Hydrogen Bonding Interactions in Amorphous Indomethacin and Its Amorphous Solid Dispersions with Poly(vinylpyrrolidone) and Poly(vinylpyrrolidone-co-vinyl acetate) Studied Using 13C Solid-State NMR

Molecular Pharmaceutics

Volumn 12, Issue 12, 2015, Pages 4518-4528

  Yuan, Xiaoda ^a   Xiang, Tian Xiang ^a   Anderson, Bradley D ^a   Munson, Eric J ^a  

^a University of Kentucky   (United States)

Author keywords

amorphous; hydrogen bond; indomethacin; PVP; PVP VA; solid dispersion; solid state NMR

Indexed keywords

AMIDE; CARBON; CARBON 13; CARBONYL DERIVATIVE; CARBOXYLIC ACID; HYDROGEN; INDOMETACIN; POLY(VINYLPYRROLIDONE CO VINYL ACETATE); POLYMER; POLYSTYRENE; POVIDONE; POVIDONE DERIVATIVE; UNCLASSIFIED DRUG; POLY(N-VINYLPYRROLIDINE); POLY(VINYLPYRROLIDONE-CO-VINYL-ACETATE); POLYVINYL DERIVATIVE; PYRROLIDINE DERIVATIVE; SOLVENT; VINYL ACETATE; VINYL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL INTERACTION; CHEMICAL REACTION; CONTROLLED STUDY; DECONVOLUTION; DIMERIZATION; DISPERSION; ENTHALPY; ENTROPY; EVAPORATION; FRACTIONATION; HYDROGEN BOND; ISOTOPE LABELING; MOLECULAR DYNAMICS; MOLECULE; PRIORITY JOURNAL; SOLID STATE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE IMAGING; PROCEDURES;

AMIDES; CARBON; CARBOXYLIC ACIDS; HYDROGEN BONDING; INDOMETHACIN; MAGNETIC RESONANCE IMAGING; MOLECULAR DYNAMICS SIMULATION; POLYVINYLS; PYRROLIDINES; SOLVENTS; VINYL COMPOUNDS;

EID: 84948977091     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/acs.molpharmaceut.5b00705     Document Type: Article

References (46)

