Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings

Kubinyi, 1995, Strategies and recent technologies in drug discovery, Pharmazie, 50, 647 Moos, 1993, Recent Advances in the Generation of Molecular Diversity, Annu. Rep. Med. Chem., 28, 315, 10.1016/S0065-7743(08)60903-3 Patel, 1996, Applications of small-molecule combinatorial chemistry to drug discovery, Drug Discov. Today, 1, 134, 10.1016/1359-6446(96)89062-3 Baum, 1994, Combinatorial approaches provide fresh leads for medicinal chemistry, Chem. Eng. News February, 7, 20, 10.1021/cen-v072n006.p020 Chow, 1995, Using backpropagation networks for the estimation of aqueous activity coefficients of aromatic compounds, J. Chem. Inf. Comput. Sci., 35, 723, 10.1021/ci00026a009 Andrews, 1984, Functional group contributions to drug-receptor interactions, J. Med. Chem., 27, 1648, 10.1021/jm00378a021 Navia, 1996, Design principles for orally bioavailable drugs, Drug. Dev. Today, 1, 179, 10.1016/1359-6446(96)10020-9 Pardridge, 1995, Transport of small molecules through the blood-brain barrier: biology and methodology, Adv. Drug Deliv. Rev., 15, 5, 10.1016/0169-409X(95)00003-P Cohen, 1972, Diffusion of small non-electrolytes across liposome membranes, Nature, 236, 173, 10.1038/236173a0 Testa, 1996, Lipophilicity in molecular modelling, Pharm. Res., 13, 335, 10.1023/A:1016024005429 Moriguchi, 1992, Simple method of calculating octanol/water partition coefficient, Chem. Pharm. Bull., 40, 127, 10.1248/cpb.40.127 Moriguchi, 1994, Comparison of log P values for drugs calculated by several methods, Chem. Pharm. Bull., 42, 976, 10.1248/cpb.42.976 Leo, 1995, Critique of recent comparison of log P calculation methods, Chem. Pharm. Bull., 43, 512, 10.1248/cpb.43.512 Abraham, 1994, Hydrogen bonding. 32. An analysis of water-octanol and water-alkane partitioning and the delta log P parameter of Seiler, J. Pharm. Sci., 83, 1085, 10.1002/jps.2600830806 Paterson, 1994, A non-aqueous partitioning system for predicting the oral absorption potential of peptides, Quant. Struct.-Act. Relatsh., 13, 4, 10.1002/qsar.19940130103 Hillgren, 1995, In vitro systems for studying intestinal drug absorption, Med. Res. Rev., 15, 83, 10.1002/med.2610150202 Abraham, 1993, Hydrogen bonding. 31. Construction of a scale of solute effective or summation hydrogen-bond basicity, J. Phys. Org. Chem., 6, 660, 10.1002/poc.610061204 Raevsky, 1992, Complete thermodynamic description of Hbonding in the framework of multiplicative approach, Quant. Struct.-Act. Relatsh., 11, 49, 10.1002/qsar.19920110109 Raevsky, 1995, HBond contribution to octanol-water partition coefficients of polar compounds, Quant. Struct.-Act. Relatsh., 14, 433, 10.1002/qsar.19950140504 Lipinski, 1995, Computational alerts for potential absorption problems: profiles of clinically tested drugs 1995, Prediction of Drug Transport Through Membranes 1993 Lipinski, 1994, Biologically relevant UV-based solubility assays Reichardt, 1988, Solvents and Solvent Effects in Organic Chemistry, 27 Bodor, 1991, Neural network studies. 