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Volumn 40, Issue 5, 2010, Pages 430-440

Estimation of drug solubility in water, PEG 400 and their binary mixtures using the molecular structures of solutes

Author keywords

ADME; Cosolvent; PEG; Polyethylene glycol; QSAR; QSPR; Solubility

Indexed keywords

ALLOPURINOL; AZATHIOPRINE; CAFFEINE; GUANINE; MACROGOL 400; SOLVENT; STRYCHNINE; URIC ACID; WATER; XANTHINE; DRUG; MACROGOL DERIVATIVE; SOLUTION AND SOLUBILITY;

EID: 77953911489     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2010.04.016     Document Type: Article
Times cited : (15)

References (50)
  • 1
    • 0032841864 scopus 로고    scopus 로고
    • The correlation and prediction of the solubility of compounds in water using an amended solvation energy relationship
    • Abraham M.H., Le J. The correlation and prediction of the solubility of compounds in water using an amended solvation energy relationship. J. Pharm. Sci. 1999, 88:868-880.
    • (1999) J. Pharm. Sci. , vol.88 , pp. 868-880
    • Abraham, M.H.1    Le, J.2
  • 2
    • 10844219583 scopus 로고    scopus 로고
    • Consensus kNN QSAR: a versatile method for predicting the estrogenic activity of organic compounds in silico. A comparative study with five estrogen receptors and a large, diverse set of ligands
    • Asikainen A.H., Ruuskanen J., Tuppurainen K.A. Consensus kNN QSAR: a versatile method for predicting the estrogenic activity of organic compounds in silico. A comparative study with five estrogen receptors and a large, diverse set of ligands. J. Environ. Sci. Tech. 2004, 38:6724-6729.
    • (2004) J. Environ. Sci. Tech. , vol.38 , pp. 6724-6729
    • Asikainen, A.H.1    Ruuskanen, J.2    Tuppurainen, K.A.3
  • 3
    • 0022046495 scopus 로고
    • Calculation of water solubility of organic compounds with UNIFAC-derived parameters
    • Banerjee S. Calculation of water solubility of organic compounds with UNIFAC-derived parameters. Environ. Sci. Technol. 1985, 19:369-370.
    • (1985) Environ. Sci. Technol. , vol.19 , pp. 369-370
    • Banerjee, S.1
  • 4
    • 15244339914 scopus 로고    scopus 로고
    • In silico predictions of drug solubility and permeability: two rate-limiting barriers to oral drug absorption
    • Bergström C.A.S. In silico predictions of drug solubility and permeability: two rate-limiting barriers to oral drug absorption. Basic Clin. Pharmacol. Toxicol. 2005, 96:156-161.
    • (2005) Basic Clin. Pharmacol. Toxicol. , vol.96 , pp. 156-161
    • Bergström, C.A.S.1
  • 5
    • 0036179239 scopus 로고    scopus 로고
    • Experimental and computational screening models for prediction of aqueous drug solubility
    • Bergström C.A.S., Norinder U., Luthman K., Artursson P. Experimental and computational screening models for prediction of aqueous drug solubility. Pharm. Res. 2002, 19:182-188.
    • (2002) Pharm. Res. , vol.19 , pp. 182-188
    • Bergström, C.A.S.1    Norinder, U.2    Luthman, K.3    Artursson, P.4
  • 6
    • 0041698448 scopus 로고    scopus 로고
    • Molecular Descriptors influencing melting point and their role in classification of solid drugs
    • Bergström C.A.S., Norinder U., Luthman K., Artursson P. Molecular Descriptors influencing melting point and their role in classification of solid drugs. J. Chem. Inf. Comput. Sci. 2003, 43:1177-1185.
    • (2003) J. Chem. Inf. Comput. Sci. , vol.43 , pp. 1177-1185
    • Bergström, C.A.S.1    Norinder, U.2    Luthman, K.3    Artursson, P.4
  • 7
    • 0036489458 scopus 로고    scopus 로고
    • On combining recursive partitioning and simulated annealing to detect groups of biologically active compounds
    • Blower P., Fligner M., Verducci J., Bjoraker J. On combining recursive partitioning and simulated annealing to detect groups of biologically active compounds. J. Chem. Inf. Comput. Sci. 2002, 42:393-404.