1. Hancock, B. C.; Zografi, G. Characteristics and significance of the amorphous state in pharmaceutical systems J. Pharm. Sci. 1997, 86 (1) 1-12 10.1021/js9601896
2. Chiou, W. L.; Riegelman, S. Pharmaceutical applications of solid dispersion systems J. Pharm. Sci. 1971, 60 (9) 1281-1302 10.1002/jps.2600600902
3. Miyazaki, T.; Yoshioka, S.; Aso, Y.; Kojima, S. Ability of polyvinylpyrrolidone and polyacrylic acid to inhibit the crystallization of amorphous acetaminophen J. Pharm. Sci. 2004, 93, 2710-2717 10.1002/jps.20182
4. Van den Mooter, G.; Wuyts, M.; Blaton, N.; Busson, R.; Grobet, P.; Augustijns, P.; Kinget, R. Physical stabilization of amorphous ketoconazole in solid dispersions with polyvinylpyrrolidone K25 Eur. J. Pharm. Sci. 2001, 12, 261-269 10.1016/S0928-0987(00)00173-1
5. Yoshioka, M.; Hancock, B. C.; Zografi, G. Inhibition of indomethacin crystallization in poly(vinylpyrrolidone) coprecipitates J. Pharm. Sci. 1995, 84 (8) 983-986 10.1002/jps.2600840814
6. Taylor, L. S.; Zografi, G. Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions Pharm. Res. 1997, 14, 1691-1698 10.1023/A:1012167410376
7. Matsumoto, T.; Zografi, G. Physical properties of solid molecular dispersions of indomethacin with poly(vinylpyrrolidone) and poly(vinylpyrrolidone-co-vinyl-acetate) in relation to indomethacin crystallization Pharm. Res. 1999, 16 (11) 1722-1728 10.1023/A:1018906132279
8. Rumondor, A. C. F.; Marsac, P. J.; Stanford, L. A.; Taylor, L. S. Phase behavior of poly(vinylpyrrolidone) containing amorphous solid dispersions in the presence of moisture Mol. Pharmaceutics 2009, 6 (5) 1492-1505 10.1021/mp900050c
9. Marsac, P. J.; Konno, H.; Taylor, L. S. A comparison of the physical stability of amorphous felodipine and nifedipine systems Pharm. Res. 2006, 23, 2306-2316 10.1007/s11095-006-9047-9
10. Miyoshi, T.; Takegoshi, K.; Hikichi, K. High-resolution solid-state 13C nuclear magnetic resonance study of a polymer complex: poly(methacrylic acid)/poly(ethylene oxide) Polymer 1996, 37 (1) 11-18 10.1016/0032-3861(96)81594-1
11. Miyoshi, T.; Takegoshi, K.; Hikichi, K. High-resolution solid state 13C n.m.r. study of the interpolymer interaction, morphology and chain dynamics of the poly(acrylic acid)/poly(ethylene oxide) complex Polymer 1997, 38 (10) 2315-2320 10.1016/S0032-3861(96)00799-9
12. 13C 2D exchange NMR Macromolecules 1999, 32 (26) 8914-8917 10.1021/ma991012b
13. Xiang, T.-X.; Anderson, B. D. Molecular dynamics simulation of amorphous indomethacin Mol. Pharmaceutics 2013, 10 (1) 102-114 10.1021/mp3000698
14. Xiang, T.-X.; Anderson, B. D. Molecular dynamics simulation of amorphous indomethacin-poly(vinylpyrrolidone) glasses: Solubility and hydrogen bonding interactions J. Pharm. Sci. 2013, 102 (3) 876-891 10.1002/jps.23353
15. Yamamoto, T.; Shibayama, M.; Nomura, S. Structure and properties of fatigued segmented poly(urethaneurea)s III. Quantitative analyses of hydrogen bond Polym. J. 1989, 21 (11) 895-903 10.1295/polymj.21.895
16. Coleman, M. M.; Painter, P. C. Hydrogen bonded polymer blends Prog. Polym. Sci. 1995, 20 (1) 1-59 10.1016/0079-6700(94)00038-4
17. Kaneniwa, N.; Otsuka, M.; Hayashi, T. Physicochemical characterization of indomethacin polymorphs and the transformation kinetics in ethanol Chem. Pharm. Bull. 1985, 33 (8) 3447-3455 10.1248/cpb.33.3447
18. Andrew, E. R.; Bradbury, A.; Eades, R. G. Removal of dipolar broadening of nuclear magnetic resonance spectra of solids by specimen rotation Nature 1959, 183 (4678) 1802-1803 10.1038/1831802a0
19. Pines, A.; Gibby, M. G.; Waugh, J. S. Proton-enhanced NMR of dilute spins in solids J. Chem. Phys. 1973, 59 (2) 569-590 10.1063/1.1680061
20. Dixon, W. T.; Schaefer, J.; Sefcik, M. D.; Stejskal, E. O.; McKay, R. A. Total suppression of sidebands in CPMAS C-13 NMR J. Magn. Reson. 1982, 49 (2) 341-345 10.1016/0022-2364(82)90199-8
21. Fung, B. M.; Khitrin, A. K.; Ermolaev, K. An improved broadband decoupling sequence for liquid crystals and solids J. Magn. Reson. 2000, 142 (1) 97-101 10.1006/jmre.1999.1896
22. 13C solid-state NMR standard Solid State Nucl. Magn. Reson. 2006, 30 (3-4) 125-129 10.1016/j.ssnmr.2006.06.001
