Physical chemistry of supersaturated solutions and implications for oral absorption

Advanced Drug Delivery Reviews

Volumn 101, Issue , 2016, Pages 122-142

  Taylor, Lynne S ^a   Zhang, Geoff G Z ^b  

^a PURDUE UNIVERSITY   (United States)

^b ABBVIE INC   (United States)

Author keywords

Absorption; Amorphous; Liquid liquid phase separation; Membrane transport rate; Solubility; Solubility enhancement

Indexed keywords

ABSORPTION; AMORPHOUS MATERIALS; BIOCHEMISTRY; CRYSTALLIZATION; DISSOLUTION; LIQUIDS; MICROCRYSTALS; PHYSICAL CHEMISTRY; SOLUBILITY; SUPERSATURATION;

ABSORPTION PROCESS; AMORPHOUS SOLID DISPERSIONS; FAST DISSOLUTIONS; LIQUID-LIQUID PHASE SEPARATION; MEMBRANE TRANSPORT; POORLY SOLUBLE DRUGS; SOLUBILITY ENHANCEMENT; SUPERSATURATED SOLUTIONS;

PHASE SEPARATION;

LOPINAVIR; RITONAVIR; DRUG;

AMORPHOUS SOLID DISPERSION; CRYSTALLIZATION; DISPERSION; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG FORMULATION; DRUG SOLUBILITY; FLUORESCENCE SPECTROSCOPY; HUMAN; IONIC STRENGTH; LIGHT SCATTERING; LIQUID LIQUID PHASE SEPARATION; MEMBRANE TRANSPORT; PH; PHASE SEPARATION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REVIEW; SOLUBILIZATION; THERMODYNAMICS; BIOAVAILABILITY; CHEMISTRY; INTESTINE ABSORPTION; LIQUID LIQUID EXTRACTION; METABOLISM; MICELLE; ORAL DRUG ADMINISTRATION; SOLUBILITY; SOLUTION AND SOLUBILITY;

ADMINISTRATION, ORAL; BIOLOGICAL AVAILABILITY; CRYSTALLIZATION; DRUG COMPOUNDING; HUMANS; INTESTINAL ABSORPTION; LIQUID-LIQUID EXTRACTION; MICELLES; PHARMACEUTICAL PREPARATIONS; SOLUBILITY; SOLUTIONS;

EID: 84963595085     PISSN: 0169409X     EISSN: 18728294     Source Type: Journal    
DOI: 10.1016/j.addr.2016.03.006     Document Type: Review

References (109)

