메뉴 건너뛰기




Volumn 5, Issue 2, 2000, Pages 49-58

Computational methods for the prediction of 'drug-likeness'

Author keywords

[No Author keywords available]

Indexed keywords

ALPRENOLOL; ATENOLOL; CARBAMAZEPINE; CIPROFLOXACIN; DIAZEPAM; ENALAPRILAT; FLUINDOSTATIN; FOSCARNET; HYDROCHLOROTHIAZIDE; KETOPROFEN; LACTULOSE; MANNITOL; METOLAZONE; METOPROLOL; NITROGEN; NORDAZEPAM; OLSALAZINE; OXAZEPAM; OXPRENOLOL; OXYGEN; PHENAZONE; PINDOLOL; PRACTOLOL; RAFFINOSE; SALAZOSULFAPYRIDINE; SULPIRIDE; TERBUTALINE; TRANEXAMIC ACID; UNINDEXED DRUG; VERAPAMIL;

EID: 0033981358     PISSN: 13596446     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1359-6446(99)01451-8     Document Type: Review
Times cited : (546)

References (56)
  • 1
    • 0033178249 scopus 로고    scopus 로고
    • Pharmacokinetics and metabolism in early drug discovery
    • Smith D.A., van de Waterbeemd H. Pharmacokinetics and metabolism in early drug discovery. Curr. Opin. Chem. Biol. 3:1999;373-378.
    • (1999) Curr. Opin. Chem. Biol , vol.3 , pp. 373-378
    • Smith, D.A.1    Van De Waterbeemd, H.2
  • 2
    • 0030787532 scopus 로고    scopus 로고
    • A human colonic cell line sharing similarities with enterocytes as a model to examine oral absorption: Advantages and limitations of the Caco-2 model
    • Delie F., Rubas W.A. A human colonic cell line sharing similarities with enterocytes as a model to examine oral absorption: Advantages and limitations of the Caco-2 model. Crit. Rev. Ther. Drug Carrier Syst. 14:1997;221-286.
    • (1997) Crit. Rev. Ther. Drug Carrier Syst. , vol.14 , pp. 221-286
    • Delie, F.1    Rubas, W.A.2
  • 3
    • 0032949615 scopus 로고    scopus 로고
    • MDCK (Madin-Darby canine kidney) cells: A tool for membrane permeability screening
    • Irvine J.et al. MDCK (Madin-Darby canine kidney) cells: A tool for membrane permeability screening. J. Pharm. Sci. 88:1999;28-33.
    • (1999) J. Pharm. Sci. , vol.88 , pp. 28-33
    • Irvine, J.1
  • 5
    • 0033179183 scopus 로고    scopus 로고
    • Recognizing molecules with drug-like properties
    • Walters W.P.et al. Recognizing molecules with drug-like properties. Curr. Opin. Chem. Biol. 3:1999;384-387.
    • (1999) Curr. Opin. Chem. Biol. , vol.3 , pp. 384-387
    • Walters, W.P.1
  • 6
    • 0031133147 scopus 로고    scopus 로고
    • Similarity measures for rational set selection and analysis of combinatorial libraries: The diverse property-derived (DPD) approach
    • Lewis R.A.et al. Similarity measures for rational set selection and analysis of combinatorial libraries: The diverse property-derived (DPD) approach. J. Chem. Inf. Comput. Sci. 37:1997;599-614.
    • (1997) J. Chem. Inf. Comput. Sci. , vol.37 , pp. 599-614
    • Lewis, R.A.1
  • 7
    • 0030756360 scopus 로고    scopus 로고
    • Reactive compounds and in vitro false positives in HTS
    • Rishton G.M. Reactive compounds and in vitro false positives in HTS. Drug Discovery Today. 2:1997;382-384.
    • (1997) Drug Discovery Today , vol.2 , pp. 382-384
    • Rishton, G.M.1
  • 8
    • 0002606755 scopus 로고    scopus 로고
    • Virtual screening - An overview
    • Walters W.P.et al. Virtual screening - An overview. Drug Discovery Today. 3:1998;160-178.
