New perspectives of 19F MAS NMR in the characterization of amorphous forms of atorvastatin in dosage formulations

International Journal of Pharmaceutics

Volumn 409, Issue 1-2, 2011, Pages 62-74

  Brus, Jiri ^a   Urbanova, Martina ^a   Sedenkova, Ivana ^a   Brusova, Hana ^b  

^a INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Czech Republic)

^b Zentiva Prague   (Czech Republic)

Author keywords

19F MAS NMR; Amorphous solids; Atorvastatin; Factor analysis; Pharmaceuticals; Polymorphism

Indexed keywords

ATORVASTATIN; FLUORINE; HEPTANOIC ACID DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMOMETRIC ANALYSIS; CONTROLLED STUDY; DRUG STRUCTURE; FACTORIAL ANALYSIS; FLUORINE NUCLEAR MAGNETIC RESONANCE; INFRARED SPECTROSCOPY; INTERMETHOD COMPARISON; PRIORITY JOURNAL; QUALITATIVE ANALYSIS; QUANTITATIVE ANALYSIS; RELIABILITY; TABLET FORMULATION; X RAY DIFFRACTION; CHEMISTRY; COMPARATIVE STUDY; CRYSTALLIZATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POWDER DIFFRACTION; REPRODUCIBILITY; TIME;

CRYSTALLIZATION; FACTOR ANALYSIS, STATISTICAL; FLUORINE; HEPTANOIC ACIDS; MAGNETIC RESONANCE SPECTROSCOPY; POWDER DIFFRACTION; PYRROLES; REPRODUCIBILITY OF RESULTS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TIME FACTORS;

EID: 79954990292     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2011.02.030     Document Type: Article

References (33)