1. [1] 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 Deliv. Rev. 23 (1997), 3–25.
2. [2] Loftsson, T., Brewster, M.E., Pharmaceutical applications of cyclodextrins: basic science and product development. J. Pharm. Pharmacol. 62 (2010), 1607–1621.
3. [3] Porter, C.J.H., Pouton, C.W., Cuine, J.F., Charman, W.N., Enhancing intestinal drug solubilisation using lipid-based delivery systems. Adv. Drug Deliv. Rev. 60 (2008), 673–691.
4. [4] Rabinow, B.E., Nanosuspensions in drug delivery. Nat. Rev. Drug Discov. 3 (2004), 785–796.
5. [5] Merisko-Liversidge, E., Liversidge, G.G., Nanosizing for oral and parenteral drug delivery: a perspective on formulating poorly-water soluble compounds using wet media milling technology. Adv. Drug Deliv. Rev. 63 (2011), 427–440.
6. [6] Andronis, V., Zografi, G., Crystal nucleation and growth of indomethacin polymorphs from the amorphous state. J. Non-Cryst. Solids 271 (2000), 236–248.
7. [7] Saleki-Gerhardt, A., Ahlneck, C., Zografi, G., Assessment of disorder in crystalline solids. Int. J. Pharm. 101 (1994), 237–247.
8. [8] Ahlneck, C., Zografi, G., The molecular basis of moisture effects on the physical and chemical stability of drugs in the solid state. Int. J. Pharm. 62 (1990), 87–95.
9. [9] Simonelli, A., Mehta, S., Higuchi, W., Dissolution rates of high energy polyvinylpyrrolidone (PVP)-sulfathiazole coprecipitates. J. Pharm. Sci. 58 (1969), 538–549.
10. [10] Simonelli, A.P., Mehta, S.C., Higuchi, W.I., Dissolution rates of high energy sulfathiazole-povidone coprecipitates II: characterization of form of drug controlling its dissolution rate via solubility studies. J. Pharm. Sci., 65(3), 1976, 355.
11. [11] 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. 99 (2010), 3787–3806.
12. [12] Murdande, S.B., Pikal, M.J., Shanker, R.M., Bogner, R.H., Solubility advantage of amorphous pharmaceuticals: I. A thermodynamic analysis. J. Pharm. Sci. 99 (2010), 1254–1264.
13. [13] Marsac, P.J., Shamblin, S.L., Taylor, L.S., Theoretical and practical approaches for prediction of drug-polymer miscibility and solubility. Pharm. Res. 23 (2006), 2417–2426.
14. [14] Sun, Y., Tao, J., Zhang, G.G.Z., Yu, L., Solubilities of crystalline drugs in polymers: an improved analytical method and comparison of solubilities of indomethacin and nifedipine in PVP, PVP/VA, and PVAc. J. Pharm. Sci. 99 (2010), 4023–4031.
15. [15] Cai, T., Zhu, L., Yu, L., Crystallization of organic glasses: effects of polymer additives on bulk and surface crystal growth in amorphous nifedipine. Pharm. Res. 28 (2011), 2458–2466.
16. [16] Kwong, A.D., Kauffman, R.S., Hurter, P., Mueller, P., Discovery and development of telaprevir: an NS3-4 A protease inhibitor for treating genotype 1 chronic hepatitis C virus. Nat. Biotechnol. 29 (2011), 993–1003.
17. [17] Shah, N., Iyer, R.M., Mair, H.-J., Choi, D.S., Tian, H., Diodone, R., Fähnrich, K., Pabst-Ravot, A., Tang, K., Scheubel, E., Grippo, J.F., Moreira, S.A., Go, Z., Mouskountakis, J., Louie, T., Ibrahim, P.N., Sandhu, H., Rubia, L., Chokshi, H., Singhal, D., Malick, W., Improved human bioavailability of vemurafenib, a practically insoluble drug, using an amorphous polymer-stabilized solid dispersion prepared by a solvent-controlled coprecipitation process. J. Pharm. Sci. 102 (2013), 967–981.
18. [18] Taylor, L.S., Zografi, G., Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions. Pharm. Res. 14 (1997), 1691–1698.
19. [19] Yalkowsky, S.H., Solubility and Solubilization in Aqueous Media. 1999, Oxford University Press, New York.
20. [20] Sandler, S.I., Chemical, Biochemical, and Engineering Thermodynamics. 2006, John Wiley, Hoboken, N.J.
