Analysis of solid-state transformations of pharmaceutical compounds using vibrational spectroscopy

Journal of Pharmacy and Pharmacology

Volumn 61, Issue 8, 2009, Pages 971-988

  Heinz, Andrea ^a   Strachan, Clare J ^a,b   Gordon, Keith C ^a   Rades, Thomas ^a  

^a UNIVERSITY OF OTAGO   (New Zealand)

^b UNIVERSITY OF HELSINKI   (Finland)

Author keywords

Amorphous; Hydrate; Near infrared spectroscopy; Polymorphism; Terahertz pulsed spectroscopy

Indexed keywords

AMPICILLIN; AZITHROMYCIN; BACLOFEN; CAFFEINE; CARBAMAZEPINE; CIMETIDINE; ERYTHROMYCIN; FAMOTIDINE; FENOFIBRATE; FLUCONAZOLE; IBUPROFEN; INDOMETACIN; KETOPROFEN; LACTOSE; LISINOPRIL; NAPROXEN; NICLOSAMIDE; NIFEDIPINE; NITROFURANTOIN; PARACETAMOL; PIROXICAM; RANITIDINE; RISEDRONIC ACID; SULFATHIAZOLE; THEOPHYLLINE; TREHALOSE; DRUG;

CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG FORMULATION; DRUG GRANULATION; DRUG STORAGE; DRUG TRANSFORMATION; INFRARED SPECTROSCOPY; NEAR INFRARED SPECTROSCOPY; NONHUMAN; RAMAN SPECTROMETRY; REVIEW; SCANNING ELECTRON MICROSCOPY; SOLID STATE; SOLVATE; TERAHERTZ SPECTROSCOPY; CHEMISTRY; METHODOLOGY; PHARMACEUTICS; PHASE TRANSITION; SOLUBILITY; SPECTROSCOPY; VIBRATION;

CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; PHARMACEUTICAL PREPARATIONS; PHASE TRANSITION; SOLUBILITY; SPECTRUM ANALYSIS; TECHNOLOGY, PHARMACEUTICAL; VIBRATION;

EID: 85047682766     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/jpp.61.08.0001     Document Type: Review

References (146)

