Study of the amorphous glibenclamide drug: Analysis of the molecular dynamics of quenched and cryomilled material

Molecular Pharmaceutics

Volumn 7, Issue 5, 2010, Pages 1692-1707

  Wojnarowska, Z ^a   Grzybowska, K ^a   Adrjanowicz, K ^a   Kaminski, K ^a   Paluch, M ^a   Hawelek, L ^a   Wrzalik, R ^a   Dulski, M ^a   Sawicki, W ^b   Mazgalski, J ^c   Tukalska, A ^c   Bieg, T ^d  

^a UNIVERSITY OF SILESIA   (Poland)

^b MEDICAL UNIVERSITY OF GDANSK   (Poland)

^c Pharmaceutical Works Polpharma SA   (Poland)

^d SILESIAN UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

amide imidic acid tautomerism; cryogrinding; Glibenclamide; molecular dynamics; thermal decomposition

Indexed keywords

AMIDE; GLIBENCLAMIDE; IMIDE;

ANALYTIC METHOD; ARTICLE; BROADBAND DIELECTRIC SPECTROSCOPY; COOLING; DIELECTRIC CONSTANT; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DECOMPOSITION; DRUG DEGRADATION; DRUG SOLUBILITY; INFRARED SPECTROSCOPY; ISOMERISM; MEASUREMENT; MOLECULAR DYNAMICS; PRIORITY JOURNAL; SOLID STATE; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; X RAY POWDER DIFFRACTION;

ADMINISTRATION, ORAL; CALORIMETRY, DIFFERENTIAL SCANNING; CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; DIELECTRIC SPECTROSCOPY; DRUG STABILITY; GLYBURIDE; HUMANS; HYPOGLYCEMIC AGENTS; MOLECULAR DYNAMICS SIMULATION; POWDER DIFFRACTION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SPECTRUM ANALYSIS;

EID: 77956431273     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp100077c     Document Type: Article

References (38)