21. [21] Mullin, J.W., Crystallization. fourth ed., 2001, Butterworths, London.
22. [22] Paus, R., Ji, Y., Vahle, L., Sadowski, G., Predicting the solubility advantage of amorphous pharmaceuticals: a novel thermodynamic approach. Mol. Pharm. 12 (2015), 2823–2833.
23. [23] Parks, G., Snyder, L., Cattoir, F., Studies on glass. XI. Some thermodynamic relations of glassy and alpha-crystalline glucose. J. Chem. Phys. 2 (1934), 595–598.
24. [24] Parks, G., Thomas, S., Light, D., Studies on glass XII. Some new heat capacity data for organic glasses. The entropy and free energy of dl-lactic acid. J. Chem. Phys. 4 (1936), 64–69.
25. [25] Brick, M.C., Palmer, H.J., Whitesides, T.H., Formation of colloidal dispersions of organic materials in aqueous media by solvent shifting. Langmuir 19 (2003), 6367–6380.
26. [26] 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. 27 (2010), 2704–2714.
27. [27] Hancock, B.C., Parks, M., What is the true solubility advantage for amorphous pharmaceuticals?. Pharm. Res. 17 (2000), 397–404.
28. [28] Sousa, L. Almeida e, Reutzel-Edens, S.M., Stephenson, G.A., Taylor, L.S., Assessment of the amorphous “solubility” of a group of diverse drugs using new experimental and theoretical approaches. Mol. Pharm. 12 (2014), 484–495.
29. [29] Mosquera-Giraldo, L.I., Taylor, L.S., Glass–liquid phase separation in highly supersaturated aqueous solutions of telaprevir. Mol. Pharm. 12 (2014), 496–503.
30. [30] Zografi, G., Hancock, B., Water–solid interactions in pharmaceutical systems. Crommelin, D.J.A., Midha, K.K., Nagai, T., (eds.) Topics in Pharmaceutical Sciences 1993, Proceedings of International Congress on Pharmaceutical Sciences F.I.P., 1994, Medpharm Scientific, Stuttgart, Germany, 405–419.
31. [31] Ceolin, R., Barrio, M., Tamarit, J.-L., Veglio, N., Perrin, M.-A., Espeau, P., Liquid–liquid miscibility gaps and hydrate formation in drug–water binary systems: pressure–temperature phase diagram of lidocaine and pressure–temperature–composition phase diagram of the lidocaine–water system. J. Pharm. Sci. 99 (2010), 2756–2765.
32. [32] Rietveld, I.B., Perrin, M.-A., Toscani, S., Barrio, M., Nicolai, B., Tamarit, J.-L., Ceolin, R., Liquid–liquid miscibility gaps in drug–water binary systems: crystal structure and thermodynamic properties of prilocaine and the temperature–composition phase diagram of the prilocaine–water system. Mol. Pharm. 10 (2013), 1332–1339.
33. [33] Campbell, A.N., Campbell, A.J.R., Concentrations, total and partial vapor pressures, surface tensions and viscosities, in the systems phenol–water and phenol–water–4% succinic acid. J. Am. Chem. Soc. 59 (1937), 2481–2488.
34. [34] Deneau, E., Steele, G., An in-line study of oiling out and crystallization. Org. Process. Res. Dev. 9 (2005), 943–950.
35. [35] Ilevbare, G.A., Taylor, L.S., Liquid–liquid phase separation in highly supersaturated aqueous solutions of poorly water-soluble drugs: implications for solubility enhancing formulations. Cryst. Growth Des. 13 (2013), 1497–1509.
36. [36] Bonnett, P.E., Carpenter, K.J., Dawson, S., Davey, R.J., Solution crystallisation via a submerged liquid–liquid phase boundary: oiling out. Chem. Commun., 2003, 698–699.
37. [37] Gower, L.B., Biomimetic model systems for investigating the amorphous precursor pathway and its role in biomineralization. Chem. Rev. 108 (2008), 4551–4627.
38. [38] Tung, H.-H., Paul, E.L., Midler, M., McCauley, J.A., Crystallization of Organic Compounds. 2008, John Wiley & Sons, Inc., 107.
39. [39] Jackson, M.J., Kestur, U.S., Hussain, M.A., Taylor, L.S., Dissolution of danazol amorphous solid dispersions: supersaturation and phase behavior as a function of drug loading and polymer type. Mol. Pharm. 13 (2016), 223–231.
