Methods of amorphization and investigation of the amorphous state

Acta Pharmaceutica

Volumn 63, Issue 3, 2013, Pages 305-334

  Einfal, Tomaž ^a   Planinšek, Odon ^a   Hrovat, Klemen ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

amorphous solid preparation; calorimetry; crystallinity; spectroscopy

Indexed keywords

ACRIDINE; BUDESONIDE; CARBAMAZEPINE; EXCIPIENT; IBUPROFEN; INDOMETACIN; ITRACONAZOLE; PHENOTHIAZINE; PIROXICAM; SIMVASTATIN; SULFATHIAZOLE;

AMORPHIZATION; BIOAVAILABILITY; CHEMICAL REACTION; COOLING; CRYSTAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; DISSOLUTION; ENTHALPY; FREEZE DRYING; INFRARED SPECTROSCOPY; INVERSE GAS CHROMATOGRAPHY; LIQUID; MICROCALORIMETRY; NEAR INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE; RAMAN SPECTROMETRY; REVIEW; SCANNING ELECTRON MICROSCOPY; SOLID STATE; SPRAY DRYING; TERAHERTZ SPECTROSCOPY; THERMODYNAMICS; X RAY POWDER DIFFRACTION;

ANIMALS; BIOLOGICAL AVAILABILITY; CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; DESICCATION; FREEZE DRYING; HUMANS; POWDERS; X-RAY DIFFRACTION;

EID: 84887362639     PISSN: 13300075     EISSN: 18469558     Source Type: Journal    
DOI: 10.2478/acph-2013-0026     Document Type: Review

References (157)

1. B. C. Hancock and G. Zografi, Characteristics and significance of the amorphous state in pharmaceutical systems, J. Pharm. Sci. 86 (1997) 1-12; DOI: 10.1021/js9601896
2. L. Yu, Amorphous pharmaceutical solids: preparation, characterization and stabilization, Adv. Drug Delivery Rev. 48 (2001) 27-42; DOI: 10.1016/S0169-409X(01)00098-9
3. G. L. Amidon, H. Lennernäs, V. P. Shah and J. R. Crison, A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability, Pharm. Res. 12 (1995) 413-420; DOI: 10.1023/A:1016212804288
4. P. Poole, T. Grande, C. Angell and P. McMillan, Polymorphic phase transitions in liquids and glasses, Science 275 (1997) 322-323; DOI: 10.1126/science.275.5298.322
5. A. Saleki-Gerhardt, J. G. Stowell, S. R. Byrn and G. Zografi, Hydration and dehydration of crystalline and amorphous forms of raffinose, J. Pharm. 84 (1995) 318-323
6. L. R. L. Hilden and K. R. K. Morris, Physics of amorphous solids, J. Pharm. 93 (2003) 3-12; DOI: 10.1002/jps.10489
7. K. A. Graeser, C. J. Strachan, J. E. Patterson, K. C. Gordon and T. Rades, Physicochemical properties and stability of two differently prepared amorphous forms of simvastatin, Cryst. Growth Des. 8 (2008) 128-135; DOI: 10.1021/cg700913m
8. P. Karmwar, K. Graeser, K. C. Gordon, C. J. Strachan and T. Rades, Investigation of properties and recrystallisation behaviour of amorphous indomethacin samples prepared by different methods, Int. J. Pharm. 417 (2011) 94-100; DOI: 10.1016/j.ijpharm.2010.12.019
9. M. Otsuka, J-I. Nishizawa, N. Fukura and T. Sasaki, Characterization of poly-amorphous indomethacin by terahertz spectroscopy, J. Infrared Milli. Terahz. Waves 33 (2012) 953-962; DOI: 10. 1007/s10762-012-9910-1
10. R. Lefort, A. De Gusseme, J. F. Willart, F. Danède and M. Descamps, Solid state NMR and DSC methods for quantifying the amorphous content in solid dosage forms: an application to ball-milling of trehalose, Int. J. Pharm. 280 (2004) 209-219; DOI: 10.1016/j.ijpharm.2004.05.012
11. D. Kivelson, J. Pereda, K. Luu, M. Lee, H. Sakai, A. Ha, I. Cohen and G. Tarjus, Facts and speculation concerning low-temperature polymorphism in glass formers, Symp. Ser. 676 (1997), 224-232; DOI: 10.1021/bk-1997-0676.ch017
12. J. E. Patterson, M. B. James, A. H. Forster, R. W. Lancaster, J. M. Butler and T. Rades, The influence of thermal and mechanical preparative techniques on the amorphous state of four poorly soluble compounds, J. Pharm. Sci. 94 (2005) 1998-2012; DOI: 10.1002/jps.20424
13. D. Q. D. Craig, V. L. V. Kett, J. R. J. Murphy and D. M. D. Price, The measurement of small quantities of amorphous material-should we be considering the rigid amorphous fraction, Pharm. Res. 18 (2001) 1081-1082
14. D. Turnbull, Under what conditions can a glass be formed?, Contemp. Phys. 10 (1969) 473-488; DOI: 10.1080/00107516908204405
