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A comparative study of complexation methods for cefdinir-hydroxypropyl-β-cyclodextrin system

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Abstract

The aim of this study was to investigate the effect of hydroxypropyl-β-cyclodextrin (HPβCD) on the solubility and dissolution rate of Cefdinir (CEF). The methods that were employed to prepare CEF–HPβCD complexes were Kneading (KN), Co-evaporation (CE), Spray drying (SD) and a novel approach of Microwave irradiation (MWI). The formation of inclusion complexes with HPβCD in the solid state, were characterized by Differential Scanning Calorimetry (DSC), Fourier Transformation Infrared spectroscopy (FTIR), Proton Nuclear Magnetic Resonance Spectroscopy (NMR), X Ray Diffraction (XRD) and Scanning Electron Microscopy (SEM) studies, and comparative studies on the in vitro dissolution of CEF were carried out. Phase solubility profile with HPβCD was classified as AL type, indicating the formation of 1:1 stoichiometric inclusion complexes. Characterization of binary systems by DSC, FTIR, NMR, XRD and SEM indicated that SD and MWI method resulted in formation of true complexes. Binary systems showed significant increase in dissolution rate as compared to plain drug. Amongst the various binary systems, MWI products were prepared in least time with better yield and highest dissolution rate.

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References

  1. Cabri, W., Ghetti, P., Alpegiani, M., Pozzi, Giovanni., Justo-Erbez, A., Perez-Martinez, J.I., Villalon-Rubio, R., Monedero-Perales, M.C., Munoz-Rubio, A.: Cefdinir: a comparative e study of anhydrous vs monohydrate form Microstructure and tableting behaviour. Eur. J. Pharm. Biopharm 64, 212–221 (2006). doi:10.1016/j.ejpb.2006.05.007

    Article  CAS  Google Scholar 

  2. Inamoto, Y., Chiba, T., Kamimura, T., Takaya, T.: FK 482, a new orally active cephalosporin synthesis and biological properties. J. Antibiot. 41, 828–830 (1988)

    CAS  Google Scholar 

  3. Szejtli, J.: Cyclodextrin Technology, pp. 1–78. Kluwer Academic Publishers, Dordrecht (1988)

    Google Scholar 

  4. Duchene, D., Wouessidjewe, D.: Pharmaceutical uses of cyclodextrins and derivatives. Drug Dev. Ind. Pharm. 16(17), 2487–2499 (1990)

    Article  CAS  Google Scholar 

  5. Loftsson, T., Bjornsdottir, S., Palsdottir, G., Bodor, N.: Cyclodextrins. The effects of 2-hydroxypropyl-β-cyclodextrin on the solubility and stability of chlorambucil and melphalan in a aqueous solution. Int. J. Pharm 57, 63–72 (1989)

    Article  CAS  Google Scholar 

  6. Bekers, O., Beijnen, J.M., Kempers, Y.A.G., Bult, A., Underberg, J.M.: Eeeects of cyclodextrins on N-trifluoroacetyl-doxorubicin-14-valerate (AD-32) stability and solubility in aqueous media. Int. J. Pharm 68, 271–276 (1991)

    Article  CAS  Google Scholar 

  7. Vila-Jato, J.L., Blanco, J., Torres, J.J.: Biopharmaceutical aspects of the tolbutamide-β-cyclodextrin inclusion compound. II Farmaco Edizione Pratica 643(2), 37–45 (1988)

    Google Scholar 

  8. Le Bas, D., Rysanek, N.: Structural aspects of cyclodextrins. In: Duchene, D. (ed.) Cyclodextrins and Their Industrial Uses, pp. 105–125. Editions de SAnte, Paris (1987)

  9. Loftsson, T., Brewster, M.E., Derendorf, H., Bodor, N.: 2-Hydroxypropyl-β-cyclodextrin. Properties and usage in pharmaceutical formulations. Pharm. Ztg. Wiss. 136(1–4), 5–10 (1991)

    Google Scholar 

  10. Esclusa-Diaz, M.T., Torres-Labandeira, J.J., Kata, M., Vila-Jato, J.L.: Inclusion complexation of glibenclamide with 2-hydroxypropyl- β-cyclodextrin in solution and in solid state. Eur. J. Pharm. Biopharm. 1, 291–296 (1994)

    CAS  Google Scholar 

  11. Ribeiro, L., Carvalho, R.A., Ferreira, D.C., Veiga, F.J.B.: Multicomponent complex formation between vinpocetine, cyclodextrins, tartaric acid and water soluble polymers monitored by NMR and solubility studies. Eur. J. Pharm. Sci. 24, 1–13 (2005)

    Article  CAS  Google Scholar 

  12. Parmar, K.R., Patel, K.A., Shah, S.R., Sheth, N.R.: Inclusion complexes of lamotrigine and hydroxypropyl-β-cyclodextrin: solid state characterization and dissolution studies. J. Incl. Phenom. Macrocycl. Chem. 65, 263–268 (2009)

