Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 2. Prediction of blood-brain barrier penetration

Journal of Pharmaceutical Sciences

Volumn 88, Issue 8, 1999, Pages 815-821

  Clark, David E ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; BLOOD BRAIN BARRIER; CALCULATION; CHEMICAL STRUCTURE; LIBRARY; PREDICTION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SURFACE PROPERTY; TRANSPORT KINETICS;

EID: 0032811868     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js980402t     Document Type: Article

References (30)

1. De Vries, H. E.; Kuiper, J.; De Boer, A. G.; Van Berkel, T. J. C.; Breimer, D. D. The Blood-Brain Barrier in Neuroinflammatory Diseases. Pharmacol. Rev. 1997, 49, 143-155.
2. Pardridge, W. M. CNS Drug Design Based on Principles of Blood-Brain Barrier Transport. J. Neurochem. 1998, 70, 1781-1792.
3. Abraham, M. H.; Takacs-Novak, K.; Mitchell, R. C. On the Partition of Ampholytes: Application to Blood-Brain Distribution. J. Pharm. Sci. 1997, 86, 310-315.
4. Eddy, E. P.; Maleef, B. E.; Hart, T. K; Smith, P. L. In Vitro Models to Predict Blood-Brain Barrier Permeability. Adv. Drug Deliv. Rev. 1997, 23, 185-198.
5. Reichel, A.; Begley, D. J. Potential of Immobilized Artificial Membranes for Predicting Drug Penetration Across the Blood-Brain Barrier. Pharm. Res. 1998, 15, 1270-1274.
6. Kansy, M.; van de Waterbeemd, H. Hydrogen-Bonding Capacity and Brain Penetration. Chimia 1992, 46, 299-303.
7. Young, R. C.; Mitchell, R. C.; Brown, T. H.; Ganellin, C. R.; Griffiths, R.; Jones, M.; Rana, K. K.; Saunders: D.; Smith, I. R.; Sore, N. E.; Wilks, T. J. Development of a New Physicochemical Model for Brain Penetration and Application to the Design of Centrally Acting H2 Receptor Histamine Antagonists. J. Med. Chem. 1988, 31, 656-671.
8. Calder, J. A.; Ganellin, C. R. Predicting the Brain-Penetrating Capability of Histaminergic Compounds. Drug Des. Discov. 1994, 11, 259-268.
9. Abraham, M. H.; Chadha, H. S.; Mitchell, R. C. Hydrogen Bonding. 33. Factors that Influence the Distribution of Solutes Between Blood and Brain. J. Pharm. Sci. 1994, 83, 1257-1268.
10. Abraham, M. H.; Chadha, H. S.; Mitchell, R. C. Hydrogen Bonding. Part 36. Determination of Blood Brain Distribution Using Octanol-Water Partition Coefficients. Drug Des. Discov. 1995, 13, 123-131.
11. Abraham, M. H.; McGowan, J. C. The Use of Characteristic Volumes to Measure Cavity Terms in Reversed Phase Liquid Chromatography. Chromatographia 1987, 23, 243-246.
12. Livingstone, D. Data Analysis for Chemists. Oxford University Press: Oxford, 1995; pp 126-127.
13. Lombardo, F.; Blake, J. F.; Curatolo, W. J. Computation of Brain-Blood Partitioning of Organic Solutes via Free Energy Calculations. J. Med. Chem. 1996, 39, 4750-4755.
14. Hawkins, G. D.; Liotard, D. A.; Cramer, C. J.; Truhlar, D. G. OMNISOL: Fast Prediction of Free Energies of Solvation and Partition Coefficients. J. Org. Chem. 1998, 63, 4305-4313.
15. Norinder, U.; Sjöberg, P.; Österberg, T. Theoretical Calculation and Prediction of Brain-Blood Partitioning of Organic Solutes Using MolSurf Parametrization and PLS Statistics. J. Pharm. Sci. 1998, 87, 952-959.
