Investigation of the impact of annealing on global molecular mobility in glasses: Optimization for stabilization of amorphous pharmaceuticals

Journal of Pharmaceutical Sciences

Volumn 97, Issue 9, 2008, Pages 3865-3882

  Luthra, Suman A ^a   Hodge, Ian M ^b   Pikal, Michael J ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b ROCHESTER INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Aging; Annealing; Differential scanning calorimetry; Distribution of relaxation times; Enthalpy relaxation; Glass; Glass transition; Isothermal microcalorimetry; Kohlraush Williams Watts (KWW) equation; Lyophilization; Pharmaceutical stability; Relaxation time

Indexed keywords

ASPARTAME; GLASS; POVIDONE; SUCROSE; TREHALOSE;

ARTICLE; DIFFERENTIAL SCANNING CALORIMETRY; ENTHALPY; FREEZE DRYING; ISOTHERM; MICROCALORIMETRY; MOLECULAR DYNAMICS;

EID: 53549127558     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21255     Document Type: Article

References (51)

1. Luthra S, Hodge IM, Pikal MJ. 2007. Effects of annealing on enthalpy relaxation in lyophilized disaccharide formulations: Mathematical modeling of DSC curves. (in press).
2. Hancock BC, Zografi G. 1997. Characteristics and significance of the amorphous state in pharmaceutical systems. J Pharm Sci 86:1-12.
3. Guo Y, Byrn SR, Zografi G. 2000. Physical characteristics and chemical degradation of amorphous quinapril hydrochloride. J Pharm Sci 89:128-143.
4. Shamblin SL, Hancock BC, Pikal MJ. 2006. Coupling between chemical reactivity and structural relaxation in pharmaceutical glasses. Pharm Res 23:2254-2268.
5. Duddu SP, Zhang G, Dal Monte PR. 1997. The relationship between protein aggregation and molecular mobility below the glass transition temperature of lyophilized formulations containing a monclonal antibody. Pharm Res 14:596-600.
6. Yoshioka S, Tajima S, Aso Y, Kojima S. 2003. Inactivation and aggregation of b-galactosidase in lyophilized formulation described by Kohlrausch-Williams- Watts stretched exponential function. Pharm Res 20:1655-1660.
7. Alie J, Menegotto J, Cardon P, Duplaa H, Caron A, Lacabanne C, Bauer M. 2004. Dielectric study of the molecular mobility and the isothermal crystallization kinetics of an amorphous pharmaceutical drug substance. J Pharm Sci 93:218-233.
8. Bhugra C, Shmeis R, Krill SL, Pikal MJ. 2006. Predictions of onset of crystallization from experimental relaxation times I-correlation of molecular mobility from temperatures above the glass transition to temperatures below the glass transition. Pharm Res 23:2277-2290.
9. Yoshioka S, Aso Y. 2005. A quantitative assessment of the significance of molecular mobility as a determinant for the stability of lyophilized insulin formulations. Pharm Res 22:1358-1364.
10. Chang L, Shepherd D, Sun J, Ouellette D, Grant KL, Tang X, Pikal MJ. 2005. Mechanism of protein stabilization by sugars during freeze-drying and storage: Native structure preservation, specific interaction, and/or immobilization in a glassy matrix? J Pharm Sci 94:1427-1444.
11. Abdul-Fattah Ahmad M, Dellerman Karen M, Bogner Robin H, Pikal Michael J. 2006. The effect of annealing on the stability of amorphous solids: Chemical stability of freeze-dried Moxalactam. J Pharm Sci 96(5):1237-1250.
12. Hill SA, MacNaughtan W, Farhat LA, Noel TR, Parker R, Ring SG, Whitcombe MJ. 2005. The effect of thermal history on the Maillard reaction in a glassy matrix. J Agric Food Chem 53:10213-10218.