1. Grant DJW. Theory and origin of polymorphism. In: Brittain HG, ed. Polymorphism in Pharmaceutical Solids. New York: Marcel Dekker, 2000: 1-33.
2. Yu L. Amorphous pharmaceutical solids: preparation, characterization and stabilization. Adv Drug Deliv Rev 2001; 48: 27-42.
3. Giron D et al. Solid-state of pharmaceutical compounds - impact of the ICH Q6 guideline on industrial development. J Therm Anal Cal 2004; 77: 709-747.
4. Byrn SR. Solid-state Chemistry of Drugs. West Lafayette, Indiana: SSCI, Inc., 1999.
5. Rodríguez-Spong B et al. General principles of pharmaceutical solid polymorphism: a supramolecular perspective. Adv Drug Deliv Rev 2004; 56: 241-274.
6. Lohani S, Grant DJW. Polymorphism in the Pharmaceutical Industry. Weinheim, Germany: Wiley-VCH Verlag, 2006.
7. Brittain HG, ed. Polymorphism in Pharmaceutical Solids. New York: Marcel Dekker, Inc., 2000.
8. Craig DQM et al. The relevance of the amorphous state to pharmaceutical dosage forms: glassy drugs and freeze dried systems. Int J Pharm 1999; 179: 179-207.
9. Hancock BC, Zografi G. Characteristics and significance of the amorphous state in pharmaceutical systems. J Pharm Sci 1997; 86: 1-12.
10. Morris KR et al. Theoretical approaches to physical transformations of active pharmaceutical ingredients during manufacturing processes. Adv Drug Deliv Rev 2001; 48: 91-114.
11. Govindarajan R, Suryanarayanan R. Processing-induced phase transformations and their implications on pharmaceutical product quality. In: Hilfiker R, ed. Polymorphism in the Pharmaceutical Industry. Weinheim, Germany: Wiley-VCH Verlag, 2006: 333-364.
12. Zhang GGZ et al. Phase transformation considerations during process development and manufacture of solid oral dosage forms. Adv Drug Deliv Rev 2004; 56: 371-390.
13. Bernstein J. Polymorphism in Molecular Crystals. Oxford: Oxford University Press, 2002.
14. Gillon AL et al. Hydration in molecular crystals - a Cambridge Structural Database analysis. Cryst Growth Des 2003; 3: 663-673.
15. Guillory JK. Generation of polymorphs, hydrates, solvates, and amorphous solids. In: Brittain HG, ed. Polymorphism in Pharmaceutical Solids. New York: Marcel Dekker, Inc., 2000: 183-225.
16. Han J, Suryanarayanan R. Influence of environmental conditions on the kinetics and mechanism of dehydration of carbamazepine dihydrate. Pharm Dev Technol 1998; 3: 587-596.
17. Suihko E et al. Dehydration of theophylline monohydrate - a two step process. Int J Pharm 1997; 158: 47-55.
18. Garnier S et al. Dehydration mechanism and crystallisation behaviour of lactose. J Therm Anal Cal 2002; 68: 489-502.
19. Petit S, Coquerel G. The amorphous state. In: Hilfiker R, ed. Polymorphism in the Pharmaceutical Industry. Weinheim, Germany: Wiley-VCH Verlag, 2006: 259-286.
20. Bugay DE. Characterization of the solid state: spectroscopic techniques. Adv Drug Deliv Rev 2001; 48: 43-65.
21. Stephenson GA et al. Characterization of the solid state: quantitative studies. Adv Drug Deliv Rev 2001; 48: 67-90.
22. Brittain HG. Spectral methods for the characterization of polymorphs and solvates. J Pharm Sci 1997; 86: 405-412.
23. Wartewig S, Neubert RHH. Pharmaceutical applications of Mid-IR and Raman spectroscopy. Adv Drug Deliv Rev 2005; 57: 1144-1170.
24. Brittain HG ed. Physical Characterization of Pharmaceutical Solids. New York: Marcel Dekker, Inc., 1995.
25. Zeitler JA et al. Terahertz pulsed spectroscopy and imaging in the pharmaceutical setting - a review. J Pharm Pharmacol 2007; 59: 209-223.
26. Workman JJ. Review of process and non-invasive near-infrared and infrared spectroscopy: 1993-1999. Appl Spectrosc Rev 1999; 34: 1-89.
27. Nguyen NAT et al. Physicochemical characterization of the various solid forms of carbovir, an antiviral nucleoside. J Pharm Sci 1994; 83: 1116-1123.
