Reliability of logP predictions based on calculated molecular descriptors: A critical review

Current Medicinal Chemistry

Volumn 9, Issue 20, 2002, Pages 1819-1829

  Eros, D ^a   Kovesdi I ^a   Orfi, L ^a   Takacs Novak K ^a   Acsady Gy ^a   Keri Gy ^a  

^a SEMMELWEIS UNIVERSITY   (Hungary)

Author keywords

Combinatorial libraries; Drugs; In silico screening; Lipophilicity; LogP prediction; Neural network

Indexed keywords

ACEBUTOLOL; ASCORBIC ACID; ATENOLOL; BENZOIC ACID; BUSPIRONE; CEFALOTIN; CHLORPROMAZINE; CLOBAZAM; CODEINE; DEXTROMORAMIDE; DISOPYRAMIDE; FLUMEQUINE; GLUTAMINE; LEVOMEPROMAZINE; LIDOCAINE; MEFENAMIC ACID; METHOTREXATE; METIPRANOLOL; METOPROLOL; MEXILETINE; NALOXONE; OFLOXACIN; OXPRENOLOL; PAPAVERINE; PENBUTOLOL; PENICILLAMINE; PHENFORMIN; PILOCARPINE; PINDOLOL; UNINDEXED DRUG;

ACCURACY; ANALYTIC METHOD; ANALYTICAL PARAMETERS; ARTIFICIAL NEURAL NETWORK; AUTOMATION; COMBINATORIAL LIBRARY; COMPUTER PROGRAM; CONTROLLED STUDY; DATA BASE; INTERMETHOD COMPARISON; LINEAR REGRESSION ANALYSIS; MATHEMATICAL ANALYSIS; MATHEMATICAL COMPUTING; MULTIPLE REGRESSION; PHYSICAL CHEMISTRY; PREDICTION; QUALITY CONTROL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RELIABILITY; REVIEW; STATISTICAL ANALYSIS; VALIDATION PROCESS;

EID: 0036383632     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867023369042     Document Type: Review

References (55)

