Solid-state stability of human insulin II. Effect of water on reactive intermediate partitioning in lyophiles from pH 2-5 solutions: Stabilization against covalent dimer formation

Journal of Pharmaceutical Sciences

Volumn 86, Issue 6, 1997, Pages 645-653

  Strickley, Robert G ^a,b   Anderson, Bradley D ^a  

^a UNIVERSITY OF UTAH   (United States)

^b GENENTECH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INSULIN; RECOMBINANT HUMAN INSULIN; WATER;

AQUEOUS SOLUTION; ARTICLE; DRUG DEGRADATION; DRUG STABILITY; FREEZE DRYING; PH;

EID: 0030997388     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js9700311     Document Type: Article

References (60)

1. Darrington, R. T.; Anderson, B. D. The role of intramolecular nucleophilic catalysis and the effects of self-association on the deamidation of human insulin at low pH. Pharm. Res. 1994, 11, 784-793.
2. Bhatt, N. P.; Patel, K.; Borchardt, R. T. Chemical pathways of peptide degradation. I. Deamidation of adrenocorticotropic hormone. Pharm. Res. 1990, 7, 593-599.
3. Oliyai, C.; Borchardt, R. T. Chemical pathways of peptide degradation. IV. Pathways, kinetics, and mechanism of degradation of an aspartyl residue in a model hexapeptide. Pharm. Res. 1993, 10, 95-102.
4. Powell, M. F. Peptide stability in aqueous parenteral formulations: Prediction of chemical stability based on primary structure. In Formulation and Delivery of Proteins and Peptides; Cleland, J. L.; Langer, R., Eds.; American Chemical Society: Washington, DC., 1994; pp 100-117.
5. Lura, R.; Schirch, V. Role of peptide conformation in the rate and mechanism of deamidation of asparaginyl residues. Biochemistry 1988, 27, 7671-7677.
6. Geiger, T.; Clarke, S. Deamidation, isomerization, and racemization at asparaginyl and aspartyl residues in peptides: Succinimide-linked reactions that contribute to protein degradation. J. Biol. Chem. 1987, 262, 785-794.
7. Oliyai, C.; Patel, J. P.; Carr, L.; Borchardt, R. T. Chemical pathways of peptide degradation. VII. Solid state chemical instability of an aspartyl residue in a model hexapeptide. Pharm. Res. 1994, 11, 901-908.
8. Shahrohk, Z.; Eberlein, G.; Buckley, D.; Paranandi, M. V.; Aswad, D. W.; Stratton, P.; Mischak, R.; Wang, Y. J. Major degradation products of basic fibroblast growth factor: Detection of succinimide and iso-aspartate in place of aspartate. Pharm. Res. 1994, 11, 936-944.
9. Darrington, R. T.; Anderson, B. D. Evidence for a common intermediate in insulin deamidation and covalent dimer formation: Effects of pH and aniline trapping in dilute acidic solutions. J. Pharm. Sci. 1995, 84, 275-282.
10. Brange, J.; Havelund, S.; Hougaard, P. Chemical stability of insulin. 2. Formation of higher molecular weight transformation products during storage of pharmaceutical preparations. Pharm. Res. 1992, 9, 727-734.
11. Brange, J. Chemical stability of insulin 4. Mechanisms and kinetics of chemical transformation in pharmaceutical formulation. Acta Pharm. Nord. 1992, 4, 209-222.
12. Costantino, H. R.; Langer, R.; Klibanov, A. M. Moisture-induced aggregation of lyophilized insulin. Pharm. Res. 1994, 11, 21-29.
13. Wang, Y.-C. J.; Hanson, M. A. Parenteral formulations of proteins and peptides; stability and stabilizers. J. Parenteral Sci. Technol. 1988, 42, S1-S24.
14. Yoshioka, S.; Aso, Y.; Izutsu, K.; Terao, T. Aggregates formed during storage of β-galactosidase in solution and in the freeze-dried state. Pharm. Res. 1993, 10, 687-691.
15. Gu, L.; Fausnaugh, J. Stability and characterization of human interleukin-1β. In Stability and Characterization of Protein and Peptide Drugs; Wang, Y. J.; Pearlman, R., Eds.; Plenum: New York, 1993; Vol. 5, pp 221-248.
16. Costantino, H. R.; Langer, R.; Klibanov, A. M. Aggregation of a lyophilized pharmaceutical protein, recombinant human albumin: effect of moisture and stabilization by excipients. Biotechnology 1995, 13, 493-496.