    • (1998) Drug Discovery Today , vol.3 , pp. 160-178
    • Walters, W.P.1
  • 9
    • 0033194752 scopus 로고    scopus 로고
    • Strategic pooling of compounds for high-throughput screening
    • Hann M.et al. Strategic pooling of compounds for high-throughput screening. J. Chem. Inf. Comput. Sci. 39:1999;897-902.
    • (1999) J. Chem. Inf. Comput. Sci. , vol.39 , pp. 897-902
    • Hann, M.1
  • 10
    • 0032015361 scopus 로고    scopus 로고
    • Identification of biological activity profiles using substructural analysis and genetic algorithms
    • Gillet V.J.et al. Identification of biological activity profiles using substructural analysis and genetic algorithms. J. Chem. Inf. Comput. Sci. 38:1998;165-179.
    • (1998) J. Chem. Inf. Comput. Sci. , vol.38 , pp. 165-179
    • Gillet, V.J.1
  • 11
    • 0032572819 scopus 로고    scopus 로고
    • Can we learn to distinguish between drug-like and non-drug-like molecules?
    • Ajayet al. Can we learn to distinguish between drug-like and non-drug-like molecules? J. Med. Chem. 41:1998;3314-3324.
    • (1998) J. Med. Chem. , vol.41 , pp. 3314-3324
    • Ajay1
  • 12
    • 0032572816 scopus 로고    scopus 로고
    • A scoring scheme for discriminating between drugs and nondrugs
    • Sadowski J., Kubinyi H. A scoring scheme for discriminating between drugs and nondrugs. J. Med. Chem. 41:1998;3325-3329.
    • (1998) J. Med. Chem. , vol.41 , pp. 3325-3329
    • Sadowski, J.1    Kubinyi, H.2
  • 14
    • 0001334658 scopus 로고    scopus 로고
    • Design principles for orally bioavailable drugs
    • Navia M.A., Chaturvedi P.R. Design principles for orally bioavailable drugs. Drug Discovery Today. 1:1996;179-189.
    • (1996) Drug Discovery Today , vol.1 , pp. 179-189
    • Navia, M.A.1    Chaturvedi, P.R.2
  • 15
    • 0000312699 scopus 로고    scopus 로고
    • Physicochemical and drug-delivery considerations for oral drug bioavailability
    • Chan O.H., Stewart B.H. Physicochemical and drug-delivery considerations for oral drug bioavailability. Drug Discovery Today. 1:1996;461-473.
    • (1996) Drug Discovery Today , vol.1 , pp. 461-473
    • Chan, O.H.1    Stewart, B.H.2
  • 16
    • 0033199346 scopus 로고    scopus 로고
    • Absorption prediction from physicochemical parameters
    • Krämer, S.D. (1999) Absorption prediction from physicochemical parameters. Pharm. Sci. Technol. Today 2, 373-380; 2, 426 (corrigendum).
    • (1999) Pharm. Sci. Technol. Today , vol.2 , pp. 373-380
    • Krämer, S.D.1
  • 17
    • 0032704733 scopus 로고    scopus 로고
    • (corrigendum)
    • Krämer, S.D. (1999) Absorption prediction from physicochemical parameters. Pharm. Sci. Technol. Today 2, 373-380; 2, 426 (corrigendum).
    • Pharm. Sci. Technol. Today , vol.2 , pp. 426
  • 18
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski C.A.et al. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 23:1997;3-25.
    • (1997) Adv. Drug Deliv. Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1
  • 19
    • 0026597449 scopus 로고
    • Simple method of calculating octanol/water partition coefficient
    • Moriguchi I.et al. Simple method of calculating octanol/water partition coefficient. Chem. Pharm. Bull. 40:1992;127-130.
