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Renu Chadha University Institute of Pharmaceutical Sciences, Panjab University, Chandigarh 160014, India

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Poonam Arora University Institute of Pharmaceutical Sciences, Panjab University, Chandigarh 160014, India

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Sushma Gupta University Institute of Pharmaceutical Sciences, Panjab University, Chandigarh 160014, India

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Dharamvir Singh Jain Department of Chemistry, Panjab University, Chandigarh 160014, India

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Abstract

The work is undertaken to evaluate the effect of Tween 80 on the complexing ability of β-cyclodextrins to encapsulate the poorly soluble antiretroviral agent, nevirapine. The phase solubility diagram indicates 1:1 stoichiometry and is supported by electronspray ionization mass spectrometry. The complexes were characterized by DSC, FT-IR, and XRD in the solid state. The ternary systems were autoclaved before being lyophilized for the best results. Proton NMR suggests that the methyl pyridine ring of the drug is involved in inclusion and enters from the wider side of the cavity which was confirmed by COESY NMR. Solution calorimetry, a direct method to determine the thermodynamic parameters, was used to determine the complexation constant (K) and other thermodynamic properties. The process is associated with negative ΔH and positive ΔS indicating a stable inclusion complex. The value of K follows the order β-CD < HP-β-CD < M-β-CD. The molar enthalpy of solution in autoclaved solid formulation is less endothermic as compared to additive molar enthalpy of solution obtained by summation of enthalpy of solution of individual components suggesting synergistic interaction between the drug and its constituents. A threefold increase of the in vitro permeability flux was observed for binary systems which was elevated to fourfold for autoclaved ternary complexes.

  • 1. Budavari S , (ed) (1996) The Merck index, an encyclopedia of chemicals, drugs, and biological. Merck, Rahway, p. 1114.

  • 2. Kasim, NA, Whitehouse, M, Ramachandran, C, Bermejo, M, Lennernäs, H, Hussain, AS, Junginger, HE, Stavchansky, SA, Midha, KK, Shah, VP, Amidon, GL. Molecular properties of WHO essential drugs and provisional biopharmaceutical classification. Mol Pharm. 2004;1: 1 8596. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 3. Zielenkiewicz, W, Koz′biał, M, Golankiewicz, BZ, Poznan′ ski, J. Enhancement of aqueous solubility of tricyclic acyclovir derivatives by their complexation with hydroxypropyl-b-cyclodextrin. J Therm Anal Calorim. 2010;101:555560. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 4. Patyi, G, Bódis, A, Antal, I, Vajna, B, Nagy, ZS, Marosi, G. Thermal and spectroscopic analysis of inclusion complex of spironolactone prepared by evaporation and hot melt methods. J Therm Anal Calorim. 2010;102:349355. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 5. Zielenkiewicz, W, Terekhova, IV, Koz′biał, M, Kumeev, RS. Thermodynamic study on inclusion complex formation of riboflavin with hydroxypropyl-b-cyclodextrin in water. J Therm Anal Calorim. 2010;101:595600. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 6. Chowdary KPR , Srinivas SV, () Influence of hydrophilic polymers on celecoxib complexation with hydroxypropyl β-cyclodextrin. J AAPS PharmSciTech. 2006;7: ,(3): article 79.

    • Search Google Scholar
    • Export Citation
  • 7. Loftsson, T, Masson, M. The effects of water-soluble polymers on cyclodextrins and cyclodextrin solubilization of drugs. J Drug Del Sci Tech. 2004;14:3543.

    • Search Google Scholar
    • Export Citation
  • 8. Valero, M, Esteban, B, Peläez, R, Rodrïguez, LJ. Naproxen:hydroxypropyl-β-cyclodextrin:polyvinylpyrrolidine ternary complex formation. J Incl Phenom Macrocycl Chem. 2004;48:157163. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 9. Barillaro V , Dive G, Bertholet P, Evrard B, Delattre L, Frederich M, Ziémons E, Piel G, (2007) Theoretical and experimental investigations of organic acids/cyclodextrin complexes and their consequences upon the formation of miconazole/cyclodextrin/acid ternary inclusion complexes. Int J Pharm. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 10. Ribeiro, L, Carvalho, RA, Ferreira, DC, Veiga, FJ. Multicomponent complex formation between vinpocetine, cyclodextrins, tartaric acid and water-soluble polymers monitored by NMR and solubility studies. Eur J Pharm Sci. 2005;24:113. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 11. Li N , Liu N, Zhao X, Gao Y, Zheng L, Zhang J, Yu L, () Complex formation of ionic liquid surfactant and β-cyclodextrin. Colloids Surf A Physicochem Eng Asp. 2007;292(2–3):196201. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 12. Bakshi, MS. Cationic mixed micelles in the presence of beta-cyclodextrin: a host-guest study. J Colloid Interface Sci. 2007;27: 1 7883.

