Using polymeric precipitation inhibitors to improve the absorption of poorly water-soluble drugs: A mechanistic basis for utility

Journal of Drug Targeting

Volumn 18, Issue 10, 2010, Pages 704-731

  Warren, Dallas B ^a   Benameur, Hassan ^b   Porter, Christopher J H ^a   Pouton, Colin W ^a  

^a MONASH UNIVERSITY   (Australia)

^b CAPSUGEL   (France)

Author keywords

Bioavailability; Crystallization; Danazol; Inhibition; Lipid formulation; Metastable; Polymer; Solid dispersion; Supersaturation

Indexed keywords

ACETAZOLAMIDE; BICALUTAMIDE; BICARBONATE; CAFFEINE; CARBAMAZEPINE; CELECOXIB; CELLULOSE DERIVATIVE; DANAZOL; ESTRADIOL; EUDRAGIT; FELODIPINE; HYDROCORTISONE; HYDROCORTISONE ACETATE; HYDROXYPROPYLCELLULOSE; HYDROXYPROPYLMETHYLCELLULOSE; HYDROXYPROPYLMETHYLCELLULOSE ACETATE SUCCINATE; ITRACONAZOLE; LIPID; MACROGOL 6000; PACLITAXEL; PARACETAMOL; POLOXAMER; POLYMER; POLYMERIC PRECIPITATION INHIBITOR; POVIDONE; SALICYLIC ACID; TACROLIMUS; UNCLASSIFIED DRUG; UNINDEXED DRUG; VALDECOXIB; WATER;

ANALYTIC METHOD; CHEMICAL REACTION; CRYSTALLIZATION; DIELECTRIC CONSTANT; DISPERSION; DRUG ABSORPTION; DRUG ADSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG FORMULATION; DRUG IMPURITY; DRUG SOLUBILITY; GASTROINTESTINAL TRACT; HYDROGEN BOND; INTESTINE FLUID; MAXIMUM PLASMA CONCENTRATION; MOLECULAR WEIGHT; PRECIPITATION; PREDICTION; PRIORITY JOURNAL; REVIEW; SOLVATION; SUPERSATURATION; TEMPERATURE; THERMODYNAMICS; TURBIDITY; VISCOSITY;

ANIMALS; BIOLOGICAL AVAILABILITY; CHEMICAL PRECIPITATION; DANAZOL; HUMANS; PHARMACEUTICAL PREPARATIONS; POLYMERS; SOLUTIONS; WATER;

EID: 78149438214     PISSN: 1061186X     EISSN: 10292330     Source Type: Journal    
DOI: 10.3109/1061186X.2010.525652     Document Type: Review

References (111)

