, J.P., and Leo, A., J. Pharm. Sci., 76 (1987) 663.
2. Van Belle, K., Sarre, S., Ebinger, G., and Michotte, Y., J. Pharmacol. Exp. Ther., 272 (1995) 1217.
3. Kelder, J., Grootenhuis, P.D.J., Bayada, D.M., Delbressine, L.P.C., and Ploemen, J.- P., Pharm. Res., 16 (1999) 1514.
4. Lin, J.H., and Y, L.A., Pharmacol. Rev., 49 (1997) 403.
5. Norinder, U., Sjöberg, P., and Österberg, T., J. Pharm. Sci., 87 (1998) 952.
6. Luco, J.M., J. Chem. Inf. Comput. Sci., 39 (1999) 396.
7. Crivori, P., Cruciani, G., Carrupt, P.-A., and Testa, B., J. Med. Chem., 43 (2000) 2204.
8. Feher, M., Sourial, E., and Schmidt, J.M., Int. J. Pharm. Sci., 201 (2000) 239.
9. Liu, R., Sun, H., and So, S.-S., J. Chem. Inf. Comput. Sci., 41 (2001) 1623.
10. Platts, J.A., Abraham, M.H., Zhao, Y.H., Hersey, A., Ijaz, L., and Butina, D., Eur. J. Med. Chem., 36 (2001) 719.
11. Hou, T., and Xu, X., J. Mol. Model, 8 (2002) 337.
12. Rose, K., Hall, L.H., and Kier, L.B., J. Chem. Inf. Comput. Sci., 42 (2002) 651.
13. Kier, L.B., and Hall, L.H., Molecular Structure Description: The Electrotopological State, Academic Press, San Diego, 1999.
14. Norinder, U., and Haeberlein, M., Adv. Drug Deliv. Rep., 54 (2002) 291.
15. Kramer, S.D., Pharm. Sci. Techn. Today, 2 (1999) 373.
16. Clark, D.E., Comb. Chem. H. T. S., 4 (2001) 477.
17. Clark, D.E., J. Pharm. Sci., 88 (1999) 815.
18. van de Waterbeemd, H., and Kansy, M., Chimia, 46 (1992) 299.
19. Abraham, M.H., Chandha, H.S., and Mitchell, R.C., Drug Des. Discov., 13 (1995) 123.
20. Young, R.C., Mitchell, R., Brown, T.H., Ganellin, C.R., Griffith, R., Jones, M., Rana, K.K., Saunders, D., Smith, I.R., Sore, N.E., and Wilks, T.K., J. Med. Chem., 31 (1988) 656.
21. Lombardo, F., Blake, J.F., and Curatolo, W.J., J. Med. Chem., 39 (1996) 4750.
22. Keserü, G.M., and Molnár, L., J. Chem. Inf. Comput. Sci., 41 (2001) 120.
23. Kaznessis, Y.N., Show, M.E., and Blankley, C.J., J. Comput.-Aided Mol. Des., 15 (2001) 697.
24. Cox, S.R., and Williams, D.E., J. Comput. Chem., 2 (1981) 304.
25. Stone, A.J., Chem. Phys. Lett., 83 (1981) 233.
26. Gasteiger, J., and Marsili, M., Tetrahedron, 36 (1980) 3219.
27. Beck, B., Glen, R.C., and Clark, T., J. Comput. Chem., 18 (1997) 744.
28. Beck, B., Horn, A., Carpenter, J.E., and Clark, T., J. Chem. Inf. Comput. Sci., 38 (1998) 1214.
29. Derwent World Drug Index (Derwent WDI), Derwent Information, 14 Great Queen Street, London WC2B 5DF, U.K., 1997.
30. Cruciani, G., Crivori, P., Carrupt, P.-A., and Testa, B., J. Mol. Struct. (Theochem), 503 (2000) 17.
31. Ooms, F., Weber, P., Carrupt, P.-A., and Testa, B., Biochim. Biophys. Acta Mol. Basis Dis., 1587 (2002) 118.
32. Sjöberg, P., In van de Waterbeemd, H., Testa, B., and Flokers, G. (Eds.), Computer-Assisted Lead Finding and Optimization, Verlag Helvetica Chimica Acta, Basel, Switzerland, 1997, pp. 81-92.
33. Ertl, P., Rohde, B., and Selzer, P., J. Med. Chem., 43 (2000) 3714.
34. Abraham, M.H., Chanda, H.S., and Mitchell, R.C., J. Pharm. Sci., 83 (1994) 1257.
35. Lin, J.H., Chen, I.-W., and Lin, T.-H., J. Pharmacol. Exp. Ther., 271 (1994) 1197.
36. Salmien, T., Pulli, A., and Taskinen, J., J. Pharmaceut. Biomed. Anal., 15 (1997) 469.
37. Calder, J.A.D., and Ganellin, R., Drug Des. Discov., 11 (1994) 259.
38. Rauhut, G., Alex, A., Chandrasekhar, J., Steinke, T., Sauer, W., Beck, B., Hutter, M., Gedeck, P., and Clark, T., VAMP Version 6.5, Oxford Molecular, Erlangen, Germany, 1997.
39. Baker, J., J. Comput. Chem., 7 (1986) 385.
40. Miller, W.G., OpenStat2, Version 6.1, West DeMoines, Iowa.
41. Lipinski, C.A., Lombardo, F., Dominy, B.W., and Feeney, P.J., Adv. Drug Deliv. Rev., 23 (1997) 3.
42. Meyer, A.Y., Chem. Soc. Rev., 15 (1986) 449.
43. Cronce, D.T., Famini, G.R., De Soto, J.A., and Wilson, L.Y., J. Chem. Soc., Perkin Trans. 2 (1998) 1293.
44. Breindl, A., Beck, B., Clark, T., and Glen, R.C., J. Mol. Model., 3 (1997) 142.
45. McCall, A.L., Mellington, W.R., and Wurtman, R., Life Sci., 31 (1982) 2709.
46. Schinkel, A.H., Wagenaar, E., Carla, A.A.M., and van Deemter, L., J. Clin. Invest., 97 (1996) 2517.
47. Clark, T., Rauhut, G., and Breindl, A., J. Mol. Model., 1 (1995) 22.
48. Pascual-Ahuir, J.L., Silla, E., and Tuñon, I., J. Comput. Chem., 15 (1994) 1127.
49. Leach, A.R., Molecular Modelling: Principles and Applications, Addison Wesley Longman Ltd, Harlow, Essex, U.K., 1996.
50. Rinaldi, D., and Rivail, J.L., Theor. Chim. Acta, 32 (1974) 243.
51. Mu, L., Drago, R.S., and Richardson, D.E., J. Chem. Soc., Perkin Trans. 2 (1998) 159.
52. Murray, J.S., Lane, P., Brinck, T., Paulsen, K., Grice, M.E., and Politzer, P., J. Phys. Chem., 97 (1993) 9369.
53. Brüstle, M., Beck, B., Schindler, T., King, W., Mitchell, T., and Clark, T., J. Med. Chem., 45 (2002) 3345.