    • (2002) J. Chem. Inf. Comput. Sci. , vol.42 , pp. 393-404
    • Blower, P.1    Fligner, M.2    Verducci, J.3    Bjoraker, J.4
  • 9
    • 0345424863 scopus 로고    scopus 로고
    • Center for Drug Evaluation and Research, Rockville, MD, CDER/FDA
    • Center for Drug Evaluation and Research, 2000. Guidance for Industry. Rockville, MD, CDER/FDA.
    • (2000) Guidance for Industry
  • 10
    • 0041731599 scopus 로고    scopus 로고
    • Prediction of aqueous solubility of a diverse set of compounds using quantitative structure-property relationships
    • Cheng A., Merz K.M. Prediction of aqueous solubility of a diverse set of compounds using quantitative structure-property relationships. J. Med. Chem. 2003, 46:3572-3580.
    • (2003) J. Med. Chem. , vol.46 , pp. 3572-3580
    • Cheng, A.1    Merz, K.M.2
  • 12
    • 25844468887 scopus 로고    scopus 로고
    • EMEA, Concept Paper on BCS-Based Biowaiver. EMEA, London, EMEA/CHMP/EWP/213035/2007
    • EMEA, 2007. Committee for Medicinal Products for Human Use, Concept Paper on BCS-Based Biowaiver. EMEA, London, EMEA/CHMP/EWP/213035/2007.
    • (2007) Committee for Medicinal Products for Human Use
  • 13
    • 33750305816 scopus 로고    scopus 로고
    • The effect of variable selection on nonlinear modelling of oestrogen receptor binding
    • Ghafourian T., Cronin T.D.M. The effect of variable selection on nonlinear modelling of oestrogen receptor binding. QSAR Comb. Sci. 2006, 25:824-835.
    • (2006) QSAR Comb. Sci. , vol.25 , pp. 824-835
    • Ghafourian, T.1    Cronin, T.D.M.2
  • 14
    • 0037208311 scopus 로고    scopus 로고
    • Recursive median partitioning for virtual screening of large databases
    • Godden J.W., Furr J.R., Bajorath J. Recursive median partitioning for virtual screening of large databases. J. Chem. Inf. Comput. Sci. 2003, 43:182-188.
    • (2003) J. Chem. Inf. Comput. Sci. , vol.43 , pp. 182-188
    • Godden, J.W.1    Furr, J.R.2    Bajorath, J.3
  • 15
    • 0034778812 scopus 로고    scopus 로고
    • Issues in representation of molecular structure: the development of molecular connectivity
    • Hall L.H., Kier L.B. Issues in representation of molecular structure: the development of molecular connectivity. J. Mol. Graph. Model. 2001, 20:4-18.
    • (2001) J. Mol. Graph. Model. , vol.20 , pp. 4-18
    • Hall, L.H.1    Kier, L.B.2
  • 16
    • 0030769940 scopus 로고    scopus 로고
    • Analysis of a large structure-activity data set using recursive partitioning
    • Hawkins D.M., Young S.S., Rusinko A. Analysis of a large structure-activity data set using recursive partitioning. Quant. Struct. Act. Relat. 1997, 16:296-302.
    • (1997) Quant. Struct. Act. Relat. , vol.16 , pp. 296-302
    • Hawkins, D.M.1    Young, S.S.2    Rusinko, A.3
  • 17
    • 0017702985 scopus 로고
    • Use of solvent cavity area and number of packed solvent molecules around a solute in regard to hydrocarbon solubilities and hydrophobic interactions
    • Hermann R.B. Use of solvent cavity area and number of packed solvent molecules around a solute in regard to hydrocarbon solubilities and hydrophobic interactions. Proc. Natl. Acad. Sci. USA 1977, 74:4144-4145.
    • (1977) Proc. Natl. Acad. Sci. USA , vol.74 , pp. 4144-4145
    • Hermann, R.B.1
  • 18
  • 20
    • 1542741028 scopus 로고    scopus 로고
    • ADME evaluation in drug discovery. 4. Prediction of aqueous solubility based on atom contribution approach
    • Hou T.J., Xi K., Zhang W., Xu X.J. ADME evaluation in drug discovery. 4. Prediction of aqueous solubility based on atom contribution approach. J. Chem. Inf. Comput. Sci 2004, 44:266-275.