28. Fletton RA et al. A comparative spectroscopic investigation of 3 pseudopolymorphs of testosterone using solid-state IR and high-resolution solid-state NMR. Spectrochim Acta A Mol Biomol Spectrosc 1987; 43: 1111-1120.
29. Kalinkova GN, Dimitrova L. Infrared spectroscopic studies of the antibiotic cefamandole nafate. Vib Spectrosc 1995; 10: 41-47.
30. Bartolomei M et al. Solid-state investigation of fluocinolone acetonide. J Pharm Biomed Anal 1997; 15: 1813-1820.
31. Agatonovic-Kustrin S et al. Determination of polymorphic forms of ranitidine-HCl by DRIFTS and XRPD. J Pharm Biomed Anal 2001; 25: 741-750.
32. McMahon LE et al. Characterization of dihydrates prepared from carbamazepine polymorphs. J Pharm Sci 1996; 85: 1064-1069.
33. Variankaval NE et al. Crystallization of beta-estradiol in an acrylic transdermal drug delivery system. J Biomed Mater Res 1999; 44: 397-406.
34. Matsumoto T, Zografi G. Physical properties of solid molecular dispersions of IM with poly(vinylpyrrolidone) and poly(vinylpyrrolidone-co- vinyl-acetate) in relation to indomethacin crystallisation. Pharm Res 1999; 16: 1722-1728.
35. Tong P, Zografi G. A study of amorphous molecular dispersions of indomethacin and its sodium salt. J Pharm Sci 2001; 90: 1991-2004.
36. Takahashi H et al. Acetaminophen particle design using chitosan and a spray-drying technique. Chem Pharm Bull 2005; 53: 37-41.
37. Taylor LS, Zografi G. Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions. Pharm Res 1997; 14: 1691-1697.
38. Bugay DE et al. Quantitation of cefepim·2HCl dihydrate in cefepime·2HCl monohydrate by diffuse reflectance IR and powder X-ray diffraction techniques. J Pharm Biomed Anal 1996; 15: 49-61.
39. Hartauer KJ et al. Diffuse reflectance infrared Fourier-transform spectroscopy for the quantitative-analysis of mixtures of polymorphs. Int J Pharm 1992; 85: 163-174.
40. Otsuka M, Kaneniwa N. Effect of grinding on the degree of crystallinity of cephalexin powder. Chem Pharm Bull 1983; 31: 4489-4495.
41. Kaneniwa N et al. Effect of tabletting on the degree of crystallinity and on the dehydration and decomposition points of cephalexin crystalline powder. Chem Pharm Bull 1985; 33: 802-809.
42. Bakeev KA, Ciurczak EW. Near-infrared spectroscopy as a process analytical tool - Part 1: Laboratory applications. Spectroscopy 2003; 18: 32-35.
43. Reich G. Near-infrared spectroscopy and imaging: basic principles and pharmaceutical applications. Adv Drug Deliv Rev 2005; 57: 1109-1143.
44. Eustaquio A et al. Determination of paracetamol in intact tablets by use of near infrared transmittance spectroscopy. Anal Chim Acta 1999; 383: 283-290.
45. Laasonen M et al. Development and validation of a near-infrared method for the quantitation of caffeine in intact single tablets. Anal Chem 2003; 75: 754-760.
46. McGoverin CM et al. Quantification of binary polymorphic mixtures of ranitidine hydrochloride using NIR spectroscopy. Vib Spectrosc 2006; 41: 225-231.
47. Savolainen M et al. Determination of amorphous content in the pharmaceutical process environment. J Pharm Pharmacol 2007; 59: 161-170.
48. Blanco M et al. Characterization and analysis of polymorphs by near-infrared spectrometry. Anal Chim Acta 2004; 502: 221-227.
49. Blanco M et al. Application of NIR spectroscopy in polymorphic analysis: study of pseudo-polymorphs stability. J Pharm Sci 2005; 94: 1336-1342.
50. Rantanen J et al. Improved understanding of factors contributing to quantification of anhydrate/hydrate powder mixtures. Appl Spectrosc 2005; 59: 942-951.
51. Blanco M, Villar A. Development and validation of a method for the polymorphic analysis of pharmaceutical preparations using near infrared spectroscopy. J Pharm Sci 2003; 92: 823-830.
52. Rantanen J et al. On-line monitoring of moisture content in an instrumented fluidized bed granulator with a multi-channel NIR moisture sensor. Powder Technol 1998; 99: 163-170.