13. Pikal MJ, Reddy RD, Shalaev EY, Ziegler CB. 2005. Method of stabilizing disordered cefovecin sodium salt using thermal annealing. ed.: 2005-IB955 [2005102274] Pfizer Products, Inc., USA. p 19.
14. Mardaleishvili IR, Anisimov VM. 1987. b-Transition and relaxation of impurities in molecules in their reactions in glass polymers. Izvestiya Akademii NaukSSSR, Seriya Khimicheskaya 6:1431-1432.
15. Hodge IM. 1995. Physical aging in polymer glasses. Science 267:1945-1947.
16. Hutchinson JM. 1995. Physical aging of polymers. Prog Polym Sci 20:703-760.
17. Andronis V, Zografi G. 1997. Molecular mobility of supercooled amorphous indomethacin, determined by dynamic mechanical analysis. Pharm Res 14: 410-414.
18. Badii F, Martinet C, Mitchell JR, Farhat IA. 2006. Enthalpy and mechanical relaxation of glassy gelatin films. Food Hydrocolloids 20:879-884.
19. Carpentier L, Decressain R, Gusseme A, Neves C, Descamps M. 2006. Molecular mobility in glass forming fananserine: A dielectric, NMR, and TMDSC investigation. Pharm Res 23:798-805.
20. Masuda K, Tabata S, Sakata Y, Hayase T, Yonemochi E, Terada K. 2005. Comparison of molecular mobility in the glassy state between amorphous indomethacin and salicin based on spin-lattice relaxation times. Pharm Res 22:797-805.
21. Aso Y, Yoshioka S. 2006. Molecular mobility of nifedipine-PVP and phenobarbital-PVP solid dispersions as measured by 13C-NMR spin-lattice relaxation time. J Pharm Sci 95:318-325.
22. Yoshioka S, Aso Y, Kojima S. 2002. Different molecular motions in lyophilized protein formulations as determined by laboratory and rotating frame spin-lattice relaxation times. J Pharm Sci 91:2203-2210.
23. Gunawan L, Johari GP, Shanker RM. 2006. Structural relaxation of acetaminophen glass. Pharm Res 23:967-979.
24. Hancock BC, Shamblin SL, Zografi G. 1995. Molecular mobility of amorphous pharmaceutical solids below their glass-transition temperatures. Pharm Res 12(6):799-806.
25. Shamblin SL, Zografi G. 1998. Enthalpy relaxation in binary amorphous mixtures containing sucrose. Pharm Res 15:1828-1834.
26. Liu J, Rigsbee Daniel R, Stotz C, Pikal Michael J. 2002. Dynamics of pharmaceutical amorphous solids: The study of enthalpy relaxation by isothermal microcalorimetry. J Pharm Sci 91:1853-1862.
27. Kawakami K, Pikal MJ. 2005. Calorimetric investigation of the structural relaxation of amorphous materials: Evaluating validity of the methodologies. J Pharm Sci 94:948-965.
28. Duddu SP, Sokoloski TD. 1995. Dielectric analysis in the characterization of amorphous pharmaceutical solids. 1. Molecular mobility in poly(vinyl-pyrrolidone)-water systems in the glassy state. J Pharm Sci 84:773-776.
29. Shmeis RA, Wang Z, Krill SL. 2004. A mechanistic investigation of an amorphous pharmaceutical and its solid dispersions, part I: A comparative analysis by thermally stimulated depolarization current and differential scanning calorimetry. Pharm Res 21:2025-2030.
30. Roozen MJGW, Hemminga MA, Walstra P. 1991. Molecular motion in glassy water-malto-oligosac-charide (maltodextrin) mixtures as studied by conventional and saturation-transfer spin-probe e.s.r. spectroscopy. Carbohydr Res 215:229-237.
31. Struik LCE. 1978. Physical aging in amorphous polymers and other materials Elsevier, Amsterdam: p 242.
32. Noel TR, Parker R, Brownsey GJ, Farhat IA, Mac-Naughtan W, Ring SG. 2005. Physical aging of starch, maltodextrin, and maltose. J Agric Food Chem 53:8580-8585.
