Skip to main content
SpringerLink
Log in

Preparation and physicochemical characterization of omeprazole:methyl-beta-cyclodextrin inclusion complex in solid state

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

In this work, we illustrate the usefulness of cyclodextrins, namely, methyl-β-cyclodextrin (MβCD), an amorphous, methylated derivative of the natural β-cyclodextrin (βCD), as a tool to form an inclusion complex with omeprazole (OME), a poorly water soluble drug. Solid binary systems between OME and MβCD were prepared experimentally in a stoichiometry 1:1 by different techniques (physical mixing, kneading, spray-drying and freeze-drying). Afterward these products were characterized by Fourier transformation-infrared spectroscopy (FTIR); X-ray diffractometry (XRD) and scanning electron microscopy (SEM). The results obtained suggest that spray-drying and freeze-drying methods yield a higher degree of amorphous entities suggesting the formation of inclusion complexes between OME and MβCD.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Rosenblatt K.M., Bunjes H., Seeling A., Oelschlãger H.: Investigations on the thermal behavior of omeprazole and other sulfoxides. Pharmazie, 60, 503–507 (2005).

    CAS  Google Scholar 

  2. Biswas K., Bandypadhyay U., Chattopadhyay I., Varadaraj A., Ali E., Banerjee R.K.: A novel antioxidant and antiapoptotic role of omeprazole to block gastric ulcer through scavenging of hydroxyl radical. Journal of Biological Chemistry. 10993–11001 (2003).

  3. Arias M.J., Moyano J.R., Muñoz P., Ginés J.M., Justo A., Giordano F.: Study of omeprazole-γ- cyclodextrin complexation in the solid state .Drug Development and Industrial Pharmacy 26, 253–259 (2000).

    Article  CAS  Google Scholar 

  4. Ventura C.A., Giannone I., Musumeci T., Pignatello R., Ragni L., Landolfi C., Milanese C., Paolino D., Puglisi G.: Physico-chemical characterization of disoxaril dimethyl-β-cyclodextrin inclusion complex and in vitro permeation studies. European Journal of Medicinal Chemistry 41, 233–240 (2006).

    Article  CAS  Google Scholar 

  5. Ribeiro L.S.S., Ferreira D.C., Veiga F.J.B.: Physicochemical investigation of the effects of water-soluble polymers on vinpocetine complexation with β-cyclodextrin and its sulfobutyl ether derivative in solution and solid state. European Journal of Pharmaceutical Sciences. 20, 253–266 (2003).

    Article  CAS  Google Scholar 

  6. Rao V.M., Haslam J.L., Stella V.J.: Controlled and complete release of a model poorly water-soluble drug, prednisolone, from hydroxypropyl methylcellulose matrix tablets using (SBE)7m-β-cyclodextrin as a solubilizing agent. Journal of Pharmaceutical Sciences. 90, 807–816 (2001).

    Article  CAS  Google Scholar 

  7. Moyano J.R., Ginés J.M., Arias M.J., Rabasco A.M.: Study of the dissolution characteristics of oxazepam via complexation with β-cyclodextrin. International Journal of Pharmaceutics. 114, 95–102 (1995).

    Article  CAS  Google Scholar 

  8. Mura P., Zerrouk N., Faucci M.T., Maestrelli F., Chemtob C.: Comparative study of ibuproxam complexation with amorphous β-cyclodextrin derivatives in solution and in the solid state. European Journal of Pharmaceutics and Biopharmaceutics. 54, 181–191 (2002).

    Article  CAS  Google Scholar 

  9. Marzocchi L., Moyano J.R., Muñoz P., Arias M.J., Giordano F.: Current status of ATP-ase proton pump inhibitor complexation with cyclodextrins. Biological Journal of Armenia Special issue: Cyclodextrins. 176–193 (2001).

  10. Fernandes C.M., Vieira M.T., Veiga F.J.B.: Physicochemical characterization and in vitro dissolution behavior of nicardipine-cyclodextrin inclusions compounds. European Journal of Pharmaceutical Science. 15, 79–88 (2002).

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was financially supported by a grant (Praxis SFRH/BD/19175/2004) from FCT (Fundação para a Ciência e a Tecnologia, Portugal). The authors would like to thank assistance of Margarida Henriques by XRD and SEM acquisitions (Instituto Pedro Nunes, Coimbra), Belmac Laboratory, S.A. (Barcelona, Spain) for the kindly donation of OME and Roquette (Lestrem, France) for their support providing βCD and MβCD.

Author information

Authors and Affiliations

  1. Laboratory of Pharmaceutical Technology, Faculty of Pharmacy, University of Coimbra, Coimbra, 3000-295, Portugal

    Ana Figueiras & Francisco Veiga

  2. Pharmaceutical Studies Center, Faculty of Pharmacy, University of Coimbra, Coimbra, Portugal

    Ana Figueiras, Laura Ribeiro & Francisco Veiga

  3. Department of Mechanical Engineering, Faculty of Sciences and Technology, University of Coimbra, Coimbra, Portugal

    M. Teresa Vieira

Authors
  1. Ana Figueiras
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Laura Ribeiro
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Teresa Vieira
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Francisco Veiga
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Francisco Veiga.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Figueiras, A., Ribeiro, L., Vieira, M.T. et al. Preparation and physicochemical characterization of omeprazole:methyl-beta-cyclodextrin inclusion complex in solid state. J Incl Phenom Macrocycl Chem 57, 173–177 (2007). https://doi.org/10.1007/s10847-006-9200-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-006-9200-4

Keywords

Search

Navigation