    • (1992) Chem. Pharm. Bull. , vol.40 , pp. 127-130
    • Moriguchi, I.1
  • 20
    • 0032600640 scopus 로고    scopus 로고
    • A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases
    • Ghose A.K.et al. A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. J. Comb. Chem. 1:1999;55-68.
    • (1999) J. Comb. Chem. , vol.1 , pp. 55-68
    • Ghose, A.K.1
  • 21
    • 0030481554 scopus 로고    scopus 로고
    • Estimation of Caco-2 cell permeability using calculated molecular descriptors
    • van de Waterbeemd H.et al. Estimation of Caco-2 cell permeability using calculated molecular descriptors. Quant. Struct.-Act. Relatsh. 15:1996;480-490.
    • (1996) Quant. Struct.-Act. Relatsh. , vol.15 , pp. 480-490
    • Van De Waterbeemd, H.1
  • 22
    • 0031404654 scopus 로고    scopus 로고
    • Theoretical calculation and prediction of Caco-2 cell permeability using MolSurf parametrization and PLS statistics
    • Norinder U.et al. Theoretical calculation and prediction of Caco-2 cell permeability using MolSurf parametrization and PLS statistics. Pharm. Res. 14:1997;1786-1791.
    • (1997) Pharm. Res. , vol.14 , pp. 1786-1791
    • Norinder, U.1
  • 23
    • 0026513211 scopus 로고
    • The influence of peptide structure on transport across Caco-2 cells. II. Peptide bond modification which results in improved permeability
    • Conradi R.A.et al. The influence of peptide structure on transport across Caco-2 cells. II. Peptide bond modification which results in improved permeability. Pharm. Res. 9:1992;435-439.
    • (1992) Pharm. Res. , vol.9 , pp. 435-439
    • Conradi, R.A.1
  • 24
    • 0030030608 scopus 로고    scopus 로고
    • Correlation of drug absorption with molecular surface properties
    • Palm K.et al. Correlation of drug absorption with molecular surface properties. J. Pharm. Sci. 85:1996;32-39.
    • (1996) J. Pharm. Sci. , vol.85 , pp. 32-39
    • Palm, K.1
  • 25
    • 0031872134 scopus 로고    scopus 로고
    • Predicting drug absorption from molecular surface properties based on molecular dynamics simulations
    • Krarup L.H.et al. Predicting drug absorption from molecular surface properties based on molecular dynamics simulations. Pharm. Res. 15:1998;972-978.
    • (1998) Pharm. Res. , vol.15 , pp. 972-978
    • Krarup, L.H.1
  • 26
    • 0032585545 scopus 로고    scopus 로고
    • Evaluation of dynamic polar molecular surface area as predictor of drug absorption: Comparison with other computational and experimental predictors
    • Palm K.et al. Evaluation of dynamic polar molecular surface area as predictor of drug absorption: Comparison with other computational and experimental predictors. J. Med. Chem. 41:1998;5382-5392.
    • (1998) J. Med. Chem. , vol.41 , pp. 5382-5392
    • Palm, K.1
  • 27
    • 0033014577 scopus 로고    scopus 로고
    • Prediction of membrane permeability to peptides from calculated dynamic molecular surface properties
    • Stenberg P.et al. Prediction of membrane permeability to peptides from calculated dynamic molecular surface properties. Pharm. Res. 16:1999;205-212.
    • (1999) Pharm. Res. , vol.16 , pp. 205-212
    • Stenberg, P.1
  • 28
    • 0030914681 scopus 로고    scopus 로고
    • Polar molecular surface properties predict the intestinal absorption of drugs in humans
    • Palm K.et al. Polar molecular surface properties predict the intestinal absorption of drugs in humans. Pharm. Res. 14:1997;568-571.
    • (1997) Pharm. Res. , vol.14 , pp. 568-571
    • Palm, K.1
  • 29
    • 0032979004 scopus 로고    scopus 로고
    • Theoretical calculation and prediction of intestinal absorption of drugs in humans using MolSurf parametrization and PLS statistics
    • Norinder U.et al. Theoretical calculation and prediction of intestinal absorption of drugs in humans using MolSurf parametrization and PLS statistics. Eur. J. Pharm. Sci. 8:1999;49-56.