    • (2004) J. Chem. Inf. Comput. Sci , vol.44 , pp. 266-275
    • Hou, T.J.1    Xi, K.2    Zhang, W.3    Xu, X.J.4
  • 21
    • 4043112708 scopus 로고    scopus 로고
    • Structural interpretation of the topological index. 2. The molecular connectivity index, the kappa index, and the atom-type E-state index
    • Hu Q.N., Liang Y.-Z., Yin H., Peng X.-L., Fang K.-T. structural interpretation of the topological index. 2. The molecular connectivity index, the kappa index, and the atom-type E-state index. J. Chem. Inf. Comput. Sci. 2004, 44:1193-1201.
    • (2004) J. Chem. Inf. Comput. Sci. , vol.44 , pp. 1193-1201
    • Hu, Q.N.1    Liang, Y.-Z.2    Yin, H.3    Peng, X.-L.4    Fang, K.-T.5
  • 22
    • 47349119393 scopus 로고    scopus 로고
    • Prediction of drug solubility from molecular structure using a drug-like training set
    • Huuskonen J., Livingstone D.J., Manallack D.T. Prediction of drug solubility from molecular structure using a drug-like training set. SAR QSAR Environ. Res. 2008, 19:191-212.
    • (2008) SAR QSAR Environ. Res. , vol.19 , pp. 191-212
    • Huuskonen, J.1    Livingstone, D.J.2    Manallack, D.T.3
  • 23
    • 0032061266 scopus 로고    scopus 로고
    • Aqueous solubility prediction of drugs based on molecular topology and neural network modeling
    • Huuskonen J., Salo M., Taskinen J. Aqueous solubility prediction of drugs based on molecular topology and neural network modeling. J. Chem. Inf. Comput. Sci. 1998, 38:450-456.
    • (1998) J. Chem. Inf. Comput. Sci. , vol.38 , pp. 450-456
    • Huuskonen, J.1    Salo, M.2    Taskinen, J.3
  • 24
    • 33747183101 scopus 로고    scopus 로고
    • Recent progress in the computational prediction of aqueous solubility and absorption
    • Johnson S.R., Zheng W. Recent progress in the computational prediction of aqueous solubility and absorption. AAPS J. 2006, 8:4. (http://www.aapsj.org).
    • (2006) AAPS J. , vol.8 , pp. 4
    • Johnson, S.R.1    Zheng, W.2
  • 25
    • 0032904970 scopus 로고    scopus 로고
    • Comparison of various cosolvency models for calculating solute solubility in water-cosolvent mixtures
    • Jouyban-Gharamaleki A., Valaee L., Barzegar-Jalali M., Clark B.J., Acree W.E. Comparison of various cosolvency models for calculating solute solubility in water-cosolvent mixtures. Int. J. Pharm. 1999, 177:93-101.
    • (1999) Int. J. Pharm. , vol.177 , pp. 93-101
    • Jouyban-Gharamaleki, A.1    Valaee, L.2    Barzegar-Jalali, M.3    Clark, B.J.4    Acree, W.E.5
  • 26
    • 0035273557 scopus 로고    scopus 로고
    • Estimation of the aqueous solubility of organic molecules by the group contribution approach
    • Klopman G., Zhu H. Estimation of the aqueous solubility of organic molecules by the group contribution approach. J. Chem. Inf. Comput. Sci. 2001, 41:439-445.
    • (2001) J. Chem. Inf. Comput. Sci. , vol.41 , pp. 439-445
    • Klopman, G.1    Zhu, H.2
  • 27
    • 0030759733 scopus 로고    scopus 로고
    • A comparison of AQUAFAC group q-values to their corresponding CLOGP f-values
    • Lee Y.C., Pinsuwan S., Yalkowsky S.H. A comparison of AQUAFAC group q-values to their corresponding CLOGP f-values. Chemosphere 1997, 35:775-782.
    • (1997) Chemosphere , vol.35 , pp. 775-782
    • Lee, Y.C.1    Pinsuwan, S.2    Yalkowsky, S.H.3
  • 28
    • 0034461768 scopus 로고    scopus 로고
    • Drug-like properties and the causes of poor solubility and poor permeability
    • Lipinski C.A. Drug-like properties and the causes of poor solubility and poor permeability. J. Pharmacol. Toxicol. Methods 2000, 44:235-249.
