Prediction of drug exposure in the brain from the chemical structure

AAPS Advances in the Pharmaceutical Sciences Series

Volumn 10, Issue , 2014, Pages 317-338

  Fridén, Markus ^a  

^a ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOLYTE;

ARTICLE; BLOOD BRAIN BARRIER; BRAIN FUNCTION; CHEMICAL STRUCTURE; COMPUTER MODEL; DRUG BINDING; DRUG DESIGN; DRUG EXPOSURE; DRUG PENETRATION; DRUG STRUCTURE; DRUG TARGETING; HYDROGEN BOND; LIPID SOLUBILITY; LOGBB; PHARMACOKINETIC ASSAY; PHYSICOCHEMICAL MODEL; PRIORITY JOURNAL; SURFACE AREA;

EID: 84928650350     PISSN: 22107371     EISSN: 2210738X     Source Type: Book Series    
DOI: 10.1007/978-1-4614-9105-7_11     Document Type: Article

References (50)

1. Abraham MH, Hersey A (2007) In silico models to predict brain uptake. In: Comprehensive medicinal chemistry II (anonymous), John B. Taylor and David J. Triggle. Elsevier Ltd., London, p 745
2. Abraham MH (2004a) The factors that influence permeation across the blood-brain barrier. Eur J Med Chem 39:235-240
3. Abraham MH (2004b) The factors that influence permeation across the blood-brain barrier. Eur J Med Chem 39:235-240
4. Abraham MH, Ibrahim A, Zissimos AM, Zhao YH, Comer J, Reynolds DP (2002) Application of hydrogen bonding calculations in property based drug design. Drug Discov Today 7: 1056-1063
5. Abraham MH, Chadha HS, Mitchell RC (1994) Hydrogen bonding. 33. Factors that influence the distribution of solutes between blood and brain. J Pharm Sci 83:1257-1268
6. Bendels S, Kansy M, Wagner B, Huwyler J (2008) In silico prediction of brain and CSF permeation of small molecules using PLS regression models. Eur J Med Chem 43:1581-1592
7. Broccatelli F, Larregieu CA, Cruciani G, Oprea TI, Benet LZ (2012) Improving the prediction of the brain disposition for orally administered drugs using BDDCS. Adv Drug Deliv Rev 64:95-109
8. Chen H, Winiwarter S, Friden M, Antonsson M, Engkvist O (2011) In silico prediction of unbound brain-to-plasma concentration ratio using machine learning algorithms. J Mol Graph Model 29:985-995
9. Clark DE (2003) In silico prediction of blood-brain barrier permeation. Drug Discov Today 8:927-933
10. de Lange EC, de Boer BA, Breimer DD (1999) Microdialysis for pharmacokinetic analysis of drug transport to the brain. Adv Drug Deliv Rev 36:211-227
11. Demel MA, Kramer O, Ettmayer P, Haaksma EE, Ecker GF (2009) Predicting ligand interactions with ABC transporters in ADME. Chem Biodivers 6:1960-1969
12. Ecker GF, Stockner T, Chiba P (2008) Computational models for prediction of interactions with ABC-transporters. Drug Discov Today 13:311-317
13. Ecker GF, Noe CR (2004) In silico prediction models for blood-brain barrier permeation. Curr Med Chem 11:1617-1628
14. Ekins S, Ecker GF, Chiba P, Swaan PW (2007) Future directions for drug transporter modelling. Xenobiotica 37:1152-1170
15. Elmquist WF, Sawchuk RJ (1997) Application of microdialysis in pharmacokinetic studies. Pharm Res 14:267-288
16. Friden M, Winiwarter S, Jerndal G, Bengtsson O, Wan H, Bredberg U, Hammarlund-Udenaes M, Antonsson M (2009) Structure-brain exposure relationships in rat and human using a novel data set of unbound drug concentrations in brain interstitial and cerebrospinal fluids. J Med Chem 52:6233-6243
17. Friden M, Gupta A, Antonsson M, Bredberg U, Hammarlund-Udenaes M (2007) In vitro methods for estimating unbound drug concentrations in the brain interstitial and intracellular fluids. Drug Metabol Dispos 35:1711-1719
18. Ghose AK, Herbertz T, Hudkins RL, Dorsey BD, Mallamo JP (2012) Knowledge-based, central nervous system (CNS) lead selection and lead optimization for CNS drug discovery. ACS Chem Neurosci 3:50-68
19. Gratton JA, Abraham MH, Bradbury MW, Chadha HS (1997) Molecular factors influencing drug transfer across the blood-brain barrier. J Pharm Pharmacol 49:1211-1216
20. Gupta A, Chatelain P, Massingham R, Jonsson EN, Hammarlund-Udenaes M (2006) Brain distribution of cetirizine enantiomers: comparison of three different tissue-to-plasma partition coefficients: K(p), K(p, u), and K(p, uu). Drug Metabol Dispos 34:318-323
21. Hammarlund-Udenaes M, Bredberg U, Friden M (2009) Methodologies to assess brain drug delivery in lead optimization. Curr Top Med Chem 9:148-162
22. Hammarlund-Udenaes M, Friden M, Syvänen S, Gupta A (2008) On the rate and extent of drug delivery to the brain. Pharm Res 25:1737-1750
23. Hammarlund-Udenaes M (2000) The use of microdialysis in CNS drug delivery studies. Pharmacokinetic perspectives and results with analgesics and antiepileptics. Adv Drug Deliv Rev 45:283-294