53. Rantanen J et al. In-line moisture measurement during granulation with a four-wavelength near infrared sensor: an evaluation of particle size and binder effects. Eur J Pharm Biopharm 2000; 50: 271-276.
54. Frake P et al. Process control and end-point determination of a fluid bed granulation by application of near infra-red spectroscopy. Int J Pharm 1997; 151: 75-80.
55. Derksen MWJ et al. The use of near-infrared spectroscopy in the efficient prediction of a specification for the residual moisture content of a freeze-dried product. J Pharm Biomed Anal 1998; 17: 473-480.
56. Zhou GX et al. In-line measurement of a drug substance via near infrared spectroscopy to ensure a robust crystallization process. J Pharm Sci 2006; 95: 2337-2347.
57. Gu XJ, Jiang W. Characterization of polymorphic forms of fluconazole using Fourier-transform Raman-spectroscopy. J Pharm Sci 1995; 84: 1438-1441.
58. Raghavan K et al. A Spectroscopic investigation of losartan polymorphs. Pharm Res 1993; 10: 900-904.
59. Szelagiewicz M et al. In situ characterization of polymorphic forms: the potential of Raman techniques. J Therm Anal Cal 1999; 57: 23-43.
60. Söderholm S et al. Raman spectra of fructose and glucose in the amorphous crystalline states. J Raman Spectrosc 1999; 30: 1009-1018.
61. Tudor A et al. The qualitative and quantitative analysis of chlorpropamide polymorphic mixtures by near-infrared Fourier transform Raman spectroscopy. Pharm Res 1993; 10: 1772-1776.
62. Langkilde FW et al. Quantitative FT-Raman analysis of two crystal forms of a pharmaceutical compound. J Pharm Biomed Anal 1997; 15: 687-696.
63. Taylor LS, Zografi G. The quantitative analysis of crystallinity using FT-Raman spectroscopy. Pharm Res 1998; 15: 755-761.
64. Campbell Roberts SN et al. Quantitative analysis of mannitol polymorphs. FT-Raman spectroscopy. J Pharm Biomed Anal 2002; 28: 1135-1147.
65. De Spiegeleer B et al. Determination of the relative amounts of three crystal forms of a benzimidazole drug in complex finished formulations by FT-Raman spectroscopy. J Pharm Biomed Anal 2005; 39: 275-280.
66. Kontoyannis CG. Quantitative determination of Caco3 and glycine in antacid tablets by laser Raman-spectroscopy. J Pharm Biomed Anal 1995; 13: 73-76.
67. Ryder AG et al. Identifications and quantitative measurements of narcotics in solid mixtures using near-IR Raman spectroscopy and multivariate analysis. J Forensic Sci 1999; 44: 1013-1019.
68. Ryder AG et al. Quantitative analysis of cocaine in solid mixtures using Raman spectroscopy and chemometric methods. J Raman Spectrosc 2000; 31: 221-227.
69. Skoulika SG, Georgiou CA. Rapid quantitative determination of ciprofloxacin in pharmaceuticals by use of solid-state FT-Raman spectroscopy. Appl Spectrosc 2001; 55: 1259-1265.
70. Szostak R, Mazurek S. Quantitative determination of acetylsalicylic acid and acetaminophen in tablets by FT-Raman spectroscopy. Analyst 2002; 127: 144-148.
71. Szostak R, Mazurek S. FT-Raman quantitative determination of ambroxol in tablets. J Mol Struct 2004; 704: 229-233.
72. Chantry GW. Submillimetre Spectroscopy: a Guide to the Theoretical and Experimental Physics of the Far Infrared. London: Academic Press Inc., 1971.
73. Strachan CJ et al. Using terahertz pulsed spectroscopy to study crystallinity of pharmaceutical materials. Chem Phys Lett 2004; 390: 20-24.
74. Newnham DA, Taday PF. Pulsed terahertz attenuated total reflection spectroscopy. Appl Spectrosc 2008; 62: 394-398.
75. Zeitler JA et al. Temperature dependent terahertz pulsed spectroscopy of carbamazepine. Thermochim Acta 2005; 436: 71-77.
76. Day GM et al. Understanding the influence of polymorphism on phonon spectra: lattice dynamics calculations and terahertz spectroscopy of carbamazepine. J Phys Chem B 2006; 110: 447-456.