1. Alonzo DE, Zhang GG, Zhou D, Gao Y, Taylor LS. (2010). Understanding the behavior of amorphous pharmaceutical systems during dissolution. Pharm Res, 27, 608-618.
2. Alsenz J, Meister E, Haenel E. (2007). Development of a partially automated solubility screening (PASS) assay for early drug development. J Pharm Sci, 96, 1748-1762.
3. Appel LE, Babcock WC, Friesen DT, Ray RJ, Shamblin SL, Shanker RM, Smithey DT. (2006). Pharmaceutical dosage forms comprising a low-solubility drug and a polymer. US Patent WO/2006/024944. March 9.
4. Bakatselou V, Oppenheim RC, Dressman JB. (1991). Solubilization and wetting effects of bile salts on the dissolution of steroids. Pharm Res, 8, 1461-1469.
5. Bansal SS, Kaushal AM, Bansal AK. (2007). Molecular and thermodynamic aspects of solubility advantage from solid dispersions. Mol Pharm, 4, 794-802.
6. Bodvik R, Dedinaite A, Karlson L, Bergstrom M, Baverback P, Pedersen JS, Edward K, Karlsson G, Varga I, Claesson PM. (2010). Aggregation and network formation of aqueous methylcellulose and hydroxypropylmethylcellulose solutions. Colloids Surf A-Physicochem Eng Asp, 354, 162-171.
7. Brewster ME, Neeskens P, Peeters J. (2007). Solubilization of itraconazole as a function of cyclodextrin structural space. J Inclusion Phenom Macrocycl Chem, 57, 561-566.
8. Brewster ME, Vandecruys R, Peeters J, Neeskens P, Verreck G, Loftsson T. (2008). Comparative interaction of 2-hydroxypropylbeta- cyclodextrin and sulfobutylether-beta-cyclodextrin with itraconazole: phase-solubility behavior and stabilization of supersaturated drug solutions. Eur J Pharm Sci, 34, 94-103.
9. Brouwers J, Brewster ME, Augustijns P. (2009). Supersaturating drug delivery systems: the answer to solubility-limited oral bioavailability? J Pharm Sci, 98, 2549-2572.
10. Chiou WL. (1977). Pharmaceutical applications of solid dispersion systems: X-ray diffraction and aqueous solubility studies on griseofulvin-polyethylene glycol 6000 systems. J Pharm Sci, 66, 989-991.
11. Chutimaworapan S, Ritthidej GC, Yonemochi E, Oguchi T, Yamamoto K. (2000). Effect of water-soluble carriers on dissolution characteristics of nifedipine solid dispersions. Drug Dev Ind Pharm, 26, 1141-1150.
12. Clarysse S, Psachoulias D, Brouwers J, Tack J, Annaert P, Duchateau G, Reppas C, Augustijns P. (2009). Postprandial changes in solubilizing capacity of human intestinal fluids for BCS class II drugs. Pharm Res, 26, 1456-1466.
13. Crowley KJ, Zografi G. (2003). The effect of low concentrations of molecularly dispersed poly(vinylpyrrolidone) on indomethacin crystallization from the amorphous state. Pharm Res, 20, 1417-1422.
14. Curatolo W, Nightingale JA, Herbig SM. (2009). Utility of hydroxypropylmethylcellulose acetate succinate (HPMCAS) for initiation and maintenance of drug supersaturation in the GI milieu. Pharm Res, 26, 1419-1431.
15. Dai WG, Dong LC, Shi X, Nguyen J, Evans J, Xu Y, Creasey AA. (2007). Evaluation of drug precipitation of solubility-enhancing liquid formulations using milligram quantities of a new molecular entity (NME). J Pharm Sci, 96, 2957-2969.
16. DiNunzio JC, Miller DA, Yang W, McGinity JW, Williams RO 3rd. (2008). Amorphous compositions using concentration enhancing polymers for improved bioavailability of itraconazole. Mol Pharm, 5, 968-980.
17. Doherty WOS, Fellows CM, Gorjian S, Senogles E, Cheung WH. (2004). Inhibition of calcium oxalate monohydrate by poly(acrylic acid)s with different end groups. J Appl Polym Sci, 91, 2035-2041.
18. Donnet M, Aimable A, Lematre J, Bowen P. (2010). Contribution of aggregation to the growth mechanism of seeded calcium carbonate precipitation in the presence of polyacrylic acid. J Phys Chem B, 114, 12058-12067.