1. S.-G. An, and Y.-T. Sohn Crystal forms of atorvastatin Arch. Pharm. Res. 32 2009 933 936
2. Aronhime, J., Lidon-Hadas, R., Niddam, V., Lifshitz, R., 2003. Atorvastatin hemi-calcium form VII. US Patent 6605636 (12.8.2003).
3. Aronhime, J., Lifshitz, R., Niddam, V., Lidon-Hadas, R., Wizel, S., 2006. Novel crystal forms of atorvastatin hemi-calciun and processes for their preparation as well as novel processes for preparing other forms. US Patent 7144916 (5.12.2006).
4. 19F-NMR for assessing the molecular mobility of flufenamic acid in solid dispersions Chem. Pharm. Bull. 57 2009 61 64
5. Ayalon, A., Levinger, M., Royblat, S., Niddam, V., Lifshitz, R., Aronhime, J., 2008. Polymorphic form of atorvastatin calcium. US Patent 7411075 (12.8.2008).
6. J. Bauer, S. Spanton, R. Henry, J. Quick, W. Dziki, W. Porter, and J. Morris Ritonavir: an extraordinary example of conformational polymorphism Pharm. Res. 18 2001 859 866 (Pubitemid 32783524)
7. N. Blagden, M. de Matas, P.T. Gavan, and P. York Crystal engineering of active pharmaceutical ingredients to improve solubility and dissolution rate Adv. Drug Deliv. Rev. 59 2007 617 630 (Pubitemid 47285407)
8. Briggs, C.A., Jennings, R.A., Wade, R., Harasawa, K., Ichikawa, S., Minohara, K., Naskagawa, S., 1999. Warner Lambert Co. US Patent 5969156 (19.10.1999).
9. J. Brus Heating of samples induced by fast magic-angle spinning Solid State Nucl. Magn. Reson. 16 2000 151 160 (Pubitemid 34867568)
10. J. Brus, and A. Jegorov Through-bonds and through-space solid-state NMR correlations at natural isotopic abundance: signal assignment and structural study of simvastatin J. Phys. Chem. A 108 2004 3955 3964
11. N.J. Claydenaq, R.J. Lehnertb, and S. Tumocka Factor analysis of time domain NMR data: crystallinity of poly(tetrafluoroethylene) Anal. Chim. Acta 344 1997 261 269
12. D.Q.M. Craig, P.G. Royall, V.L. Kett, and M.L. Hopton The relevance of the amorphous state to pharmaceutical dosage forms: glassy drugs and freeze dried system Int. J. Pharm. 179 1999 179 207 (Pubitemid 29131430)
13. C.D. Eads, C.M. Furnish, I. Noda, K.D. Juhlin, D.A. Cooper, and S.W. Morrall Molecular factor analysis applied to collections of NMR spectra Anal. Chem. 76 2004 1982 1990 (Pubitemid 38451517)
14. Gogulapati, V.P.R., Chavakula, R., Bandami, M., Gorantla, S.R., 2004. Crystalline form of atorvastatin hemi-calcium. US Patent 20090240064 (24.09.2004).
15. K.A. Graeser, C.J. Strachan, J.E. Patterson, K.C. Gordon, and T. Rades Physicochemical properties and stability of two differently prepared amorphous forms of simvastatin Cryst. Growth Des. 8 2008 128 135
16. Greco, K., Bogner, R., 2010. Crystallization of amorphous indomethacin during dissolution: effect of processing and annealing. Mol. Pharm. (on-line publication: 13.5.2010).
17. J.M. Griffin, D.R. Martin, and S.P. Brown Distinguishing anhydrous and hydrous forms of an active pharmaceutical ingredient in a tablet formulation using solid-state NMR spectroscopy Angew. Chem. Int. Ed. 46 2007 8036 8038 (Pubitemid 350033483)
18. R.K. Harris NMR studies of organic polymorphs & solvates Analyst 131 2006 351 373
19. R.K. Harris, R. Cadars, L. Emsley, J.R. Yates, C.J. Pickard, R.K.R. Jettid, and U.J. Griesserd NMR crystallography of oxybuprocaine hydrochloride, Modification II° Phys. Chem. Chem. Phys. 9 2007 360 368
20. R.K. Harris Applications of solid-state NMR to pharmaceutical polymorphism and related matters J. Pharm. Pharmacol. 59 2007 225 239 (Pubitemid 46203061)
21. A. Heinz, C.J. Strachan, F. Atassi, K.C. Gordon, and T. Rades Characterizing an amorphous system exhibiting trace crystallinity: a case study with saquinavir Cryst. Growth Des. 8 2008 119 127
22. A. Heinz, K.C. Gordon, M.C. McGoverin, T. Rades, and C.J. Strachan Understanding the solid-state forms of fenofibrate - a spectroscopic and computational study Eur. J. Pharm. Biopharm. 71 2009 100 108
23. E.R. Henry, and J. Hofrichter Singular value decomposition: application to analysis of experimental data Methods Enzymol. 210 1992 129 192
24. M. Husak, A. Jegorov, J. Brus, van W. Beek, P. Patison, M. Christensen, V. Favre-Nicolin, and J. Maixner Metergoline II: structure solution from powder diffraction data with preferred orientation and from microcrystal Struct. Chem. 19 2008 517 525 (Pubitemid 351937970)
25. M. Husak, B. Kratochvil, A. Jegorov, J. Brus, J. Maixner, and J. Rohlíček Simvastatin: structure solution of two new low-temperature phases from synchrotron powder diffraction and ss-NMR Struct. Chem. 21 2010 511 518
26. J.M. Koonst, and P.D. Ellis Applicability of factor analysis in solid state NMR Anal. Chem. 67 1995 4309 4315
27. B.K. Levine Chemometrics Anal. Chem. 70 1998 209 228 (Review)
28. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Fluorine in medicinal chemistry Chem. Soc. Rev. 37 2008 320 330
29. G. Shete, V. Puri, L. Kumar, and A.K. Bansal Solid state characterization of commercial crystalline and amorphous atorvastatin calcium samples J. Pharm. Sci. Technol. 11 2010 598 609
30. Tessler, L., Aronhime, J., Lifshitz, R., Maidan-Hanoch, D., Hasson, N., 2008. Novel crystal forms of atorvastatin hemi-calcium and processes for their preparation as well as novel processes for preparing other forms. US Patent 7456297 (25.11.2008).
31. 13C CPMAS NMR spectroscopy Int. J. Pharm. 394 2010 18 25
32. L. Yu Amorphous pharmaceutical solids: preparation, characterization and stabilization Adv. Drug Deliv. Rev. 48 2001 27 42 (Pubitemid 32454482)
33. A. Zakrzewski, and M. Zakrzewski Solid State Characterization of Pharmaceuticals 2006 Pergamon