    Google Scholar 

  13. Szente, L., Atwood, J.L., Davies, J.E.D., MacNicol, D.D., Vogtle, F.: Comprehensive Supramolecular Chemistry, vol. 3, p. 243. Elsevier Science Ltd., Oxford (1996)

    Google Scholar 

  14. Zhao, D.Y., Yang, S.G., Hu, M., Ma, X.Y.: Structural study of inclusion complex of andrographolide with β-cyclodextrin prepared under microwave irradiation. Chin. Chem. Lett. 14, 155–158 (2003)

    CAS  Google Scholar 

  15. Zhao, D., Liao, K., Ma, X., Yan, N.: Study of supramolecular inclusion of β-cyclodextrin with andrographolide. J. Incl. Phenom. Macrocycl. Chem. 43, 259–264 (2002)

    Article  CAS  Google Scholar 

  16. Kappe, C.O.: Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed. 43, 6250–6284 (2004)

    Article  CAS  Google Scholar 

  17. Zhou, J., Shi, C., Mei, B., Yuan, R., Fu, Z.: Research on the technology and the mechanical properties of the microwave processing of polymer. J. Mater. Process. Tech. 137, 156–158 (2003)

    Article  CAS  Google Scholar 

  18. Passerini, N., Albertini, B., González-Rodríguez, M.L., Cavallari, C., Rodriguez, L.: Preparation and characterisation of ibuprofen–poloxamer 188 granules obtained by melt granulation. Eur. J. Pharm. Biopharm. 15, 71–78 (2002)

    CAS  Google Scholar 

  19. Moneghini, M., Bellich, B., Baxa, P., Princivalle, F.: Microwave generated solid dispersions containing Ibufrofen. Int. J. Pharm. 361, 125–130 (2008)

    Article  CAS  Google Scholar 

  20. Wen, X., Tan, F., Jing, Z., Liu, Z.: Preparation and study the 1:2 inclusion complex of carvedilol with β-cyclodextrin. J. Pharm. Biomed. Anal. 34(3), 517–523 (2004)

    Article  CAS  Google Scholar 

  21. Aleem, O., Kuchekar, B., Pore, Y., Late, S.: Effect of β-cyclodextrin and hydroxypropyl β-cyclodextrin complexation on physicochemical properties and antimicrobial activity of Cefdinir. J. Pharm. Biomed. Anal. 47, 535–540 (2008). doi:10.1016/jpba.2008.02.006

    Article  CAS  Google Scholar 

  22. Ren, Y., Gao, J., Han, B., Ma, X.: Medical composition containing cyclodextrin inclusion compound of cefdinir and its preparation method. PCT Int. Appl. PCT/CN2008/000514 (2008)

  23. Higuchi, T., Connors, K.A.: Phase-solubility techniques. Adv. Anal. Chem. Instrum. 4, 117–212 (1965)

    CAS  Google Scholar 

  24. Bodmeier, R., Chen, H.: Preparation of biodegradable poly (±) lactide microparticles using a spray-drying technique. J. Pharm. Pharma¢ol 40, 754–757 (1988)

    Article  CAS  Google Scholar 

  25. Benesi, H., Hildebrand, J.: A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbon. J. Am. Chem. Soc. 71, 2701–2705 (1949)

    Article  Google Scholar 

  26. Spulber, M., Pinteala, M., Harbagiu, V., Simionescu, B.C.: Inclusion complexes of Sulconazole with b-cyclodextrin and hydroxypropyl β-cyclodextrin: characterization in aqueous solution and in solid state. J. Incl. Phenom. Macrocycl. Chem. 61, 41–51 (2008)

    Article  CAS  Google Scholar 

  27. Esclusa-Diaz, M.T., Guimaraens-Mfndez, M., Pfrez-Marcos, M.B., Vila-Jato, J.L., Torres-Labandeira, J.J.: Characterization and in vitro dissolution behaviour of ketoconazole/β- and 2-hydroxypropyl-β-cyclodextrin inclusion compounds. Int. J. Pharm. 143, 203–210 (1996)

    Article  CAS  Google Scholar 

  28. Vij, M., Garse, H., Dand, N., Kadam, V., Hirlekar, R.: Effect of preparation method on complexation of Cefdinir with β-cyclodextrin. J. Inc. Phenom. Macrocycl. Chem. (2009). doi:10.1007/s10847-009-9666-y

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Acknowledgment

The authors would like to place on record their sincere gratitude to Alkem Research Lab. Ltd (India) for kindly gifting Cefdinir and Wacker Fine Chemical Corporation (Germany) for generously providing HPβCD.

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Correspondence to Hirlekar Rajashree.

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Mohit, V., Harshal, G., Neha, D. et al. A comparative study of complexation methods for cefdinir-hydroxypropyl-β-cyclodextrin system. J Incl Phenom Macrocycl Chem 71, 57–66 (2011). https://doi.org/10.1007/s10847-010-9901-6

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  • DOI: https://doi.org/10.1007/s10847-010-9901-6

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