    • Search Google Scholar
    • Export Citation
  • 13. Tomasella, FP, Zuting, P, Love, LJC. Effects of selected alcohols on chiral recognition via cyclodextrin inclusion complexation. Supramol Chem. 1992;25–30: 1 04781029.

    • Search Google Scholar
    • Export Citation
  • 14. Cirri, M, Maestrelli, S, Orlandini, S, Furlanetto, S, Pinzauti, S, Mura, P. Determination of stability constant values of flurbiprofen-cyclodextrin complexes using different techniques. J Pharm Biomed Anal. 2005;37:9951002. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 15. Cirri, M, Maestrelli, S, Corti, G, Mura, P. Simultaneous effect of cyclodextrin complexation, pH and hydrophilic polymers on naproxen solubilization. J Pharm Biomed Anal. 2006;42:126131. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 16. Martin Del valle, EM. Cyclodextrins and their uses: a review. Process Biochem. 2004;39:10331046. .

  • 17. Loftsson, T, Hreinsdottir, D, Masson, M. Evaluation of cyclodextrin solubilization of drugs. Int J Pharm. 2005;302:1828. .

  • 18. Zielenkiewicz, W, Terekhova, IV, Wszelaka-Rylik, M, Kumeev, RS. Thermodynamics of inclusion complex formation of hydroxypropylated α- and β-cyclodextrins with aminobenzoic acids in water. J Therm Anal Calorim. 2010;101:1523. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 19. Royall, PG, Gaisford, S. Application of solution calorimetry in pharmaceutical and biopharmaceutical research. Curr Pharm Biotechnol. 2005;6:215222. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 20. Mingquan G , Suoqing Z, Fengrui S, Daowu W, Zhiqiang L, Shuying L, () Studies on the non-covalent complexes between oleanolic acid and cyclodextrins electroscopy ionization tandem mass spectrometry. J Mass Spectrom. 2003;38(7):723731. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 21. Soares-Sobrinho J-L , Felts de La M, Soares R, Rolim-Neto P-J, Juan J. Torres L, Physicochemical study of solid-state benznidazole–cyclodextrin complexes. J Therm Anal Calorim. Published online 17 December 2010. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 22. Ali H , Al M, Elwya H, Shehadib I, Ademc A, (2009) Physicochemical properties of antifungal drug–cyclodextrin complexes prepared by supercritical carbon dioxide and by conventional techniques. J Pharm Biomed Anal 49:227–233.

    • Search Google Scholar
    • Export Citation
  • 23. Veiga, FJB, Fernandes, CM, Carvalho, RA, Geraldes, FGC. Molecular modelling and 1H-NMR: ultimate tools for the investigation of tolbutamide: β-cyclodextrin and tolbutamide: hydroxypropyl-β-cyclodextrin complexes. Chem Pharm Bull. 2001;49: 10 12511256. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 24. Chadha, R, Jain, DVS, Aggarawal, A, Singh, S, Thakur, D. Binding constants of inclusion complexes of nitroimidazoles with β-cyclodextrins in the absence and presence of PVP. Thermochim Acta. 2007;459:111115. .

    • Crossref
    • Search Google Scholar
    • Export Citation
  • 25. Liu, L, Guo, Q-X. The driving forces in the inclusion complexation of cyclodextrins. J Incl Phenom Macrocycl Chem. 2002;42:114. .

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Journal of Thermal Analysis and Calorimetry
Language English
Size A4
Year of
Foundation
1969
Volumes
per Year
1
Issues
per Year
24
Founder Akadémiai Kiadó
Founder's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
Publisher Akadémiai Kiadó
Springer Nature Switzerland AG
Publisher's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
CH-6330 Cham, Switzerland Gewerbestrasse 11.
Responsible
Publisher
Chief Executive Officer, Akadémiai Kiadó
ISSN 1388-6150 (Print)
ISSN 1588-2926 (Online)

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