Solid-state amorphization of rebamipide and investigation on solubility and stability of the amorphous form

References

• Maddileti D, Swapna B, Nangia A. Tetramorphs of the antibiotic drug trimethoprim: characterization and stability. Crystal Growth Des 2015;15:1745–56.
   Web of Science ®Google Scholar
• Łaszcz M, Trzcińska K, Witkowska A, et al. Phase transition studies of dutasteride crystalline forms. CrystEngComm 2015;17:2346–52.
   Web of Science ®Google Scholar
• Du Y, Zhang H, Xue J. Vibrational spectroscopic study of polymorphism and polymorphic transformation of the anti-viral drug lamivudine. Spectrochim Acta A 2015;137:1158–63.
   Web of Science ®Google Scholar
• Lim RTY, Ng WK, Tan RBH. Dissolution enhancement of indomethacin via amorphization using co-milling and supercritical co-precipitation processing. Powder Technol 2013;240:79–87.
   Web of Science ®Google Scholar
• Lim RTY, Ng WK, Widjaja E. Comparison of the physical stability and physicochemical properties of amorphous indomethacin prepared by co-milling and supercritical anti-solvent co-precipitation. J Supercriti Fluid 2013;79:186–201.
   Web of Science ®Google Scholar
• Kanaujia P, Poovizhi P, Ng WK, et al. Amorphous formulations for dissolution and bioavailability enhancement of poorly soluble APIs. Powder Technol 2015;285:2–15.
   Web of Science ®Google Scholar
• Surwase SA, Itkonen L, Aaltonen J, et al. Polymer incorporation method affects the physical stability of amorphous indomethacin in aqueous suspension. Eur J Pharm Biopharm 2015;96:32–43.
   PubMed Web of Science ®Google Scholar
• Xia D, Wu JX, Cui F, et al. Solvent-mediated amorphous-to-crystalline transformation of nitrendipine in amorphous particle suspensions containing polymers. Eur J Pharm Sci 2012;46:446–54.
   PubMed Web of Science ®Google Scholar
• Murdande SB, Pikal MJ, Shanker RM, et al. Solubility advantage of amorphous pharmaceuticals: II. Application of quantitative thermodynamic relationships for prediction of solubility enhancement in structurally diverse insoluble pharmaceuticals. Pharm Res 2010;27:2704–14.
   PubMed Web of Science ®Google Scholar
• Chawla G, Gupta P, Thilagavathi R, et al. Characterization of solid-state forms of celecoxib. Eur J Pharm Sci 2003;20:305–17.
   PubMed Web of Science ®Google Scholar
• Caron V, Willart JF, Lefort R, et al. Solid state amorphization kinetic of alpha lactose upon mechanical milling. Carbohydr Res 2011;346:2622–8.
   PubMed Web of Science ®Google Scholar
• Willart JF, Durand M, Briggner LE, et al. Solid-state amorphization of linaprazan by mechanical milling and evidence of polymorphism. J Pharm Sci 2013;102:2214–20.
   PubMed Web of Science ®Google Scholar
• Bahl D, Bogner RH. Amorphization of indomethacin by co-grinding with neusilin US2: amorphization kinetics, physical stability and mechanism. Pharm Res 2006;23:2317–25.
   PubMed Web of Science ®Google Scholar
• Bolla G, Mittapalli S, Nangia A. Pentamorphs of acedapsone. Crystal Growth Des 2014;14:5260–74.
   Web of Science ®Google Scholar
• Wlodarski K, Sawicki W, Paluch KJ, et al. The influence of amorphization methods on the apparent solubility and dissolution rate of tadalafil. Eur J Pharm Sci 2014;62:132–40.
   PubMed Web of Science ®Google Scholar
• Willart JF, Descamps M. Solid state amorphization of pharmaceuticals. Mol Pharm 2008;5:905–20.
   PubMed Web of Science ®Google Scholar
• Sussich F, Cesaro A. Trehalose amorphization and recrystallization. Carbohydr Res 2008;343:2667–74.
   PubMed Web of Science ®Google Scholar
• Macfhionnghaile P, Hu Y, Gniado K, et al. Effects of ball-milling and cryomilling on sulfamerazine polymorphs: a quantitative study. J Pharm Sci 2014;103:1766–78.
   PubMed Web of Science ®Google Scholar
• Hu Y, Macfhionnghaile P, Caron V, et al. Formation, physical stability, and quantification of process-induced disorder in cryomilled samples of a model polymorphic drug. J Pharm Sci 2013;102:93–103.
   PubMed Web of Science ®Google Scholar
• Xu K, Zheng S, Zhai Y, et al. Two solid forms of tauroursodeoxycholic acid and the effects of milling and storage temperature on solid-state transformations. Int J Pharm 2015;486:185–94.
   PubMed Web of Science ®Google Scholar
• Caron V, Tajber L, Corrigan OI, et al. A comparison of spray drying and milling in the production of amorphous dispersions of sulfathiazole/polyvinylpyrrolidone and sulfadimidine/polyvinylpyrrolidone. Mol Pharm 2011;8:532–42.
   PubMed Web of Science ®Google Scholar
• Caron V, Hu Y, Tajber L, et al. Amorphous solid dispersions of sulfonamide/Soluplus® and sulfonamide/PVP prepared by ball milling. AAPS PharmSciTech 2013;14:464–74.
   PubMed Web of Science ®Google Scholar
• Zidan AS, Rahman Z, Sayeed V, et al. Crystallinity evaluation of tacrolimus solid dispersions by chemometric analysis. Int J Pharm 2012;423:341–50.