40. [40] Ilevbare, G.A., Liu, H., Pereira, J., Edgar, K.J., Taylor, L.S., Influence of additives on the properties of nanodroplets formed in highly supersaturated aqueous solutions of ritonavir. Mol. Pharm. 10 (2013), 3392–3403.
41. [41] 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. 101 (2012), 815–825.
42. [42] Tachibana, T., Nakamura, A., A method for preparing an aqueous colloidal dispersion of organic materials by using water-soluble polymers: dispersion of Β-carotene by polyvinylpyrrolidone. Kolloid Z. Z. Polym. 203 (1965), 130–133.
43. [43] Indulkar, A.S., Box, K.J., Taylor, R., Ruiz, R., Taylor, L.S., pH-dependent liquid–liquid phase separation of highly supersaturated solutions of weakly basic drugs. Mol. Pharm., 2015.
44. [44] Alonzo, D.E., Gao, Y., Zhou, D.L., Mo, H.P., Zhang, G.G.Z., Taylor, L.S., Dissolution and precipitation behavior of amorphous solid dispersions. J. Pharm. Sci. 100 (2011), 3316–3331.
45. [45] Van Eerdenbrugh, B., Raina, S., Hsieh, Y.-L., Augustijns, P., Taylor, L., Classification of the crystallization behavior of amorphous active pharmaceutical ingredients in aqueous environments. Pharm. Res. 31 (2014), 969–982.
46. [46] Raghavan, S.L., Trividic, A., Davis, A.F., Hadgraft, J., Crystallization of hydrocortisone acetate: influence of polymers. Int. J. Pharm. 212 (2001), 213–221.
47. [47] Alonzo, D.E., Raina, S., Zhou, D., Gao, Y., Zhang, G.G.Z., Taylor, L.S., Characterizing the impact of hydroxypropylmethyl cellulose on the growth and nucleation kinetics of felodipine from supersaturated solutions. Cryst. Growth Des. 12 (2012), 1538–1547.
48. [48] Chen, J., Mosquera-Giraldo, L.I., Ormes, J.D., Higgins, J.D., Taylor, L.S., Bile salts as crystallization inhibitors of supersaturated solutions of poorly water-soluble compounds. Cryst. Growth Des. 15 (2015), 2593–2597.
49. [49] Raina, S.A., Eerdenbrugh, B.V., Alonzo, D.E., Mo, H., Zhang, G.G.Z., Gao, Y., Taylor, L.S., Trends in the precipitation and crystallization behavior of supersaturated aqueous solutions of poorly water-soluble drugs assessed using synchrotron radiation. J. Pharm. Sci. 104 (2015), 1981–1992.
50. [50] Murdande, S.B., Pikal, M.J., Shanker, R.M., Bogner, R.H., Aqueous solubility of crystalline and amorphous drugs: challenges in measurement. Pharm. Dev. Technol. 16 (2010), 187–200.
51. [51] Ozaki, S., Kushida, I., Yamashita, T., Hasebe, T., Shirai, O., Kano, K., Evaluation of drug supersaturation by thermodynamic and kinetic approaches for the prediction of oral absorbability in amorphous pharmaceuticals. J. Pharm. Sci. 101 (2012), 4220–4230.
52. [52] Lindfors, L., Forssén, S., Skantze, P., Skantze, U., Zackrisson, A., Olsson, U., Amorphous drug nanosuspensions. 2. Experimental determination of bulk monomer concentrations. Langmuir 22 (2006), 911–916.
53. [53] Raina, S., Alonzo, D., Zhang, G.Z., Gao, Y., Taylor, L., Using environment-sensitive fluorescent probes to characterize liquid–liquid phase separation in supersaturated solutions of poorly water soluble compounds. Pharm. Res. 32 (2015), 3660–3673.
54. [54] Thomson, J.A., Schurtenberger, P., Thurston, G.M., Benedek, G.B., Binary liquid phase separation and critical phenomena in a protein/water solution. Proc. Natl. Acad. Sci. 84 (1987), 7079–7083.
55. [55] Lafferrere, L., Hoff, C., Veesler, S., Study of liquid–liquid demixing from drug solution. J. Cryst. Growth 269 (2004), 550–557.
56. [56] Haiss, W., Thanh, N.T.K., Aveyard, J., Fernig, D.G., Determination of size and concentration of gold nanoparticles from UV–vis spectra. Anal. Chem. 79 (2007), 4215–4221.