33. Borde B, Bizot H, Vigier G, Buleon A. 2002. Calorimetric analysis of the structural relaxation in partially hydrated amorphous polysaccharides. II. Phenomenological study of physical ageing. Carbohydr Polym 48:111-123.
34. Dilworth SE, Buckton G, Gaisford S, Ramos R. 2004. Approaches to determine the enthalpy of crystallisation, and amorphous content, of lactose from isothermal calorimetric data. Int J Pharm 284:83-94.
35. Vemuri NM, Chrzan Z, Cavatur R. 2004. Use of isothermal microcalorimetry in pharmaceutical preformulation studies - part I. Monitoring crystalline phase transitions. J Therm Anal Calorimetry 78:47-54.
36. Kawakami K, Numa T, Ida Y. 2002. Assessment of amorphous content by microcalorimetry. J Pharm Sci 91:417-423.
37. Murti Vemuri N, Chrzan Z, Cavatur R. 2004. Use of isothermal microcalorimetry in pharmaceutical preformulation studies, part I. Monitoring crystalline phase transitions. J Therm Anal Calorimetry 78:47-54.
38. Tool AQ. 1946. Relation between inelastic deform-ability and thermal expansion of glass in its annealing range. J Am Ceramic Soc 29:240-253.
39. Hodge IM, Berens AR. 1982. Effects of annealing and prior history on enthalpy relaxation in glassy polymers. 2. Mathematical modeling. Macromolecules 15:762-770.
40. Claudy P, Jabrane S, Letoffe JM. 1997. Annealing of a glycerol glass: Enthalpy, fictive temperature and glass transition temperature change with annealing parameters. Thermochim Acta 293:1-11.
41. Shamblin SL, Tang XL, Chang LQ, Hancock BC, Pikal MJ. 1999. Characterization of the time scales of molecular motion in pharmaceutically important glasses. J Phys Chem B 103:4113-4121.
42. Pikal MJ, Rigsbee Daniel R, Roy ML. 2007. Solid state chemistry of proteins: I. Glass transition behavior in freeze dried disachharide formulations of human growth hormone (hGH). J Pharm Sci 96(10): 2765-2776.
43. Shultz AR, Young AL. 1980. DSC on freeze-dried poly(methyl methacrylate)-polystyrene blends. Macromolecules 13:663-668.
44. Hodge IM. 1994. Enthalpy relaxation and recovery in amorphous materials. J Non-Cryst Solids 169: 211-266.
45. Moynihan CT, Macedo PB, Montrose CJ, Gupta PK, DeBolt MA, Dill JF, Dom BE, Drake PW, Easteal AJ, 1976. Thermodynamic and transport properties of liquids near the glass transition temperature. Structural relaxation in vitreous materials. Ann NY Acad Sci 279(Glass Transition Nat. Glassy State): 15-35.
46. Royall PG, Craig DQM, Doherty C. 1998. Characterization of the glass transition of an amorphous drug using modulated DSC. Pharm Res 15:1117-1121.
47. Sartor G, Mayer E, Johari GP. 1994. Thermal history and enthalpy relaxation of an interpenetrating network polymer with exceptionally broad relaxation time distribution. J Polym Sci B Polym Phys 32:683-689.
48. Green JL, Fan J, Angell CA. 1994. The protein-glass analogy: New insight from homopeptide comparisons. J Phys Chem 98:13780-13790.
49. Ruedisser S, Hallbrucker A, Mayer E, Johari GP. 1997. Enthalpy, entropy, and structural relaxation behaviors of A- and B-DNA in their vitrified states and the effect of water on the dynamics of B-DNA. J Phys Chem B 101:266-277.
50. Sartor G, Johari GP. 1996. Structural relaxation of a vitrified high-protein food, beef, and the phase transformations of its water content. J Phys Chem 100:10450-10463.
51. Vyazovkin S, Dranca I. 2006. Probing beta relaxation in pharmaceutically relevant glasses by using DSC. Pharm Res 23:422-428.