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Volumn 13, Issue 4, 2013, Pages 1497-1509

Liquid-liquid phase separation in highly supersaturated aqueous solutions of poorly water-soluble drugs: Implications for solubility enhancing formulations

Author keywords

[No Author keywords available]

Indexed keywords

AMORPHOUS SOLID DISPERSIONS; COLLOID FORMATION; CRYSTALLINE SOLIDS; LIQUID-LIQUID PHASE SEPARATION; METASTABLE REGION; POLY(VINYL PYRROLIDONE); POORLY WATER-SOLUBLE DRUGS; SUPERSATURATED AQUEOUS SOLUTIONS;

EID: 84875776484     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg301679h     Document Type: Article
Times cited : (292)

References (49)
  • 1
    • 47749106894 scopus 로고    scopus 로고
    • Stoichiometry and physical chemistry of promiscuous aggregate-based inhibitors
    • Coan, K. E. D.; Shoichet, B. K. Stoichiometry and physical chemistry of promiscuous aggregate-based inhibitors J. Am. Chem. Soc. 2008, 130, 9606-9612
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 9606-9612
    • Coan, K.E.D.1    Shoichet, B.K.2
  • 2
    • 64549152003 scopus 로고    scopus 로고
    • Promiscuous aggregate-based inhibitors promote enzyme unfolding
    • Coan, K. E. D.; Maltby, D. A.; Burlingame, A. L.; Shoichet, B. K. Promiscuous aggregate-based inhibitors promote enzyme unfolding J. Med. Chem. 2009, 52, 2067-2075
    • (2009) J. Med. Chem. , vol.52 , pp. 2067-2075
    • Coan, K.E.D.1    Maltby, D.A.2    Burlingame, A.L.3    Shoichet, B.K.4
  • 4
    • 15444366107 scopus 로고    scopus 로고
    • Concentration and pH dependent aggregation of hydrophobic drug molecules and relevance to oral bioavailability
    • Frenkel, Y. V.; Clark, A. D.; Das, K.; Wang, Y.-H.; Lewi, P. J.; Janssen, P. A. J.; Arnold, E. Concentration and pH dependent aggregation of hydrophobic drug molecules and relevance to oral bioavailability J. Med. Chem. 2005, 48, 1974-1983
    • (2005) J. Med. Chem. , vol.48 , pp. 1974-1983
    • Frenkel, Y.V.1    Clark, A.D.2    Das, K.3    Wang, Y.-H.4    Lewi, P.J.5    Janssen, P.A.J.6    Arnold, E.7
  • 5
    • 0037326367 scopus 로고    scopus 로고
    • Effects of synthetic lipids on solubilization and colloid stability of hydrophobic drugs
    • Pacheco, L. F.; Carmona-Ribeiro, A. M. Effects of synthetic lipids on solubilization and colloid stability of hydrophobic drugs J. Colloid Interface Sci. 2003, 258, 146-154
    • (2003) J. Colloid Interface Sci. , vol.258 , pp. 146-154
    • Pacheco, L.F.1    Carmona-Ribeiro, A.M.2
  • 6
    • 0141923641 scopus 로고    scopus 로고
    • Identification and prediction of promiscuous aggregating inhibitors among known drugs
    • Seidler, J.; McGovern, S. L.; Doman, T. N.; Shoichet, B. K. Identification and prediction of promiscuous aggregating inhibitors among known drugs J. Med. Chem. 2003, 46, 4477-4486
    • (2003) J. Med. Chem. , vol.46 , pp. 4477-4486
    • Seidler, J.1    McGovern, S.L.2    Doman, T.N.3    Shoichet, B.K.4
  • 8
    • 0042071139 scopus 로고    scopus 로고
    • Formation of colloidal dispersions of organic materials in aqueous media by solvent shifting
