Evolution of the physicochemical properties of marketed drugs: Can history foretell the future?

Drug Discovery Today

Volumn 16, Issue 21-22, 2011, Pages 976-984

  Faller, Bernard ^a   Ottaviani, Giorgio ^a   Ertl, Peter ^a   Berellini, Giuliano ^b   Collis, Alan ^b  

^a NOVARTIS PHARMA AG   (Switzerland)

^b NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CENTRAL NERVOUS SYSTEM AGENTS; CYTOSTATIC AGENT; DRUG; NEW DRUG; PHOSPHOTRANSFERASE INHIBITOR;

DATA ANALYSIS SOFTWARE; DRUG MECHANISM; DRUG PENETRATION; DRUG RESEARCH; DRUG TARGETING; HUMAN; HYDROGEN BOND; HYDROPHILICITY; HYDROPHOBICITY; PARTICLE SIZE; PHYSICAL CHEMISTRY; PREDICTION; REVIEW;

BIOLOGICAL AGENTS; DRUG APPROVAL; DRUG INDUSTRY; FORECASTING; HUMANS; MOLECULAR STRUCTURE; PHARMACEUTICAL PREPARATIONS; PHYSICOCHEMICAL PHENOMENA; SMALL MOLECULE LIBRARIES; UNITED STATES; UNITED STATES FOOD AND DRUG ADMINISTRATION;

EID: 80255141850     PISSN: 13596446     EISSN: 18785832     Source Type: Journal    
DOI: 10.1016/j.drudis.2011.07.003     Document Type: Review

References (30)

1. C.A. Lipinski Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Deliv. Rev. 23 1997 3 25 (Pubitemid 27046991)
2. G. Cruciani VolSurf: a new tool for the pharmacokinetic optimization of lead compounds Eur. J. Pharm. Sci. 11 Suppl. 2 2000 S29 S39
3. G. Cruciani Molecular fields in quantitative structure-permeation relationships: the VolSurf approach J. Mol. Struct. 503 2000 17 30
4. J.L. Medina-Franco Visualization of the chemical space in drug discovery Curr. Comp. Aid. Drug Des. 4 2008 322 333
5. M. Bruestle Descriptors, physical properties, and drug-likeness J. Med. Chem. 45 2002 3345 3355
6. P.D. Leeson, and B. Springthorpe The influence of drug-like concepts on decision-making in medicinal chemistry Nat. Rev. Drug Discov. 6 2007 881 890 (Pubitemid 350042396)
7. J.R. Empfield, and P.D. Leeson Lessons learned from candidate drug attrition IDrugs 13 2010 869 873
8. M.J. Waring Defining optimum lipophilicity and molecular weight ranges for drug candidates: molecular weight dependent lower log D limits based on permeability Bioorg. Med. Chem. Lett. 19 2009 2844 2851
9. M.P. Gleeson Probing the links between in vitro potency, ADMET and physicochemical parameters Nat. Rev. Drug Discov. 10 2011 197 208
10. T.I. Oprea, and J. Gottfries Chemography: the art of navigating in chemical space J. Comb. Chem. 3 2001 157 166 (Pubitemid 33614499)
11. T.I. Oprea Pharmacokinetically based mapping device for chemical space navigation J. Comb. Chem. 4 2002 258 266
12. S. Wold Multivariate data analysis in chemistry Chemom. Math. Stat. Chem. 138 1984 17 96
13. C. Lipinski, and A. Hopkins Navigating chemical space for biology and medicine Nature 432 2004 855 861 (Pubitemid 40037141)
14. P.D. Leeson, and A.M. Davis Time-related differences in the physical property profiles of oral drugs J. Med. Chem. 47 2004 6338 6348 (Pubitemid 39587257)
15. S. Sciabola Predicting kinase selectivity profiles using Free-Wilson QSAR analysis J. Chem. Inf. Model. 48 2008 1851 1867
16. S. Frantz, and A. Smith New drug approvals for 2002 Nat. Rev. Drug Discov. 2 2003 95 96 (Pubitemid 37361640)
17. S. Frantz 2003 approvals: a year of innovation and upward trends Nat. Rev. Drug Discov. 3 2004 103 105
18. S. Frantz 2004 approvals: the demise of the blockbuster? Nat. Rev. Drug Discov. 4 2005 93 94 (Pubitemid 40277473)
19. S. Frantz 2005 approvals: safety first Nat. Rev. Drug Discov. 5 2006 92 93
20. J. Owens 2006 drug approvals: finding the niche Nat. Rev. Drug Discov. 6 2007 99 101
21. B. Hughes 2007 FDA drug approvals: a year of flux Nat. Rev. Drug Discov. 7 2008 107 109
22. B. Hughes 2008 FDA drug approvals Nat. Rev. Drug Discov. 8 2009 93 96
23. F. Wohnsland, and B. Faller High-throughput permeability pH profile and high-throughput alkane/water log P with artificial membranes J. Med. Chem. 44 2001 923 930 (Pubitemid 32861617)
24. W.J. Egan Prediction of drug absorption using multivariate statistics J. Med. Chem. 43 2000 3867 3877
25. J. Karlsson, and P. Artursson A method for the determination of cellular permeability coefficients and aqueous boundary layer thickness in monolayers of intestinal epithelial (Caco-2) cells grown in permeable filter chambers Int. J. Pharm. 71 1991 55 64
26. I. Hidalgo, and J. Li Carrier-mediated transport and efflux mechanisms in Caco-2 cells Adv. Drug Deliv. Rev. 22 1996 53 56
27. D.A. Smith The effect of plasma protein binding on in vivo efficacy: misconceptions in drug discovery Nat. Rev. Drug Discov. 9 2010 929 993
28. S. Schmidt Significance of protein binding in pharmacokinetics and pharmacodynamics J. Pharm. Sci. 99 2010 1107 1122
29. R.S. Obach Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds Drug Metab. Dispos. 36 2008 1385 1405 (Pubitemid 351929323)
30. K.D. Read, and S. Braggio Assessing brain free fraction in early drug discovery Drug. Metab. Toxicol. 6 2010 337 344