57. [57] Mougan, M.A., Coello, A., Jover, A., Meijide, F., Vazquez Tato, J., Spectrofluorimeters as light-scattering apparatus: application to polymers molecular weight determination. J. Chem. Educ., 72, 1995, 284.
58. [58] Hsieh, Y.L., Ilevbare, G.A., Van Eerdenbrugh, B., Box, K.J., Sanchez-Felix, M.V., 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. 29 (2012), 2738–2753.
59. [59] Wang, J., Matayoshi, E., Solubility at the molecular level: development of a critical aggregation concentration (CAC) assay for estimating compound monomer solubility. Pharm. Res. 29 (2012), 1745–1754.
60. [60] Goddard, E.D., Turro, N.J., Kuo, P.L., Ananthapadmanabhan, K.P., Fluorescence probes for critical micelle concentration determination. Langmuir 1 (1985), 352–355.
61. [61] Kalyanasundaram, K., Thomas, J.K., Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems. J. Am. Chem. Soc. 99 (1977), 2039–2044.
62. [62] Kalyanasundaram, K., Thomas, J.K., Solvent-dependent fluorescence of pyrene-3-carboxaldehyde and its applications in the estimation of polarity at micelle-water interfaces. J. Phys. Chem. 81 (1977), 2176–2180.
63. [63] Chandar, P., Somasundaran, P., Turro, N.J., Fluorescence probe investigation of anionic polymer-cationic surfactant interactions. Macromolecules 21 (1988), 950–953.
64. [64] Zana, R., Yiv, S., Strazielle, C., Lianos, P., Effect of alcohol on the properties of micellar systems: I. Critical micellization concentration, micelle molecular weight and ionization degree, and solubility of alcohols in micellar solutions. J. Colloid Interface Sci. 80 (1981), 208–223.
65. [65] Demchenko, A.P., Mély, Y., Duportail, G., Klymchenko, A.S., Monitoring biophysical properties of lipid membranes by environment-sensitive fluorescent probes. Biophys. J. 96 (2009), 3461–3470.
66. [66] Sousa, L. Almeida e, Reutzel-Edens, S.M., Stephenson, G.A., Taylor, L.S., Supersaturation potential of salt, co-crystal, and amorphous forms of a model weak base. Cryst. Growth Des. 16 (2016), 737–748.
67. [67] LaPlante, S.R., Aubry, N., Bolger, G., Bonneau, P., Carson, R., Coulombe, R., Sturino, C., Beaulieu, P.L., Monitoring drug self-aggregation and potential for promiscuity in off-Target In Vitro pharmacology screens by a practical NMR Strategy. J. Med. Chem. 56 (2013), 7073–7083.
68. [68] Trasi, N.S., Taylor, L.S., Thermodynamics of highly supersaturated aqueous solutions of poorly water-soluble drugs—impact of a second drug on the solution phase behavior and implications for combination products. J. Pharm. Sci. 104 (2015), 2583–2593.
69. [69] Jackson, M.J., Dissolution Behavior of Amorphous Solid Dispersions. 2015, Purdue University.
70. [70] Twist, J., Zatz, J., Influence of solvents on paraben permeation through idealized skin model membranes. J. Soc. Cosmet. Chem. 37 (1986), 429–444.
71. [71] Yalkowsky, S.H., Flynn, G.L., Correlation and prediction of mass transport across membranes II: influence of vehicle polarity on flux from solutions and suspensions. J. Pharm. Sci. 63 (1974), 1276–1280.
72. [72] Megrab, N.A., Williams, A., Barry, B., Oestradiol permeation through human skin and silastic membrane: effects of propylene glycol and supersaturation. J. Control. Release 36 (1995), 277–294.
73. [73] Pellett, M., Castellano, S., Hadgraft, J., Davis, A., The penetration of supersaturated solutions of piroxicam across silicone membranes and human skin in vitro. J. Control. Release 46 (1997), 205–214.
74. [74] Moser, K., Kriwet, K., Froehlich, C., Naik, A., Kalia, Y.N., Guy, R.H., Permeation enhancement of a highly lipophilic drug using supersaturated systems. J. Pharm. Sci. 90 (2001), 607–616.