    • Brick, M. C.; Palmer, H. J.; Whitesides, T. H. Formation of colloidal dispersions of organic materials in aqueous media by solvent shifting Langmuir 2003, 19, 6367-6380
    • (2003) Langmuir , vol.19 , pp. 6367-6380
    • Brick, M.C.1    Palmer, H.J.2    Whitesides, T.H.3
  • 9
    • 84875765122 scopus 로고    scopus 로고
    • Solid dispersions of α-Mangostin Improve its aqueous solubility through self-assembly of nanomicelles
    • Aisha, A. F. A.; Ismail, Z.; Abu-Salah, K. M.; Majid, A. M. S. A. Solid dispersions of α-Mangostin Improve its aqueous solubility through self-assembly of nanomicelles J. Pharm. Sci. 2011, 1-11
    • (2011) J. Pharm. Sci. , pp. 1-11
    • Aisha, A.F.A.1    Ismail, Z.2    Abu-Salah, K.M.3    Majid, A.M.S.A.4
  • 10
    • 0001732876 scopus 로고
    • A method for preparing an aqueous colloidal dispersions of organic materials by using water-soluble polymers: Dispersion of β-carotene by polyvinylprrolidone
    • Tachibana, T.; Nakamura, A. A method for preparing an aqueous colloidal dispersions of organic materials by using water-soluble polymers: Dispersion of β-carotene by polyvinylprrolidone Kolloid Z. Z. Polym. 1965, 203, 130-133
    • (1965) Kolloid Z. Z. Polym. , vol.203 , pp. 130-133
    • Tachibana, T.1    Nakamura, A.2
  • 12
    • 4344609538 scopus 로고    scopus 로고
    • Study of liquid-liquid demixing form drug solution
    • Lafferrère, L.; Hoff, C.; Veesler, S. Study of liquid-liquid demixing form drug solution J. Cryst. Growth 2004, 269, 550-557
    • (2004) J. Cryst. Growth , vol.269 , pp. 550-557
    • Lafferreìre, L.1    Hoff, C.2    Veesler, S.3
  • 14
    • 0035525921 scopus 로고    scopus 로고
    • Nucleation, growth and pseudo-polymorphic behavior of citric acid as monitored in situ by attenuated total reflection fourier transform infrared spectroscopy
    • Groen, H.; Roberts, K. J. Nucleation, growth and pseudo-polymorphic behavior of citric acid as monitored in situ by attenuated total reflection fourier transform infrared spectroscopy J. Phys. Chem. B 2001, 105, 10723-10730
    • (2001) J. Phys. Chem. B , vol.105 , pp. 10723-10730
    • Groen, H.1    Roberts, K.J.2
  • 15
    • 0035244965 scopus 로고    scopus 로고
    • Novel Phenomenon of crystallization an emulsification of hydrophobic solute in aqueous solution
    • Maeda, K.; Aoyama, Y.; Fukui, K.; Hirota, S. Novel Phenomenon of crystallization an emulsification of hydrophobic solute in aqueous solution J. Colloid Interface Sci. 2001, 234, 217-222
    • (2001) J. Colloid Interface Sci. , vol.234 , pp. 217-222
    • Maeda, K.1    Aoyama, Y.2    Fukui, K.3    Hirota, S.4
  • 16
    • 84866733801 scopus 로고    scopus 로고
    • PH-induced precipitation behavior of weakly basic compounds: Determination of extent and duration of supersaturation using potentiometric titration and correlation to solid state properties