77. Aaltonen J et al. Solid form screening - A review. Eur J Pharm Biopharm 2009; 71: 23-37.
78. Aaltonen J et al. Perspectives in the use of spectroscopy to characterise pharmaceutical solids. Int J Pharm 2008; 364: 159-169.
79. Strachan C et al. Using terahertz pulsed spectroscopy to quantify pharmaceutical polymorphism and crystallinity. J Pharm Sci 2005; 94: 837-846.
80. Taday PF et al. Using terahertz pulse spectroscopy to study the crystalline structure of a drug: a case study of the polymorphs of ranitidine hydrochloride. J Pharm Sci 2003; 92: 831-838.
81. Zeitler JA et al. Drug hydrate systems and dehydration processes studied by terahertz pulsed spectroscopy. Int J Pharm 2007; 334: 78-84.
82. Kogermann K et al. Investigating dehydration from compacts using terahertz pulsed, Raman, and near-infrared spectroscopy. Appl Spectrosc 2007; 61: 1265-1274.
83. Beebe KR et al. Chemometrics: a practical guide. New York: John Wiley & Sons, Inc., 1998.
84. Gabrielsson J et al. Multivariate methods in pharmaceutical applications. J Chemometr 2002; 16: 141-160.
85. Wold S et al. PLS-regression: a basic tool of chemometrics. Chemometr Intell Lab Syst 2001; 58: 109-130.
86. Starbuck C et al. Process optimization of a complex pharmaceutical polymorphic system via in situ Raman spectroscopy. Cryst Growth Des 2002; 2: 515-522.
87. Boerrigter SXM et al. In situ observation of epitaxial polymorphic nucleation of the model steroid methyl analogue 17 norethindrone. J Phys Chem B 2002; 106: 4725-4731.
88. Ferrari ES, Davey RJ. Solution-mediated transformation of alpha to beta L-glutamic acid: rate enhancement due to secondary nucleation. Cryst Growth Des 2004; 4: 1061-1068.
89. Ono T et al. Quantitative measurement of the polymorphic transformation of L-glutamic acid using in-situ Raman spectroscopy. Cryst Growth Des 2004; 4: 465-469.
90. Schöll J et al. In situ monitoring and modeling of the solvent-mediated polymorphic transformation of L-glutamic acid. Cryst Growth Des 2006; 6: 881-891.
91. Wang F et al. An investigation of solvent mediated polymorphic transformation of progesterone using in situ Raman spectroscopy. Org Proc Res Dev 2000; 4: 391-395.
92. Hu YR et al. Estimation of the transition temperature for an enantiotropic polymorphic system from the transformation kinetics monitored using Raman spectroscopy. J Pharm Biomed Anal 2007; 45: 546-551.
93. O'Brien LE et al. Use of in situ FT-Raman spectroscopy to study the kinetics of the transformation of carbamazepine polymorphs. J Pharm Biomed Anal 2004; 36: 335-340.
94. Gamberini MC et al. Solid state characterization of chloramphenicol palmitate. Raman spectroscopy applied to pharmaceutical polymorphs. J Mol Struct 2006; 785: 216-224.
95. Gamberini MC et al. Vibrational study of tamoxifen citrate polymorphism. J Mol Struct 2007; 840: 29-37.
96. Ali HRH et al. Vibrational spectroscopic characterisation of salmeterol xinafoate polymorphs and a preliminary investigation of their transformation using simultaneous in situ portable Raman spectroscopy and differential scanning calorimetry. Anal Chim Acta 2008; 620: 103-112.
97. Kauffman JF et al. Raman detected differential scanning calorimetry of polymorphic transformations in acetaminophen. J Pharm Biomed Anal 2008; 48: 1310-1315.
98. Wildfong PLD et al. Demonstration of a shear-based solid-state phase transformation in a small molecular organic system: Chlorpropamide. J Pharm Sci 2007; 96: 1100-1113.
99. De Beer TRM et al. Implementation of a process analytical technology system in a freeze-drying process using Raman Spectroscopy for in-line process monitoring. Anal Chem 2007; 79: 7992-8003.
100. Romero-Torres S et al. Monitoring of mannitol phase behavior during freeze-drying using non-invasive Raman spectroscopy. PDA J Pharm Sci Technol 2007; 61: 131-145.