15. C. Angell, Structural instability and relaxation in liquid and glassy phases near the fragile liquid limit, J. Non-Cryst. Solids 102 (1988) 205-221; DOI: 10.1016/0022-3093(88)90133-0
16. J. Liu, D. Rigsbee, C. Stotz and M. Pikal, Dynamics of pharmaceutical amorphous solids: The study of enthalpy relaxation by isothermal microcalorimetry, J. Pharm. Sci. 91 (2002) 1853-1862; DOI:10.1002/jps.10181
17. D. Grant, Polymorphism in Pharmaceutical Solids, Marcel Dekker, Basel 1999, pp. 183-227
18. K. A. Graeser, J. E. Patterson, J. A. Zeitler, K. C. Gordon and T. Rades, Correlating thermodynamic and kinetic parameters with amorphous stability, Eur. J. Pharm. Sci. 37 (2009) 492-498; DOI: 10.1016/j.ejps.2009.04.005
19. J. W. Lee, L. C. Thomas and S. J. Schmidt, Effects of heating conditions on the glass transition parameters of amorphous sucrose produced by melt-quenching, J. Agric. Food Chem. 59 (2011) 3311-3319; DOI: 10.1021/jf104853s
20. H. Miyanishi, T. Nemoto, M. Mizuno, H. Mimura, S. Kitamura, Y. Iwao, S. Noguchi and S. Itai, Evaluation of crystallization behavior on the surface of nifedipine solid dispersion powder using inverse gas chromatography, Pharm. Res. 30 (2013) 502-511; DOI: 10.1007/s11095-012-0896-0
21. M. G. Abiad, D. C. Gonzalez, B. Mert, O. H. Campanella and M. T. Carvajal, A novel method to measure the glass and melting transitions of pharmaceutical powders, Int. J. Pharm. 396 (2010) 23-29; DOI: 10.1016/j.ijpharm.2010.06.001
22. H. Takeuchi, S. Nagira, H. Yamamoto and Y. Kawashima, Solid dispersion ppagess of tolbutamide prepared with fine silica ppagess by the spray-drying method, Powder Technol. 141 (2004) 187-195; DOI: 10.1016/j,powtec.2004.03.007
23. R. C. Rowe, P. J. Sheskey, W. G. Cook and M. F. Fenton, Colloidal Silicon Dioxide, in Handbook of Pharmaceutical Excipients, Pharmaceutical Press, London 2000, pp. 143-145
24. H. Takeuchi, T. Handa and Y. Kawashima, Spherical solid dispersion containing amorphous tolbutamide embedded in enteric coating polymers or colloidal silica prepared by spray-drying technique, Chem. Pharm. Bull. 35 (1987) 3800-3806
25. I. Chuang and G. Maciel, Probing hydrogen bonding and the local environment of silanols on silica surfaces via nuclear spin cross polarization dynamics, J. Am. Chem. Soc. 118 (1996) 401-406; DOI: 10.1021/ja951550d
26. J. Broadhead, S. K. E. Rouan and C. T. Rhodes, The spray drying of pharmaceuticals, Drug. Dev. Ind. Pharm. 18 (1992) 11-12; DOI: 10.3109/03639049209046327
27. R. Vehring, Pharmaceutical ppages engineering via spray drying, Pharm. Res. 25 (2008) 999-1022; DOI: 10.1007/s11095-007-9475-1
28. K. Haque and Y. H. Roos, Crystallization and X-ray diffraction of spray-dried and freeze-dried amorphous lactose, Carbohyd. Res. 340 (2005) 293-301; DOI: 10.1016/j.carres.2004.11.026
29. D. Chiou, T. A. G. Langrish and R. Braham, The effect of temperature on the crystallinity of lactose powders produced by spray drying, J. Food Eng. 86 288-293; DOI: 10.1016/j.jfoodeng.2007. 10.005
30. S. P. Bhardwaj, K. K. Arora, E. Kwong, A. Templeton, S. D. Clas and R. Suryanarayanan, Correlation between molecular mobility and physical stability of amorphous itraconazole, Mol. Pharm. 10 (2013) 694-700; DOI: 10.1021/mp300487u
31. M. Vogt, K. Kunath and J. B. Dressman, Dissolution enhancement of fenofibrate by micronization, cogrinding and spray-drying: comparison with commercial preparations, Eur. J. Pharm. Biopharm. 68 (2008) 283-288; DOI: 10.1016/j.ejpb.2007.05.010
32. D. Q. Craig, P. G. Royall, V. L. Kett and M. L. Hopton, The relevance of the amorphous state to pharmaceutical dosage forms: glassy drugs and freeze dried systems, Int. J. Pharm. 179 (1999) 179-207; DOI: 10.1016/S0378-5173(98) 00338-X
33. J. Liu, Physical characterization of pharmaceutical formulations in frozen and freeze-dried solid states: techniques and applications in freeze-drying development, Pharm. Dev. Technol. 11 (2006) 3-28; DOI: 10.1080/10837450500463729
34. S. P. Bhardwaj and R. Suryanarayanan, Molecular mobility as an effective predictor of the physical stability of amorphous trehalose, Mol. Pharm. 9 (2012) 3209-3217; DOI: 10.1021/mp300302g