75. [75] Miller, J.M., Beig, A., Carr, R.A., Spence, J.K., Dahan, A., A win–win solution in oral delivery of lipophilic drugs: supersaturation via amorphous solid dispersions increases apparent solubility without sacrifice of intestinal membrane permeability. Mol. Pharm. 9 (2012), 2009–2016.
76. [76] Brouwers, J., Brewster, M.E., Augustijns, P., Supersaturating drug delivery systems: the answer to solubility-limited oral bioavailability?. J. Pharm. Sci. 98 (2009), 2549–2572.
77. [77] Yalkowsky, S.H., Perspective on improving passive human intestinal absorption. J. Pharm. Sci. 101 (2012), 3047–3050.
78. [78] Higuchi, T., Physical chemical analysis of percutaneous absorption process from creams and ointments. J. Soc. Cosmet. Chem., 11, 1960.
79. [79] Raina, S., Zhang, G.Z., Alonzo, D., Wu, J., Zhu, D., Catron, N., Gao, Y., Taylor, L., Impact of solubilizing additives on supersaturation and membrane transport of drugs. Pharm. Res., 2015, 1–15.
80. [80] Raina, S.A., Zhang, G.G.Z., Alonzo, D.E., Wu, J., Zhu, D., Catron, N.D., Gao, Y., Taylor, L.S., Enhancements and limits in drug membrane transport using supersaturated solutions of poorly Water soluble drugs. J. Pharm. Sci. 103 (2014), 2736–2748.
81. [81] Sassene, P.J., Knopp, M.M., Hesselkilde, J.Z., Koradia, V., Larsen, A., Rades, T., Müllertz, A., Precipitation of a poorly soluble model drug during in vitro lipolysis: characterization and dissolution of the precipitate. J. Pharm. Sci. 99 (2010), 4982–4991.
82. [82] Stappaerts, J., Geboers, S., Snoeys, J., Brouwers, J., Tack, J., Annaert, P., Augustijns, P., Rapid conversion of the ester prodrug abiraterone acetate results in intestinal supersaturation and enhanced absorption of abiraterone: in vitro, rat in situ and human in vivo studies. Eur. J. Pharm. Biopharm. 90 (2015), 1–7.
83. [83] Childs, S.L., Kandi, P., Lingireddy, S.R., Formulation of a danazol cocrystal with controlled supersaturation plays an essential role in improving bioavailability. Mol. Pharm. 10 (2013), 3112–3127.
84. [84] Poelma, F., Breäs, R., Tukker, J., Crommelin, D., Intestinal absorption of drugs. The influence of mixed micelles on the disappearance kinetics of drugs from the small intestine of the rat. J. Pharm. Pharmacol. 43 (1991), 317–324.
85. [85] Katneni, K., Charman, S.A., Porter, C.J.H., Permeability assessment of poorly water-soluble compounds under solubilizing conditions: the reciprocal permeability approach. J. Pharm. Sci. 95 (2006), 2170–2185.
86. [86] Lee, B.H., Christian, S.D., Tucker, E.E., Scamehorn, J.F., Solubilization of mono-and dichlorophenols by hexadecylpyridinium chloride micelles. Effects of substituent groups. Langmuir 6 (1990), 230–235.
87. [87] Goto, A., Endo, F., The distribution of alkyl paraben in aqueous sodium lauryl sulfate micellar solutions: III. The gel filtration of solubilized systems. J. Colloid Interface Sci. 66 (1978), 26–32.
88. [88] Croy, S.R., Kwon, G.S., Polysorbate 80 and Cremophor EL micelles deaggregate and solubilize nystatin at the core–corona interface. J. Pharm. Sci. 94 (2005), 2345–2354.
89. [89] Shore, P.A., Brodie, B.B., Hogben, C.A.M., The gastric secretion of drugs: a pH partition hypothesis. J. Pharmacol. Exp. Ther. 119 (1957), 361–369.
90. [90] Xie, T., Taylor, L.S., Dissolution performance of high drug loading celecoxib amorphous solid dispersions formulated with polymer combinations. Pharm. Res., 2015, 1–12.
91. [91] Luner, P.E., Babu, S.R., Mehta, S.C., Wettability of a hydrophobic drug by surfactant solutions. Int. J. Pharm. 128 (1996), 29–44.
