Differential molecular interactions between the crystalline and the amorphous phases of celecoxib

Journal of Pharmacy and Pharmacology

Volumn 57, Issue 10, 2005, Pages 1271-1278

  Gupta, Piyush ^a   Thilagavathi, R ^a   Chakraborti, Asit K ^a   Bansal, Arvind K ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CELECOXIB; FLUORINE; HYDROGEN; NITROGEN; PYRAZOLE;

ARTICLE; COMPUTER PROGRAM; CRYSTAL; DRUG SOLUBILITY; DRUG STABILITY; ELECTRON; HYDROGEN BOND; INFRARED SPECTROSCOPY; KINETICS; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PHYSICAL PHASE; SOLID STATE; STRENGTH; VITRIFICATION; X RAY DIFFRACTION;

CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRAZOLES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SULFONAMIDES;

EID: 27544514480     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/jpp.57.10.0005     Document Type: Article

References (26)

1. Adsmond, D. A., Grant, D. J. W. (2001) Hydrogen bonding in sulfonamides. J. Pharm. Sci. 90: 2058-2077
2. Alvarez, F., Arbe, A., Colmenero, J. (2000) Methyl group dynamics above the glass transition temperature: a molecular dynamics simulation in polyisoprene. Chem. Phys. 261: 47-59
3. Anonymous (1997) Computational chemistry becoming a "must-have" tool. Chem. Eng. News May 12: cover story
4. Brock, C. P., Dunitz, J. D. (1994) Towards a grammar of crystal packing. Chem. Mater. 6: 1118-1127
5. Chawla, G., Gupta, P., Thilagavathi, R., Chakraborti, A. K., Bansal, A. K. (2003) Characterization of solid-state forms of celecoxib. Eur. J. Pharm. Sci. 20: 305-317
6. Desiraju, G. R. (2003) In search of clarity. Nature 423: 485
7. Dev, R. V., Rekha, K. S., Vyas, K., Mohanti, S. B., Kumar, P. R., Reddy, G. O. (1999) Celecoxib, a COX-II inhibitor. Acta Crystallogr. C55: IUC9900161
8. Donohue, J. (1952) The hydrogen bond in organic crystals. J. Phys. Chem. 56: 502-510
9. Etter, M. C., MacDonald, J. C., Bernstein, J. (1990) Graph-set analysis of hydrogen-bond patterns in organic crystals. Acta Crystallogr. B46: 256-262
10. Gestoso, P., Brisson, J. (2001) Effect of hydrogen bonds on the amorphous phase of a polymer as determined by atomistic molecular modelling. Comput. Theor. Polym. Sci. 11: 263-271
11. Gupta, P., Kakumanu, V. K., Bansal, A. K. (2004) Stability and solubility of celecoxib-PVP amorphous dispersions: a molecular perspective. Pharm. Res. 21: 1762-1769
12. Halgren, T. A. (1996) Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. J. Comput. Chem. 17: 490-519
13. Jeffrey, G. A. (1997) An introduction to hydrogen bonding. Oxford University Press, New York
14. Kakumanu, V. K., Bansal, A. K. (2002) Enthalpy relaxation studies of celecoxib amorphous mixtures. Pharm. Res. 19: 1873-1878
15. Kaushal, A. M., Gupta, P., Bansal, A. K. (2004) Amorphous drug delivery systems: molecular aspects, design and performance. Crit. Rev. Ther. Drug Carrier Syst. 21: 133-193
16. Kirkpatrick, S., Gelatt, C. D., Vecchi, M. P. (1983) Optimization by simulated annealing. Science 220: 671-680
17. Langer, M., Holtje, M., Urbanetz, N. A., Brandt, B., Holtje, H.-D., Lippold, B. C. (2003) Investigations on the predictability of the formation of glassy solid solutions of drugs in sugar alcohols. Int. J. Pharm. 252: 167-179
18. Li, T., Kildsig, D. O., Park, K. (1997) Computer simulation of molecular diffusion in amorphous polymers. J. Control. Release 48: 57-66
19. Lin-Vien, D., Colthup, N. B., Fateley, W. G., Grasselli, J. G. (1991) The handbook of infrared and Roman characteristic frequencies of organic molecules. Academic Press, Inc., San Diego, California
20. Nakamoto, K., Margoshes, M., Rundle, R. E. (1955) Stretching frequencies as a function of distances in hydrogen bonds. J. Am. Chem. Soc. 77: 6480-6486
21. Paradkar, A. R., Chauhan, B., Yamamuri, S., Pawar, A. P. (2003) Preparation and characterization of glassy celecoxib. Drug Dev. Ind. Pharm. 29: 739-744
22. 2 in amorphous poly(ethylene terephthalate) and related aromatic polyesters. Polymer 44: 6713-6724
23. Roberge, M., Prud'homme, R. E., Brisson, J. E. (2004) Molecular modelling of the uniaxial deformation of amorphous polyethylene terephthalate. Polymer 45: 1401-1411
24. Steiner, T. (2002) The hydrogen bond in the solid state. Angew. Chem. Int. Ed. 41: 48-76
25. Tang, X. C., Pikal, M. J., Taylor, L. S. (2002) A spectroscopic investigation of hydrogen bond patterns in crystalline and amorphous phases in dihydropyridine calcium channel blockers. Pharm. Res. 19: 477-483
26. Yoshioka, S., Aso, Y., Kojima, S. (2003) Prediction of glass transition temperature of freeze-dried formulations by molecular dynamics simulation. Pharm. Res. 20: 873-878