19. Dunitz JD, Bernstein J. (1995). Disappearing polymorphs. Acc Chem Res, 28, 193-200.
20. Ebewele RO. (2000). Polymer Science and Technology, Boca Raton: CRC Press.
21. Erlich L, Yu D, Pallister DA, Levinson RS, Gole DG, Wilkinson PA, Erlich RE, Reeve LE, Viegas TX. (1999). Relative bioavailability of danazol in dogs from liquid-filled hard gelatin capsules. Int J Pharm, 179, 49-53.
22. Friesen DT, Shanker R, Crew M, Smithey DT, Curatolo WJ, Nightingale JA. (2008). Hydroxypropyl methylcellulose acetate succinate-based spray-dried dispersions: an overview. Mol Pharm, 5, 1003-1019.
23. Gao P, Akrami A, Alvarez F, Hu J, Li L, Ma C, Surapaneni S. (2009). Characterization and optimization of AMG 517 supersaturatable self-emulsifying drug delivery system (S-SEDDS) for improved oral absorption. J Pharm Sci, 98, 516-528.
24. Gao P, Guyton ME, Huang T, Bauer JM, Stefanski KJ, Lu Q. (2004). Enhanced oral bioavailability of a poorly water soluble drug PNU- 91325 by supersaturatable formulations. Drug Dev Ind Pharm, 30, 221-229.
25. Gao P, Morozowich W. (2006). Development of supersaturatable selfemulsifying drug delivery system formulations for improving the oral absorption of poorly soluble drugs. Expert Opin Drug Deliv, 3, 97-110.
26. Gao P, Rush BD, Pfund WP, Huang T, Bauer JM, Morozowich W, Kuo MS, Hageman MJ. (2003). Development of a supersaturable SEDDS (S-SEDDS) formulation of paclitaxel with improved oral bioavailability. J Pharm Sci, 92, 2386-2398.
27. Garekani HA, Ford JL, Rubinstein MH, Rajabi-Siahboomi AR. (2000). Highly compressible paracetamol: I: crystallization and characterization. Int J Pharm, 208, 87-99.
28. Gift AD, Luner PE, Luedeman L, Taylor LS. (2008). Influence of Polymeric Excipients on Crystal Hydrate Formation Kinetics in Aqueous Slurries. J Pharm Sci, 97, 5198-5211.
29. Guo S, Zhang L, Wang Z, Liu J. (2002). [Effects of conditioned medium derived from different keratinocytes on proliferation and collagen synthesis of hypertrophic scar fibroblasts]. Zhonghua Zheng Xing Wai Ke Za Zhi, 18, 83-85.
30. Gupta P, Thilagavathi R, Chakraborti AK, Bansal AK. (2005). Role of molecular interaction in stability of celecoxib-PVP amorphous systems. Mol Pharm, 2, 384-391.
31. Guzmán HR, Tawa M, Zhang Z, Ratanabanangkoon P, Shaw P, Gardner CR, Chen H, Moreau JP, Almarsson O, Remenar JF. (2007). Combined use of crystalline salt forms and precipitation inhibitors to improve oral absorption of celecoxib from solid oral formulations. J Pharm Sci, 96, 2686-2702.
32. Hilton JE, Summers MP. (1986). The effect of wetting agents on the dissolution of indomethacin solid dispersion systems. Int J Pharm, 31, 157-164.
33. Iervolino M, Cappello B, Raghavan SL, Hadgraft J. (2001). Penetration enhancement of ibuprofen from supersaturated solutions through human skin. Int J Pharm, 212, 131-141.
34. Jannink G, Cloizeaux JD. (1990). Polymers in solution. J Phys: Condensed Matter, 2, 1.
35. Janssens S, Nagels S, Armas HN, DAutry W, Van Schepdael A, Van den Mooter G. (2008). Formulation and characterization of ternary solid dispersions made up of itraconazole and two excipients, TPGS 1000 and PVPVA 64, that were selected based on a supersaturation screening study. Eur J Pharm Biopharm, 69, 158-166.
36. Kachrimanis K, Ktistis G, Malamataris S. (1998). Crystallisation conditions and physicomechanical properties of ibuprofen- Eudragit (R) S100 spherical crystal agglomerates prepared by the solvent-change technique. Int J Pharm, 173, 61-74.
