[en] The inclusion of miconazole into cyclodextrin cavity has been demonstrated by different authors. Preliminary studies have shown which fragment of the molecule is involved in the inclusion. In the present study, AM1 approximate molecular orbital calculations have been performed on several cyclodextrins complexes ( CD, HP CD and HP CD) with miconazole and acidic compounds (maleic, fumaric and L-tartaric acids) as partners.
For all the binary complexes, the inclusion of the dichlorobenzene–CH2–O-group leads to the most stable complex. For the ternary complexes, depending on their conformation and/or their structures, the acids can either stabilize or destabilize the complex. All the theoretical results were in good agreement with experimental data of miconazole inclusion yields into cyclodextrins. This work clearly demonstrates that the structure of both cyclodextrin and acid plays a key-role in the formation of inclusion complexes.
scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.
Bibliography
Amato M.E., Djedaini F., Pappalardo G.C., Perly B., and Scarlata G. Molecular modeling of β-cyclodextrin complexes with nootropic drugs. J. Pharm. Sci. 81 (1992) 1157-1161
Barillaro V., Bertholet P., Henry de Hassonville S., Ziémons E., Evrard B., Delattre L., and Piel G. Effect of acidic ternary compounds on the formation of miconazole/cyclodextrin inclusion complexes by means of supercritical carbon dioxide. J. Pharm. Pharm. Sci. 7 (2004) 378-388
Barillaro V., Evrard B., Delattre L., and Piel G. Oral bioavailability in pigs of a miconazole/hydroxypropyl-γ-cyclodextrin/L-tartaric acid inclusion complex produced by supercritical carbon dioxide processing. AAPS J. 7 (2005) (article 16)
Dewar M.J.S., Zoebisch E.G., Healy E.F., and Stewart J.J.P. AM1: a new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 107 (1985) 3902-3909
Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Chen W., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ciolowski J., Oritz J.V., Baboul A.G.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanyakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Jonhson B., Wong M.W., Andres J.L., Head-Gordon M., Replogle E.S., and Pople J.A. Gaussian 98 (1998) A.7
Harata K. The structure of the cyclodextrin complex 20. Crystal-structure of uncomplexed hydrated γ-cyclodextrin. Bull. Chem. Soc. Jpn. 60 (1987) 2763-2767
Lipkowitz K.B. Applications of computational chemistry to the study of cyclodextrins. Chem. Rev. 98 (1998) 1829-1873
Loftsson T., and Brewster M.E. Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J. Pharm. Sci. 85 (1996) 1017-1025
MC Quarrie D.A. Statistical Thermodynamics (1973), Harper & Row, New York
Mura P., Bettinetti G., Melani F., and Manderioli A. Interaction between naproxen and chemically modified β-cyclodextrins in the liquid and solid state. Eur. J. Pharm. Sci. 3 (1995) 347-355
Mura P., Liguori A., Bramanti G., Bettinetti G.P., Campisi E., and Faggi E. Improvement of dissolution properties and microbiological activity of miconazole and econazole by cyclodextrin complexation. Eur. J. Pharm. Biopharm. 38 (1992) 119-123
Piel G., Dive G., Evrard B., Van Hees T., Henry de Hassonville S., and Delattre L. Molecular modeling study of β- and γ-cyclodextrin complexes with miconazole. Eur. J. Pharm. Sci. 13 (2001) 271-279
Piel G., Evrard B., Fillet M., Llabres G., and Delattre L. Development of a non-surfactant parenteral formulation of miconazole by the use of cyclodextrins. Int. J. Pharm. 169 (1998) 15-22
Redenti E., Szente L., and Szejtli J. Drug/cyclodextrin/hydroxy acid multicomponent systems. Properties and pharmaceutical applications. J. Pharm. Sci. 89 (2000) 1-8
Steiner T., and Koellner G. Crystalline β-cyclodextrin hydrate at various humidities: fast, continuous and reversible dehydration studied by X-ray diffraction. J. Am. Chem. Soc. 116 (1994) 5122-5128
Tenjarla S., Puranajoti P., Kasina R., and Mandal T. Preparation, characterisation, and evaluation of miconazole-cyclodextrin complexes for improved oral and topical delivery. J. Pharm. Sci. 87 (1998) 425-429
Van Hees T., Piel G., Henry de Hassonville S., Evrard B., and Delattre L. Determination of the free/included piroxicam ratio in cyclodextrin complexes: comparison between UV spectroscopy and differential scanning calorimetry. Eur. J. Pharm. Sci. 15 (2002) 347-353
Zia V., Rajewski R.A., and Stella V.J. Effect of cyclodextrin charge on complexation of neutral and charged substrates: comparison of (SBE)7M-βCD to HP-β-CD. Pharm. Res. 18 (2001) 667-673
Similar publications
Sorry the service is unavailable at the moment. Please try again later.
This website uses cookies to improve user experience. Read more
Save & Close
Accept all
Decline all
Show detailsHide details
Cookie declaration
About cookies
Strictly necessary
Performance
Strictly necessary cookies allow core website functionality such as user login and account management. The website cannot be used properly without strictly necessary cookies.
This cookie is used by Cookie-Script.com service to remember visitor cookie consent preferences. It is necessary for Cookie-Script.com cookie banner to work properly.
Performance cookies are used to see how visitors use the website, eg. analytics cookies. Those cookies cannot be used to directly identify a certain visitor.
Used to store the attribution information, the referrer initially used to visit the website
Cookies are small text files that are placed on your computer by websites that you visit. Websites use cookies to help users navigate efficiently and perform certain functions. Cookies that are required for the website to operate properly are allowed to be set without your permission. All other cookies need to be approved before they can be set in the browser.
You can change your consent to cookie usage at any time on our Privacy Policy page.