35. K. P. O'Donnell, Z. Cai, P. Schmerler and R. O. I. Williams, Atmospheric freeze drying for the reduction of powder electrostatics of amorphous, low density, high surface area pharmaceutical powders, Drug Dev. Ind. Pharm. 39 (2013) 205-217; DOI: 10.3109/03639045.2012.669385
36. Y. Li, J. Han, G. G. Zhang, D. J. Grant and R. Suryanarayanan, In situ dehydration of carbamazepine dihydrate: Anovel technique to prepare amorphous anhydrous carbamazepine, Pharm. Dev. Technol. 5 (2000) 257-266; DOI: 10.1081/PDT-100100540
37. F. Sussich and A. Cesaro, Trehalose amorphization and recrystallization, Carboh. Res. 343 2667-2674; DOI: 10.1016/j.carres.2008.08.008
38. B. Bennett and G. Cole, Secondary Pharmaceutical Production: An Engineering Guide, IChemE 2003, pp. 111-201
39. D. M. Parikh, Handbook of Pharmaceutical Granuation Technology, Taylor and Francis, London 2005, pp. 491-512
40. R. Liu, Water-InsolubleDrug Formulation, Taylor and Francis, London 2008, pp. 88-455
41. R. Price and P. M. Young, On the physical transformations of processed pharmaceutical solids, Micron. 36 (2005) 519-524; DOI: 10.1016/j.micron.2005.04. 003
42. G. Zhang, C. Gu, M. Zell, R. Burkhardt, E. Munson and D. Grant, Crystallization and transitions of sulfamerazine polymorphs, J. Pharm. Sci. 91 (2002) 1089-1100; DOI: 10.1002/jps.10100
43. P. Thanatuksorn, K. Kawai, K. Kajiwara and T. Suzuki, Effects of ball-milling on the glass transition of wheat flour constituents, J. Sci. Food Agric. 89 (2009) 430-435; DOI: 10.1002/jsfa.3463
44. J. F. Willart and M. Descamps, Solid state amorphization of pharmaceuticals, Mol. Pharmaceutics 5 (2008) 905-920; DOI: 10.1021/mp800092t
45. A. Revesz, Melting behavior and origin of strain in ball-milled nanocrystalline Al powders, J. Mater. Sci. 40 (2005) 1643-1646; DOI: 10.1007/s10853-005-0664-1
46. S. Karki, T. Friscic, W. Jones and W. D. S. Motherwell, Screening for pharmaceutical cocrystal hydrates via neat and liquid-assisted grinding, Mol. Pharmaceutics 4 (2007) 347-354; DOI: 10. 1021/mp0700054
47. K. Chadwick, R. Davey and W. Cross, How does grinding produce co-crystals? Insights from the case of benzophenone and diphenylamine, CrystEngComm 9 (2007) 732-734; DOI: 10.1039/ b709411f
48. T. Shakhtshneider, Phase transformations and stabilization of metastable states of molecular crystals under mechanical activation, Solid State Ionics 101 (1997) 851-856; DOI: 10.1016/S0167-2738(97)00224-5
49. E. Dudognon, J. Willart, V. Caron, F. Capet, T. Larsson and M. Descamps, Formation of budesonide/ alpha-lactose glass solutions by ball-milling, Solid State Commun. 138 (2006) 68-71; DOI: 10.1016/j.ssc.2006.02.007
50. I. Tsukushi, O. Yamamuro and T. Matsuo, Solid state amorphization of organic molecular crystals using a vibrating mill, Solid State Commun. 94 (1995) 1013-1013; DOI: 10.1016/0038-1098 (95)00161-1
51. J. Font, J. Muntasell and E. Cesari, Amorphization of organic compounds by ball milling, Mater. Res. Bull. 32 (1997) 1691-1696; DOI: 10.1016/S0025-5408(97)00162-1
52. J. Willart, V. Caron, R. Lefort, F. Danède, D. Prevost and M. Descamps, Athermal character of the solid state amorphization of lactose induced by ball milling, Solid State Commun. 132 (2004) 693-696; DOI: 10.1016/j.ssc.2004.09.007
53. M. Otsuka, H. Ohtani, N. Kaneniwa and S. Higuchi, Isomerization of lactose in solid-state by mechanical stress during grinding, J. Pharm. Pharmacol. 43 (1991) 148-153; DOI: 10.1111/j.2042-7158.1991.tb06656.x
54. J. Willart, A. De Gusseme, S. Hemon, G. Odou, F. Danède and M. Descamps, Direct crystal to glass transformation of trehalose induced by ball milling, Solid State Commun. 119 (2001) 501-505; DOI: 10.1016/S0038-1098(01) 00283-6
55. A. J. Megarry, J. Booth and J. Burley, Amorphous trehalose dihydrate by cryogenic milling, Carbohyd. Res. 346 (2011) 1061-1064; DOI: 10.1016/j.carres.2011.03.011
56. J. F. Willart, N. Dujardin, E. Dudognon, F. Danède and M. Descamps, Amorphization of sugar hydrates upon milling, Carbohyd. Res. 345 (2010) 1613-1616; DOI: 10.1016/j.carres.2010.04.014
57. P. Okamoto and N. Lam, Physics of crystal-to-glass transformations, Solid State Phys. 52 (1999) 1-135; DOI: 10.1016/S0081-1947(08)60018-1