24. Hitchcock SA, Pennington LD (2006) Structure-brain exposure relationships. J Med Chem 49:7559-7583
25. Johansson U, Sonstrod C, Norinder U, Bostrom H (2011) Trade-off between accuracy and interpretability for predictive in silico modeling. Future Med Chem 3:647-663
26. Kakee A, Terasaki T, Sugiyama Y (1996) Brain efflux index as a novel method of analyzing efflux transport at the blood-brain barrier. J Pharmacol Exp Therapeut 277:1550-1559
27. Kalvass JC, Maurer TS (2002) Influence of nonspecific brain and plasma binding on CNS exposure: implications for rational drug discovery. Biopharm Drug Dispos 23:327-338
28. Kelder J, Grootenhuis PD, Bayada DM, Delbressine LP, Ploemen JP (1999) Polar molecular surface as a dominating determinant for oral absorption and brain penetration of drugs. Pharm Res 16:1514-1519
29. Lanevskij K, Dapkunas J, Juska L, Japertas P, Didziapetris R (2011) QSAR analysis of blood-brain distribution: the influence of plasma and brain tissue binding. J Pharm Sci 100:2147-2160
30. Levin VA (1980) Relationship of octanol/water partition coefficient and molecular weight to rat brain capillary permeability. J Med Chem 23:682-684
31. Liu X, Tu M, Kelly RS, Chen C, Smith BJ (2004) Development of a computational approach to predict blood-brain barrier permeability. Drug Metab Dispos 32:132-139
32. Luco JM (1999) 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 39:396-404
33. Martin I (2004) Prediction of blood-brain barrier penetration: are we missing the point? Drug Discov Today 9:161-162
34. Matsson P (2007) ATP-Binding cassette efflux transporters and passive membrane permeability in drug absorption and disposition. Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Pharmacy 67:68
35. McAinsh J, Cruickshank JM (1990) Beta-blockers and central nervous system side effects. Pharmacol Therapeut 46:163-197
36. Mehdipour AR, Hamidi M (2009) Brain drug targeting: a computational approach for overcoming blood-brain barrier. Drug Discov Today 14:1030-1036
37. Norinder U, Haeberlein M (2002) Computational approaches to the prediction of the blood-brain distribution. Adv Drug Deliv Rev 54:291-313
38. Osterberg T, Norinder U (2000) Prediction of polar surface area and drug transport processes using simple parameters and PLS statistics. J Chem Inf Comput Sci 40:1408-1411
39. Palm K, Stenberg P, Luthman K, Artursson P (1997) Polar molecular surface properties predict the intestinal absorption of drugs in humans. Pharm Res 14:568-571
40. Pardridge WM (2004) Log(BB), PS products and in silico models of drug brain penetration. Drug Discov Today 9:392-393
41. Plowright AT, Nilsson K, Antonsson M, Amin K, Broddefalk J, Jensen J, Lehmann A, Jin S, St-Onge S, Tomaszewski MJ, Tremblay M, Walpole CS, Wei Z, Yang H, Ulander J (2012) Discovery of agonists of cannabinoid receptor 1 with restricted CNS penetration aimed for treatment of gastroesophageal reflux disease. J Med Chem. doi:10.1021/jm301511h
42. Seelig A, Landwojtowicz E (2000) Structure-activity relationship of P-glycoprotein substrates and modifiers. Eur J Pharm Sci 12:31-40
43. van de Waterbeemd H, Smith DA, Jones BC (2001) Lipophilicity in PK design: methyl, ethyl, futile. J Comput Aided Mol Des 15:273-286
44. van de Waterbeemd H, Camenisch G, Folkers G, Chretien JR, Raevsky OA (1998) Estimation of blood-brain barrier crossing of drugs using molecular size and shape, and H-bonding descriptors. J Drug Target 6:151-165
45. Wager T, Hou X, Verhoest PR, Villalobos A (2010) Moving beyond rules: the development of a central nervous system multiparameter optimization (CNS MPO) approach to enable alignment of druglike properties. ACS Chem Neurosci 1:435-449
46. Winiwarter S, Hilgendorf C (2008) Modeling of drug-transporter interactions using structural information. Curr Opin Drug Discov Devel 11:95-103
47. Winiwarter S, Ridderström M, Ungell AL, Andersson TB, Zamora I, Zamora I (2007) Use of molecular descriptors for absorption, distribution, metabolism, and excretion predictions. In: comprehensive medicinal chemistry II (anonymous), John B. Taylor and David J. Triggle. Elsevier Ltd., London, p 745
48. Wold S (2001) PLS-regression: a basic tool of chemometrics. Chemometr Intell Lab 58:109-130
49. Wold S (1991) Validation of QSAR’s. Quant Struct: Act Relat 10:191-193
50. Young RC, Mitchell RC, Brown TH, Ganellin CR, Griffiths R, Jones M, Rana KK, Saunders D, Smith IR, Sore NE (1988) Development of a new physicochemical model for brain penetration and its application to the design of centrally acting H2 receptor histamine antagonists. J Med Chem 31:656-671