Molecular dynamics in supercooled liquid and glassy states of antibiotics: Azithromycin, clarithromycin and roxithromycin studied by dielectric spectroscopy. Advantages given by the amorphous state

Molecular Pharmaceutics

Volumn 9, Issue 6, 2012, Pages 1748-1763

  Adrjanowicz, K ^a   Zakowiecki, D ^b   Kaminski, K ^a   Hawelek, L ^a,c   Grzybowska, K ^a   Tarnacka, M ^a   Paluch, M ^a   Cal, K ^d  

^a UNIVERSITY OF SILESIA   (Poland)

^b Pharmaceutical Works Polpharma SA   (Poland)

^c INSTITUTE OF NON FERROUS METALS   (Poland)

^d MEDICAL UNIVERSITY OF GDANSK   (Poland)

Author keywords

amorphous active pharmaceutical ingredients; antibiotics; dielectric spectroscopy; glass transition; molecular dynamics

Indexed keywords

AZITHROMYCIN; CLARITHROMYCIN; GLASS; ROXITHROMYCIN;

ARTICLE; CALORIMETRY; CONTROLLED STUDY; COOLING; DRUG SOLUBILITY; DRUG STABILITY; ELECTROCHEMICAL IMPEDANCE SPECTROSCOPY; GLASS TRANSITION TEMPERATURE; LIQUID; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; PHYSICAL MOBILITY; PRIORITY JOURNAL; ROOM TEMPERATURE; THERMODYNAMICS; X RAY DIFFRACTION;

ANTI-BACTERIAL AGENTS; AZITHROMYCIN; CLARITHROMYCIN; DIELECTRIC SPECTROSCOPY; DRUG STABILITY; MOLECULAR DYNAMICS SIMULATION; ROXITHROMYCIN; TEMPERATURE; X-RAY DIFFRACTION;

EID: 84862019970     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp300067r     Document Type: Article

References (49)

