Thermal Analysis and Calorimetric Methods for the Characterization of New Crystal Forms

Preformulation in Solid Dosage Form Development

Volumn , Issue , 2008, Pages 279-321

  Murphy, Denette K ^a   Rabel, Shelley ^b  

^a BRISTOL MYERS SQUIBB   (United States)

^b ALZA CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 75449113115     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.3109/9780849360862-14     Document Type: Chapter

References (73)

1. Byrn SR, Ralph PR, Joseph SG. Solid-state Chemistry of Drugs. 2nd ed. West Lafayette: SSCI Inc, 1999:574.
2. Brittain HG. Polymorphism in Pharmaceutical Solids. New York: Marcel Dekker, 1999.
3. Haleblian J, McCrone W. Pharmaceutical applications of polymorphism. J Pharm Sci 1969; 58(8):911-929.
4. Bernstein J. Polymorphism in Molecular Crystals. International Union of Crystallography Monographs on Crystallography 14. Oxford: Oxford University Press, 2002:410.
5. Yu L, Reutzel SM, Stephenson GA. Physical characterization of polymorphic drugs: an integrated characterization strategy. Pharm Sci Technol Today 1998; 1(3):118-27.
6. Rodríguez-Spong B, Price CP, Jayasankar A, Matzger AJ, Rodríguez-Hornedo N. General principles of pharmaceutical solid polymorphism: a supramolecular perspective. Adv Drug Delivery Rev 2004; 56(3):241-74.
7. Burger A, Ramberger R. On the polymorphism of pharmaceuticals and other molecular crystals. I. Theory of thermodynamic rules. Mikrochimica Acta 1979; 2(3-4):259-71.
8. Burger A, Ramberger R. On the polymorphism of pharmaceuticals and other molecular crystals. II. Applicability of thermodynamic rules. Mikrochimica Acta 1979; 2(3-4):273-316.
9. Burger A. Thermodynamic and other aspects of the polymorphism of drugs. Pharm Int 1982; 3(5):158-63.
10. Grunenberg A, Henck JO, Siesler HW. Theoretical derivation and practical application of energy/temperature diagrams as an instrument in preformulation studies of polymorphic drug substances. Int J Pharm 1996; 129 (147-58).
11. Yu L, Stephenson GA, Mitchell CA, et al. Thermochemistry and conformational polymorphism of a hexamorphic crystal system. J Am Chem Soc 2000; 122(4):585-91.
12. Yu L. Inferring thermodynamic stability relationship of polymorphs from melting data. J Pharm Sci 1995; 84(8):966-74.
13. Richardson MJ. The derivation of thermodynamic properties by DSC: free energy curves and phase stability. Thermochim Acta 1993; 229:1-14.
14. Van Hecke GR, Kaji K, Sorai M. Heat capacity of the discotic mesogen, 2,3,6,7,10,11-hexa-n-octanoyloxytriphenylene: a complex solid-state polymorphism. Mol Cryst Liq Cryst 1986; 136(2-4):197-220.
15. McCrone WC. Fusion Methods in Chemical Microscopy. New York: Interscience Publishers, Inc., 1957.
16. Behme RJ, Brooke D. Heat of fusion measurement of a low melting polymorph of carbamazepine that undergoes multiple-phase changes during differential scanning calorimetry analysis. J Pharm Sci 1991; 80(10):986-90.
17. Giron D. Thermal analysis and calorimetric methods in the characterisation of polymorphs and solvates. Thermochim Acta 1995; 248:1-59.
18. Gu CH, Grant DJW. Estimating the relative stability of polymorphs and hydrates from heats of solution and solubility data. J Pharm Sci 2001; 90(9): 1277-87.
19. Byrn SR, Lin CT. The effect of crystal packing and defects on desolvation of hydrate crystals of caffeine and L-(-)-1,4 cyclohexane-1-alanine. J Am Chem Soc 1976; 98:4004-5.
20. Lin CT, Byrn SR. Desolvation of solvated organic crystals. Mol Cryst Liq Cryst 1979; 50:99-104.
21. Taylor LS, York P. Characterization of the phase transitions of trehalose dihydrate on heating and subsequent dehydration. J Pharm Sci 1998; 87(3): 347-55.
22. Giron D. Contribution of thermal methods and related techniques to the rational development of pharmaceuticals part 1. Pharm Sci Technol Today 1998; 1(5):191-9.
23. Morris KR, Rodríguez-Hornedo N. Hydrates. In: Swarbrick J, ed. Encyclopedia of Pharmaceutical Technology. New York: Marcel Dekker, Inc., 1993.
