Thermodynamics, molecular mobility and crystallization kinetics of amorphous griseofulvin

Molecular Pharmaceutics

Volumn 5, Issue 6, 2008, Pages 927-936

  Zhou, Deliang ^a   Zhang, Geoff G Z ^a   Law, Devalina ^a   Grant, David J W ^b   Schmitt, Eric A ^a,c  

^a ABBOTT LABORATORIES   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

^c ABBOTT LABORATORIES   (United States)

Author keywords

Amorphous; Crystallization; Griseofulvin; John mehl avrami (JMA); Molecular mobility; Nucleation; Stability

Indexed keywords

GRISEOFULVIN;

ARTICLE; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG FORMULATION; DRUG STABILITY; DRUG STRUCTURE; ENTROPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR DYNAMICS; PHASE TRANSITION; PHOTOCHEMICAL QUENCHING; PRIORITY JOURNAL; THERMAL ANALYSIS; THERMODYNAMICS; THERMOSTABILITY; X RAY DIFFRACTION;

ANTIBIOTICS, ANTIFUNGAL; CALORIMETRY, DIFFERENTIAL SCANNING; CRYSTALLIZATION; DRUG STABILITY; GLASS; GRISEOFULVIN; HEATING; KINETICS; MOLECULAR STRUCTURE; MOTION; THERMODYNAMICS; TRANSITION TEMPERATURE;

EID: 64649098724     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp800169g     Document Type: Article

References (48)

