Beta-cyclodextrin complexes of celecoxib: molecular-modeling, characterization, and dissolution studies

AAPS PharmSci. 2004 Mar 5;6(1):E7. doi: 10.1208/ps060107.


Celecoxib, a specific inhibitor of cycloxygenase-2 (COX-2) is a poorly water-soluble nonsteroidal anti-inflammatory drug with relatively low bioavailability. The effect of beta-cyclodextrin on the aqueous solubility and dissolution rate of celecoxib was investigated. The possibility of molecular arrangement of inclusion complexes of celecoxib and beta-cyclodextrin were studied using molecular modeling and structural designing. The results offer a better correlation in terms of orientation of celecoxib inside the cyclodextrin cavity. Phase-solubility profile indicated that the solubility of celecoxib was significantly increased in the presence of beta-cyclodextrin and was classified as A(L)-type, indicating the 1:1 stoichiometric inclusion complexes. Solid complexes prepared by freeze drying, evaporation, and kneading methods were characterized using differential scanning calorimetry, powder x-ray diffractometry, and scanning electron microscopy. In vitro studies showed that the solubility and dissolution rate of celecoxib were significantly improved by complexation with beta-cyclodextrin with respect to the drug alone. In contrast, freeze-dried complexes showed higher dissolution rate than the other complexes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents, Non-Steroidal / chemistry*
  • Calorimetry, Differential Scanning
  • Celecoxib
  • Cyclodextrins / chemistry*
  • Microscopy, Electron, Scanning
  • Models, Molecular
  • Powders / chemistry
  • Protein Conformation
  • Pyrazoles
  • Solubility
  • Sulfonamides / chemistry*
  • X-Ray Diffraction
  • beta-Cyclodextrins*


  • Anti-Inflammatory Agents, Non-Steroidal
  • Cyclodextrins
  • Powders
  • Pyrazoles
  • Sulfonamides
  • beta-Cyclodextrins
  • Celecoxib
  • betadex