    • (2000) J. Pharmacol. Toxicol. Methods , vol.44 , pp. 235-249
    • Lipinski, C.A.1
  • 29
    • 0036742053 scopus 로고    scopus 로고
    • Poor aqueous solubility - an industry wide problem in drug delivery
    • Lipinski C.A. Poor aqueous solubility - an industry wide problem in drug delivery. Am. Pharm. Rev. 2002, 5:82-85.
    • (2002) Am. Pharm. Rev. , vol.5 , pp. 82-85
    • Lipinski, C.A.1
  • 30
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Del. Rev. 1997, 23:3-25.
    • (1997) Adv. Drug Del. Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 31
    • 0030056288 scopus 로고    scopus 로고
    • Improved method for estimating water solubility from octanol water partition coefficient
    • Meylan W.M., Howard P.H., Boethling R.S. Improved method for estimating water solubility from octanol water partition coefficient. Environ. Toxicol. Chem. 1996, 15:100-106.
    • (1996) Environ. Toxicol. Chem. , vol.15 , pp. 100-106
    • Meylan, W.M.1    Howard, P.H.2    Boethling, R.S.3
  • 32
    • 57649213892 scopus 로고    scopus 로고
    • Simultaneous feature selection and parameter optimisation using an artificial ant colony: case study of melting point prediction
    • O'Boyle N.M., Palmer D.S., Nigsch F., Mitchell J.B.O. Simultaneous feature selection and parameter optimisation using an artificial ant colony: case study of melting point prediction. Chem. Centr. J. 2008, 2:21.
    • (2008) Chem. Centr. J. , vol.2 , pp. 21
    • O'Boyle, N.M.1    Palmer, D.S.2    Nigsch, F.3    Mitchell, J.B.O.4
  • 34
    • 0010253751 scopus 로고
    • Solubility of salicylic acid as a function of dielectric constant
    • Paruta A.N., Sciarrone B.J., Lordi N.G. Solubility of salicylic acid as a function of dielectric constant. J. Pharm. Sci. 1964, 53:1349-1353.
    • (1964) J. Pharm. Sci. , vol.53 , pp. 1349-1353
    • Paruta, A.N.1    Sciarrone, B.J.2    Lordi, N.G.3
  • 35
    • 1242314687 scopus 로고    scopus 로고
    • A quantitative structure-property relationship for predicting drug solubility in PEG 400/water cosolvent systems
    • Rytting E., Lentz K.A., Chen X.Q., Qian F., Venkatesh S. A quantitative structure-property relationship for predicting drug solubility in PEG 400/water cosolvent systems. Pharm. Res. 2004, 21:237-244.
    • (2004) Pharm. Res. , vol.21 , pp. 237-244
    • Rytting, E.1    Lentz, K.A.2    Chen, X.Q.3    Qian, F.4    Venkatesh, S.5
  • 36
    • 27644595841 scopus 로고    scopus 로고
    • Aqueous and co-solvent solubility data for drug-like organic compounds
    • Article 10
    • Rytting, E., Lentz, K.A., Chen, X.Q., Qian, F., Venkatesh, S., 2005. Aqueous and co-solvent solubility data for drug-like organic compounds. AAPS J. 7, Article 10 (). http://www.aapsj.org/.
    • (2005) AAPS J. , vol.7
    • Rytting, E.1    Lentz, K.A.2    Chen, X.Q.3    Qian, F.4    Venkatesh, S.5
  • 37
    • 38349173396 scopus 로고    scopus 로고
    • Combined 4D-fingerprint and clustering based membrane-interaction QSAR analyses for constructing consensus Caco-2 cell permeation virtual screens
    • Santos O.A., Hopfinger A.J. Combined 4D-fingerprint and clustering based membrane-interaction QSAR analyses for constructing consensus Caco-2 cell permeation virtual screens. J. Pharm. Sci. 2008, 97:566-583.