37. Kachrimanis K, Malamataris S. (1999). Crystallization of paracetamol from ethanol-water solutions in the presence of polymers. J Pharm Pharmacol, 51, 1219-1227.
38. Kachrimanis K, Nikolakakis I, Malamataris S. (2000). Spherical crystal agglomeration of ibuprofen by the solvent-change technique in presence of methacrylic polymers. J Pharm Sci, 89, 250-259.
39. Karavas E, Georgarakis E, Sigalas MP, Avgoustakis K, Bikiaris D. (2007). Investigation of the release mechanism of a sparingly water-soluble drug from solid dispersions in hydrophilic carriers based on physical state of drug, particle size distribution and drug-polymer interactions. Eur J Pharm Biopharm, 66, 334-347.
40. Karavas E, Ktistis G, Xenakis A, Georgarakis E. (2006). Effect of hydrogen bonding interactions on the release mechanism of felodipine from nanodispersions with polyvinylpyrrolidone. Eur J Pharm Biopharm, 63, 103-114.
41. Kashchiev D, van Rosmalen GM. (2003). Review: nucleation in solutions revisited. Crystal Res Technol, 38, 555-574.
42. Katzhendler I, Azoury R, Friedman M. (1998). Crystalline properties of carbamazepine in sustained release hydrophilic matrix tablets based on hydroxypropyl methylcellulose. J Control Release, 54, 69-85.
43. Kawaguchi H, Hirai H, Sakai K, Sera S, Nakajima T, Ebisawa Y, Koyama K. (1992). Crystallization of inorganic-compounds in polymer-solutions. 1. Control of shape and form of calciumcarbonate. Colloid Polym Sci, 270, 1176-1181.
44. Kim IW, Robertson RE, Zand R. (2005). Effects of some nonionic polymeric additives on the crystallization of calcium carbonate. Crystal Growth Des, 5, 513-522.
45. Kohri N, Yamayoshi Y, Xin H, Iseki K, Sato N, Todo S, Miyazaki K. (1999). Improving the oral bioavailability of albendazole in rabbits by the solid dispersion technique. J Pharm Pharmacol, 51, 159-164.
46. Kondo S, Sugimoto I. (1987). Enhancement of transdermal delivery by superfluous thermodynamic potential. I. Thermodynamic analysis of nifedipine transport across the lipoidal barrier. J Pharmacobiodyn, 10, 587-594.
47. Konno H, Handa T, Alonzo DE, Taylor LS. (2008). Effect of polymer type on the dissolution profile of amorphous solid dispersions containing felodipine. Eur J Pharm Biopharm, 70, 493-499.
48. Konno H, Taylor LS. (2006). Influence of different polymers on the crystallization tendency of molecularly dispersed amorphous felodipine. J Pharm Sci, 95, 2692-2705.
49. Kossel W. (1934). The energetics of surface procedures. Annalen Der Physik, 413, 457-480.
50. Kossena GA, Charman WN, Boyd BJ, Dunstan DE, Porter CJ. (2004). Probing drug solubilization patterns in the gastrointestinal tract after administration of lipid-based delivery systems: a phase diagram approach. J Pharm Sci, 93, 332-348.
51. Kostewicz ES, Wunderlich M, Brauns U, Becker R, Bock T, Dressman JB. (2004). Predicting the precipitation of poorly soluble weak bases upon entry in the small intestine. J Pharm Pharmacol, 56, 43-51.
52. Kulak AN, Iddon P, Li Y, Armes SP, Cö;lfen H, Paris O, Wilson RM, Meldrum FC. (2007). Continuous structural evolution of calcium carbonate particles: a unifying model of copolymer-mediated crystallization. J Am Chem Soc, 129, 3729-3736.
53. Kumar S, Chawla G, Bansal AK. (2008a). Role of additives like polymers and surfactants in the crystallization of mebendazole. Yakugaku Zasshi, 128, 281-289.
54. Kumar S, Chawla G, Bansal AK. (2008b). Spherical crystallization of mebendazole to improve processability. Pharm Dev Technol, 13, 559-568.
55. Kushida I, Ichikawa M, Asakawa N. (2002). Improvement of dissolution and oral absorption of ER-34122, a poorly water-soluble dual 5-lipoxygenase/ cyclooxygenase inhibitor with anti-inflammatory activity by preparing solid dispersion. J Pharm Sci, 91, 258-266.