   PubMed Web of Science ®Google Scholar
• Singh A, Van den Mooter G. Spray drying formulation of amorphous solid dispersions. Adv Drug Deliv Rev 2016; 100:27–50.
   PubMed Web of Science ®Google Scholar
• Yu L. Amorphous pharmaceutical solids: preparation, characterization and stabilization. Adv Drug Deliv Rev 2001;48:27–42.
   PubMed Web of Science ®Google Scholar
• Balani PN, Ng WK, Tan RBH. Influence of excipients in comilling on mitigating milling-induced amorphization or structural disorder of crystalline pharmaceutical actives. J Pharm Sci 2009;99:2462–74.
   Web of Science ®Google Scholar
• Bhugra C, Pikal MJ. Role of thermodynamic, molecular, and kinetic factors in crystallization from the amorphous state. J Pharm Sci 2008;97:1329–49.
   PubMed Web of Science ®Google Scholar
• Qi S, Avalle P, Saklatvala R, et al. An investigation into the effects of thermal history on the crystallisation behaviour of amorphous paracetamol. Eur J Pharm Biopharm 2008;69:364–71.
   PubMed Web of Science ®Google Scholar
• Li N, Taylor LS, Mauer LJ. The physical and chemical stability of amorphous (−)-epi-gallocatechin gallate: effects of water vapor sorption and storage temperature. Food Res Int 2014;58:112–23.
   Web of Science ®Google Scholar
• Lee SH, Bae JH, Park Y, et al. Sulfonic acid salts of donepezil and stabilization of amorphous donepezil via formation of amorphous salts. Crystal Growth Des 2015;15:3123–30.
   Web of Science ®Google Scholar
• Jondhale S, Bhise S, Pore Y. Physicochemical investigations and stability studies of amorphous gliclazide. AAPS PharmSciTech 2012;13:448–59.
   PubMed Web of Science ®Google Scholar
• Pradhan R, Tran TH, Choi JY, et al. Development of a rebamipide solid dispersion system with improved dissolution and oral bioavailability. Arch Pharm Res 2014;38:522–33.
   PubMed Web of Science ®Google Scholar
• Tung NT, Park CW, Oh TO, et al. Formulation of solid dispersion of rebamipide evaluated in a rat model for improved bioavailability and efficacy. J Pharm Pharmacol 2011;63:1539–47.
   PubMed Web of Science ®Google Scholar
• Cho HY, Yoon H, Park GK, et al. Pharmacokinetics and bioequivalence of two formulations of rebamipide 100-mg tablets: a randomized, single-dose, two-period, two-sequence crossover study in healthy Korean male volunteers. Clin Ther 2009;31:2712–21.
   PubMed Web of Science ®Google Scholar
• Park CW, Tung NT, Rhee YS, et al. Physicochemical, pharmacokinetic and pharmacodynamic evaluations of novel ternary solid dispersion of rebamipide with poloxamer 407. Drug Dev Ind Pharm 2013;39:836–44.
   PubMed Web of Science ®Google Scholar
• Dolomanov OV, Bourhis LJ, Gildea RJ, et al. OLEX2: a complete structure solution, refinement and analysis program. J Appl Crystallogr 2009;42:339–41.
   Web of Science ®Google Scholar
• Sheldrick GM. Crystal structure refinement with SHELXL. Acta Crystallogr C 2015;71:3–8.
   PubMed Web of Science ®Google Scholar
• Lu T, Chen C. Uncertainty evaluation of humidity sensors calibrated by saturated salt solutions. Measurement 2007;40:591–9.
   Web of Science ®Google Scholar
• Ondrušová D, Jona E, Šimon P. Thermal properties of N-ethyl-N-phenyl-dithiocarbamates and their influence on the kinetics of cure. J Therm Anal Calorim 2002;67:147–52.
   Web of Science ®Google Scholar
• Willart JF, De Gusseme A, Hemon S, et al. Direct crystal to glass transformation of trehalose induced by ball milling. Solid State Commun 2001;119:501–5.
   Web of Science ®Google Scholar
• Willart JF, Carpentier L, Danede F, et al. Solid-state vitrification of crystalline griseofulvin by mechanical milling. J Pharm Sci 2012;101:1570–7.
   PubMed Web of Science ®Google Scholar
• Shah B, Kakumanu VK, Bansal AK. Analytical techniques for quantification of amorphous/crystalline phases in pharmaceutical solids. J Pharm Sci 2006;95:1641–65.
   PubMed Web of Science ®Google Scholar
• Black D, Lovering EG. Estimation of the degree of crystallinity in digoxin by X-ray and infrared methods. J Pharm Pharmacol 1977;29:684–7.
   PubMed Web of Science ®Google Scholar
• Bandarkar FS, Vavia PR. An optimized commercially feasible milling technique for molecular encapsulation of meloxicam in β-cyclodextrin. Drug Dev Ind Pharm 2011;37:1318–28.
   PubMed Web of Science ®Google Scholar
• Zimeri JE, Kokini JL. The effect of moisture content on the crystallinity and glass transition temperature of inulin. Carbohyd Polym 2002;48:299–304.
   Web of Science ®Google Scholar
• Chattoraj S, Bhugra C, Telang C, et al. Origin of two modes of non-isothermal crystallization of glasses produced by milling. Pharm Res 2012;29:1020–32.
   PubMed Web of Science ®Google Scholar