1. Elliott, S. R. Amorphous semiconductors. Nature 1979, 282, 560-560.
2. Demetriou, M. D.; Launey, M. E; Garrett, G.; Schramm, J. P.; Hofmann, D. C.; Johnson, W. L.; Ritchie, R. O. A damage-tolerant glass. Nat. Mater. 2011, 10, 123-128.
3. Levine, H. Amorphous food and pharmaceutical systems; Royal Society of Chemistry: Cambridge, 2002.
4. Gambling, W. A. The rise and rise of optical fibers. IEEE J. Sel. Top. Quantum Electron. 2000, 6 (6), 1084.
5. Johari, G. P.; Goldstein M.; Simba R. (eds). The glass transition and nature of the glassy state. Ann. N.Y. Acad. Sci. 1976, 279, 117
6. Johari, G. P.; Goldstein, M. Viscous Liquids and the Glass Transition. III. Secondary Relaxations in Aliphatic Alcohols and Other Nonrigid Molecules. J. Chem. Phys. 1971, 55, 4245.
7. Murdande, S. B.; Pikal, M. J.; Shanker, M.; Bogner, R. H. Solubility Advantage of Amorphous Pharmaceuticals: II. Application of Quantitative Thermodynamic Relationships for Prediction of Solubility Enhancement in Structurally Diverse Insoluble Pharmaceuticals. Pharm. Res. 2010, 27 (12), 2704-2714.
8. Jagadeesh Babu, N.; Nangia, A. Solubility Advantage of Amorphous Drugs and Pharmaceutical Cocrystals. Cryst. Growth Des. 2011, 11 (7), 2662-2679.
9. Gupta, P.; Bansal, A. K. Devitrification of Amorphous Celecoxib. AAPS PharmSciTech 2005, 6 (2), E223-E230. (Pubitemid 41631749)
10. Parker, R.; Gunning, Y. M.; Lalloue, B.; Noel, T. R.; Ring, S. G. Glassy state dynamics, its significance for biostabilization and role of carbohydrates. In Amorphous food and pharmaceutical systems; Levine, H., Ed.; The Royal Society of Chemistry: Cambridge, 2002; pp 73-87.
11. Yoshioka, S.; Aso, Y. Correlations between molecular mobility and chemical stability during storage of amorphous pharmaceuticals. J. Pharm. Sci. 2007, 96 (5), 960-81. (Pubitemid 46797468)
12. Shamblin, S. L.; Hancock, B. C.; Pikal, M. J. Coupling between Chemical Reactivity and Structural Relaxation in Pharmaceutical Glasses. Pharm. Res. 2006, 23, 2254-2268. (Pubitemid 44515010)
13. Aso, Y.; Yoshioka, S.; Kojima, S. Relationship between the crystallization rates of amorphous nifedipine, phenobarbital and flopropione and their molecular mobility ad measured by their enthalpy relaxation and 1HNMR relaxation time. J. Pharm. Sci. 2000, 89 (3), 408-416. (Pubitemid 30152440)
14. Hikima, T.; Hanaya, T.; Oguni, N. β-Molecular Rearrangement Process, But Not an α-Process, as Governing the Homogeneous Crystal-Nucleation Rate in a Supercooled Liquid. Bull. Chem. Soc. Jpn. 1996, 69 (7), 1863-1868.
15. Karmwar, P.; Graeser, K.; Gordon, K. C.; Strachan, C. J.; Rades, T. Investigation of properties and recrystallisation behaviour of amorphous indomethacin samples prepared by different methods. Int. J. Pharm. 2011, 417 (1-2), 94-100.
16. Crowley, K. J.; Zografi, G. Cryogenic grinding of indomethacin polymorphs and solvates: assessment of amorphous phase formation and amorphous phase physical stability. J. Pharm. Sci. 2002, 91, 492-507. (Pubitemid 34139812)
17. Medical Microbiology, 4th ed.; Baron, S., Ed.; University of Texas Medical Branch: Galveston, TX, 1996.
18. Kurath, P.; Jones, P. H.; Egan, R. S.; Perun, T. Acid degradation of erythromycin A and erythromycin B. Experientia 1971, 27, 362.
19. Yonemochi, E.; Kitahara, S.; Maeda, S.; Yamamura, T.; Oguchi, S.; Yamamoto, K. Physicochemical properties of amorphous clarithromycin obtained by grinding and spray drying. Eur. J. Pharm. Sci. 1999, 7, 331-338. (Pubitemid 29080746)
20. Biradar, S. V.; Patil, A. R.; Sudarsan, G. V.; Pokharkar, V. B. A comparative study of approaches used to improve solubility of roxithromycin. Powder Technol. 2006, 169 (1), 22-32. (Pubitemid 44485137)
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, 395.
22. Johari, G. P.; Goldstein, M. Viscous Liquids and the Glass Transition. III. Secondary Relaxations in Aliphatic Alcohols and Other Nonrigid Molecules. J. Chem. Phys. 1971, 55, 4245.
23. Schneider, U.; Brand, R.; Lunkenheimer, P.; Loidl, A. Excess Wing in the Dielectric Loss of Glass Formers: A Johari-Goldstein β- Relaxation? Phys. Rev. Lett. 2000, 84, 5560-5563.
24. Havriliak, S.; Negami, S. A complex plane representation of dielectric and mechanical relaxation processes in some polymers. Polymer 1967, 8 (4), 161.