56. Lapasin R, Pricl S. (1995). Rheology of Industrial Polysaccharides: Theory and Applications. London: Blackie Academic and Profession.
57. Lin S-Y, Yang J-C. (1987). Drug interactions in pharmaceutical formulations. Part VII: Solubility and thermodynamic parameters of diazepam in pluronic surfactant solutions. Acta Pharm Technol, 33, 222-224.
58. Lindfors L, Forssén S, Westergren J, Olsson U. (2008). Nucleation and crystal growth in supersaturated solutions of a model drug. J Colloid Interface Sci, 325, 404-413.
59. Lioliou MG, Paraskeva CA, Koutsoukos PG, Payatakes AC. (2006). Calcium sulfate precipitation in the presence of water-soluble polymers. J Colloid Interface Sci, 303, 164-170.
60. Liu R. (ed. 2008) Water-Insoluble Drug Formulation Boca Raton: CRC Press
61. Liu YL, Liu YC, Zhang JY, Lu YM, Shen DZ, Fan XW. (2006). ZnO hexagonal prisms grown onto p-Si (111) substrate from poly (vinylpyrrolidone) assisted electrochemical assembly. J Crystal Growth, 290, 405-409.
62. Loftsson T, Fririksdóttir H, Gumundsdóttir TK. (1996). The effect of water-soluble polymers on aqueous solubility of drugs. Int J Pharm, 127, 293-296.
63. Machefer S, Huddar MM, Schnitzlein K. (2008). Effect of polymer admixtures on the growth habit of ionic crystals. Study on crystal growth kinetics of potassium dihydrogen phosphate in water/ polyol mixtures. J Crystal Growth, 310, 5347-5356.
64. Mallick S, Dey PK, Sannigrahi S, Mitra A. (2004). Crystallization of a non-steroidal anti-inflammatory drug from ethanol-water solution in presence of polymers: physicochemical characterization and release behaviour from suppositories. Acta Pol Pharm, 61, 447-453.
65. Martinez-Cruz N, Carrillo-Romo F, Jaramillo-Vigueras D. (2004). Effect of molecular weight of polystyrensulfonic acid sodium salt polymers on the precipitation kinetics of sodium bicarbonate. J Crystal Growth, 270, 573-581.
66. Matteucci ME, Brettmann BK, Rogers TL, Elder EJ, Williams RO 3rd, Johnston KP. (2007). Design of potent amorphous drug nanoparticles for rapid generation of highly supersaturated media. Mol Pharm, 4, 782-793.
67. Megrab NA, Williams AC, Barry BW. (1995). Estradiol permeation through human skin and silastic membrane-effects of propylene-glycol and supersaturation. J Control Release, 36, 277-294.
68. Miller DA, DiNunzio JC, Yang W, McGinity JW, Williams RO 3rd. (2008). Enhanced in vivo absorption of itraconazole via stabilization of supersaturation following acidic-to-neutral pH transition. Drug Dev Ind Pharm, 34, 890-902.
69. Mirza S, Miroshnyk I, Heinä;mä;ki J, Antikainen O, Rantanen J, Vuorela P, Vuorela H, Yliruusi J. (2009). Crystal morphology engineering of pharmaceutical solids: tabletting performance enhancement. AAPS PharmSciTech, 10, 113-119.
70. Mullin JW. (2001). Crystallization. Oxford: Butterworth-Heinemann.
71. Munoz-Espi R, Burger C, Krishnan CV, Chu B. (2008). Polymercontrolled crystallization of molybdenum oxides from peroxomolybdates: structural diversity and application to catalytic epoxidation. Chem Mater, 20, 7301-7311.
72. Newa M, Bhandari KH, Li DX, Kwon TH, Kim JA, Yoo BK, Woo JS, Lyoo WS, Yong CS, Choi HG. (2007). Preparation, characterization and in vivo evaluation of ibuprofen binary solid dispersions with poloxamer 188. Int J Pharm, 343, 228-237.
73. O'Driscoll KM, Corrigan OI. (1982). Chlorothiazide- polyvinylpyrrolidone (PVP) interactions: influence on membrane permeation (everted rat intestine) and dissolution. Drug Dev Ind Pharm, 8, 547-564.