24. TA Instruments. DSC 2920 Differential Scanning Calorimeter Operator’s Manual. New Castle: TA Instruments, 1995.
25. Griesser UJ, Burger A. The effect of water vapor pressure on desolvation kinetics of caffeine 4/5-hydrate. Int J Pharm 1995; 120:83-93.
26. Suzuki E, Shirotani K, Tsuda Y, Sekiguchi K. Studies on methods of particle size reduction of medicinal compound: XXIII. Water content and dehydration behavior of crystalline caffeine hydrate. Chem Pharm Bull 1985; 33:5028-35.
27. Wendlandt WW. Thermal analysis. In: Winefordner IM, ed. Chemical Analysis: a Series on Monographs in Analytical Chemistry and Its Applications. 3rd ed. Vol. 19. New York: John Wiley & Sons, 1964:814.
28. Morris KR. Structural aspects of hydrates and solvates. In: Brittain HG, ed. Polymorphism in Pharmaceutical Solids. New York: Marcel Dekker, Inc., 1999.
29. Zhu H, Grant DJW. Dehydration behavior of nedocromil magnesium pentahydrate. Int J Pharm 2001; 215:251-62.
30. Monkhouse DC, Van Campen L. Solid-state reactions-theoretical and experimental aspects. Drug Dev Ind Pharm 1984; 10(8-9):1175-276.
31. Ford JL, Timmins P. Pharmaceutical thermal analysis techniques and applications. In: Rubinstein MH, ed. Ellis Horwood Series in Pharmaceutical Technology. Chichester: Ellis Horwood Limited, 1989:313.
32. Han J, Suryanarayanan R. Influence of environmental conditions on the kinetics and mechanism of dehydration of carbamazepine dihydrate. Pharm Dev Technol 1998; 3(4):587-96.
33. Zhu H, Xu J, Varlashkin P, Long S, Kidd C. Dehydration, hydration behavior, and structural analysis of fenoprofen calcium. J Pharm Sci 2001; 90(7):845-59.
34. Taylor LS, York P. Effect of particle size and temperature on the dehydration kinetics of trehalose dihydrate. Int J Pharm 1998; 167:215-21.
35. Sheng J, Venkatesh GM, Duddu SP, Grant DJW. Dehydration behavior of eprosartan dihydrate. J Pharm Sci 1999; 88(10):1021-29.
36. Vyazovkin S, Wight CA. Isothermal and noniosthermal reaction kinetics in solids: in search of ways toward consensus. J Phys Chem 1997; 101:8279-8284.
37. Vyazovkin S, Wight CA. Kinetics in solids. Annu Rev Phys Chem 1997; 48: 125-49.
38. Zhou D, Schmitt EA, Zhang GGZ, et al. Model-free treatment of the dehydration kinetics of nedocromil sodium trihydrate. J Pharm Sci 2003; 92(7): 1367-76.
39. Dong Z, Salsbury JS, Zhou D, et al. Dehydration kinetics of neotame monohydrate. J Pharm Sci 2002; 91(6):1423-31.
40. Foreman J, Sauerbrunn SR, Marcozzi CL. Exploring the sensitivity of thermal analysis techniques to the glass transition. TA Instruments, Application Note TA-082.
41. Hancock BC, Zografi G. Characterization and significance of the amorphous state in pharmaceutical systems. J Pharm Sci 1997; 86:1-11.
42. Rabel SR, JA Jona, Maurin MB. Applications of modulated differential scanning calorimetry in preformulation studies. J Pharm Biomed Anal 1999; 21: 339-45.
43. Shamblin SL, Zografi G. Enthalpy relaxation in binary amorphous mixtures containing sucrose. Pharm Res 1998; 15(12):1828-34.
44. Coleman NJ, Craig DQM. Modulated temperature differential scanning calorimetry: a novel approach to pharmaceutical thermal analysis. Int J Pharm 1996; 135:13-29.
45. Saleki-Gerhardt A, Ahlneck C, Zografi G. Assessment of disorder in crystalline solids. Int J Pharm 1994; 101:237-47.
46. Duddu SP, Grant DJW. The use of thermal analysis in the assessment of crystal disruption. Thermochim Acta 1995; 248:131-45.
47. Pikal MJ, Lukes AL, Lang JE, Gaines K. Quantitative crystallinity determinations for b-lactam antibiotics by solution calorimetry: correlations with stability. J Pharm Sci 1978; 67(6):767-73.
48. Gao D, Rytting JH. Use of solution calorimetry to determine the extent of crystallinity of drugs and excipients. Int J Pharm 1997; 151(2):183-92.