    • Hsieh, Y.; Ilevbare, G. A.; Van Eerdenbrugh, B.; Box, K.; Sanchez-Felix, M.; Taylor, L. S. pH-induced precipitation behavior of weakly basic compounds: Determination of extent and duration of supersaturation using potentiometric titration and correlation to solid state properties Pharm. Res. 2012, 20, 2738-2753
    • (2012) Pharm. Res. , vol.20 , pp. 2738-2753
    • Hsieh, Y.1    Ilevbare, G.A.2    Van Eerdenbrugh, B.3    Box, K.4    Sanchez-Felix, M.5    Taylor, L.S.6
  • 17
    • 52949150391 scopus 로고    scopus 로고
    • Effect of polymer type on the dissolution profile of amorphous solid dispersions containing felodipine
    • Konno, H.; Handa, T.; Alonzo, D. E.; Taylor, L. S. Effect of polymer type on the dissolution profile of amorphous solid dispersions containing felodipine Eur. J. Pharm. Biopharm. 2008, 20, 493-499
    • (2008) Eur. J. Pharm. Biopharm. , vol.20 , pp. 493-499
    • Konno, H.1    Handa, T.2    Alonzo, D.E.3    Taylor, L.S.4
  • 18
    • 77953171784 scopus 로고    scopus 로고
    • Understanding the behavior of amorphous pharmaceutical systems during dissolution
    • Alonzo, D.; Zhang, G.; Zhou, D.; Gao, Y.; Taylor, L. S. Understanding the behavior of amorphous pharmaceutical systems during dissolution Pharm. Res. 2010, 27, 608-618
    • (2010) Pharm. Res. , vol.27 , pp. 608-618
    • Alonzo, D.1    Zhang, G.2    Zhou, D.3    Gao, Y.4    Taylor, L.S.5
  • 19
    • 76649105411 scopus 로고    scopus 로고
    • Solubility advantage of amorphous pharmaceuticals I. A thermordynamic analysis
    • Murdande, S. B.; Pikal, M. J.; Shanker, R. M.; Bogner, R. H. Solubility advantage of amorphous pharmaceuticals I. A thermordynamic analysis J. Pharm. Sci. 2009, 99, 1254-1264
    • (2009) J. Pharm. Sci. , vol.99 , pp. 1254-1264
    • Murdande, S.B.1    Pikal, M.J.2    Shanker, R.M.3    Bogner, R.H.4
  • 20
    • 78651288987 scopus 로고    scopus 로고
    • Solubility advantage of amorphous pharmaceuticals II. Application of quantitative thermodynamic relationships for prediction of solubility enhancement in structurally diverse insoluble pharmaceuticals
    • Murdande, S. B.; Pikal, M. J.; Shanker, R. M.; Bogner, R. H. Solubility advantage of amorphous pharmaceuticals II. Application of quantitative thermodynamic relationships for prediction of solubility enhancement in structurally diverse insoluble pharmaceuticals Pharm. Res. 2010, 27, 2704-2714
    • (2010) Pharm. Res. , vol.27 , pp. 2704-2714
    • Murdande, S.B.1    Pikal, M.J.2    Shanker, R.M.3    Bogner, R.H.4
  • 21
    • 36849125484 scopus 로고
    • Thermodynamic driving force in nucleation and growth processes
    • Hoffman, J. D. Thermodynamic driving force in nucleation and growth processes J. Chem. Phys. 1958, 29, 1192-1193
    • (1958) J. Chem. Phys. , vol.29 , pp. 1192-1193
    • Hoffman, J.D.1
  • 22
    • 33749447574 scopus 로고    scopus 로고
    • A comparison of the physical stability of amorphous felodipine and nifedipine systems
    • Marsac, P. J.; Konno, H.; Taylor, L. S. A comparison of the physical stability of amorphous felodipine and nifedipine systems Pharm. Res. 2006, 23, 2306-2316
    • (2006) Pharm. Res. , vol.23 , pp. 2306-2316