1. Pikal, M. J.; Lukes, A. L.; Lang, J. E.; Gaines, K. Quantitative crystallinity determinations for /?-lactam antibiotics by solution calorimetry: Correlations with stability. J. Pharm. Sci. 1978, 67, 767-772.
2. Aso, Y.; Yoshioka, S.; Otsuka, T.; Kojima, S. The physical stability of amorphous nifedipine determined by isothermal microcalorimetry. Chem. Pharm. Bull. 1995, 43, 300-303.
3. Hancock, B. C.; Shamblin, S. L.; Zografi, G. Molecular mobility of amorphous pharmaceutical solids below their glass transition temperature. Pharm. Res. 1995, 12, 799-806.
4. Hancock, B. C.; Zografi, G. Characteristics and significance of the amorphous state in pharmaceutical systems. J. Pharm. Sci. 1997, 86, 1-12.
5. Duddu, S. P.; Zhang, G.; Dal Monte, P. R. The relationship between protein aggregation and molecular mobility below the glass transition temperature of lyophilized formulations containing a monoclonal antibody. Pharm. Res. 1997, 14, 596-600.
6. Shamblin, S. L.; Tang, X.; Chang, L.; Hancock, B. C.; Pikal, M. J. Characterization of the time scales of molecular motion in pharmaceutically important glasses. J. Phys. Chem. 1999, 103B, 4113-4121.
7. Yoshioka, S.; Aso, Y.; Kojima, S. Temperature dependence of bimolecular reactions associated with molecular mobility in lyophilized formulations. Pharm. Res. 2000, 17, 925-929.
8. Aso, Y.; Yoshioka, S.; Kojima, S. Explanation of the crystallization rate of amorphous nifedipine and phenobarbital from their molecular mobility as measured by 13C nuclear magnetic resonance relaxation time and the relaxation time obtained from the heating rate dependence of the glass transition temperature. J. Pharm. Sci. 2001, 90, 798-806.
9. Guo, Y.; Byrn, S. R.; Zografi, G. Physical characteristics and chemical degradation of amorphous quinapril hydrochloride. J. Pharm. Sci. 2000, 89, 128-143.
10. Yoshioka, S.; Aso, Y. A quantitative assessment of the significance of molecular mobility as a determinant for the stability of lyophilized insulin formulation. Pharm. Res. 2005, 22, 1358-1364.
11. Yoshioka, S.; Aso, Y.; Miyazaki, T. Negligible contribution of molecular mobility to the degradation rate of insulin lyophilized with poly(vinylpyrrolidone). J. Pharm. Sci. 2006, 95, 939-13.
12. Zhou, D.; Zhang, G. G. Z.; Law, D.; Grant, D. J. W.; Schmitt, E. A. Physical stability of amorphous pharmaceuticals: Importance of configurational thermodynamic quantities and molecular mobility. J. Pharm. Sci. 2002, 91, 1863-1872.
13. Zhou, D.; Grant, D. J. W.; Zhang, G. G. Z.; Law, D.; Schmitt, E. A. A calorimetric investigation of thermodynamic and molecular mobility contributions to the physical stability of two pharmaceutical glasses. J. Pharm. Sci. 2007, 96, 71-83.
14. Moynihan, C. T.; Easteal, A. J.; Wilder, J.; Tucker, J. Dependence of the glass transition temperature on heating and cooling rate. J. Phys. Chem. 1974, 78, 2673-2677.
15. Moynihan, C. T.; S.-K., L.; Tatsumisago, M.; Minami, T. Estimation of activation energies for structural relaxation and viscous flow from DTA and DSC experiments. Thermochim. Acta 1996, 280-281, 153-162.
16. Townley, E.; Roden, P. High-performance liquid chromatographic analysis of griseofulvin in drug substance and solid dosage forms: Separation of impurities and metabolites. J. Pharm. Sci. 1980, 69, 523-526.
17. Hodge, I. M. Enthalpy relaxation and recovery in amorphous materials. J. Non-Cryst. Solids 1994, 169, 211-266.
18. Tool, A. Q.; Eichlin, C. G. Variations caused in the heating curves of glass by heat treatment. J. Am. Ceram. Soc. 1931, 14, 276-308.
19. Tool, A. Q. Relation between inelastic deformability and thermal expansion of glass in its annealing range. J. Am. Ceram. Soc. 1946, 29, 240-253.
20. Ritland, H. N. Limitations of the fictive temperature concept. J. Am. Ceram. Soc. 1956, 39, 403-406.
21. Narayanaswamy, O. S. Model of structural relaxation in glass. J. Am. Ceram. Soc. 1971, 54, 491-498.
22. Scherer, G. W. Use of the Adam-Gibbs equation in the analysis of structural relaxation. J. Am. Ceram. Soc. 1984, 67, 504-511.
23. Hodge, I. M. Effects of annealing and prior history on enthalpy relaxation in glassy polymers. 6. Adam-Gibbs formulation of nonlinearity. Macromolecules 1987, 20, 2897-2908.
24. Avrami, M. Kinetics of phase change. I. General theory. J. Chem. Phys. 1939, 7, 1103-1112.
25. Avrami, M. Kinetics of phase change. II. Transformation-time relations for random distribution of nuclei. J. Chem. Phys. 1940, 8, 212-224.
26. Avrami, M. Kinetics of phase change. III. Granulation, phase change, and microstructure. J. Chem. Phys. 1941, 9, 177-184.
27. Johnson, W. A.; Mehl, R. F. Reaction kinetics in processes of nucleation and growth. Trans. Am. Inst. Min. Metall. Eng. 1939, 135, 416-442.
28. Maffezzoli, A.; Kenny, J. M.; Torre, L. On the physical dimensions of the Avrami constant. Thermochim. Acta 1995, 269/270, 185-190.
29. Schmitt, E. A.; Law, D.; Zhang, G. G. Z. Nucleation and crystallization kinetics of hydrated amorphous lactose above the glass transition temperature. J. Pharm. Sci. 1999, 88, 291-296.
30. Woldt, E. The relationship between isothermal and nonisothermal description of Johnson-Mehl-Avrami-Kolmogorov kinetics. J. Phys. Chem. Solids 1992, 53, 521-527.
31. Kissinger, H. E. Variation of peak temperature with heating rate in differential thermal analysis. J. Res. Natl. Bur. Stand. 1956, 57, 217-221.
32. Kissinger, H. E. Reaction kinetics in differential thermal analysis. Anal. Chem. 1957, 29, 1702-1706.
33. Doolittle, A. K. Studies in Newtonian flow. II. The dependence of the viscosity of liquids on free-space. J. Appl. Phys. 1951, 22, 1471-1475.
34. Cohen, M. H.; Turnbull, D. Molecular transport in liquids and glasses. J. Chem. Phys. 1959, 31, 1164-1169.
35. Turnbull, D.; Cohen, M. H. Free-volume model of amorphous phase glass transitions. J. Chem. Phys. 1961, 34, 120-125.
36. Turnbull, D.; Cohen, M. H. On free-volume model of liquid-glass transitions. J. Chem. Phys. 1970, 52, 3038-3041.
37. Goldstein, M. Viscous liquids and the glass transition. V. Sources of the excess specific heat of the liquid. J. Chem. Phys. 1976, 64, 4767-4774.
38. Byrn, S. R.; Pfeiffer, R. R. and Stowell, J. G. Solid-State Chemistry of Drugs, 2nd ed.; SSCI Inc: West Lafayette, IN, 1999,; p 452.
39. Zhou, D.; Schmitt, E. A.; Zhang, G. G.; Law, D.; Vyazovkin, S.; Wight, C. A.; Grant, D. J. W. Crystallization kinetics of amorphous nifedipine studied by model-fitting and model-free approaches. J. Pharm. Sci. 2003, 92, 1779-1792.
40. Zhou, D.; Grant, D. J. W. Model dependence of the activation energy derived from nonisothermal kinetic data. J. Phys. Chem. 2004, 108A, 4239-4246.
41. Vyazovkin, S.; Wight, C. A. Isothermal and non-isothermal kinetics of thermally stimulated reactions of solids. Int. Rev. Phys. Chem. 1998, 17, 407-433.
42. Fujara, F.; Geil, B.; Sillescu, H.; Fleischer, G. Translational and rotational diffusion in supercooled orthoterphenyl close to the glass transition. Z. Phys. B 1992, 88, 195-204.
43. Ngai, K. L.; Magill, J. H.; PLazek, D. J. Flow, diffusion and crystallization of supercooled liquid: Revisited. J. Chem. Phys. 2000, 112, 1887-1892.
44. Hikima, T.; Adachi, Y.; Hanaya, M.; Oguni, M. Determination of potentially homogeneous-nucleation-based crystallization in o-terphenyl and an interpretation of the nucleation-enhancement mechanism. Phys. Rev.B1995, 52, 3900-8.
45. Wu, T.; Yu, L. Origin of enhanced crystal growth kinetics near Tg probed with indomethacin polymorphs. J. Phys. Chem. B 2006, 110, 15694-15699.
46. g without and with polyvinylpyrrolidone. J. Pharm. Sci. 2007, 96, 1131-1138.
47. Sun, Y.; Xi, H.; Chen, S.; Ediger, M. D.; Yu, L. Crystallization near glass transition: transition from diffusion-controlled to diffusionless crystal growth studied with seven polymorphs. J. Phys. Chem. 2008, 112, 661-664.
48. Sun, Y.; Xi, H.; Ediger, M. D.; Yu, L. Diffusionless crystal growth from glass has precursor in equilibrium liquid. J. Phys. Chem. B 2008, 112, 661-664.