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Volumn 87, Issue 12, 1998, Pages 1590-1596

Enthalpy-entropy compensation for the solubility of drugs in solvent mixtures: Paracetamol, acetanilide, and nalidixic acid in dioxane-water

Author keywords

[No Author keywords available]

Indexed keywords

ACETANILIDE; DIOXANE; NALIDIXIC ACID; PARACETAMOL; PHENACETIN; PHOSPHOLIPID; WATER;

EID: 0031774542     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js980149x     Document Type: Article
Times cited : (233)

References (26)
  • 1
    • 0020666212 scopus 로고    scopus 로고
    • Enthalpy-Entropy Compensation Analysis of Pharmaceutical, Biochemical and Biological Systems. 1983, 73, 115-144.
    • Tomlinson, E. Enthalpy-Entropy Compensation Analysis of Pharmaceutical, Biochemical and Biological Systems. Int. J. Pharm. 1983, 73, 115-144.
    • Int. J. Pharm.
    • Tomlinson, E.1
  • 2
    • 0025343507 scopus 로고    scopus 로고
    • B.; Diederich, F. Strenght of Molecular Complexation of Apolar Solutes in Water and in Organic Solvents Is Predictable by Linear Free Energy Relationships: A general Model for Solvation Effects on Apolar Binding. 1990, 112, 339-343.
    • Smithrud, D. B.; Diederich, F. Strenght of Molecular Complexation of Apolar Solutes in Water and in Organic Solvents Is Predictable by Linear Free Energy Relationships: A general Model for Solvation Effects on Apolar Binding. J. Am. Chem. Soc. 1990, 112, 339-343.
    • J. Am. Chem. Soc.
    • Smithrud, D.1
  • 3
    • 33847798413 scopus 로고    scopus 로고
    • R.; Hunter, W. G.; Grieger, R. A. Enthalpy-entropy compensation. 2. Separation of the chemical from the statistical effect. 1976, 80, 2341-2351.
    • Krug, R. R.; Hunter, W. G.; Grieger, R. A. Enthalpy-entropy compensation. 2. Separation of the chemical from the statistical effect. J. Phys. Chem. 1976, 80, 2341-2351.
    • J. Phys. Chem.
    • Krug, R.1
  • 4
    • 0011400993 scopus 로고    scopus 로고
    • Davis, S. S. Interactions between large organic ions of opposite and unequal charge. III. Enthalpy-entropy linear compensation and application of solvophobic theory. 1980, 76, 563-572.
    • Tomlinson, E.; Davis, S. S. Interactions between large organic ions of opposite and unequal charge. III. Enthalpy-entropy linear compensation and application of solvophobic theory. J. Colloid interface Sci. 1980, 76, 563-572.
    • J. Colloid Interface Sci.
    • Tomlinson, E.1
  • 5
    • 0028393186 scopus 로고    scopus 로고
    • L.; Pfeiffer, P. E.; Doner, L. W.; Sapers, G. M.; Brewster, G. N.; Hicks, K. B. Binding geometry, stoichiometry, and thermodynamics of cyclomalto-oligosaccharide (cyclodextrin) inclusion complex formation with chlorogenic acid, the major substrate of apple polyphenol oxidase. 1994, 256, 13-27.
    • Irwin, P. L.; Pfeiffer, P. E.; Doner, L. W.; Sapers, G. M.; Brewster, G. N.; Hicks, K. B. Binding geometry, stoichiometry, and thermodynamics of cyclomalto-oligosaccharide (cyclodextrin) inclusion complex formation with chlorogenic acid, the major substrate of apple polyphenol oxidase. Carbohydr. Res. 1994, 256, 13-27.
    • Carbohydr. Res.
    • Irwin, P.1
  • 6
    • 0028207026 scopus 로고    scopus 로고
    • H.; Clouser, D.; O'Neil, J. Thermodynamics of transfer of indocarbocyanides from gel to fluid phases of phospholipid bilayers. 1994, 1191, 164-172.
    • Spink, C. H.; Clouser, D.; O'Neil, J. Thermodynamics of transfer of indocarbocyanides from gel to fluid phases of phospholipid bilayers. Biochim. Biophys. Acta 1994, 1191, 164-172.
    • Biochim. Biophys. Acta
    • Spink, C.1
  • 7
    • 84901955233 scopus 로고    scopus 로고
    • K.; Conn, M. M.; Rebek Jr., J. Hydrogen bonding in water using synthetic receptors. 1995,52, 1208-1212.
    • Kato, Y. K.; Conn, M. M.; Rebek Jr., J. Hydrogen bonding in water using synthetic receptors. Proc. Natl. Acad. Sci. U.S.A. 1995,52, 1208-1212.