101. Norris T et al. Determination of end-points for polymorph conversions of crystalline organic compounds using on-line near-infrared spectroscopy. Analyst 1997; 122: 549-552.
102. Févotte G et al. Applications of NIR spectroscopy to monitoring and analyzing the solid state during industrial crystallization processes. Int J Pharm 2004; 273: 159-169.
103. Aaltonen J et al. Polymorph screening using near-infrared spectroscopy. Anal Chem 2003; 75: 5267-5273.
104. Li WY et al. Determination of polymorph conversion of an active pharmaceutical ingredient in wet granulation using NIR calibration models generated from the premix blends. J Pharm Sci 2005; 94: 2800-2806.
105. Desai SR et al. Thermoanalytical study of polymorphic transformation in fluconazole drug. Thermochim Acta 2003; 399: 81-89.
106. Rossi A et al. Solid-state characterization of paracetamol metastable polymorphs formed in binary mixtures with hydroxypropylmethylcellulose. Thermochim Acta 2003; 406: 55-67.
107. Févotte G. New perspectives for the on-line monitoring of pharmaceutical crystallization processes using in situ infrared spectroscopy. Int J Pharm 2002; 241: 263-278.
108. Shakhtshneider TP. Phase transformations and stabilization of metastable states of molecular crystals under mechanical activation. Solid State Ionics 1997; 101: 851-856.
109. Chieng N et al. Effect of milling conditions on the solid-state conversion of ranitidine hydrochloride form 1. Int J Pharm 2006; 327: 36-44.
110. Cheng W-T, Lin S-Y. Famotidine polymorphic transformation in the grinding process significantly depends on environmental humidity or water content. Int J Pharm 2008; 357: 164-168.
111. Cheng W-T et al. Raman microspectroscopic mapping or thermal system used to investigate milling-induced solid-state conversion of famotidine polymorphs. J Raman Spectrosc 2007; 38: 1595-1601.
112. Bauer-Brandl A. Polymorphic transitions of cimetidine during manufacture of solid dosage forms. Int J Pharm 1996; 140: 195-206.
113. Zeitler JA et al. Characterization of temperature-induced phase transitions in five polymorphic forms of sulfathiazole by terahertz pulsed spectroscopy and differential scanning calorimetry. J Pharm Sci 2006; 95: 2486-2498.
114. Upadhya PC et al. Characterization of crystalline phase-transformations in theophylline by time-domain terahertz spectroscopy. Spectrosc Lett 2006; 39: 215-224.
115. Herman J et al. Formation of theophylline monohydrate during the pelletization of microcrystalline cellulose anhydrous theophylline blends. Int J Pharm 1988; 42: 15-18.
116. Ando H et al. Effect of moisture on crystallization of theophylline in tablets. Drug Dev Ind Pharm 1992; 18: 453-467.
117. Otsuka M et al. Effect of geometric factors on hydration kinetics of theophylline anhydrate tablets. J Pharm Sci 1992; 81: 1189-1193.
118. Räsänen E et al. Novel identification of pseudopolymorphic changes of theophylline during wet granulation using near infrared spectroscopy. J Pharm Sci 2001; 90: 389-396.
119. Jørgensen A et al. Hydrate formation during wet granulation studied by spectroscopic methods and multivariate analysis. Pharm Res 2002; 19: 1285-1291.
120. Wikström H et al. In-line monitoring of hydrate formation during wet granulation using Raman spectroscopy. J Pharm Sci 2005; 94: 209-219.
121. Aaltonen J et al. In situ measurement of solvent-mediated phase transformations during dissolution testing. J Pharm Sci 2006; 95: 2730-2737.
122. Lehto P et al. Simultaneous measurement of liquid-phase and solid-phase transformation kinetics in rotating disc and channel flow cell dissolution devices. Int J Pharm 2008; 363: 66-72.