58. H. Fecht, Defect-induced melting and solid-state amorphization, Nature 356 (1992) 133-135; DOI: 10.1016/S0081-1947(08)60018-1
59. M. Descamps, J. F. Willart, E. Dudognon and V. Caron, Transformation of pharmaceutical compounds upon milling and comilling: the role of Tg, J. Pharm. Sci. 96 (2007) 1398-1407; DOI: 10. 1002/jps.20939
60. J. Willart, N. Descamps, V. Caron, F. Capet, F. Danède and M. Descamps, Formation of lactose-mannitol molecular alloys by solid state vitrification, Solid State Commun. 138 (2006) 194-199; DOI: 10.1016/j.ssc.2006. 02.034
61. G. Martin and P. Bellon, Driven alloys, Solid State Phys. 50 (1997) 189-331
62. S. Qi, I. Weuts, S. De Cort, S. Stokbroekx, R. Leemans, M. Reading, P. Belton and D. Q. M. Craig, An investigation into the crystallisation behaviour of an amorphous cryomilled pharmaceutical material above and below the glass transition temperature, J. Pharm. Sci. 99 (2010) 196-208; DOI: 10.1002/jps.21811
63. K. J. Crowley and G. Zografi, Cryogenic grinding of indomethacin polymorphs and solvates: assessment of amorphous phase formation and amorphous phase physical stability, J. Pharm. Sci. 91 (2002) 492-507; DOI: 10.1002/jps.10028
64. J. Carstensen, Advanced Pharmaceutical Solids, Marcel Dekker, New York 2001, pp. 107-117
65. C. Sun and D. J. Grant, Influence of crystal shape on the tableting performance of L-lysine monohydrochloride dihydrate, J. Pharm. Sci. 90 (2001) 569-579; DOI: 10.1002/1520-6017(200105)90: 5<569::AID-JPS1013>3.0.CO;2-4
66. V. Chikhalia, R. T. Forbes, R. A. Storey and M. Ticehurst, The effect of crystal morphology and mill type on milling induced crystal disorder, Eur. J. Pharm. Sci. 27 (2006) 19-26; DOI: 10.1016/ j.ejps.2005.08.013
67. T. Watanabe, S. Hasegawa, N. Wakiyama, A. Kusai and M. Senna, Comparison between polyvinylpyrrolidone and silica nanoppagess as carriers for indomethacin in a solid state dispersion, Int. J. Pharm. 250 (2003) 283-286; DOI: 10.1016/S0378-5173(02)00549-5
68. A. Ali, K. Yamamoto, A. Elsayed, F. Habib and Y. Nakai, Molecular behavior of flufenamic acid in physical and ground mixtures with florite, Chem. Pharm. Bull. 40 (1992) 1289-1294
69. H. Sekizaki, K. Danjo, H. Eguchi, Y. Yonezawa, H. Sunada and A. Otsuka, Solid-state interaction of ibuprofen with polyvinylpyrrolidone, Chem. Pharm. Bull. 43 (1995) 988-993
70. V. Boldyrev, T. Shakhtshneider, L. Burleva and V. Severstev, Preparation of the disperse systems of sulfathiazole-polyvinylpyrrolidone by mechanical activation, Drug Dev. Ind. Pharm. 20 (1994) 1103-1114
71. N. Kaneniwa and A. Ikekava, Solubilization of Water-insoluble organic powders by ball-milling in the presence of polyvinylpyrrolidone, Chem. Pharm. Bull. 23 (1975) 2973-2986
72. N. Kaneniwa, A. Ikekava and M. Sumi, A decrease in crystallinity of amobarbital by mechanical treatment in presence of diluents, Chem. Pharm. Bull. 26 (1978) 2734-2743
73. H. Takeuchi, S. Nagira, H. Yamamoto and Y. Kawashima, Solid dispersion ppagess of amorphous indomethacin with fine porous silica ppagess by using spray-drying method, Int. J. Pharm. 293 (2005) 155-164; DOI: 10.1016/j.ijpharm.2004.12.019
74. M. Fujii, H. Okada, Y. Shibata, H. Teramachi, M. Kondoh and Y. Watanabe, Preparation, characterization, and tableting of a solid dispersion of indomethacin with crospovidone, Int. J. Pharm. 293 (2005) 145-153; DOI: 10.1016/j.ijpharm.2004.12.018
75. Y. Nakai, E. Fukuoka, S. Nakajima and Y. Iida, Effect of grinding on physical and chemical properties of crystalline medicinals with microcrystalline cellulose. 2. Retention of volatile medicinals in ground mixture, Chem. Pharm. Bull. 26 (1978) 2983-2989
76. M. Cirri, F. Maestrelli, S. Furlanetto and P. Mura, Solid-state characterization of glyburide-cyclodextrin co-ground products, J. Therm. Anal. Calorim. 77 (2004) 413-422; DOI: 10.1023/B: JTAN.0000038982.40315.8f
77. T. Shakhtshneider, M. Vasiltchenko, A. Politov and V. Boldyrev, The mechanochemical preparation of solid disperse systems of ibuprofen-polyethylene glycol, Int. J. Pharm. 130 (1996) 25-32; DOI: 10.1016/0378-5173(95)04244-X