74. Oaki Y, Imai H. (2005). Morphological evolution of inorganic crystal into zigzag and helical architectures with an exquisite association of polymer: a novel approach for morphological complexity. Langmuir, 21, 863-869.
75. Oner M, Dogan O, Oner G. (1998). The influence of polyelectrolytes architecture on calcium sulfate dihydrate growth retardation. J Crystal Growth, 186, 427-437.
76. Overhoff KA, McConville JT, Yang W, Johnston KP, Peters JI, Williams RO 3rd. (2008). Effect of stabilizer on the maximum degree and extent of supersaturation and oral absorption of tacrolimus made by ultra-rapid freezing. Pharm Res, 25, 167-175.
77. Overhoff KA, Moreno A, Miller DA, Johnston KP, Williams RO 3rd. (2007). Solid dispersions of itraconazole and enteric polymers made by ultra-rapid freezing. Int J Pharm, 336, 122-132.
78. Pellett MA, Castellano S, Hadgraft J, Davis AF. (1997a). The penetration of supersaturated solutions of piroxicam across silicone membranes and human skin in vitro. J Control Release, 46, 205-214.
79. Pellett MA, Roberts MS, Hadgraft J. (1997b). Supersaturated solutions evaluated with an in vitro stratum corneum tape stripping technique. Int J Pharm, 151, 91-98.
80. Perng C-Y, Kearney AS, Patel K, Palepu NR, Zuber G. (1998). Investigation of formulation approaches to improve the dissolution of SB-210661, a poorly water soluble 5-lipoxygenase inhibitor. Int J Pharm, 176, 31-38.
81. Plaizier-Vercammen JA. (1983). Interaction of povidone with aromatic compounds IV: effects of macromolecule molecular weight, solvent dielectric constant, and ligand solubility on complex formation. J Pharm Sci, 72, 1042-1044.
82. Plaizier-Vercammen JA, De Nève RE. (1982). Interaction of povidone with aromatic compounds III: thermodynamics of the binding equilibria and interaction forces in buffer solutions at varying pH values and varying dielectric constant. J Pharm Sci, 71, 552-556.
83. Plaizier-Vercammen JA, De Nève RE. (1981). Interaction of povidone with aromatic compounds II: evaluation of ionic strength, buffer concentration, temperature, and pH by factorial analysis. J Pharm Sci, 70, 1252-1256.
84. Raghavan SL, Kiepfer B, Davis AF, Kazarian SG, Hadgraft J. (2001a). Membrane transport of hydrocortisone acetate from supersaturated solutions; the role of polymers. Int J Pharm, 221, 95-105.
85. Raghavan SL, Schuessel K, Davis A, Hadgraft J. (2003). Formation and stabilisation of triclosan colloidal suspensions using supersaturated systems. Int J Pharm, 261, 153-158.
86. Raghavan SL, Trividic A, Davis AF, Hadgraft J. (2001b). Crystallization of hydrocortisone acetate: influence of polymers. Int J Pharm, 212, 213-221.
87. Raghavan SL, Trividic A, Davis AF, Hadgraft J. (2000). Effect of cellulose polymers on supersaturation and in vitro membrane transport of hydrocortisone acetate. Int J Pharm, 193, 231-237.
88. Rodríguez-Hornedo N, Murphy D. (1999). Significance of controlling crystallization mechanisms and kinetics in pharmaceutical systems. J Pharm Sci, 88, 651-660.
89. Sangwal K. (2007). Additives and Crystallization Processes: From Fundamentals to Applications. Chichester: John Wiley & Sons.
90. Sekikawa H, Nakano M, Arita T. (1978a). [Dissolution behaviors and gastrointestinal absorption of sulfisoxazole in sulfisoxazole- polyvinylpyrrolidone coprecipitate (authors transl)]. Yakugaku Zasshi, 98, 62-66.
91. Sekikawa H, Nakano M, Arita T. (1978b). Inhibitory effect of poly(vinylpyrrolidone) on the crystallization of drugs. Chem Pharm Bull, 26, 118-126.
92. Simonelli AP, Mehta SC, Higuchi WI. (1976). 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, 355-361.