    • (1999) Eur. J. Pharm. Sci. , vol.8 , pp. 49-56
    • Norinder, U.1
  • 30
    • 0033587166 scopus 로고    scopus 로고
    • Molecular hashkeys: A novel method for molecular characterization and its application for predicting important pharmaceutical properties of molecules
    • Ghuloum A.M.et al. Molecular hashkeys: A novel method for molecular characterization and its application for predicting important pharmaceutical properties of molecules. J. Med. Chem. 42:1999;1739-1748.
    • (1999) J. Med. Chem. , vol.42 , pp. 1739-1748
    • Ghuloum, A.M.1
  • 31
    • 0032112107 scopus 로고    scopus 로고
    • Prediction of human intestinal absorption of drug compounds from molecular structure
    • Wessel M.D.et al. Prediction of human intestinal absorption of drug compounds from molecular structure. J. Chem. Inf. Comput. Sci. 38:1998;726-735.
    • (1998) J. Chem. Inf. Comput. Sci. , vol.38 , pp. 726-735
    • Wessel, M.D.1
  • 32
    • 0032795192 scopus 로고    scopus 로고
    • Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 1. Prediction of intestinal absorption
    • Clark D.E. Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 1. Prediction of intestinal absorption. J. Pharm. Sci. 88:1999;807-814.
    • (1999) J. Pharm. Sci. , vol.88 , pp. 807-814
    • Clark, D.E.1
  • 33
    • 0032480901 scopus 로고    scopus 로고
    • Correlation of human jejunal permeability (in vivo) of drugs with experimentally and theoretically derived parameters. A multivariate data analysis approach
    • Winiwarter S.et al. Correlation of human jejunal permeability (in vivo) of drugs with experimentally and theoretically derived parameters. A multivariate data analysis approach. J. Med. Chem. 41:1998;4939-4949.
    • (1998) J. Med. Chem. , vol.41 , pp. 4939-4949
    • Winiwarter, S.1
  • 34
    • 0032410164 scopus 로고    scopus 로고
    • Estimation of blood-brain barrier crossing of drugs using molecular size and shape, and H-bonding descriptors
    • van de Waterbeemd H.et al. Estimation of blood-brain barrier crossing of drugs using molecular size and shape, and H-bonding descriptors. J. Drug Targeting. 6:1998;151-165.
    • (1998) J. Drug Targeting , vol.6 , pp. 151-165
    • Van De Waterbeemd, H.1
  • 35
    • 0033002003 scopus 로고    scopus 로고
    • Strategies toward predicting peptide cellular permeability from computed molecular descriptors
    • Goodwin J.T.et al. Strategies toward predicting peptide cellular permeability from computed molecular descriptors. J. Pept. Res. 53:1999;355-369.
    • (1999) J. Pept. Res. , vol.53 , pp. 355-369
    • Goodwin, J.T.1
  • 36
    • 0032321367 scopus 로고    scopus 로고
    • Quantitative estimation of hydrogen bond contribution to permeability and absorption processes of some chemicals and drugs
    • Raevsky O.A., Schaper K.-J. Quantitative estimation of hydrogen bond contribution to permeability and absorption processes of some chemicals and drugs. Eur. J. Med. Chem. 33:1998;799-807.
    • (1998) Eur. J. Med. Chem. , vol.33 , pp. 799-807
    • Raevsky, O.A.1    Schaper, K.-J.2
  • 37
    • 0031959341 scopus 로고    scopus 로고
    • CNS drug design based on principles of blood-brain barrier transport
    • Pardridge W.M. CNS drug design based on principles of blood-brain barrier transport. J. Neurochem. 70:1998;1781-1792.