1. Estimation of the aqueous solubility of organic compounds, J. Am. Chem. Soc., 113, 9480, 10.1021/ja00025a009 Gavezzotti, 1994, Are crystal structures predictable?, Acc. Chem. Res., 27, 309, 10.1021/ar00046a004 Polymorph Predictor, Molecular Simulations Inc., Burlington, MA. Abraham, 1993, Scales of solute hydrogen-bonding: their construction and application to physicochemical and biochemical processes, Chem. Soc. Rev., 22, 73, 10.1039/cs9932200073 Abraham, 1987, The use of characteristic volumes to measure cavity terms in reversed phase liquid chromatography, Chromatographia, 23, 243, 10.1007/BF02311772 Taft, 1985, The molecular properties governing solubilities of organic nonelectrolytes in water, Nature, 315, 384, 10.1038/313384a0 Kamlet, 1993, Linear solvation energy relationships: an improved equation for correlation and prediction of aqueous solubilities of aromatic solutes including polycyclic aromatic hydrocarbons and polychlorinated biphenyls, Prog. Phys. Org. Chem., 19, 295, 10.1002/9780470171981.ch5 Abraham, 1994, Hydrogen bonding. 33. Factors that influence the distribution of solutes between blood and brain, J. Pharm. Sci., 83, 1257, 10.1002/jps.2600830915 Brinck, 1993, Octanol/water partition coefficients expressed in terms of solute molecular surface areas and electrostatic potentials, J. Org. Chem., 58, 7070, 10.1021/jo00077a028 Murray, 1991, Correlations between the solvent hydrogen-bond-donating parameter α and the calculated molecular surface electrostatic potential, J. Org. Chem., 56, 6715, 10.1021/jo00023a045 Murray, 1991, Correlations between the solvent hydrogen bond acceptor parameter β and the calculated molecular electrostatic potential, J. Org. Chem., 56, 3734, 10.1021/jo00011a060 Famini, 1992, Using theoretical descriptors in quantitative structure activity relationships: some physicochemical properties, J. Phys. Org. Chem., 5, 395, 10.1002/poc.610050704 Headley, 1994, Analysis of solute/solvent interactions for the acidity of acetic acids by theoretical descriptors, J. Org. Chem., 59, 8040, 10.1021/jo00105a020 Ruelle, 1994, Prediction of carbazole solubility and its dependence upon the solvent nature, Int. J. Pharm., 104, 125, 10.1016/0378-5173(94)90187-2 Ruelle, 1991, A new predictive equation for the solubility of drugs based on the thermodynamics of mobile disorder, Pharm. Res., 8, 840, 10.1023/A:1015891126287 Ruelle, 1994, Solubility predictions for solid nitriles and tertiary amides based on the mobile order theory, Pharm. Res., 11, 201, 10.1023/A:1018990904867 Yalkowski, 1980, Solubility and partitioning 1: solubility of nonelectrolytes in water, J. Pharm. Sci., 69, 912, 10.1002/jps.2600690814 Abramovitz, 1990, Estimation of aqueous solubility and melting point of PCB congeners, Chemosphere, 21, 1221, 10.1016/0045-6535(90)90142-G Yalkowski, 1993, Estimation of the solubility of complex organic compounds, Chemosphere, 26, 1239, 10.1016/0045-6535(93)90179-9 Leo, 1993, Calculating log Poct from structures, Chem. Rev., 93, 1281, 10.1021/cr00020a001 Abramovitz, 1990, Melting point, boiling point, and symmetry, Pharm. Res., 7, 942, 10.1023/A:1015949907825 Dannenfelser, 1993, Molecular symmetry and related properties, SAR & QSAR Environ. Res., 1, 273, 10.1080/10629369308029892 Suzuki, 1991, Development of an automatic estimation system for both the partition coefficient and aqueous solubility, J. Comput. Aided Mol. Des., 5, 149, 10.1007/BF00129753 Myrdal, 1995, Aquafac 3: aqueous functional group activity coefficients; application to the estimation of aqueous solubility, Chemosphere, 30, 1619, 10.1016/0045-6535(95)00026-5 Bodor, 1992, A new method for the estimation of the aqueous solubility of organic compounds, J. Pharm. Sci., 81, 954, 10.1002/jps.2600810924 Nelson, 1994, Prediction of aqueous solubility of organic compounds, J. Chem. Int. Comput. Sci., 34, 601, 10.1021/ci00019a019