93. Smith BR, Alexander AE. (1970). The effect of additives on the process of crystallization II. Further studies on calcium sulphate (1). J Colloid Interface Sci, 34, 81-90.
94. Suzuki H, Sunada H. (1998a). Influence of water-soluble polymers on the dissolution of nifedipine solid dispersions with combined carriers. Chem Pharm Bull, 46, 482-487.
95. Suzuki H, Sunada H. (1998b). Some factors influencing the dissolution of solid dispersions with nicotinamide and hydroxypropylmethylcellulose as combined carriers. Chem Pharm Bull, 46, 1015-1020.
96. Tanno F, Nishiyama Y, Kokubo H, Obara S. (2004). Evaluation of hypromellose acetate succinate (HPMCAS) as a carrier in solid dispersions. Drug Dev Ind Pharm, 30, 9-17.
97. Taylor LS, Zografi G. (1997). Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions. Pharm Res, 14, 1691-1698.
98. Teberekidis VI, Sigalas MP. (2007). Theoretical study of hydrogen bond interactions of felodipine with polyvinylpyrrolidone and polyethyleneglycol. J Mol Struct Theochem, 803, 29-38.
99. Tian F, Baldursdottir S, Rantanen J. (2009). Effects of polymer additives on the crystallization of hydrates: a molecular-level modulation. Mol Pharm, 6, 202-210.
100. Tonge SR, Tighe BJ. (2001). Responsive hydrophobically associating polymers: a review of structure and properties. Adv Drug Deliv Rev, 53, 109-122.
101. Usui F, Maeda K, Kusai A, Nishimura K, Keiji Y. (1997). Inhibitory effects of water-soluble polymers on precipitation of RS-8359. Int J Pharm, 154, 59-66.
102. Van Speybroeck M, Mols R, Mellaerts R, Thi TD, Martens JA, Van Humbeeck J, Annaert P, Van den Mooter G, Augustijns P. (2010). Combined use of ordered mesoporous silica and precipitation inhibitors for improved oral absorption of the poorly soluble weak base itraconazole. Eur J Pharm Biopharm, 75, 354-365.
103. Vandecruys R, Peeters J, Verreck G, Brewster ME. (2007). Use of a screening method to determine excipients which optimize the extent and stability of supersaturated drug solutions and application of this system to solid formulation design. Int J Pharm, 342, 168-175.
104. Vargeese AA, Joshi SS, Krishnamurthy VN. (2008). Role of poly(vinyl alcohol) in the crystal growth of ammonium perchlorate. Crystal Growth Des, 8, 1060-1066.
105. Vasconcelos T, Sarmento B, Costa P. (2007). Solid dispersions as strategy to improve oral bioavailability of poor water soluble drugs. Drug Discov Today, 12, 1068-1075.
106. Vogt M, Kunath K, Dressman JB. (2008a). Dissolution improvement of four poorly water soluble drugs by cogrinding with commonly used excipients. Eur J Pharm Biopharm, 68, 330-337.
107. Vogt M, Vertzoni M, Kunath K, Reppas C, Dressman JB. (2008b). Cogrinding enhances the oral bioavailability of EMD 57033, a poorly water soluble drug, in dogs. Eur J Pharm Biopharm, 68, 338-345.
108. Wen H, Morris KR, Park K. (2005). Hydrogen bonding interactions between adsorbed polymer molecules and crystal surface of acetaminophen. J Colloid Interface Sci, 290, 325-335.
109. Yamashita K, Nakate T, Okimoto K, Ohike A, Tokunaga Y, Ibuki R, Higaki K, Kimura T. (2003). Establishment of new preparation method for solid dispersion formulation of tacrolimus. Int J Pharm, 267, 79-91.
110. Yokoi Y, Yonemochi E, Terada K. (2005). Effects of sugar ester and hydroxypropyl methylcellulose on the physicochemical stability of amorphous cefditoren pivoxil in aqueous suspension. Int J Pharm, 290, 91-99.
111. Ziller KH, Rupprecht H. (1988). Control of crystal growth in drug suspensions: 1. Design of a control unit and application to acetaminophen suspensions. Drug Dev Ind Pharm, 14, 2341-2370.