17. Strickley, R. G.; Anderson, B. D. Solid-state stability of human insulin I. Mechanism and the effect of water on the kinetics of degradation of lyophiles from pH 2-5 solutions. Pharm. Res. 1996, 13, 1142-1153.
18. Darrington, R. T.; Anderson, B. D. Effects of insulin concentration and self-association of its A-21 cyclic anhydride intermediate to desamido insulin and covalent dimer. Pharm. Res. 1995, 12, 1077-1084.
19. Hageman, M. J.; Bauer, J. M.; Possert, P. L.; Darrington, R. T. Preformulation studies oriented toward sustained delivery of recombinant somatotropins. J. Agric. Food Chem. 1992, 40, 348-355.
20. Brange, J.; Hallund, O.; Sorensen, E. Chemical stability of insulin 5. Isolation, characterization and identification of insulin transformation products. Acta Pharm. Nord. 1992, 4, 223-232.
21. Townsend, M. W.; DeLuca, P. P. Nature of aggregates formed during storage of freeze-dried ribonuclease A. J. Pharm. Sci. 1991, 80, 63-66.
22. Eckhardt, B. M.; Oeswein, J. Q.; Bewley, T. A. Effect of freezing on aggregation of human growth hormone. Pharm. Res. 1991, 8, 1360-1364.
23. Gu, L. C.; Erdos, E. A.; Chiang, H.-S.; Calderwood, T.; Tsai, K.; Visor, G. C.; Duffy, J.; Hsu, W.-C.; Foster, L. C. Stability of interleukin 1β (IL-1β) in aqueous solution: analytical methods, kinetics, products, and solution formulation implications. Pharm. Res. 1991, 8, 485-490.
24. Robbins, D. C.; Cooper, S. M.; Fineberg, S. E.; Mead, P. M. Antibodies to covalent aggregates of insulin in blood of insulin-using diabetic patients. Diabetes 1987, 36, 838-841.
25. Wang, Y. J.; Pearlman, R. Stability and Characterization of Protein and Peptide Drugs, Case Histories; Wang, Y. J.; Pearlman, R., Eds.; Plenum: New York and London, 1993; Vol. 5.
26. Pikal, M. J. Freeze-drying of proteins: Process, formulation and stability. In Formulation and Delivery of Proteins and Peptides; Cleland, J. L.; Langer, R., Eds.; American Chemical Society: Washington, D.C., 1994; pp 120-133.
27. Pearlman, R.; Nguyen, T. H. Pharmaceutics of protein drugs. J. Pharm. Pharmacol. 1992, 44 (Suppl.), 178-185.
28. Manning, M. C.; Patel, K.; Borchardt, R. T. Stability of protein pharmaceuticals. Pharm. Res. 1989, 6, 903-918.
29. Pikal, M. J.; Dellerman, K. M.; Roy, M. L.; Riggin, R. M. The effects of formulation variables on the stability of freeze-dried human growth hormone. Pharm. Res. 1991, 8, 427-436.
30. Pearlman, R.; Bewley, T. A. Stability and characterization of human growth hormone. In Stability and Characterization of Protein and Peptide Drugs: Case Histories; Wang, Y. J.; Pearlman, R., Eds.; Plenum: New York, 1993; Vol. 5, pp 1-58.
31. Hageman, M. J. Water sorption and solid state stability of proteins. In Stability of Protein Pharmaceuticals: Chemical and Physical Pathways of Protein Degradation; Ahern, T. J.; Manning, M. C., Eds.; Plenum: New York, 1992.
32. Davio, S. R.; Hageman, M. J. Characterization and formulation considerations for recombinantly derived bovine somatotropin. In Stability and Characterization of Protein and Peptide Drugs Case Histories; Wang, Y. J.; Pearlman, R., Eds.; Plenum: New York, 1993; Vol. 5, pp 59-89.
33. Nguyen, T. H.; Ward, C. Stability characterization and formulation development of alteplase, a recombinant tissue plasminogen activator. In Stability and Characterization of Protein and Peptide Drugs; Wang, Y. J.; Pearlman, R., Eds.; Plenum: New York, 1993; Vol. 5, pp 91-134.
34. Oksanen, C. A.; Zografi, G. The relationship between the glass transition temperature and water vapor absorption by poly-(vinylpyrrolidone). Pharm. Res. 1990, 7, 654-657.
35. Oksanen, C. A.; Zografi, G. Molecular mobility in mixtures of absorbed water and solid poly(vinylpyrrolidone). Pharm. Res. 1993, 10, 791-799.
36. Cohen, M. H.; Turnbull, D. Molecular transport in liquids and glasses. J. Chem. Phys. 1959, 31, 1164-1169.
37. Franks, F.; Hatley, R. H. M.; Mathias, S. F. Materials science and the production of shelf-stable biologicals. Pharm. Tech. 1992, March, 32-50.