    • Proc. Natl. Acad. Sci. U.S.A.
    • Kato, Y.1
  • 8
    • 0029836768 scopus 로고    scopus 로고
    • Bustamante, P. Nonlinear enthalpyentropy compensation for the solubility of phenacetin in dioxane-water mixtures. 1996,85,1109-1111.
    • Bustamante, C.; Bustamante, P. Nonlinear enthalpyentropy compensation for the solubility of phenacetin in dioxane-water mixtures. J. Pharm. Sci. 1996,85,1109-1111.
    • J. Pharm. Sci.
    • Bustamante, C.1
  • 9
    • 0013801936 scopus 로고    scopus 로고
    • N.; Irani, S. A. Dielectric solubility profiles in dioxane-water mixtures for several antipyretic drugs. Effect of substituents. 1965, 54, 1334-1338.
    • Paruta, A. N.; Irani, S. A. Dielectric solubility profiles in dioxane-water mixtures for several antipyretic drugs. Effect of substituents. J. Pharm. Sci. 1965, 54, 1334-1338.
    • J. Pharm. Sci.
    • Paruta, A.1
  • 10
    • 0021364376 scopus 로고    scopus 로고
    • J. W.; Mehdizadeh, M.; Chow, A. H.-L.; Fairbrother, J. E. Nonlinear van't Hoff solubility-temperature plots and their pharmaceutical interpretation. 1984,18, 25-38.
    • Grant, D. J. W.; Mehdizadeh, M.; Chow, A. H.-L.; Fairbrother, J. E. Nonlinear van't Hoff solubility-temperature plots and their pharmaceutical interpretation. Int. J. Pharm. 1984,18, 25-38.
    • Int. J. Pharm.
    • Grant, D.1
  • 11
    • 0023233968 scopus 로고    scopus 로고
    • T.; Yalkowsky, S. H. Cosolvency and deviations from Log-linear solubilization. 1987, 4, 231236.
    • Rubino, J. T.; Yalkowsky, S. H. Cosolvency and deviations from Log-linear solubilization. Pharm. Res. 1987, 4, 231236.
    • Pharm. Res.
    • Rubino, J.1
  • 12
    • 0028849912 scopus 로고    scopus 로고
    • V.; Mulski, M.; Connors, K. A. Solvent effects on Chemical processes. 10. Solubility of a-cyclodextrin in binary aqueous-organic solvents: relationships to solidphase composition. 1995, 84, 1272-1275.
    • Leiterman, R. V.; Mulski, M.; Connors, K. A. Solvent effects on Chemical processes. 10. Solubility of a-cyclodextrin in binary aqueous-organic solvents: relationships to solidphase composition. J. Pharm. Sci. 1995, 84, 1272-1275.
    • J. Pharm. Sci.
    • Leiterman, R.1
  • 13
    • 85030348395 scopus 로고    scopus 로고
    • Kashino, S.; Maeda, H. The orthorhombic form of p-hydroxyacetanilide. 1974,530, 25102512.
    • Haïsa, M.; Kashino, S.; Maeda, H. The orthorhombic form of p-hydroxyacetanilide. Acta Crystallogr. 1974,530, 25102512.
    • Acta Crystallogr.
    • Haïsa, M.1
  • 14
    • 85030340742 scopus 로고    scopus 로고
    • Kashino, S.; Kawai, R.; Maeda, H. The monoclinic form of p-hydroxyacetanilide. 1976, B32, 1283-1285.
    • Haïsa, M.; Kashino, S.; Kawai, R.; Maeda, H. The monoclinic form of p-hydroxyacetanilide. Acta Crystallogr. 1976, B32, 1283-1285.
    • Acta Crystallogr.
    • Haïsa, M.1
  • 15
    • 0021821356 scopus 로고    scopus 로고
    • H.-L.; Chow, P. K. K; Zhongshan, W.; Grant, D. J. W. Modification of acetaminophen crystals: influence of growth in aqueous solutions containing p-acetoxyacetanilide on crystal properties. 1985, 24, 239-258.
    • Chow, A. H.-L.; Chow, P. K. K; Zhongshan, W.; Grant, D. J. W. Modification of acetaminophen crystals: influence of growth in aqueous solutions containing p-acetoxyacetanilide on crystal properties. Int. J. Pharm. 1985, 24, 239-258.
    • Int. J. Pharm.
    • Chow, A.1
  • 16
    • 0029008333 scopus 로고    scopus 로고
    • of cosolvents on water content and physical properties of acetaminophen crystallized from aqueous solutions. 1995, 5, 232-237.
    • El-Said. Effect of cosolvents on water content and physical properties of acetaminophen crystallized from aqueous solutions. S. T. P. Pharma Sci. 1995, 5, 232-237.
    • S. T. P. Pharma Sci.
    • Effect, E.-S.1
  • 17
    • 0029088849 scopus 로고    scopus 로고
    • Di Martino, P.; Guyot-Hermann, A.-M. Influence of drying conditions on residual solvent contents in crystals. Part 1: Study on monocrystalline particles. 1995, 50, 607-609.