78. D. Bahl and R. H. Bogner, Amorphization of indomethacin by co-grinding with Neusilin US2: Amorphization kinetics, physical stability and mechanism, Pharm. Res. 23 (2006) 2317-2325; DOI: 10.1007/s11095-006-9062-x
79. U. Zimper, J. Aaltonen, C. M. McGoverin, K. C. Gordon, K. Krauel-Goellner and T. Rades, Quantification of process induced disorder in milled samples using different analytical techniques, Pharmaceutics 2 (2010) 30-49; DOI: 10.3390/pharmaceutics2010030
80. V. Caron, J. F. Willart, R. Lefort, P. Derollez, F. Danède and M. Descamps, Solid state amorphization kinetic of alpha lactose upon mechanical milling, Carbohyd. Res. 346 (2011) 2622-2628; DOI: 10.1016/j.carres.2011.09.004
81. J. P. Bøtker, P. Karmwar, C. J. Strachan, C. Cornett, F. Tian, Z. Zujovic, J. Rantanen and T. Rades, Assessment of crystalline disorder in cryo-milled samples of indomethacin using atomic pair-wise distribution functions, Int. J. Pharm. 417 (2011) 112-119; DOI: 10.1016/j.ijpharm.2010.12. 018
82. K. Terada, H. Kitano, Y. Yoshihashi and E. Yonemochi, Quantitative correlation between initial dissolution rate and heat of solution of drug, Pharm. Res. 17 (2000) 920-924; DOI: 10.1023/A: 1007514902161
83. Z. Lavrĩ, J. Pirnat, J. Lunik, J. Seliger, V. Agar, Z. Trontelj and S. Srcic, Application of 14N NQR to the study of piroxicam polymorphism, J. Pharm. Sci. 99 (2010) 4857-4865; DOI: 10.1002/ jps.22186
84. C. J. Strachan, T. Rades and K. C. Gordon, A theoretical and spectroscopic study of gamma-crystalline and amorphous indomethacin, J. Pharm. Pharmacol. 59 (2007) 261-269; DOI: 10.1211/ jpp.59.2.0012
85. M. Savolainen, A. Heinz, C. Strachan, K. C. Gordon, J. Yliruusi, T. Rades and N. Sandler, Screening for differences in the amorphous state of indomethacin using multivariate visualization, Eur. J. Pharm. Sci. 30 (2007) 113-123; DOI: 10.1016/j.ejps.2006.10.010
86. C. Rawle, C. Lee, C. Strachan, K. Payne, P. Manson and T. Rades, Towards characterization and identification of solid state pharmaceutical mixtures through second harmonic generation, J. Pharm. Sci. 95 (2006) 761-768; DOI: 10.1002/jps.20575
87. G. G. Buckton and P. P. Darcy, Assessment of disorder in crystalline powders - a review of analytical techniques and their application, Int. J. Pharm. 179 (1999) 141-158; DOI: 10.1016/S0378-5173(98)00335-4
88. B. Shah, V. K. Kakumanu and A. K. Bansal, Analytical techniques for quantification of amorphous/ crystalline phases in pharmaceutical solids, J. Pharm. Sci. 95 (2006) 1641-1665; DOI: 10. 1002/jps.20644
89. N. Chieng, Z. Zujovic, G. Bowmaker, T. Rades and D. Saville, Effect of milling conditions on the solid-state conversion of ranitidine hydrochloride form 1, Int. J. Pharm. 327 (2006) 36-44; DOI: 10.1016/j.ijpharm.2006.07.032
90. C. Gustafsson, H. Lennholm, T. Iversen and C. Nyström, Comparison of solid-state NMR and isothermal microcalorimetry in the assessment of the amorphous component of lactose, Int. J. Pharm. 174 (1998) 243-252; DOI: 10.1016/S0378-5173(98)00272-5
91. M. Mirmehrabi, S. Rohani, K. S. K. Murthy and B. Radatus, Characterization of tautomeric forms of ranitidine hydrochloride: thermal analysis, solid-state NMR, X-ray, J. Cryst. Growth 260 (2004) 517-526; DOI: 10.1016/j.jcrysgro.2003.08.061
92. D. C. Apperley, R. A. Fletton, R. K. Harris, R. W. Lancaster, S. Tavener and T. L. Threlfall, Sulfathiazole polymorphism studied by magic-angle spinning NMR, J. Pharm. Sci. 88 (1999) 1275-1280; DOI: 10.1021/js990175a
93. D. C. Apperley, R. K. Harris, T. Larsson and T. Malmstrom, Quantitative nuclear magnetic resonance analysis of solid formoterol fumarate and its dihydrate, J. Pharm. Sci. 92 (2003) 2487-2494; DOI: 10.1002/jps.10500
94. P. A. Tishmack, D. E. Bugay and S. R. Byrn, Solid-state nuclear magnetic resonance spectroscopy-pharmaceutical applications, J. Pharm. Sci. 92 (2003) 441-474; DOI: 10.1002/jps.10307
95. A. Gombás, I. Antal, P. Szabó-Révész, S. Marton and I. Erõs, Quantitative determination of crystallinity of alpha-lactose monohydrate by near Infrared Spectroscopy (NIRS), Int. J. Pharm. 256 (2003) 25-32; DOI: 10.1016/S0378-5173(03)00059-0
96. P. Debenedetti, Metastable Liquids: Concepts and Principles, Princeton University Press, Chichester 1996