16. Clark, D. E. Rapid Calculation of Polar Molecular Surface Area and its Application to the Prediction of Transport Phenomena. 1. Prediction of Intestinal Absorption. J. Pharm. Sci., 1999, 88, 807-814.
17. Clog P. Daylight Chemical Information Software, version 4.51. Daylight Chemical Information Inc.: 27401 Los Altos, Suite #370, Mission Viejo, CA 92691.
18. Moriguchi, I.; Hirono, S.; Liu, Q.; Nakagome, I.; Matsushita, Y. Simple Method of Calculating Octanol/Water Partition Coefficient. Chem. Pharm. Bull. 1992, 40, 127-130.
19. Sybyl 6.4.2. Tripos, Inc., 1699 S. Hanley Rd., Suite 303, St. Louis, MO 63144-2913. The SPL script was originally developed by Dr. James Blake (Pfizer, US) and has been subsequently modified by Dr. Jon Swanson (Tripos Inc.) to accommodate changes in the Tripos Sybyl Line Notation (SLN) description of substructure queries.
20. Tsar 3.1. Oxford Molecular Ltd., The Medawar Centre, Oxford Science Park, Sandford-on-Thames, Oxford, OX4 4GA, England.
21. To allow comparison with eqs 6-8, the statistics for the equations involving these quantities are PSA and molecular weight: n = 55, r = 0.845, s = 0.410, F = 64.8; PSA and molecular volume: n = 55, r = 0.849, s = 0.405, F = 66.9; PSA and nonpolar surface area: n = 55, r = 0.848, s = 0.406, F = 66.6.
22. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings. Adv. Drug Deliv. Rev. 1997, 23, 3-25.
23. Lennernäs, H. Human Jejunal Effective Permeability and its Correlation with Preclinical Drug Absorption Models. J. Pharm. Pharmacol. 1997, 49, 627-638.
24. Conradi, R. A.; Burton, P. S.; Borchardt, R. T. Physicochemical and Biological Factors that Influence a Drug's Cellular Permeability by Passive Diffusion. In Lipophilicity in Drug Action and Toxicology; Pliška, V., Testa, B., van de Waterbeemd, H., Eds.; VCH: Weinheim, 1996; pp 233-252.
25. van de Waterbeemd, H.; Camenisch, G.; Folkers, G.; Chretien, J. R.; Raevsky, O. A. Estimation of Blood-Brain Barrier Crossing of Drugs Using Molecular Size and Shape, and H-bonding Descriptors. J. Drug Target. 1998, 6, 151-165.
26. Olson, R. E.; Christ, D. D. Plasma Protein Binding of Drugs. In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed.; Academic Press: San Diego, 1996; Vol. 33, pp 327-336.
27. Rowley, M.; Kulagowski, J. J.; Watt, A. P.; Rathbone, D.; Stevenson, G. I.; Carling, R. W.; Baker, R.; Marshall, G. R.; Kemp, J. A.; Foster, A. C.; Grimwood, S.; Hargreaves, R.; Hurley, C.; Saywell, K. L.; Tricklebank, M. D.; Leeson, P. D. Effect of Plasma Protein Binding on in Vivo Activity and Brain Penetration of Glycine/NMDA Receptor Antagonists. J. Med. Chem. 1997, 40, 4053-4068.
28. Gratton, J. A.; Abraham, M. H.; Bradbury, M. W.; Chadha, H. S. Molecular Factors Influencing Drug Transfer Across the Blood-Brain Barrier. J. Pharm. Pharmacol. 1997, 49, 1211-1216.
29. Elmquist, W. F.; Sawchuk, R. J. Application of Microdialysis in Pharmacokinetic Studies. Pharm. Res. 1997, 14, 267-288.
30. Evrard, P. A.; Ragusi, C.; Boschi, G.; Verbeeck, R. K.; Scherrmann, J.-M. Simultaneous Microdialysis in Brain and Blood of the Mouse: Extracellular and Intracellular Brain Colchicine Disposition. Brain Res. 1998, 786, 122-127.