123. Vora KL et al. The use of dynamic vapour sorption and near infra-red spectroscopy (DVS-NIR) to study the crystal transitions of theophylline and the report of a new solid-state transition. Eur J Pharm Sci 2004; 22: 97-105.
124. Amado AM et al. Probing pseudopolymorphic transitions in pharmaceutical solids using Raman spectroscopy: hydration and dehydration of theophylline. J Pharm Sci 2007; 96: 1366-1379.
125. Tian F et al. Characterizing the conversion kinetics of carbamazepine polymorphs to the dihydrate in aqueous suspension using Raman spectroscopy. J Pharm Biomed Anal 2006; 40: 271-280.
126. Qu HY et al. Solvent-mediated phase transformation kinetics of an anhydrate/hydrate system. Cryst Growth Des 2006; 6: 2053-2060.
127. Mirza S et al. Solid-state properties and relationship between anhydrate and monohydrate of baclofen. J Pharm Sci 2007; 96: 2399-2408.
128. Krzyzaniak JF et al. Identification of phase boundaries in anhydrate/hydrate systems. J Pharm Sci 2007; 96: 1270-1281.
129. Hausman DS et al. Application of on-line Raman spectroscopy for characterizing relationships between drug hydration state and tablet physical stability. Int J Pharm 2005; 299: 19-33.
130. Aaltonen J et al. In-line monitoring of solid-state transitions during fluidisation. Chem Eng Sci 2007; 62: 408-415.
131. Kogermann K et al. Establishing quantitative in-line analysis of multiple solid-state transformations during dehydration. J Pharm Sci 2008; 97: 4983-4999.
132. Römer M et al. Phase transformation of erythromycin A dihydrate during fluid bed drying. J Pharm Sci 2008; 97: 4020-4029.
133. Römer M et al. Phase transformations of erythromycin A dihydrate during pelletisation and drying. Eur J Pharm Biopharm 2007; 67: 246-252.
134. Miroshnyk I et al. Insight into thermally induced phase transformations of erythromycin A dihydrate. Cryst Growth Des 2006; 6: 369-374.
135. Kogermann K et al. Qualitative in situ analysis of multiple solid-state forms using spectroscopy and partial least squares discriminant modeling. J Pharm Sci 2007; 96: 1802-1820.
136. Tan WJ, Widjaja E. Multivariate chemometric approach to thermal solid-state FT-IR monitoring of pharmaceutical drug compound. J Pharm Sci 2008; 97: 3379-3387.
137. Kojima T et al. Evaluation of hydrate formation of a pharmaceutical solid by using diffuse reflectance infrared Fourier-transform spectroscopy. J Pharm Biomed Anal 2008; 46: 788-791.
138. Sardo M et al. Pseudopolymorphic transitions of niclosamide monitored by Raman spectroscopy. J Raman Spectrosc 2008; 39: 1915-1924.
139. Wardrop J et al. Influence of solid phase and formulation processing on stability of Abbott-232 tablet formulations. J Pharm Sci 2006; 95: 2380-2392.
140. Giordano F et al. Thermal behavior of paracetamol-polymeric excipients mixtures. J Therm Anal Cal 2002; 68: 575-590.
141. Okumura T, Otsuka M. Evaluation of the microcrystallinity of a drug substance, indomethacin, in a pharmaceutical model tablet by chemometric FT-Raman spectroscopy. Pharm Res 2005; 22: 1350-1357.
142. Marsac PJ et al. Spontaneous crystallinity loss of drugs in the disordered regions of poly(ethylene oxide) in the presence of water. J Pharm Sci 2008; 97: 3182-3194.
143. Chan KLA et al. Polymorphism and devitrification of nifedipine under controlled humidity: a combined FT-Raman, IR and Raman microscopic investigation. J Raman Spectrosc 2004; 35: 353-359.
144. Zeitler JA et al. Relaxation and crystallization of amorphous carbamazepine studied by terahertz pulsed spectroscopy. J Pharm Sci 2007; 96: 2703-2709.
145. Heinz A et al. Understanding the solid-state forms of fenofibrate - a spectroscopic and computational study. Eur J Pharm Biopharm 2009; 71: 100-108.
146. SavolainenMet al. Better understanding of dissolution behaviour of amorphous drugs by in situ solid-state analysis using Raman spectroscopy. Eur J Pharm Biopharm 2009; 71: 71-79.