97. G. P. Johari, S. Ram, G. Astl and E. Mayer, Characterizing amorphous and microcrystalline solids by calorimetry, J. Non-Cryst Solids 116 (1990) 282-285; DOI: 10.1016/0022-3093(90)90703-O
98. S. Bates, G. Zografi, D. Engers, K. Morris, K. Crowley and A. Newman, Analysis of amorphous and nanocrystalline solids from their X-ray diffraction patterns, Pharm. Res. 23 (2006) 2333-2349; DOI: 10.1007/s11095-006-9086-2
99. S. J. L. Billinge and M. G. Kanatzidis, Beyond crystallography: the study of disorder, nanocrystallinity and crystallographically challenged materials with pair distribution functions, Chem. Commun. 7 (2004) 749-760; DOI: 10.1039/b309577k
100. A. S. Masadeh, E. S. Bozin, C. L. Farrow, G. Paglia, P. Juhas, S. J. L. Billinge, A. Karkamkar and M. G. Kanatzidis, Quantitative size-dependent structure and strain determination of CdSe nanoppagess using atomic pair distribution function analysis, Phys. Rev. B 76 (2007); DOI: 10. 1103/PhysRevB.76.115413
101. T. Egami and S. J. L. Billinge, Underneath the Bragg Peaks, Pergamon Press, Oxford 2003, pp. 25-101
102. T. Proffen, S. Billinge, T. Egami and D. Louca, Structural analysis of complex materials using the atomic pair distribution function - a practical guide, Z. Kristallogr. 218 (2003) 132-143; DOI: 10.1524/zkri.218.2.132.20664
103. L. Tarasov and B. E. Warren, X-ray diffraction study of liquid sodium, J. Chem. Phys. 4 (1936) 236-238; DOI: 10.1063/1.1749828
104. B. Warren, H. Krutter and O. Morningstar, Fourier-analysis of X-ray-patterns of vitreous SiO2 and B2O3, J. Am. Ceram. Soc. 75 (1992) 11-15
105. F. Zernike and J. A. Prins, Die Beugung von Röntgenstrahlen in Flüssigkeiten als Effekt der Molekülanordnung, Z. Physik 41 (1927) 184-194; DOI: 10.1007/BF01391926
106. F. Atassi, C. Mao, A. S. Masadeh and S. R. Byrn, Solid-state characterization of amorphous and mesomorphous calcium ketoprofen, J. Pharm. Sci. 99 (2009) 3684-3697; DOI: 10.1002/jps.21925
107. S. Bates, R. C. Kelly, I. Ivanisevic, P. Schields, G. Zografi and A. W. Newman, Assessment of defects and amorphous structure produced in raffinose pentahydrate upon dehydration, J. Pharm. Sci. 96 (2007) 1418-1433; DOI: 10.1002/jps.20944
108. A. Heinz, C. J. Strachan, F. Atassi, K. C. Gordon and T. Rades, Characterizing an amorphous system exhibiting trace crystallinity: Acase study with saquinavir, Crys. Growth Des. 8 (2008) 119-127; DOI: 10.1021/cg700912q
109. A. Sheth, S. Bates, F. Muller and D. Grant, Polymorphism in piroxicam, Cryst. Growth Des. 4 (2004) 1091-1098; DOI: 10.1021/cg049876y
110. A. Sheth, S. Bates, F. Muller and D. Grant, Local structure in amorphous phases of piroxicam from powder X-ray diffractometry, Cryst. Growth Des. 5 (2005) 571-578; DOI: 10.1021/cg049757i
111. M. D. Moore, A. M. Steinbach, I. S. Buckner and P. L. Wildfong, A structural investigation into the compaction behavior of pharmaceutical composites using powder X-ray diffraction and total scattering analysis, Pharm. Res. 26 (2009) 2429-2437; DOI: 10.1007/s11095-009-9954-7
112. A. Newman, D. Engers, S. Bates, I. Ivanisevic, R. C. Kelly and G. Zografi, Characterization of amorphous API: Polymer mixtures using X-ray powder diffraction, J. Pharm. Sci. 97 (2008) 4840-4856; DOI: 10.1002/jps.21352
113. K. Nollenberger, A. Gryczke, C. Meier, J. Dressman, M. U. Schmidt and S. Brühne, Pair distribution function X-ray analysis explains dissolution characteristics of felodipine melt extrusion products, J. Pharm. Sci. 98 (2009) 1476-1486; DOI: 10.1002/jps.21534
114. P. Robinson, HyperDSC, Speed DSC Technique, ESTAC8 Abstract Book, Barcelona (August 25-29, 2002), p. 101
115. Y. Roos, Melting and glass transitions of low molecular weight carbohydrates, Carbohyd. Res. 238 (1993) 39-48; DOI: 10.1016/0008-6215(93)87004- C
116. M. Brown, Introduction to Thermal Analysis: Techniques and Applications, Kluwer Academic Publishers, Amsterdam 2001
117. Perkin Elmer, Thermal Analysis Newsletter, Application Example PETAN-51, Norwalk 2000
118. P. Claudy, M. Siniti and J. El Hajri, Thermodynamic study of the glass relaxation phenomena -DSC study of annealing of maltitol glass, J. Therm. Anal. Calorim. 68 (2002) 251-264
