Predicting blood-brain barrier penetration from molecular weight and number of polar atoms

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 70, Issue 2, 2008, Pages 462-466

  Fu, Xu Chun ^a   Wang, Guo Ping ^b   Shan, Hai Li ^c   Liang, Wen Quan ^c   Gao, Jian Qing ^c  

^a ZHEJIANG UNIVERSITY CITY COLLEGE   (China)

^b ZHEJIANG UNIVERSITY   (China)

^c ZHEJIANG UNIVERSITY   (China)

Author keywords

Blood brain barrier; Molecular weight; Polar atom; Predictive model

Indexed keywords

ALPRAZOLAM; CAFFEINE; CARMUSTINE; CHLORAMBUCIL; CHLORPROMAZINE; CODEINE; DESIPRAMINE; DIDANOSINE; HYDROGEN; HYDROXYZINE; IBUPROFEN; INDOMETACIN; MIDAZOLAM; N (ALPHA ETHYLBENZYL) 3 METHYL 2 PHENYL 4 QUINOLINECARBOXAMIDE; NEVIRAPINE; NITROGEN; OXAZEPAM; OXYGEN; PENTOBARBITAL; PHENAZONE; PHENSERINE; PHYSOSTIGMINE; PROMAZINE; TERBUTYLCHLORAMBUCIL; THEOPHYLLINE; THIORIDAZINE; TRIFLUOPERAZINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VERAPAMIL; ZIDOVUDINE;

ARTICLE; ATOM; BLOOD BRAIN BARRIER; CORRELATION COEFFICIENT; DRUG BLOOD LEVEL; DRUG BRAIN LEVEL; DRUG PENETRATION; DRUG STRUCTURE; MOLECULAR WEIGHT; POLAR ATOM; PREDICTION; STEADY STATE; VALIDATION PROCESS;

BLOOD-BRAIN BARRIER; MODELS, BIOLOGICAL; MODELS, STATISTICAL; MOLECULAR WEIGHT; PERMEABILITY; PREDICTIVE VALUE OF TESTS;

EID: 52949094246     PISSN: 09396411     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejpb.2008.05.005     Document Type: Article

References (27)

1. Pardridrge W.M., and Mietus L.J. Transport of steroid hormones through the rat blood-brain barrier. J. Clin. Invest. 64 (1979) 145-154
2. 2 receptor histamine antagonists. J. Med. Chem. 31 (1988) 656-671
3. Sveigaard H.H., and Dalgaard L. Evaluation of blood-brain barrier passage of a muscarine M1 agonist and a series of analogous tetrahydropyridines measured by in vivo microdialysis. Pharm. Res. 17 (2000) 70-76
4. Gumbleton M., and Audus K.L. Progress and limitations in the use of in vitro cell cultures to serve as a permeability screen for the blood-brain barrier. J. Pharm. Sci. 90 (2001) 1681-1698
5. van de Waterbeemd H., and Kansy M. Hydrogen bonding capacity and brain penetration. Chimia 46 (1992) 299-303
6. Calder J.A.D., and Ganellin C.R. Predicting the brain-penetrating capability of histaminergic compounds. Drug Des. Discov. 11 (1994) 259-268
7. Abraham M.H., Chadha H.S., and Michell R.C. Hydrogen bonding. 33. Factors that influence the distribution of solutes between blood and brain. J. Pharm. Sci. 83 (1994) 1257-1268
8. Lombardo F., Blake J.F., and Curatolo W.J. Computation of brain-blood partitioning of organic solutes via free energy calculation. J. Med. Chem. 39 (1996) 4750-4755
9. Norinder U., Sjoberg P., and Osterberg T. Theoretical calculation and prediction of brain-blood partitioning of organic solutes using Molsurf parameterization and PLS statistics. J. Pharm. Sci. 87 (1998) 952-959
10. Clark D.E. Rapid calculation of polar surface area and its application to the prediction of transport phenomena. 2. Prediction of blood-brain barrier penetration. J. Pharm. Sci. 88 (1999) 815-821
11. 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
12. Feher M., Sourial E., and Schmidt J.M. A simple model for the prediction of blood-brain partitioning. Int. J. Pharm. 201 (2000) 239-247
13. Crivori P., Cruciani G., Carrupt P., and Testa B. Predicting blood-brain barrier permeation from three-dimensional molecular structure. J. Med. Chem. 43 (2000) 2204-2216
14. Kaznessis Y.N., Snow M.E., and Blankley C.J. Prediction of blood-brain partitioning using Monte Carlo simulations of molecules in water. J. Comput. Aid. Mol. Des. 15 (2001) 697-708
15. Rose K., and Hall L.H. Modeling blood-brain barrier partitioning using the electropological state. J. Chem. Inf. Comput. Sci. 42 (2002) 651-666
16. Ooms F., Weber T., Carrupt P.A., and Testa B. A simple model to predict blood-brain barrier permeation from 3D molecular fields. Biochim. Biophys. Acta 1587 (2002) 118-125
17. Lobell M., Molnar L., and Keseru G. Recent advances in the prediction of blood-brain partitioning from molecular structure. J. Pharm. Sci. 92 (2003) 360-370
18. Subramanian G., and Kitchen D.B. Computational models to predict blood-brain barrier permeation and CNS activity. J. Comput. Aid. Mol. Des. 17 (2003) 643-664
19. Abraham M.H. The factors that influence permeation across the blood-brain barrier. Eur. J. Med. Chem. 39 (2004) 235-240
20. Fu X.C., Song Z.F., Fu C.Y., and Liang W.Q. A simple predictive model for blood-brain barrier penetration. Pharmazie 60 (2005) 354-358
21. Abraham M.H., Chadha H.S., and Michell R.C. Hydrogen bonding. Part 36. Determination of blood brain distribution using octanol-water partition coefficients. Drug Des. Discov. 13 (1995) 123-131
22. Greig N.H., Brossi A., Pei X.F., Ingram D.K., and Soncrant T.T. In: Greenwood J., et al. (Ed). New Concepts of a Blood-Brain Barrier (1995), Plenum, New York 251-264
23. Salminen T., Pulli A., and Taskinen J. Relationship between immobilized artificial membrane chromatographic retention and the brain penetration of structurally diverse drug. J. Pharm. Biomed. Anal. 15 (1997) 469-477
24. von Sprecher A., Gerpacher M., and Anderson G.P. Neurokinin antagonists as potential therapies for inflammation and rheumatoid arthritis. Drugs 1 (1998) 73-91
25. Yazdanian M., and Glynn S.L. In vitro blood-brain barrier permeability of nevirapine compared to other HIV antiretroviral agents. J. Pharm. Sci. 87 (1998) 306-310
26. Kelder J., Grootenhuis P.D.J., Bayada D.M., Delbressine L.P.C., and Ploemen J.P. Polar molecular surface as a dominating determinant for oral absorption and brain penetration of drugs. Pharm. Res. 16 (1999) 1514-1519
27. Wold S. Cross-validatory estimation of the number of components in factor and principal component models. Technometrics 20 (1978) 397-406