92. [92] Morgen, M., Bloom, C., Beyerinck, R., Bello, A., Song, W., Wilkinson, K., Steenwyk, R., Shamblin, S., Polymeric nanoparticles for increased oral bioavailability and rapid absorption using celecoxib as a model of a low-solubility, high-permeability drug. Pharm. Res. 29 (2011), 427–440.
93. [93] Qian, F., Wang, J., Hartley, R., Tao, J., Haddadin, R., Mathias, N., Hussain, M., Solution behavior of PVP-VA and HPMC-AS-based amorphous solid dispersions and their bioavailability implications. Pharm. Res. 29 (2012), 2766–2776.
94. [94] Corrigan, O.I., Mechanisms of dissolution of fast release solid dispersions. Drug Dev. Ind. Pharm. 11 (1985), 697–724.
95. [95] Hancock, B.C., Zografi, G., The relationship between the glass transition temperature and the water content of amorphous pharmaceutical solids. Pharm. Res. 11 (1994), 471–477.
96. [96] Konno, H., Taylor, L.S., Ability of different polymers to inhibit the crystallization of amorphous felodipine in the presence of moisture. Pharm. Res. 25 (2008), 969–978.
97. [97] Rumondor, A.C.F., Jackson, M.J., Taylor, L.S., Effects of moisture on the growth rate of felodipine crystals in the presence and absence of polymers. Cryst. Growth Des. 10 (2010), 747–753.
98. [98] Raina, S.A., Alonzo, D.E., Zhang, G.G.Z., Gao, Y., Taylor, L.S., Impact of polymers on the crystallization and phase transition kinetics of amorphous nifedipine during dissolution in aqueous media. Mol. Pharm. 11 (2014), 3565–3576.
99. [99] Xie, T., Taylor, L.S., Improved release of celexocib from high drug loading amorphous solid dispersions formulated with polyacrylic acid and cellulose derivatives. Mol. Pharm. 13 (2016), 873–884.
100. [100] Purohit, H.S., Taylor, L.S., Phase separation kinetics in amorphous solid dispersions upon exposure to water. Mol. Pharm. 12 (2015), 1623–1635.
101. [101] Rumondor, A.C.F., Taylor, L.S., Effect of polymer hygroscopicity on the phase behavior of amorphous solid dispersions in the presence of moisture. Mol. Pharm. 7 (2010), 477–490.
102. [102] Rumondor, A.C.F., Stanford, L.A., Taylor, L.S., Effect of polymer type and storage relative humidity on the kinetics of felodipine crystallization from amorphous solid dispersions. Pharm. Res. 26 (2009), 2599–2606.
103. [103] Rumondor, A.C.F., Marsac, P.J., Stanford, L.A., Taylor, L.S., Phase behavior of poly(vinylpyrrolidone) containing amorphous solid dispersions in the presence of moisture. Mol. Pharm. 6 (2009), 1492–1505.
104. [104] Rumondor, A.C.F., Wikstrom, H., Van Eerdenbrugh, B., Taylor, L.S., Understanding the tendency of amorphous solid dispersions to undergo amorphous–amorphous phase separation in the presence of absorbed moisture. AAPS PharmSciTech 12 (2011), 1209–1219.
105. [105] Alonzo, D.E., Zhang, G.G.Z., Zhou, D.L., Gao, Y., Taylor, L.S., Understanding the behavior of amorphous pharmaceutical systems during dissolution. Pharm. Res. 27 (2010), 608–618.
106. [106] Chen, J., Ormes, J.D., Higgins, J.D., Taylor, L.S., Impact of surfactants on the crystallization of aqueous suspensions of celecoxib amorphous solid dispersion spray dried particles. Mol. Pharm. 12 (2015), 533–541.
107. [107] Indulkar, A.S., Gao, Y., Raina, S., Zhang, G.G.Z., Taylor, L.S., Exploiting the phenomenon of liquid–liquid phase separation to achieve enhanced and sustained membrane transport of a poorly water soluble drug. Mol. Pharm., 2016 (Submitted).
108. [108] Davis, A.F., Hadgraft, J., Effect of supersaturation on membrane transport: 1. Hydrocortisone acetate. Int. J. Pharm. 76 (1991), 1–8.
109. [109] Mudie, D.M., Murray, K., Hoad, C.L., Pritchard, S.E., Garnett, M.C., Amidon, G.L., Gowland, P.A., Spiller, R.C., Amidon, G.E., Marciani, L., Mol. Pharm., 11, 2014, 3039.