    • (1998) J. Neurochem. , vol.70 , pp. 1781-1792
    • Pardridge, W.M.1
  • 38
    • 0033526177 scopus 로고    scopus 로고
    • In vitro model for evaluating drug transport across the blood-brain barrier
    • Cecchelli R.et al. In vitro model for evaluating drug transport across the blood-brain barrier. Adv. Drug Deliv. Rev. 36:1999;165-178.
    • (1999) Adv. Drug Deliv. Rev. , vol.36 , pp. 165-178
    • Cecchelli, R.1
  • 39
    • 0033526157 scopus 로고    scopus 로고
    • Microdialysis for pharmacokinetic analysis of drug transport to the brain
    • de Lange E.C.M.et al. Microdialysis for pharmacokinetic analysis of drug transport to the brain. Adv. Drug Deliv. Rev. 36:1999;211-227.
    • (1999) Adv. Drug Deliv. Rev. , vol.36 , pp. 211-227
    • De Lange, E.C.M.1
  • 40
    • 0032804804 scopus 로고    scopus 로고
    • The design and molecular modeling of CNS drugs
    • George A. The design and molecular modeling of CNS drugs. Curr. Opin. Drug Discovery Dev. 2:1999;286-292.
    • (1999) Curr. Opin. Drug Discovery Dev. , vol.2 , pp. 286-292
    • George, A.1
  • 41
    • 0029938236 scopus 로고    scopus 로고
    • Predicting blood-brain transport of drugs: A computational approach
    • Basak S.C.et al. Predicting blood-brain transport of drugs: A computational approach. Pharm. Res. 13:1996;775-778.
    • (1996) Pharm. Res. , vol.13 , pp. 775-778
    • Basak, S.C.1
  • 42
    • 0031695039 scopus 로고    scopus 로고
    • Blood-brain barrier permeation: Molecular parameters governing passive diffusion
    • Fischer H.et al. Blood-brain barrier permeation: Molecular parameters governing passive diffusion. J. Membr. Biol. 165:1998;201-211.
    • (1998) J. Membr. Biol. , vol.165 , pp. 201-211
    • Fischer, H.1
  • 43
    • 0031048588 scopus 로고    scopus 로고
    • On the partition of ampholytes: Application to blood-brain distribution
    • Abraham M.H.et al. On the partition of ampholytes: Application to blood-brain distribution. J. Pharm. Sci. 86:1997;310-315.
    • (1997) J. Pharm. Sci. , vol.86 , pp. 310-315
    • Abraham, M.H.1
  • 44
    • 21144467893 scopus 로고
    • Hydrogen-bonding capacity and brain penetration
    • van de Waterbeemd H., Kansy M. Hydrogen-bonding capacity and brain penetration. Chimia. 46:1992;299-303.
    • (1992) Chimia , vol.46 , pp. 299-303
    • Van De Waterbeemd, H.1    Kansy, M.2
  • 45
    • 0028291586 scopus 로고
    • Predicting the brain-penetrating capability of histaminergic compounds
    • Calder J.A., Ganellin C.R. Predicting the brain-penetrating capability of histaminergic compounds. Drug Des. Discov. 11:1994;259-268.
    • (1994) Drug Des. Discov. , vol.11 , pp. 259-268
    • Calder, J.A.1    Ganellin, C.R.2
  • 46
    • 0028108085 scopus 로고
    • Hydrogen bonding. 33. Factors that influence the distribution of solutes between blood and brain
    • Abraham M.H.et al. Hydrogen bonding. 33. Factors that influence the distribution of solutes between blood and brain. J. Pharm. Sci. 83:1994;1257-1268.
    • (1994) J. Pharm. Sci. , vol.83 , pp. 1257-1268
    • Abraham, M.H.1
  • 47
    • 0040524262 scopus 로고    scopus 로고
    • Estimation of molecular free energy relation descriptors using a group contribution approach
    • Platts J.A.et al. Estimation of molecular free energy relation descriptors using a group contribution approach. J. Chem. Inf. Comput. Sci. 39:1999;835-845.