1. Mutalik, S.; Udupa, N. Glibenclamide Transdermal Patches: Physicochemical, Pharmacodynamic, and Pharmacokinetic Evaluations J. Pharm. Sci. 2004, 93 (4) 1577
2. Hartke, K., Ed. Comments to the European Pharmacopoeia, 14th ed.; WVG mbH: Stuttgart, 2001.
3. Dressman, J.; Butler, J.; Hempenstall, J.; Reppas, C. Pharm. Technol. 2001, 7, 68
4. Rupp, W.; Badian, M.; Heptner, W.; Malerczyk, V. Bioavailability and in vitro liberation of glibenclamide from a new dosage form Biopharm. Pharmacokinet., Eur. Congr., 2nd 1984, 1, 413-420
5. Ganley, J. A.; McEven, J.; Calvert, R. T.; Barker, C. J. The effect of in vivo dispension and gastric emptying on glibenclamide absorption from a novel, rapidly dissolving capsule formulation J. Pharm. Pharmacol. 1984, 36, 734-739
6. Singh, J. Effect of sodium lauryl sulfate and Tween® 80 on the therapeutic efficacy of glibenclamide tablet formulations in terms of BSL lowering in rabbits and diabetic human volunteers Drug Dev. Ind. Pharm. 1986, 12, 851-866
7. Mitrevej, A.; Sinchaipanid, N.; Junyaprasert, V.; Warintornuwat, L. Effect of grinding of β-cyclodextrin and glibenclamide on tablet properties Drug Dev. Ind. Pharm. 1996, 22, 1237-1241
8. Hassan, M. A.; Najib, N. M.; Suleiman, M. S. Characterization of glibenclamide glassy state Int. J. Pharm. 1991, 67, 131-137
9. Salem, M. S.; Najib, N. M.; Hassan, M. A.; Suleiman, M. S. Dissolution kinetics of glibenclamide glass Acta Pharm. Hung. 1997, 67, 13-17
10. Hancock, B. C.; Parks, M. What is the True Solubility Advantage for Amorphous Pharmaceuticals? Pharm. Res. 2000, 17 (4) 397-404
11. Hancock, B. C.; Zografi, G. Characteristics and significance of the amorphous state in pharmaceutical systems J. Pharm. Sci. 1997, 86, 1-12
12. Kaminski, K.; Kaminska, E.; Adrjanowicz, K.; Grzybowiska, K.; Wlodarczyk, P.; Paluch, M.; Burian, A.; Ziolo, J.; Lepek, P.; Mazgalski, J.; Sawicki, W. Dielectric relaxation studies on tramadol and its hydrochloride salt J. Pharm. Sci. 2009, 99, 94-106 1
13. Bruno, C.; Hancock, B.; Zografi, G. Characteristics and Significance of the Amorphous State in Pharmaceutical Systems J. Pharm. Sci. 1997, 86, 1
14. Huttenrauch, R.; Fricke, R.; Zielke, P. Mechanical activation of pharmaceutical systems Pharm. Res. 1985, 2, 302-306
15. Crowley, J. K.; Zografi, G. Cryogenic grinding of indomethacin polymorphs and solvates: Assesment of amorphous chase formation and amorphous chase physical stability J. Pharm. Sci. 2001, 91 (2) 492
16. Panagopoulou-Kaplani, A.; Malamataris, S. Preparation and characterization of new insoluble polymorphic form of glibenclamide Int. J. Pharm. 2000, 195, 239
17. Patterson, J. E.; James, B. M. B.; Forster, A. H.; Lancaster, R. W.; Butler, J. M.; Rades, T. The Influence of Thermal and Mechanical Preparative Techniques on the Amorphous State of Four Poorly Soluble Compounds J. Pharm. Sci. 2005, 94 (9) 1999
18. Fukami, T.; Furuishi, T.; Suzuki, T.; Hidaka, S.; Ueda, H.; Tomato, K. Improvement of solubility of polory water soluble drug by cogrinding with highly branched cyclic dextrin J. Inclusion Phenom. Macrocyclic Chem. 2006, 56, 61-64
19. Bras, A. R.; Noronha, J. P.; Antunes, A. M. M.; Cardoso, M. M.; Schonhals, A.; Affouard, F.; Dionisio, M.; Correia, N. T. Molecular motions in amorphous Ibuprofen as studied by Broadband Dielectric Spectroscopy J. Phys. Chem. B 2008, 112 (35) 11087-11099
20. Adrjanowicz, K.; Kaminski, K.; Paluch, M.; Wlodarczyk, P.; Grzybowska, K.; Wojnarowska, Z.; Hawelek, L.; Sawicki, W.; Lepek, P.; Lunio, R. Dielectric Relaxation Studies and Dissolution Behavior of Amorphous Verapamil Hydrochloride J. Pharm. Sci. 2010, 99 (2) 828-839
21. Adrjanowicz, K.; Wojnarowska, Z.; Wlodarczyk, P.; Kaminski, K.; Paluch, M.; Mazgalski, J. Molecular mobility in liquid and glassy states of Telmisartan (TEL) studied by Broadband Dielectric Spectroscopy Eur. J. Pharm. Sci. 2009, 38 (5) 395-404
22. Wojnarowska, Z.; Adrjanowicz, K.; Wlodarczyk, P.; Kaminska, E.; Kaminski, K.; Grzybowska, K.; Wrzalik, R.; Paluch, M.; Ngai, K. L. Broadband Dielectric Relaxation Study at Ambient and Elevated Pressure of Molecular Dynamics of Pharmaceutical: Indomethacin J. Phys. Chem B 2009, 113 (37) 12536-12545
23. Kohlrausch, R. Nachtrag über die elastiche Nachwirkung beim Cocon und Glasladen Ann. Phys. (Leipzig) 1847, 72, 393
24. Williams, G.; Watts, D. C. Non-symmetrical dielectric relaxation behavior arising from a simple empirical decay function Trans. Faraday Soc. 1970, 66, 80-85
25. Shamblin, S. L.; Hancock, B. C.; Dupuis, Y.; Pikal, M. J. Interpretation of relaxation time constants for amorphous pharmaceutical system J. Pharm. Sci. 1999, 89, 417-427
26. Havriliak, S.; Negami, S. A complex plane representation of dielectric and mechanical relaxation processes in some polymers Polymer 1967, 8 (4) 161
27. Cole, K. S.; Cole, R. H. Dispersion and absorption in dielectrics I. Alternating current characteristics J. Chem. Phys. 1941, 9, 341
28. Vogel, H. The law of the relation between the viscosity of liquids and the temperature Phys. Z. 1921, 22, 645-646
29. Fulcher, G. Analysis of recent measurements of the viscosity of glasses J. Am. Ceram. Soc. 1925, 8 (6) 339-355
30. Tammann, G.; Hesse, W. Die Abhängigkeit der Viscosität von der Temperatur bie unterkühlten Flüssigkeiten Z. Anorg. Allg. Chem. 1926, 156 (1) 245-257
31. Angell, C. A. Formation of glasses from liquids and biopolymers Science 1995, 267, 1924
32. Angell, C. A.; Shao, J.; Grabow, M. In Non-equilibrium phenomena in supercooled fluids, glasses and amorphous materials, Proceedings of the International Workshop, Pisa, Italy, Sept 25-29, 1995; Giordano, M.; Leporini, D.; Tosi, M. P., Eds.; World Scientific: Singapore, 1996.
33. Adrjanowicz, K.; Kaminski, K.; Paluch, M.; Wlodarczyk, P.; Grzybowska, K.; Wojnarowska, Z.; Hawelek, L.; Sawicki, W.; Lepek, P.; Lunio, R. Dielectric Relaxation Studies and Dissolution Behavior of Amorphous Verapamil Hydrochloride J. Pharm. Sci. 2010, 99 (2) 828-839
34. Ngai, K. L.; Paluch, M. Classification of secondary relaxation in glass-formers based on dynamic properties J. Chem. Phys. 2004, 120, 857
35. Ngai, K. L.; Rendell, R. W. Supercooled liquids, advances and novel applications. In Supercooled liquids: Advances and novel applications; Fourkas, J. T.; Kivelson, D.; Mohanty, U.; Nelson, K., Eds.; ACS Symposium Series 676; American Chemical Society: Washington, DC, 1997; Chapter 4, p 45.
36. Ngai, K. L.; Tsang, K. Y. Similarity of relaxation in supercooled liquids and interacting arrays of oscillators Phys. Rev. 1999, E60, 4511-4517
37. Ngai, K. L. An extended coupling model description of the evolution of dynamics with time in supercooled liquids and ionic conductors J. Phys.: Condens. Matter 2003, 15 S1107
38. g J. Pharm. Sci. 2007, 96 (5) 1398