    • Marsac, P.J.1    Konno, H.2    Taylor, L.S.3
  • 23
    • 77955232982 scopus 로고    scopus 로고
    • A classification system to assess the crystallization tendency of organic molecules from undercooled melts
    • Baird, J. A.; Van Eerdenbrugh, B.; Taylor, L. S. A classification system to assess the crystallization tendency of organic molecules from undercooled melts J. Pharm. Sci. 2010, 99, 3787-3806
    • (2010) J. Pharm. Sci. , vol.99 , pp. 3787-3806
    • Baird, J.A.1    Van Eerdenbrugh, B.2    Taylor, L.S.3
  • 24
    • 77955234073 scopus 로고    scopus 로고
    • Crystallization tendency of active pharmaceutical ingredients following rapid solvent-evaporation - Classification and comparison with crystallization tendency from undercooled melts
    • Van Eerdenburgh, B.; Baird, J. A.; Taylor, L. S. Crystallization tendency of active pharmaceutical ingredients following rapid solvent-evaporation- classification and comparison with crystallization tendency from undercooled melts J. Pharm. Sci. 2010, 99, 3826-3838
    • (2010) J. Pharm. Sci. , vol.99 , pp. 3826-3838
    • Van Eerdenburgh, B.1    Baird, J.A.2    Taylor, L.S.3
  • 27
    • 0025384405 scopus 로고
    • Fluorescence probe techniques used to study micelle formation in water-soluble block copolymers
    • Zhao, C.-L.; Winnik, M. A. Fluorescence probe techniques used to study micelle formation in water-soluble block copolymers Langmuir 1990, 6, 514-516
    • (1990) Langmuir , vol.6 , pp. 514-516
    • Zhao, C.-L.1    Winnik, M.A.2
  • 28
    • 0001696223 scopus 로고
    • The spinodal approximation by the method of scattering in (n-hexane + n-tetradecafluorohexane)
    • Pozharskaya, G. I.; Kasapova, N. L.; Skripov, V. P.; Kolpakov, Y. D. The spinodal approximation by the method of scattering in (n-hexane + n-tetradecafluorohexane) J. Chem. Thermodyn. 1984, 16, 267-272
    • (1984) J. Chem. Thermodyn. , vol.16 , pp. 267-272
    • Pozharskaya, G.I.1    Kasapova, N.L.2    Skripov, V.P.3    Kolpakov, Y.D.4
  • 29
    • 33847285901 scopus 로고    scopus 로고
    • Determining the growth mechanism of tolazamide by induction time measurement
    • Kuldipkumar, A.; Kwon, G. S.; Zhang, G. G. Z. Determining the growth mechanism of tolazamide by induction time measurement Cryst. Growth Des. 2007, 7, 234-242
    • (2007) Cryst. Growth Des. , vol.7 , pp. 234-242
    • Kuldipkumar, A.1    Kwon, G.S.2    Zhang, G.G.Z.3
  • 30
    • 0037459494 scopus 로고    scopus 로고
    • Solution crystallization via a submerged liquid-liquid phase boundary: Oiling out
    • Bonnett, P. E.; Carpenter, K. J.; Dawson, S.; Davey, R. J. Solution crystallization via a submerged liquid-liquid phase boundary: oiling out Chem. Commun. 2003, 698-699
    • (2003) Chem. Commun. , pp. 698-699
    • Bonnett, P.E.1    Carpenter, K.J.2    Dawson, S.3    Davey, R.J.4
  • 32
    • 0034886795 scopus 로고    scopus 로고
    • Physicochemical considerations in the preparation of amorphous ritonavir-poly(ethylene glycol) 8000 solid dispersions