    • (2008) J. Pharm. Sci. , vol.97 , pp. 566-583
    • Santos, O.A.1    Hopfinger, A.J.2
  • 39
    • 33845447457 scopus 로고    scopus 로고
    • Characterization of heterogeneous interaction in binary mixtures of ethylene glycol oligomer with water, ethyl alcohol and dioxane by dielectric analysis
    • Sengwa R.J., Sankhla S. Characterization of heterogeneous interaction in binary mixtures of ethylene glycol oligomer with water, ethyl alcohol and dioxane by dielectric analysis. J. Mol. Liq. 2007, 130:119-131.
    • (2007) J. Mol. Liq. , vol.130 , pp. 119-131
    • Sengwa, R.J.1    Sankhla, S.2
  • 40
    • 81855198419 scopus 로고    scopus 로고
    • Syracuse Research Corporation, Website: (accessed on March 2010)
    • Syracuse Research Corporation, 2010. Interactive PhysProp Database. Website: (accessed on March 2010). http://www.syrres.com/what-we-do/databaseforms.aspx%3Fid=386.
    • (2010) Interactive PhysProp Database
  • 41
    • 0035964449 scopus 로고    scopus 로고
    • A novel approach to the characterisation of polar liquids. Part 1: pure liquids
    • Stengele A., Stephanie R., Leuenberger H. A novel approach to the characterisation of polar liquids. Part 1: pure liquids. Int. J. Pharm. 2001, 225:123-134.
    • (2001) Int. J. Pharm. , vol.225 , pp. 123-134
    • Stengele, A.1    Stephanie, R.2    Leuenberger, H.3
  • 42
    • 0842348342 scopus 로고    scopus 로고
    • QSAR study on benzenesulphonamide carbonic anhydrase inhibitors: topological approach using Balaban index
    • Thakur A., Thakur M., Khadikar P.V., Supuran C.T., Sudele P. QSAR study on benzenesulphonamide carbonic anhydrase inhibitors: topological approach using Balaban index. Bioorg. Med. Chem. 2004, 12:789-793.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 789-793
    • Thakur, A.1    Thakur, M.2    Khadikar, P.V.3    Supuran, C.T.4    Sudele, P.5
  • 45
    • 38549151817 scopus 로고    scopus 로고
    • DrugBank: a knowledgebase for drugs, drug actions and drug targets
    • (Database issue), The DrugBank database website accessed on March 2010
    • Wishart D.S., Knox C., Guo A.C., Cheng D., Shrivastava S., Tzur D., Gautam B., Hassanali M. DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008, 36(Database issue):D901-D906. The DrugBank database website accessed on March 2010.
    • (2008) Nucleic Acids Res. , vol.36
    • Wishart, D.S.1    Knox, C.2    Guo, A.C.3    Cheng, D.4    Shrivastava, S.5    Tzur, D.6    Gautam, B.7    Hassanali, M.8
  • 47
    • 0015359870 scopus 로고
    • Solubility of nonelectrolytes in polar solvents
    • Yalkowsky S.H., Flynn G.L., Amidon G.L. Solubility of nonelectrolytes in polar solvents. J. Pharm. Sci. 1972, 61:983-984.
    • (1972) J. Pharm. Sci. , vol.61 , pp. 983-984
    • Yalkowsky, S.H.1    Flynn, G.L.2    Amidon, G.L.3
  • 49
    • 33846367299 scopus 로고    scopus 로고
    • A. Physicochemical studies of acetaminophen in Water-PEG 400 systems
    • Yurquina A., Manzur M.E., Brito P., Manzo R., Molina M.A. A. Physicochemical studies of acetaminophen in Water-PEG 400 systems. J. Mol. Liq. 2007, 133:47-53.
    • (2007) J. Mol. Liq. , vol.133 , pp. 47-53
    • Yurquina, A.1    Manzur, M.E.2    Brito, P.3    Manzo, R.4    Molina, M.A.5
  • 50
    • 45749120473 scopus 로고    scopus 로고
    • Scores of extended connectivity fingerprint as descriptors in QSPR study of melting point and aqueous solubility
    • Zhou D.S., Alelyunas Y., Liu R.F. Scores of extended connectivity fingerprint as descriptors in QSPR study of melting point and aqueous solubility. J. Chem. Inf. Model. 2008, 48:981-987.
    • (2008) J. Chem. Inf. Model. , vol.48 , pp. 981-987
    • Zhou, D.S.1    Alelyunas, Y.2    Liu, R.F.3


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