25. Stickel, F.; Fischer, E. W.; Richert, R. Dynamics of glass-forming liquids. II. Detailed comparison of dielectric relaxation, dcconductivity, and viscosity data. J. Chem. Phys. 1996, 104, 2043.
26. Hensel-Bielowka, S.; Psurek, T.; Ziolo, J.; Paluch, M. Test of the fractional Debye-Stokes-Einstein equation in low molecular weight glass-forming liquids under condition of high compression. Phys. Rev. E 2001, 63, 2301.
27. Psurek, T.; Hensel-Bielowka, S.; Ziolo, J.; Paluch, M. Decoupling between dc-conductivity and (α-) structural relaxation time in a fragile glass-forming liquid. J. Chem. Phys. 2002, 116, 9882.
28. Paluch, M.; Psurek, T.; Roland, C. M. Ionic conductivity and dielectric relaxation in poly[(phenyl glycidyl ether)-co-formaldehyde]. J. Phys.: Condens. Matter 2002, 14, 9489.
29. Psurek, T.; Ziolo, J.; Paluch, M. Analysis of decoupling of DC conductivity and structural relaxation time in epoxies with different molecular topology. Physica A 2004, 331, 353.
30. Corezzi, S; Capaccioli, S; Gallone, G; Lucchesi, M; Rolla, P. A. J. Phys.: Condens. Mat. 1999, 11, 10297-10314.
31. Crofton, D. J.; Pethrick, R. A. Dielectric studies of proton migration and relaxation in wet cellulose and its derivatives. Polymer 1981, 22, 1048.
32. Williams, G.; Watts, D. C. Non-symmetrical dielectric relaxation behaviour arising from a simple empirical decay function. Trans. Faraday Soc. 1970, 66, 80-85.
33. Kohlrausch, R. Nachtrag uber die elastiche Nachwirkung beim Cocon und Glasladen. Ann. Phys. (Leipzig) 1847, 72, 393.
34. Tombardi, E.; Ferrari, C.; Johari, G. P.; Shanker, R. M. Calorimetric relaxation in pharmaceutical molecular glasses and its utility in understanding their stability against crystallization. J. Phys. Chem. B 2008, 112, 10806-10814.
35. Ngai, K. L.; Rendell, R. W. Supercooled Liquids. In 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. Schönhals, A.; Kremer, F. In Analysis of Dielectric Spectra, Broadband Dielectric Spectroscopy; Kremer, F., Schönhals, A., Eds.; Springer Verlag: Berlin, 2002; Chapter 3,
37. Vogel, H. The law of the relation between the viscosity of liquids and the temperature. Phys. Z. 1921, 22, 645-6.
38. Fulcher, G. Analysis of recent measurements of the viscosity of glasses. J. Am. Ceram. Soc. 1925, 8 (6), 339-355.
39. Tammann, G.; Hesse Gottingen, W. Die Abhangigkeit der Viscositat von der Temperatur bie unterkuhlten Flussigkeiten. Z. Anorg. Allg. Chem. 1926, 156 (1), 245-257.
40. Angell, C. A. Liquid Fragility and the Glass Transition in Water and Aqueous Solutions. Chem. Rev. 2002, 102, 2627-265.
41. Tanaka, H. Two-order-parameter model of liquid-glass transition. I. Relation between glass transition and crystallization. J. Non-Cryst. Solids 2005, 351, 3371-3384. (Pubitemid 41528683)
42. Grzybowska, K.; Paluch, M.; Grzybowski, A.; Wojnarowska, Z.; Hawelek, L.; Kolodziejczyk, K.; Ngai, K. L. Molecular Dynamics and Physical Stability of Amorphous Anti-Glammatory Drug: Celecoxib. J. Phys. Chem. B 2010, 114, 12792-12801.
43. Adrjanowicz, K.; Wojnarowska, Z.; Grzybowska, K.; Hawelek, L.; Kaminski, K.; Paluch, M.; Kasprzycka, A. Study of molecular dynamics and crystallization phenomenon of supercooled and glassy DNA and RNA nucleosides: β-adenosine, β-thymidine and β-uridine. Phys. Rev. E 2011, 84, 051507.
44. Adrjanowicz, K.; Grzybowska, K.; Kaminski, K.; Hawelek, L.; Paluch, M.; Zakowiecki, D. Comprehensive studies on physical and chemical stability in liquid and glassy states of Telmisartan (TEL): Solubility advantages given by cryomilled and quenched material. Philos. Mag. 2011, 91, 1926-1948.
45. Wang, L.-M.; Angell, C. A.; Richert, R. Fragility and Thermodynamics in non-polymeric glassformers. J. Chem. Phys. 2006, 125, 074505.
46. Gupta, P.; Chawla, G.; Bansal, A. K. Physical Stability and Solubility Advantage from Amorphous Celecoxib: The Role of Thermodynamic Quantities and Molecular Mobility. Mol. Pharmaceutics 2004, 1 (6), 406-413.
47. Cerveny, S.; Schwartz, G. A.; Bergman, R.; Swenson, J. Glass transition and relaxation processes in supercooled water. Phys. Rev. Lett. 2004, 93, 245702.
48. Capaccioli, S.; Ngai, K. L.; Shinyashiki, N. The Johari-Goldstein beta-Relaxation of Water. J. Phys. Chem. B 2007, 111, 8197-8209.
49. Everett, J. R.; Hunt, E.; Tyler, J. W. Ketone-Hemiacetal Tautomerism in Erythromycn A in Non-aqueous Solutions. An NMR Spectroscopic Study. J. Chem. Soc., Perkin Trans. 1991, 2, 1481-1487.