    • Barthélémy, C.; Di Martino, P.; Guyot-Hermann, A.-M. Influence of drying conditions on residual solvent contents in crystals. Part 1: Study on monocrystalline particles. Pharmazie 1995, 50, 607-609.
    • Pharmazie
    • Barthélémy, C.1
  • 18
    • 0019068923 scopus 로고    scopus 로고
    • G. Determination of differential heat of solution in real solutions from variation in solubility with temperature. 1980, 69, 1241-1242.
    • Hollenbeck, R. G. Determination of differential heat of solution in real solutions from variation in solubility with temperature. J. Pharm. Sci. 1980, 69, 1241-1242.
    • J. Pharm. Sci.
    • Hollenbeck, R.1
  • 19
    • 0025205241 scopus 로고    scopus 로고
    • H.; Ahumada, A. A. Effects of solvent medium on solubility. V. Enthalpie and entropie contributions to the free energy changes of di-substituted benzene derivatives in ethanol: water and ethanol: cyclohexane mixtures. 1990, 79, 1109-1115.
    • Manzo, R. H.; Ahumada, A. A. Effects of solvent medium on solubility. V. Enthalpie and entropie contributions to the free energy changes of di-substituted benzene derivatives in ethanol: water and ethanol: cyclohexane mixtures. J. Pharm. Sci. 1990, 79, 1109-1115.
    • J. Pharm. Sci.
    • Manzo, R.1
  • 20
    • 0013801538 scopus 로고    scopus 로고
    • N.; Sciarrone, B. J.; Lordi, N. G. Dielectric solubility profiles of acetanilide and several derivatives in dioxane-water mixtures. 1965, 54, 13251333.
    • Paruta, A. N.; Sciarrone, B. J.; Lordi, N. G. Dielectric solubility profiles of acetanilide and several derivatives in dioxane-water mixtures. J, Pharm. Sci. 1965, 54, 13251333.
    • J, Pharm. Sci.
    • Paruta, A.1
  • 21
    • 0000304626 scopus 로고    scopus 로고
    • C.; Somsen, G. Solvation and hydrophobic hydration of different types of alkylamines in AT//-dimethylformamide and water mixtures. 1981, 10, 533-547.
    • Rouw, A. C.; Somsen, G. Solvation and hydrophobic hydration of different types of alkylamines in AT//-dimethylformamide and water mixtures. J. Solution Chem. 1981, 10, 533-547.
    • J. Solution Chem.
    • Rouw, A.1
  • 22
    • 0002816176 scopus 로고    scopus 로고
    • J. M.; de Visser, C.; Somsen, G. Hydrophobic hydration of tetraalkylammonium bromides in mixtures of water and some aprotic solvents. 1978, 82, 29-32.
    • Heuvelsland, W. J. M.; de Visser, C.; Somsen, G. Hydrophobic hydration of tetraalkylammonium bromides in mixtures of water and some aprotic solvents. J. Phys. Chem. 1978, 82, 29-32.
    • J. Phys. Chem.
    • Heuvelsland, W.1
  • 23
    • 0242561519 scopus 로고    scopus 로고
    • M.; Joris, L.; Mitchell, E.; Murty, T. S. S. R.; Gorrie, T. M. Studies of hydrogen-bonded complex formation. III. Thermodynamics of complexing by infrared spectroscopy and calorimetry. 1970, 92, 2365-2377.
    • Arnett, E. M.; Joris, L.; Mitchell, E.; Murty, T. S. S. R.; Gorrie, T. M. Studies of hydrogen-bonded complex formation. III. Thermodynamics of complexing by infrared spectroscopy and calorimetry. J. Am. Chem. Soc. 1970, 92, 2365-2377.
    • J. Am. Chem. Soc.
    • Arnett, E.1
  • 25
    • 0038518768 scopus 로고    scopus 로고
    • Drago, R. S. A new model for predicting solubilities and enthalpies of solution for a given solute in a series of solvents. 1997, 101, 5002-5009.
    • Bustamante, P.; Drago, R. S. A new model for predicting solubilities and enthalpies of solution for a given solute in a series of solvents. J. Phys. Chem. B 1997, 101, 5002-5009.
    • J. Phys. Chem. B
    • Bustamante, P.1
  • 26
    • 0015416726 scopus 로고    scopus 로고
    • C. Nature of acetaminophen-antipyrine complex. 1972, 61, 1661-1663.
    • Dearden, J. C. Nature of acetaminophen-antipyrine complex. J. Pharm. Sci. 1972, 61, 1661-1663.
    • J. Pharm. Sci.
    • Dearden, J.1


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