1. Pliska, V.; Testa, B.; and van de Waterbeemd, H. (eds.) Lipophilicity in Drug Action and Toxicology, Methods and Principles in Medicinal Chemistry, Vol. 4, VCH Publishers, Weinheim, Germany, 1996.
2. Abraham, M. H.; Takács-Novák, K.; Mitchell, R.C. J. Pharm. Sci., 1997, 86, 310.
3. Leo, A. J. Chemical Reviews, 1993, 93, 1281.
4. Fujita, T.; Iwasa, J.; Hansch, C. J. Am. Chem. Soc., 1964, 86, 5175.
5. Rekker, R.; Mannhold, R. Calculation of Drug Lipophilicity, VCH: Weinheim, 1992.
6. Iwase, K.; Komatau, K.; Hirono, S.; Nakagawa, S.; Moriguchi, I. Chem. Pharm. Bull., 1985, 33, 2114.
7. Bodor, N.; Gabanyi, Z.; Wong, C-K. J. Am. Chem. Soc., 1989, 111, 3783.
8. Kamlet, M.; Abboud, J.-L.; Abraham, M.; Taft, R. J Org. Chem., 1983, 48, 2877.
9. The details of this work will be published elsewhere.
10. Isis™/Base, Ver. 2.3, MDL Information Systems, Inc., San Leonardo, CA, 1990-2000. (http://www.mdli.com)
11. Takács-Novák, K.; Avdeef, A. J. Pharm. Biomed Anal., 1996, 14, 1405.
12. Nagy, P. I.; Takács-Novák, K. J. Am. Chem. Soc., 1997, 119, 4999.
13. Sangster J. LOGKOW Databank, Sangster Research Laboratories: Montreal, 1994.
14. Takács-Novák, K.; Kökösi, J.; Podányi, B.; Noszál, B.; Tsai, R. S.; Lisa, G.; Carrupt, P.-A.; Testa, B. Helv. Chim. Act., 1995, 78, 533.
15. Sirius Technical Application Notes, Riverside, Forest Row Business Park, Forest Row, East Sussex, RH18 5DW, UK. 1995, 2, 1.
16. Sangster, J. LOGKOW Databank, Sangster Research Laboratories: Montreal, 1993.
17. Hansch, C.; Leo, A.; Hoekman, D. Exploring QSAR. Hydrophobic, Electronic and Steric Constants. ACS Professional Reference Book, American Chemical Society: Washington DC, 1995.
18. Hansch, C.; Leo, A. MEDCHEM Project. Pomona College: Claremont, 1985.
19. ow) Data for Hydrophobic Organic compounds: DDT and DDE as a Case Study, U. S. Geological Survey, Water-Resources Investigations Report 01-4201, Reston, Virginia, 2001. (http://pubs. water.usgs.gov/wri01-4201)
20. 3DNET, Vichem Chemie Ltd,, Herman O. u. 15., Budapest, 1022, Hungary, 2001.
21. Connolly, M. L. J. Am. Chem. Soc., 1985, 107, 1118.
22. De Bruijn, J.; Hermkens, J. J. Quant. Struct-Act. Relat., 1990, 9, 11.
23. Bodor, N.; Buchwald, P. J. Phys. Chem., 1997, 101, 3404.
24. Meyer, A. Y. J. Chem. Soc. Rev., 1986, 15, 449.
25. Todeschini, R.; Grammatica, P. Quant. Struct.-Act. Relat., 1997, 16, 120.
26. Breindl, A.; Beck, B.; Clark, T.; Glen, R. C. J. Mol. Model., 1997, 3, 142.
27. Miller, K. J. J. Am. Chem. Soc., 1990, 112, 8533.
28. Mortier, W. J.; Genechten, K.; Gasteiger, J. J. Am. Chem. Soc., 1985, 107, 829.
29. Fedors, R. F.; Van Krevelen, D. V.; Hoftyzer, P. J. CRC Handbook of Solubility Parameters and Other Cohesion Parameters, CRC Press. New York, 1986.
30. Andrews, P. R.; Craik, D. J.; Martin, J. L. J. Med. Chem., 1984, 27, 1648.
31. Wiener, H. J. Am. Chem. Soc., 1947, 69, 2636.
32. Randic, M. J. Am. Chem. Soc., 1975, 97, 6609.
33. Katritzky, A. R.; Lobanov, V. S.; Karelson, M. J. Chem. Inf. Comput. Sci., 1998, 38, 28.
34. Bodor, N.; Huang, M, J.; Harget, A. J. Mol. Struct. (Theochem.), 1994, 309, 259.
35. Gaillard, P.; Carrupt, P.; Testa, B.; Boudon, A. J. Comput.-Aided Mol. Des., 1994, 8, 83.
36. Cronce, T. D.; Famini, G. R.; De Soto, J. A.; Wilson, L. Y. J. Chem. Soc. Perkin Trans., 1998, 2, 1293.
37. Broto, P.; Moreau, G.; Vandycke, C. Eur. J. Med. Chem., 1984, 19, 71.
38. AutoQSAR ver. 2., Vichem Chemie Ltd., 1022 Budapest, Hermann O. u., 2001.
39. Snee, R. D. Technometrics, 1997, 415.
40. Hansch, C.; Fujita, T. J. Am. Chem. Soc., 1964, 86, 1616.
41. Wold, H Research Papers in Statistics, Wiley: New York, 1966.
42. Hornik, K.; Stinchcombe, M.; White, H. Neur. Net., 1989, 5, 359.
43. Hansch, C.; Leo A. Substituent Constants for Correlation Analysis in Chemistry and Biology. Wiley: New York, 1979.
44. Takács-Novák K. Acta Pharm. Hung., 1998, 68, 39.
45. KOWWIN for Microsoft Windows, Version 1.60, Copyright (c) W. Meylan, 1993-1997. Syracuse Research Corp., New York, U.S.A.
46. SciLogP Ultra. Version 1.5. Scivision, 1999. (http://www.scivision.com)
47. http://www.daylight.com/daycgi/clogp
48. ConSystant. Version 3 13a, ExoGraphics, 1992-2000. PO Box 655, West Milford, NJ 07480.
49. Meylan, W. M.; Howard, P. H. J. Pharm. Sci., 1995, 84, 83.
50. Valko, K. "Measurements and Predictions of Physicochemical Properties" In High-Throughput ADMETox Estimation; Eds.; Darvas, F.; Dorman, G.: Eaton Publishing, Westborough, MA, 2002.
51. Károlyházi, L.; Szabó, D.; Anwair, M. A. S.; Borosy, A.; Takács-Novák, K.; Mátyus, P. J. Mol. Structure: (Theochem.), 2002, 578, 89.
52. http://www.scivision.com/gProdPage/tReviews/ SciLogPUltra/TestYourOwn.html
53. Takács-Novák, K.; Perjési, P.; Vámos, J. J. Planar Chromatogr., 2001, 14, 42.
54. Huuskonen, J. J.; Villa, A. E. P.; Tetko, I. V. J. Pharm. Sci., 1999, 88, 229.
55. Mannhold, R.; Rekker, R. F.; Sonntag, C.; Ter Laak, A. M.; Dross, K.; Polymeropoulos, E. E. J. Pharm. Sci., 1995, 84, 1410.