    • (1999) J. Chem. Inf. Comput. Sci. , vol.39 , pp. 835-845
    • Platts, J.A.1
  • 48
    • 0030462889 scopus 로고    scopus 로고
    • Computation of brain-blood partitioning of organic solutes via free energy calculations
    • Lombardo F.et al. Computation of brain-blood partitioning of organic solutes via free energy calculations. J. Med. Chem. 39:1996;4750-4755.
    • (1996) J. Med. Chem. , vol.39 , pp. 4750-4755
    • Lombardo, F.1
  • 49
    • 0031827249 scopus 로고    scopus 로고
    • Theoretical calculation and prediction of brain-blood partitioning of organic solutes using MolSurf parametrization and PLS statistics
    • Norinder U.et al. Theoretical calculation and prediction of brain-blood partitioning of organic solutes using MolSurf parametrization and PLS statistics. J. Pharm. Sci. 87:1998;952-959.
    • (1998) J. Pharm. Sci. , vol.87 , pp. 952-959
    • Norinder, U.1
  • 50
    • 0033088690 scopus 로고    scopus 로고
    • Prediction of the brain-blood distribution of a large set of drugs from structurally derived descriptors using partial least-squares (PLS) modeling
    • Luco J.M. 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. 39:1999;396-404.
    • (1999) J. Chem. Inf. Comput. Sci. , vol.39 , pp. 396-404
    • Luco, J.M.1
  • 51
    • 0032811868 scopus 로고    scopus 로고
    • Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 2. Prediction of blood-brain barrier penetration
    • Clark D.E. Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 2. Prediction of blood-brain barrier penetration. J. Pharm. Sci. 88:1999;815-821.
    • (1999) J. Pharm. Sci. , vol.88 , pp. 815-821
    • Clark, D.E.1
  • 52
    • 0343062334 scopus 로고    scopus 로고
    • Enhancing the hit-to-lead properties of lead optimization libraries
    • (in press)
    • Pickett, S.D. et al. Enhancing the hit-to-lead properties of lead optimization libraries. J. Chem. Inf. Comput. Sci. (in press).
    • J. Chem. Inf. Comput. Sci.
    • Pickett, S.D.1
  • 53
    • 0031464488 scopus 로고    scopus 로고
    • Molecular factors influencing drug transfer across the blood-brain barrier
    • Gratton J.A.et al. Molecular factors influencing drug transfer across the blood-brain barrier. J. Pharm. Pharmacol. 49:1997;1211-1216.
    • (1997) J. Pharm. Pharmacol. , vol.49 , pp. 1211-1216
    • Gratton, J.A.1
  • 54
    • 0033152287 scopus 로고    scopus 로고
    • Investigation into the correlation between the structure of hydroxypyridinones and blood-brain barrier permeability
    • Habgood M.D.et al. Investigation into the correlation between the structure of hydroxypyridinones and blood-brain barrier permeability. Biochem. Pharmacol. 57:1999;1305-1310.
    • (1999) Biochem. Pharmacol. , vol.57 , pp. 1305-1310
    • Habgood, M.D.1
  • 55
    • 0032008462 scopus 로고    scopus 로고
    • World Wide Web-based system for the calculation of substituent parameters and substituent similarity searches
    • Ertl P. World Wide Web-based system for the calculation of substituent parameters and substituent similarity searches. J. Mol. Graph. Model. 16:1998;11-13.
    • (1998) J. Mol. Graph. Model. , vol.16 , pp. 11-13
    • Ertl, P.1
  • 56
    • 0023965741 scopus 로고
    • SMILES, a chemical language and information system. 1. Introduction to methodology and encoding rules
    • Weininger D. SMILES, a chemical language and information system. 1. Introduction to methodology and encoding rules. J. Chem. Inf. Comput. Sci. 28:1988;31-36.
    • (1988) J. Chem. Inf. Comput. Sci. , vol.28 , pp. 31-36
    • Weininger, D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.