23. 207Pb MAS spectra of solid lead nitrate. An accurate, sensitive thermometer for variable-temperature MAS J. Magn. Reson., Ser. A 1995, 116 (2) 215-220 10.1006/jmra.1995.0010
24. Herzfeld, J.; Berger, A. E. Sideband intensities in NMR spectra of samples spinning at the magic angle J. Chem. Phys. 1980, 73 (12) 6021-6030 10.1063/1.440136
25. Eichele, K. HBA 1.7.3; Universität Tübingen: 2012.
26. Kistenmacher, T. J.; Marsh, R. E. Crystal and molecular structure of an antiinflammatory agent, indomethacin, 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid J. Am. Chem. Soc. 1972, 94 (4) 1340-1345 10.1021/ja00759a047
27. Chen, X.; Morris, K. R.; Griesser, U. J.; Byrn, S. R.; Stowell, J. G. Reactivity differences of indomethacin solid forms with ammonia gas J. Am. Chem. Soc. 2002, 124 (50) 15012-15019 10.1021/ja017662o
28. Apperley, D. C.; Forster, A. H.; Fournier, R.; Harris, R. K.; Hodgkinson, P.; Lancaster, R. W.; Rades, T. Characterisation of indomethacin and nifedipine using variable-temperature solid-state NMR Magn. Reson. Chem. 2005, 43 (11) 881-892 10.1002/mrc.1643
29. 13C NMR study of indomethacin polymorphism Int. J. Pharm. 2006, 318 (1-2) 146-153 10.1016/j.ijpharm.2006.03.029
30. Sperger, D. M. Solid-State NMR Analysis of Excipients and Drug-Excipient Interactions in the Amorphous State. Ph.D., University of Kansas, Lawrence, KS, 2010.
31. 13C solid-state NMR J. Am. Chem. Soc. 1998, 120 (48) 12672-12673 10.1021/ja981773e
32. 1H solid state NMR study of poly(methacrylic acid) hydrogen-bonded complexes Macromolecules 2012, 45 (15) 6015-6026 10.1021/ma300534t
33. 13C MAS NMR study of poly(methacrylic acid)-polyether complexes and multilayers Macromolecules 2014, 47 (13) 4298-4307 10.1021/ma401673n
34. 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 (2) 492-507 10.1002/jps.10028
35. Lubach, J. W.; Xu, D.; Segmuller, B. E.; Munson, E. J. Investigation of the effects of pharmaceutical processing upon solid-state NMR relaxation times and implications to solid-state formulation stability J. Pharm. Sci. 2007, 96 (4) 777-787 10.1002/jps.20684
36. 13C NMR chemical shifts of glycine residue carbonyl carbons of peptides in the solid state J. Am. Chem. Soc. 1988, 110 (11) 3380-3386 10.1021/ja00219a006
37. Gu, Z.; McDermott, A. Chemical shielding anisotropy of protonated and deprotonated carboxylates in amino acids J. Am. Chem. Soc. 1993, 115 (10) 4282-4285 10.1021/ja00063a051
38. Gu, Z.; Zambrano, R.; McDermott, A. Hydrogen bonding of carboxyl groups in solid-state amino acids and peptides: comparison of carbon chemical shielding, infrared frequencies, and structures J. Am. Chem. Soc. 1994, 116 (14) 6368-6372 10.1021/ja00093a042
39. Potrzebowski, M. J.; Schneider, C.; Tekely, P. Hydrogen bonding pattern in N-benzoyl(-dl-)-l-phenylalanines as revealed by solid-state NMR spectroscopy Chem. Phys. Lett. 1999, 313 (3-4) 569-574 10.1016/S0009-2614(99)01136-7
40. Zaugg, N. S.; Paul Steed, S.; Woolley, E. M. Intermolecular hydrogen bonding of acetic acid in carbon tetrachloride and benzene Thermochim. Acta 1972, 3 (5) 349-354 10.1016/0040-6031(72)87048-5
41. Borschel, E. M.; Buback, M. Dimerization of carboxylic acids in solution up to high pressures and temperatures. 3. Acetic acid Z. Naturforsch., A: Phys. Sci. 1988, 43 (3) 207 10.1515/zna-1988-0305
42. Semmler, J.; Irish, D. E. Estimation of the enthalpy of dimerization of acetic acid from raman spectral measurements over the temperature range 25 to 275°C J. Mol. Liq. 1990, 46 (0) 1-6 10.1016/0167-7322(90)80039-M
43. Maréchal, Y. The Hydrogen Bond and the Water Molecule: The Physics and Chemistry of Water, Aqueous and Bio Media; Elsevier: Amsterdam, 2007.
44. Yuan, X.; Sperger, D.; Munson, E. J. Investigating miscibility and molecular mobility of nifedipine-PVP amorphous solid dispersions using solid-state NMR spectroscopy Mol. Pharmaceutics 2014, 11 (1) 329-337 10.1021/mp400498n
45. Bovey, F. A.; Mirau, P. A. NMR of Polymers, 1st ed.; Academic Press: San Diego, CA, 1996.
46. 1H-NMR spin-lattice relaxation Chem. Pharm. Bull. 2007, 55 (8) 1227-1231 10.1248/cpb.55.1227