38. Rupley, J. A.; Yang, P.-H.; Tollin, G. Thermodynamics and related studies of water interacting with proteins. In Water in Polymers; Rowland, S. P., Ed.; American Chemical Society: Washington, D.C., 1980; Vol. 127, pp 11-134.
39. Hancock, B. C.; Zografi, G. The relationship between the glass transition temperature and the water content of amorphous pharmaceutical solids. Pharm. Res. 1994, 11, 471-477.
40. Hancock, B. C.; Shamblin, S. L.; Zografi, G. Molecular mobility of amorphous pharmaceutical solids below their glass transition temperatures. Pharm. Res. 1995, 12, 799-806.
41. Slade, L.; Levine, H.; Beyond water activity: Recent advances based on an alternative approach to the assessment of food quality and safety. Crit. Rev. Food Sci. Nutrit. 1991, 30, 115-360.
42. Gibbs, J. H.; DiMarzio, E. A. Nature of the glass transition and the glassy state. J. Chem. Phys. 1958, 28, 373-383.
43. Kovas, A. La contraction isotherme du volume des polymeres amorphes. J. Polym. Sci. 1958, 30, 131-147.
44. Kauzmann, W. The nature of the glassy state and the behaviour of liquids at low temperatures. Chem. Rev. 1948, 43, 219-256.
45. Barlow, A. J.; Lamb, J.; Matheson, A. J. Viscous behaviour of supercooled liquids. Proc. Roy. Soc., London Series A 1966, 292, 322-342.
46. Shalaev, E. Y.; Zografi, G. How does residual water affect the solid-state degradation of drugs in the amorphous state? J. Pharm. Sci. 1996, 85, 1137-1141.
47. Careri, G.; Gratton, E.; Yang, P.-H.; Rupley, J. A. Correlation of IR spectroscopic, heat capacity, diamagnetic susceptibility and enzymatic measurements on lysozyme powder. Nature 1980, 284, 572-573.
48. Poole, P. L.; Finney, J. L. Sequential hydration of dry proteins: A direct difference IR investigation of sequence homologs lysozyme and α-lactalbumin. Biopolymers 1984, 23, 1647-1666.
49. Chan, Y.-K.; Oda, G.; Kaplan, H. Chemical properties of the functional groups of insulin. Biochem. J. 1981, 193, 419-425.
50. Sheffer, M. G.; Kaplan, H. Unusual chemical properties of the amino groups of insulin: Implications for structure-function relationship. Can. J. Biochem. 1979, 57, 489-496.
51. Baudys, M.; Uchio, T.; Mix, D.; Wilson, D.; Kim, S. W. Physical stabilization of insulin by glycosylation. J. Pharm. Sci. 1995, 84, 28-33.
52. Turnbull, D.; Cohen, M. H. On the free-volume model of the liquid-glass transition. J. Chem. Phys. 1970, 52, 3038-3041.
53. Stein, W. D.; Nir, S. On the mass dependence of diffusion within biological membranes and polymers. J. Membr. Biol. 1971, 5, 246-249.
54. Lieb, W. R.; Stein, W. D. Simple diffusion across the membrane bilayer. In Transport and Diffusion across Cell Membranes; Stein, W. D., Ed.; Academic: Orlando, FL, 1986; pp 69-112.
55. Bell, L. N.; Hageman, M. J. Differentiating between the effects of water activity and glass transition dependent mobility on a solid state chemical reaction: aspartame degradation. J. Agric. Food Chem. 1994, 40, 873-879.
56. Barbour, N. P.; Paborji, M.; Alexander, T. C.; Coppola, W. P.; Bogardus, J. B. Stabilization of chimeric BR96-doxorubicin immunoconjugate. Pharm. Res. 1995, 12, 215-222.
57. Carpenter, J. F.; Martin, B.; Loomis, S. H.; Crowe, J. H. Long-term preservation of dried phosphofructokinase by sugars and sugar/zinc mixtures. Cryobiology 1988, 25, 372-376.
58. Chang, B. S.; Randall, C. S.; Lee, Y. S. Stabilization of lyophilized porcine pancreatic elastase. Pharm. Res. 1993, 10, 1478-1483.
59. Izutsu, K.; Yoshioka, S.; Kojima, S. Physical stability and protein stability of freeze-dried cakes during storage at elevated temperatures. Pharm. Res. 1994, 11, 995-999.
60. Colaco, C. A. L. S.; Smith, C. J. S.; Sen, S.; Roser, D. H.; Newman, Y.; Ring, S.; Roser, B. J. Chemistry of protein stabilization by trehalose. In Formulation and Delivery of Proteins and Peptides; Cleland, J. L.; Langer, R., Eds.; American Chemical Society: Washington, DC., 1994; pp 222-240.