49. Venkatesh GM, Barnett ME, Owusu-Fordjour C, Galop M. Detection of low levels of the amorphous phase in crystalline pharmaceutical materials by thermally stimulated current spectrometry. Pharm Res 2001; 18(1):98-103.
50. Briggner LE, Buckton G, Bystrom K, Darcy P. The use of isothermal microcalorimetry in the study of changes in crystallinity induced during the processing of powders. Int J Pharm 1994; 105(2):125-35.
51. Lehto VP, Laine E. Simultaneous determination of the heat and the quantity of vapor sorption using a novel microcalorimetric method. Pharm Res 2000; 17(6): 701-6.
52. Buckton G, Dove JW, Davies P. Isothermal microcalorimetry and inverse phase gas chromatography to study small changes in powder surface properties. Int J Pharm 1999; 193(1):13-9.
53. Ahmed H, Buckton G, Rawlins DA. The use of isothermal microcalorimetry in the study of small degrees of amorphous content of a hydrophobic powder. Int J Pharm 1996; 130(2):195-201.
54. Royall PG, Kett VL, Andrews CS, Craig DQM. Identification of crystalline and amorphous regions in low molecular weight materials using microthermal analysis. J Phys Chem B 2001; 105(29):7021-6.
55. Vitez IM, Newman AW, Davidovich M, Kiesnowski C. The evolution of hotstage microscopy to aid solid-state characterizations of pharmaceutical solids. Thermochim Acta 1998; 324(1-2):187-96.
56. Wang SL, Lin SY, Chen TF. Thermal-dependent dehydration process and intramolecular cyclization of lisinopril dihydrate in the solid state. Chem Pharm Bull 2000; 48(12):1890-3.
57. Wilson RJ, Beezer AE, Mitchell JC, Loh W. Determination of thermodynamic and kinetic parameters from isothermal heat conduction microcalorimetry: application to long-term reaction studies. J Phys Chem 1995; 99:7108-13.
58. Ng WL. Thermal decomposition in the solid state. Aust J Chem 1975; 281169-78.
59. Pikal MJ, Dellerman KM. Stability testing of pharmaceuticals by highsensitivity isothermal calorimetry at 25_C: cephalosporins in the solid and aqueous solution states. Int J Pharm 1989; 50(3):233-52.
60. Vickery RD, Maurin MB. Utility of microcalorimetry in the characterization of the browning reaction. J Pharm Biomed Anal 1999; 20:385-8.
61. Lehto VP, Salonen J, Laine E. Real time detection of photoreactivity in pharmaceutical solids and solutions with isothermal microcalorimetry. Pharm Res 1999; 16(3):368-73.
62. A review of DSC kinetics methods. New Castle: TA Instruments, Application Note TA-073.
63. Borchardt HJ, Daniels FJ. The application of differential thermal analysis to the study of reaction kinetics. J Am Chem Soc 1957; 79(1):41-6.
64. Swarin SJ, Wims AM. A method for determining reaction kinetics by differential scanning calorimetry. Anal Calorim 1977; 4:155-71.
65. Ozawa T. Kinetic analysis of derivative curves in thermal analysis. J Therm Anal 1970; 2(3):301-24.
66. McDaid FM, Barker SA, Fitzpatrick S, Petts CR, Craig DQM. Further investigations into the use of high sensitivity differential scanning calorimetry as a means of predicting drug-excipient interactions. Int J Pharm 2003; 252: 235-40.
67. Van Dooren AA, Mueller BW. Purity determinations of drugs with differential scanning calorimetry (DSC)-a critical review. Int J Pharm 1984; 20(3):217-33.
68. Van Dooren AA, Mueller BW. Effects of experimental variables on purity determinations with differential scanning calorimetry. Thermochim Acta 1983; 66(1-3):161-86.
69. Marti EE. Purity determination by differential scanning calorimetry. Thermochimica Acta 1972; 5:173-220.
70. Giron D. Thermal analysis of drugs and drug products. In: Swarbrick J, ed. Encyclopedia of Pharmaceutical Technology. New York: Marcel Dekker, 1996.
71. Cassel RB. Purity determination and DSC TzeroTM Technology. New Castle: TA Instruments:8.
72. Joy EF, Bonn JD, Bernard AJ Jr. Differential scanning calorimetric assessment of high purity. Thermochimica Acta 1971; 2(1):57-68.
73. Hints for good purity determination. New Castle: TA Instruments. Thermal Application Note.