    • Law, D.; Krill, S. L.; Schmitt, E. A.; Fort, J. J.; Qiu, Y.; Wang, W.; Porter, W. R. Physicochemical considerations in the preparation of amorphous ritonavir-poly(ethylene glycol) 8000 solid dispersions J. Pharm. Sci. 2001, 90, 1015-1025
    • (2001) J. Pharm. Sci. , vol.90 , pp. 1015-1025
    • Law, D.1    Krill, S.L.2    Schmitt, E.A.3    Fort, J.J.4    Qiu, Y.5    Wang, W.6    Porter, W.R.7
  • 33
    • 84861891898 scopus 로고    scopus 로고
    • Understanding polymer properties important for crystal growth inhibition - Impact of chemically diverse polymers on solution crystal growth of ritonavir
    • Ilevbare, G. A.; Liu, H.; Edgar, K. J.; Taylor, L. S. Understanding polymer properties important for crystal growth inhibition-Impact of chemically diverse polymers on solution crystal growth of ritonavir Cryst. Growth Des. 2012, 12, 3133-3143
    • (2012) Cryst. Growth Des. , vol.12 , pp. 3133-3143
    • Ilevbare, G.A.1    Liu, H.2    Edgar, K.J.3    Taylor, L.S.4
  • 34
    • 0031056536 scopus 로고    scopus 로고
    • Effects of sorbed water on the crystallization of indomethacin from the amorphous state
    • Andronis, V.; Yoshioka, M.; Zografi, G. Effects of sorbed water on the crystallization of indomethacin from the amorphous state J. Pharm. Sci. 1997, 86, 346-351
    • (1997) J. Pharm. Sci. , vol.86 , pp. 346-351
    • Andronis, V.1    Yoshioka, M.2    Zografi, G.3
  • 35
    • 0030298896 scopus 로고    scopus 로고
    • a and pH-solubility behavior of an ionizable cycle carbamate, (S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4- (trifluoromethyl)-2H-3,1-benzoxain-2-one (DMP 266)
    • a and pH-solubility behavior of an ionizable cycle carbamate, (S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1- benzoxain-2-one (DMP 266) Pharm. Dev. Technol. 1996, 1, 91-95
    • (1996) Pharm. Dev. Technol. , vol.1 , pp. 91-95
    • Rabel, S.R.1    Maurin, M.B.2    Rowe, S.M.3    Hussain, M.4
  • 36
    • 79959316849 scopus 로고    scopus 로고
    • A new validated liquid chromatographic method for the determination of loratadine and its impurities
    • Ramulu, G.; Kumar, Y. R.; Vyas, K.; Suryanarayana, M. V.; Mukkanti, K. A new validated liquid chromatographic method for the determination of loratadine and its impurities Sci. Pharm. 2011, 79, 277-291
    • (2011) Sci. Pharm. , vol.79 , pp. 277-291
    • Ramulu, G.1    Kumar, Y.R.2    Vyas, K.3    Suryanarayana, M.V.4    Mukkanti, K.5
  • 37
    • 33845491449 scopus 로고    scopus 로고
    • Interpreting Steep Dose-Response Curves in Early Inhibitor Discovery
    • Shoichet, B. K. Interpreting Steep Dose-Response Curves in Early Inhibitor Discovery J. Med. Chem. 2006, 49, 7274-7277
    • (2006) J. Med. Chem. , vol.49 , pp. 7274-7277
    • Shoichet, B.K.1
  • 38
    • 0004260819 scopus 로고    scopus 로고
    • Hydrophilic polymers. Associating polymers containing fluorocarbon hydrophobic units
    • Amis, E. J.; Hu, N.; Seery, T. A. P.; Hogen-Esch, T. E.; Yassini, M.; Hwang, F.; Hydrophilic polymers. Associating polymers containing fluorocarbon hydrophobic units. Adv. Chem. 248, 1996, 279-302.