119. M. J. Pikal, A. L. Lukes, J. E. Lang and K. Gaines, Quantitative crystallinity determinations for b-lactam antibiotics by solution calorimetry: Correlations with stability, J. Pharm. Sci. 67 (1978) 767-773; DOI: 10.1002/jps.2600670609
120. D. Gao and J. Rytting, Use of solution calorimetry to determine the extent of crystallinity of drugs and excipients, Int. J. Pharm. 151 (1997) 183-192; DOI: 10.1016/S0378-5173(97)04895-3
121. S. E. Hogan and G. Buckton, The quantification of small degrees of disorder in lactose using solution calorimetry, Int. J. Pharm. 207 (2000) 57-64; DOI: 10.1016/S0378-5173(00)00527-5
122. K. C. Thompson, J. P. Draper, M. J. Kaufman and G. S. Brenner, Characterization of the crystallinity of drugs: B02669, a case study, Pharm. Res. 11 (1994) 1362-1365; DOI: 10.1023/A:101 8919201058
123. G. H. Ward and R. K. Schultz, Process-induced crystallinity changes in albuterol sulfate and its effect on powder physical stability, Pharm. Res. 12 (1995) 773-779; DOI: 10.1023/A:1016232230 638
124. P. Harjunen, V. P. Lehto, M. Koivisto, E. Levonen, P. Paronen and K. Järvinen, Determination of amorphous content of lactose samples by solution calorimetry, Drug Dev. Ind. Pharm. 30 (2004) 809-815; DOI: 10.1081/DDC- 200030302
125. R. W. Douglas and G. A. Jones, An apparatus for the determination of small changes in density, J. Sci. Instrum. 24 (1947) 72; DOI: 10.1088/0950-7671/24/3/304
126. J. Pelsmaekers and S. Amelinckx, Simple apparatus for comparative density measurements, Rev. Sci. Instr. 32 (1961) 828-830; DOI: 10.1063/1.1717522
127. R. Suryanarayanan, Evaluation of two concepts of crystallinity using calcium gluceptate as a model compound, Int. J. Pharm. 24 (1985) 1-17; DOI: 10.1016/0378-5173(85)90140-1
128. G. M. Venkatesh, M. E. Barnett, C. Owusu-Fordjour and M. Galop, Detection of low levels of the amorphous phase in crystalline pharmaceutical materials by thermally stimulated current spectrometry, Pharm. Res. 18 (2001) 98-103, DOI: 10.1023/A:1011087012826
129. R. Huttenrauch, Molecular galenics as the basis of modern drug formation, Acta Pharm. Technol. (Suppl.) 6 (1978) 55-127
130. A. Salekigerhardt, C. Ahlneck and G. Zografi, Assessment of disorder in crystalline solids, Int. J. Pharm. 101 (1994) 237-247; DOI: 10.1016/0378- 5173(94)90219-4
131. P. M. Young, H. Chiou, T. Tee, D. Traini, H-K. Chan, F. Thielmann and D. Burnett, The use of organic vapor sorption to determine low levels of amorphous content in processed pharmaceutical powders, Drug Dev. Ind. Pharm. 33 (2007) 91-97; DOI: 10.1080/03639040600969991
132. J. Vollenbroek, G. A. Hebbink, S. Ziffels and H. Steckel, Determination of low levels of amorphous content in inhalation grade lactose by moisture sorption isotherms, Int. J. Pharm. 395 (2010) 62-70; DOI: 10.1016/j.ijpharm. 2010.04.035
133. M. Kunaver, J. Zadnik and O. Planinsek, Inverse gas chromatography-A different approach to characterization of solids and liquids, Acta Chim. Slov. 51 (2004) 373-394
134. A. Voelkel, B. Strzemiecka, K. Adamska and K. Milczewska, Inverse gas chromatography as a source of physicochemical data, J. Chromatogr. A 1216 (2009) 1551-1566; DOI: 10.1016/j.chroma. 2008.10.096
135. S. P. Chamarthy and R. Pinal, The nature of crystal disorder in milled pharmaceutical materials, Colloid. Surfaces A 331 (2008) 68-75; DOI: 10.1016/j.colsurfa.2008.06.040
136. O. Planinsek, J. Zadnik, M. Kunaver, S. Srcic and A. Godec, Structural evolution of indomethacin ppagess upon milling: time-resolved quantification and localization of disordered structure studied by IGC and DSC, J. Pharm. Sci. 99 (2010) 1968-1981; DOI: 10.1002/jps.21986
137. M. Otsuka and N. Kaneniwa, Effect of environment on crystallinity and chemical stability in solid-state of ground cephalotin sodium during storage, Drug Dev. Ind. Pharm. 17 (1990) 909-918; DOI: 10.3109/03639049109040828
138. H. Konno and L. S. Taylor, Influence of different polymers on the crystallization tendency of molecularly dispersed amorphous felodipine, J. Pharm. Sci. 95 (2006) 2692-2705; DOI: 10.1002/ jps.20697
