497
14 Quantitative Structure-Property Relationship Analysis …
18. FDA, Draft guidance for industry: waiver of in vivo bioavailability and bioequivalence studies for immediate release solid oral dosage forms containing certain active moieties/active ingredient based on a biopharmaceutics classification system, US Department of Health, Food
and Drug Administration, Center for Drug Evaluation and Research BP2, January 1999
19. Dressman JB, Amidon GL, Reppas C et al (1998) Dissolution testing as a prognostic tool for
oral drug absorption: immediate release dosage forms. Pharm Res 15:11–22
20. Meyer MC, Straughn AB, Jarvi EJ et al (1992) The bioinequivalence of carbamazepine tablets with a history of clinical failures. Pharm Res 9:1612–1616
21. Stephen RJ, Zheng W (2006) Recent progress in the computational prediction of aqueous
solubility and absorption. AAPS J 8(1):E27–E40
22. Houa T, Wangb J, Zhangc W et al (2006) Recent advances in computational prediction of
drug absorption and permeability in drug discovery. Curr Med Chem 13:2653–2667
23. Golovenko NYa, Borisyuk IYu, Kuz’min VE (2007) The dependence of “structure-property”
in the models, predictive bioavailability of drugs. Farmacom 3:27–36
24. Raevskii OA, Kazachenko IV, Raevskaya OE (2004) The calculation of the bioavailability of
drugs based on the similarity of the molecular structures. Chim-Farm Zhurn 38(10):3–8
25. Norinder U, Haeberlein M (2003) Calculated molecular properties and multivariate statistical analysis in absorption prediction. In: Drug bioavailability, methods and principles in
medicinal chemstry, Van de Waterbeemd H, Lennern SH, Artursson P. (eds.), WILEY-VCH,
Weinheim, 18:358–405
26. Lipinski CA (2000) Drug-like properties and the causes of poor solubility and poor permeability. J Pharmacol Toxicol Methods 44:235–249
27. Veber DF, Johnson SR, Cheng H-Y et al (2002) Molecular properties that influence the oral
bioavailability of drug candidates. J Med Chem 45:2615–2623
28. Lu JJ, Crimin K, Goodwin JT et al (2004) Influence of molecular flexibility and polar surface
area metrics on oral bioavailability in rat. J Med Chem 47:6104–6107
29. Hou T, Wang J, Zhang W et al (2007) ADME evaluation in drug discovery. 6. Can oral bioavailability in humans be effectively predicted by simple molecular property-based rules? J
Chem Inf Model 47:460–463
30. Hirono S, Nakagome I, Hirano H et al (1994) Non-congeneric structure–pharmacokinetic
property correlation studies using fuzzy adaptive least-squares: oral bioavailability. Biol
Pharm Bull 17:306–309
31. Bains W, Gilbert R, Sviridenko L et al (2002) Evolutionary computational methods to predict
oral bioavailability QSPRs. Curr Opin Drug Discov Devel 5(1):44–51
32. Zadeh LA (1977) Fuzzy sets and their applications to classification and clustering. In: Ryzin
JV (ed) Classification and clustering. Academic, NY, pp 251–299
33. Wessel MD, Jurs PC, Tolan JW et al (1998) Prediction of human intestinal absorption of drug
compounds from molecular structure. J Chem Inf Comput Sci 38:726–735
34. Egan WJ, Merz JKM, Baldwin JJ (2000) Prediction of drug absorption using multivariate
statistics. J Med Chem 43:3867–3877
35. Zhao YH, Abraham MH, Le J et al (2003) Evaluation of rat intestinal absorption data and
correlation with human intestinal absorption. Eur J Med Chem 38(3):233–243
36. Yoshida F, Topliss JG (2000) QSAR model for drug human oral bioavailability. J Med Chem
43:2575–2585
37. Andrews CW, Bennett L, Yu LX et al (2000) Predicting human oral bioavailability of a compound: development of a novel quantitative structure–bioavailability relationship. Pharm Res
17:639–644
38. Navia MA, Chaturvedi PR (1996) Design principles for orally bioavailable drugs. Drug Discov Today 1:179–189
39. Smith AB, Hirschmann R, Pasternak A et al (1997) An artificial antiparallel β-sheet containing a new peptidomimetic template. J Med Chem 40:2440–2444
40. Palm K, Stenberg P, Luthman K et al (1997) Polar molecular surface properties predict the
intestinal absorption of drugs in humans. Pharm Res 14:568–571
