A simple model for the prediction of blood-brain partitioning

International Journal of Pharmaceutics

Volumn 201, Issue 2, 2000, Pages 239-247

  Feher, Miklos ^a   Sourial, Elizabeth ^a   Schmidt, Jonathan M ^a  

^a Nanodesign Inc   (Canada)

Author keywords

Blood brain barrier; Drug transport; Hydrogen bonding; Partition coefficients; Polar surface area; QSAR

Indexed keywords

ACETYLSALICYLIC ACID; CHLORAMBUCIL; CIMETIDINE; CLONIDINE; ENFLURANE; FLUROXENE; HALOTHANE; ICOTIDINE; IMIPRAMINE; LUPITIDINE; MEPYRAMINE; OCTANOL; PARACETAMOL; RANITIDINE; SALICYLIC ACID; SOLVENT; TEMELASTINE; TIOTIDINE; VALPROIC ACID; WATER; ZOLANTIDINE;

ARTICLE; BLOOD BRAIN BARRIER; DRUG PENETRATION; DRUG TRANSPORT; HYDROGEN BOND; MODEL; PARTITION COEFFICIENT; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

BLOOD-BRAIN BARRIER; CHEMISTRY, PHYSICAL; DATABASES, FACTUAL; LIPIDS; MODELS, BIOLOGICAL; MODELS, STATISTICAL; MOLECULAR WEIGHT; REGRESSION ANALYSIS;

EID: 0034713376     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-5173(00)00422-1     Document Type: Article

References (19)

1. 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. 83:1994;1257-1268.
2. ACD/Labs™, version 3.6, 1998. Advanced Chemistry Development, Toronto, ON, Canada.
3. Bonate P.L. Animal models for studying transport across the blood-brain barrier. J. Neurosci. Methods. 56:1995;1-15.
4. Brown R.D., Martin Y.C. The information content of 2D and 3D structural descriptors relevant to ligand-receptor binding. J. Chem. Inf. Comput. Sci. 37:1997;1-9.
5. Bush B.L., Sheridan R.P. PATTY: a programmable atom typer and language for automatic classification of atoms in molecular databases. J. Chem. Inf. Comput. Sci. 33:1993;756-762.
6. Downs G.M., Willett P. Clustering of chemical structure databases for compound selection. van de Waterbeemd H. Advanced Computer-Assisted Techniques in Drug Discovery. 1995;Verlag Chemie, Weinheim.
7. Duffy E.M., Jorgensen W.L Prediction of Properties from Simultations: Free energies of solvation in hexadecane, Octanol, and water. J. Am. Chem. Soc. 122:2000;2878-2888.
8. Elks J., Ganellin C.R. Dictionary of Drugs. 1990;Chapman and Hall, London.
9. Ferguson D.M., Raber D.J. A new approach to probing conformational space with molecular mechanics: random incremental pulse search. J. Am. Chem. Soc. 111:1989;4371-4378.
10. Halgren T.A. Merck molecular force field. I: basis, form, scope, parametrization and performance of MMFF94. J. Comp. Chem. 17:1996;490-519.
11. Kaliszan R., Markuszewski M. Brain/blood distribution described by a combination of partition coefficient and molecular mass. Int. J. Pharm. 145:1996;9-16.
12. Levin V.A. Relationship of octanol/water partition coefficient and molecular weight to rat brain capillary permeability. J. Med. Chem. 23:1980;682-684.
13. Lombardo F., Blake J.F., Curatolo W.J. Computation of brain-blood partitioning of organic solutes via free energy calculations. J. Med. Chem. 39:1996;4750-4755.
14. Luco J.M. Prediction of the brain-blood distribution of a large set of drugs from structurally derived descriptors using partial least-squares (PLS) modeling. J. Chem. Inf. Comput. Sci. 39:1999;396-404.
15. Martin Y.C. Quantitative Drug Design: A Critical Introduction. 1978;194-198 Marcel Dekker, New York.
16. Chemical Computing Group. 1999;Montreal, Quebec, Canada.
17. 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. 87:1998;952-959.
18. Salminen T., Pulli A., Taskinen J. Relationship between immobilised artificial membrane chromatographic retention and the brain penetration of structurally diverse drugs. J. Pharm. Biomed. Anal. 15:1997;469-477.
19. 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 Targeting. 6:1998;151-165.