139. X. C. Tang, M. J. Pikal and L. S. Taylor, The effect of temperature on hydrogen bonding in crystalline and amorphous phases in dihydropyrine calcium channel blockers, Pharm. Res. 19 (2002) 484-490; DOI: 10.1023/A:1015199713635
140. L. Mackin, S. Sartnurak, I. Thomas and S. Moore, The impact of low levels of amorphous material, Int. J. Pharm. 231 (2002) 213-226; DOI: 10.1016/S0378-5173(01)00880-8
141. J. J. Seyer, P. E. Luner and M. S. Kemper, Application of diffuse reflectance near-infrared spectroscopy for determination of crystallinity, J. Pharm. Sci. 89 (2000) 1305-1316; DOI: 10.1002/ 1520-6017(200010)89:10<1305:: AID-JPS8>3.0.CO;2-Q
142. S. J. Bai, M. Rani, R. Suryanarayanan, J. F. Carpenter, R. Nayar and M. C. Manning, Quantification of glycine crystallinity by near-infrared (NIR) spectroscopy, J. Pharm. Sci. 93 (2004) 2439-2447; DOI:10.1002/jps.20153
143. P. Aldridge, C. Evans, H. Ward, S. Colgan, N. Boyer and P. Gemperline, Near-IR detection of polymorphism and process-related substances, Anal. Chem. 68 (1996) 997-1002; DOI: 10.1021/ ac950993x
144. S. Hogan and G. Buckton, The application of near infrared spectroscopy and dynamic vapor sorption to quantify low amorphous contents of crystalline lactose, Pharm. Res. 18 (2001) 112-116; DOI: 10.1023/A:1011091113734
145. G. Buckton, E. Yonemochi, J. Hammond and A. Moffat, The use of near infra-red spectroscopy to detect changes in the form of amorphous and crystalline lactose, Int. J. Pharm. 168 (1998) 231-241; DOI: 10.1016/S0378-5173(98)00095-7
146. M. Otsuka and H. Tanabe, Stability test for amorphous materials in humidity controlled 96-well plates by near-infrared spectroscopy, Drug Dev. Ind. Pharm. 38 (2012) 380-385; DOI: 10. 3109/03639045.2011.608680
147. M. Otsuka, F. Kato and Y. Matsuda, Comparative evaluation of the degree of indomethacin crystallinity by chemoinfometrical Fourier-transformed near-infrared spectroscopy and conventional powder X-ray diffractometry, AAPS PharmSci 2 (2000) E9; DOI: 10.1208/ps020109
148. P. Vandenabeele, Practical Raman Spectroscopy, Wiley, Chichosten 2013, pp. 23-80
149. P. Karmwar, K. Graeser, K. C. Gordon, C. J. Strachan and T. Rades, Effect of different preparation methods on the dissolution behaviour of amorphous indomethacin, Eur. J. Pharm. Biopharm. 80 (2012) 459-464; DOI: 10.1016/j.ejpb.2011.10.006
150. J. P. Boetker, V. Koradia, T. Rades and J. Rantanen, Atomic pairwise distribution function analysis of the amorphous phase prepared by different manufacturing routes, Pharmaceutics 4 (2012) 93-103 DOI: 10.3390/ pharmaceutics4010093
151. M. Savolainen, K. Kogermann, A. Heinz, J. Aaltonen, L. Peltonen, C. Strachan and J. Yliruusi, Better understanding of dissolution behaviour of amorphous drugs by in situ solid-state analysis using Raman spectroscopy, Eur. J. Pharm. Biopharm. 71 (2009) 71-79; DOI: 10.1016/j.ejpb. 2008.06.001
152. S. Hasegawa, T. Hamaura, N. Furuyama, S. Horikawa, A. Kusai, E. Yonemochi and K. Terada, Uniformity and physical states of troglitazone in solid dispersions determined by electron probe microanalysis and microthermal analysis, Int. J. Pharm. 280 (2004) 39-46; DOI: 10.1016/j. ijpharm.2004.04.024
153. K. Kawakami, T. Numa and Y. Ida, Assessment of amorphous content by microcalorimetry, J. Pharm. Sci. 91 (2002) 417-423; DOI: 10.1002/jps.10017
154. G. Buckton, P. Darcy, D. Greenleaf and P. Holbrook, The use of isothermal microcalorimetry in the study of changes in crystallinity of spray-dried salbutamol sulphate, Int. J. Pharm. 116 (1995) 113-118; DOI: 10.1016/0378-5173(94)00322-V
155. L. E. Briggner, G. Buckton, K. Bystrom and P. Darcy, The use of isothermal microcalorimetry in the study of changes in crystallinity induced during the processing of powders, Int. J. Pharm. 105 (1994) 125-135; DOI: 10.1016/0378-5173(94)90458-8
156. D. Giron, P. Remy, S. Thomas and E. Vilette, Quantitation of amorphicity by microcalorimetry, J. Therm. Anal. 48 (1997) 465-472; DOI: 10.1007/BF01979493
157. J. Nishizawa, N. G. Hadjiconstantinou, G. Dimonte, P. S. Lomdahl, B. L. Holian and B. J. Alder, Pioneering work of THz wave and its application for molecular sciences, AIP Conference Proceedings 708 (2004) 369-375