14 Quantitative Structure-Property Relationship Analysis …
18. FDA, Draft guidance for industry: waiver of in vivo bioavailability and bioequivalence studies for immediate release solid oral dosage forms containing certain active moieties/active ingredient based on a biopharmaceutics classification system, US Department of Health, Food
and Drug Administration, Center for Drug Evaluation and Research BP2, January 1999
19. Dressman JB, Amidon GL, Reppas C et al (1998) Dissolution testing as a prognostic tool for
oral drug absorption: immediate release dosage forms. Pharm Res 15:11–22
20. Meyer MC, Straughn AB, Jarvi EJ et al (1992) The bioinequivalence of carbamazepine tablets with a history of clinical failures. Pharm Res 9:1612–1616
21. Stephen RJ, Zheng W (2006) Recent progress in the computational prediction of aqueous
solubility and absorption. AAPS J 8(1):E27–E40
22. Houa T, Wangb J, Zhangc W et al (2006) Recent advances in computational prediction of
drug absorption and permeability in drug discovery. Curr Med Chem 13:2653–2667
23. Golovenko NYa, Borisyuk IYu, Kuz’min VE (2007) The dependence of “structure-property”
in the models, predictive bioavailability of drugs. Farmacom 3:27–36
24. Raevskii OA, Kazachenko IV, Raevskaya OE (2004) The calculation of the bioavailability of
drugs based on the similarity of the molecular structures. Chim-Farm Zhurn 38(10):3–8
25. Norinder U, Haeberlein M (2003) Calculated molecular properties and multivariate statistical analysis in absorption prediction. In: Drug bioavailability, methods and principles in
medicinal chemstry, Van de Waterbeemd H, Lennern SH, Artursson P. (eds.), WILEY-VCH,
Weinheim, 18:358–405
26. Lipinski CA (2000) Drug-like properties and the causes of poor solubility and poor permeability. J Pharmacol Toxicol Methods 44:235–249
27. Veber DF, Johnson SR, Cheng H-Y et al (2002) Molecular properties that influence the oral
bioavailability of drug candidates. J Med Chem 45:2615–2623
28. Lu JJ, Crimin K, Goodwin JT et al (2004) Influence of molecular flexibility and polar surface
area metrics on oral bioavailability in rat. J Med Chem 47:6104–6107
29. Hou T, Wang J, Zhang W et al (2007) ADME evaluation in drug discovery. 6. Can oral bioavailability in humans be effectively predicted by simple molecular property-based rules? J
Chem Inf Model 47:460–463
30. Hirono S, Nakagome I, Hirano H et al (1994) Non-congeneric structure–pharmacokinetic
property correlation studies using fuzzy adaptive least-squares: oral bioavailability. Biol
Pharm Bull 17:306–309
31. Bains W, Gilbert R, Sviridenko L et al (2002) Evolutionary computational methods to predict
oral bioavailability QSPRs. Curr Opin Drug Discov Devel 5(1):44–51
32. Zadeh LA (1977) Fuzzy sets and their applications to classification and clustering. In: Ryzin
JV (ed) Classification and clustering. Academic, NY, pp 251–299
33. Wessel MD, Jurs PC, Tolan JW et al (1998) Prediction of human intestinal absorption of drug
compounds from molecular structure. J Chem Inf Comput Sci 38:726–735
34. Egan WJ, Merz JKM, Baldwin JJ (2000) Prediction of drug absorption using multivariate
statistics. J Med Chem 43:3867–3877
35. Zhao YH, Abraham MH, Le J et al (2003) Evaluation of rat intestinal absorption data and
correlation with human intestinal absorption. Eur J Med Chem 38(3):233–243
36. Yoshida F, Topliss JG (2000) QSAR model for drug human oral bioavailability. J Med Chem
43:2575–2585
37. Andrews CW, Bennett L, Yu LX et al (2000) Predicting human oral bioavailability of a compound: development of a novel quantitative structure–bioavailability relationship. Pharm Res
17:639–644
38. Navia MA, Chaturvedi PR (1996) Design principles for orally bioavailable drugs. Drug Discov Today 1:179–189
39. Smith AB, Hirschmann R, Pasternak A et al (1997) An artificial antiparallel β-sheet containing a new peptidomimetic template. J Med Chem 40:2440–2444
40. Palm K, Stenberg P, Luthman K et al (1997) Polar molecular surface properties predict the
intestinal absorption of drugs in humans. Pharm Res 14:568–571