    • (1996) Adv. Chem. , vol.248 , pp. 279-302
    • Amis, E.J.1    Hu, N.2    Seery, T.A.P.3    Hogen-Esch, T.E.4    Yassini, M.5    Hwang, F.6
  • 40
    • 0032523141 scopus 로고    scopus 로고
    • Temperature dependence of critical micelle concentration of polyoxyethylenated non-ionic surfactants
    • Chen, L.-J.; Lin, S.-Y.; Huang, C.-C.; Chen, E.-M. Temperature dependence of critical micelle concentration of polyoxyethylenated non-ionic surfactants Colloid. Surface. A 1998, 135, 175-181
    • (1998) Colloid. Surface. A , vol.135 , pp. 175-181
    • Chen, L.-J.1    Lin, S.-Y.2    Huang, C.-C.3    Chen, E.-M.4
  • 41
    • 0001468891 scopus 로고
    • Effect of temperature on the critical micelle concentration of nonionic detergents. Thermodynamics of micelle formation
    • Schick, M. J. Effect of temperature on the critical micelle concentration of nonionic detergents. Thermodynamics of micelle formation J. Phys. Chem. 1963, 67, 1796-1799
    • (1963) J. Phys. Chem. , vol.67 , pp. 1796-1799
    • Schick, M.J.1
  • 42
    • 50549182056 scopus 로고
    • The effect of temperature on the critical micelle concentration of some paraffin-chain salts
    • Flockhart, B. D. The effect of temperature on the critical micelle concentration of some paraffin-chain salts J. Colloid Sci. 1961, 16, 484-492
    • (1961) J. Colloid Sci. , vol.16 , pp. 484-492
    • Flockhart, B.D.1
  • 43
    • 0014550327 scopus 로고
    • Some solution properties of certain surface active N-alkylpyridinium Halides I. Effect of temperature on the critical micelle concentrations
    • Stead, J. A.; Taylor, H. Some solution properties of certain surface active N-alkylpyridinium Halides I. Effect of temperature on the critical micelle concentrations J. Colloid Interface Sci. 1969, 30, 482-488
    • (1969) J. Colloid Interface Sci. , vol.30 , pp. 482-488
    • Stead, J.A.1    Taylor, H.2
  • 44
    • 0035885532 scopus 로고    scopus 로고
    • Effect of temperature on critical micelle concentration and thermodynamic potentials of micellization of anionic ammonium dodecyl sulfate and cationic octadecyl trimethyl ammonium chloride
    • Kang, K.-H.; Kim, H.-U.; Lim, K.-H. Effect of temperature on critical micelle concentration and thermodynamic potentials of micellization of anionic ammonium dodecyl sulfate and cationic octadecyl trimethyl ammonium chloride Colloid. Surface. A 2001, 189, 113-121
    • (2001) Colloid. Surface. A , vol.189 , pp. 113-121
    • Kang, K.-H.1    Kim, H.-U.2    Lim, K.-H.3
  • 46
    • 0003444425 scopus 로고    scopus 로고
    • Chemical and engineering thermodynamics
    • 3 rd ed. John Wiley and Sons
    • Sandler, S. I. Chemical and engineering thermodynamics, 3 rd ed.; John Wiley and Sons: New York, 1999.
    • (1999) New York
    • Sandler, S.I.1
  • 47
    • 0001522674 scopus 로고
    • Studies on glass II. The transition between the glassy and liquid states in the case of glucose
    • Parks, G. S.; Huffman, H. M.; Cattoir, F. R. Studies on glass II. The transition between the glassy and liquid states in the case of glucose J. Phys. Chem. 1928, 31, 1366-1379
    • (1928) J. Phys. Chem. , vol.31 , pp. 1366-1379
    • Parks, G.S.1    Huffman, H.M.2    Cattoir, F.R.3
  • 48
    • 0001539587 scopus 로고
    • Studies on glass. XI. Some thermodynamic relations of glassy and alpha-crystalline glucose
    • Parks, G. S.; Snyder, L. J.; Cattoir, F. R. Studies on glass. XI. Some thermodynamic relations of glassy and alpha-crystalline glucose J. Chem. Phys. 1934, 2, 595-598
    • (1934) J. Chem. Phys. , vol.2 , pp. 595-598
    • Parks, G.S.1    Snyder, L.J.2    Cattoir, F.R.3
  • 49
    • 1142303337 scopus 로고    scopus 로고
    • What is the true solubility advantage for amorphous pharmaceuticals?
    • Hancock, B. C.; Parks, M. What is the true solubility advantage for amorphous pharmaceuticals? Pharm. Res. 2000, 17, 397-404
    • (2000) Pharm. Res. , vol.17 , pp. 397-404
    • Hancock, B.C.1    Parks, M.2


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