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Comparative study of ibuproxam complexation with amorphous beta-cyclodextrin derivatives in solution and in the solid state.
Eur J Pharm Biopharm. 2002 Sep; 54(2):181-91.EJ

Abstract

The complexing, solubilizing and amorphizing abilities toward ibuproxam (a poorly water-soluble anti-inflammatory agent) of some randomly substituted amorphous beta-cyclodextrin derivatives (i.e. methyl- (MebetaCd), hydroxyethyl- (HEbetaCd), and hydroxypropyl- (HPbetaCd) beta-cyclodextrins) were investigated and compared with those of the parent beta-cyclodextrin. Equimolar drug-cyclodextrin solid systems were prepared by blending, cogrinding, coevaporation, and colyophilization. Drug-carrier interactions were studied in both the liquid and solid state by phase solubility analysis, supported by molecular modelling, differential scanning calorimetry, X-ray powder diffractometry, Fourier transform infrared spectroscopy and scanning electron microscopy. All the betaCd derivatives showed greater solubilizing efficacies toward ibuproxam than the parent one, due to their higher water solubility. On the contrary, a clear reduction of complexing ability was observed, indicative of some steric interferences to drug inclusion due to the presence of substituents, as confirmed by molecular modelling studies. However, this negative effect was not reflected in the dissolution behaviour (evaluated according to the dispersed amount method) of their solid binary systems, probably thanks to the greater amorphizing properties shown (DSC and X-ray analyses) by betaCd derivatives. In fact their dissolution efficiencies were not significantly different (MebetaCd) or only slightly lower (HEbetaCd and HPbetaCd) than those of the corresponding products with beta-cyclodextrin. Colyophilized products were in all cases the most effective, followed by coground and coevaporated systems, whose dissolution efficiencies were over four times higher than the corresponding physical mixtures and about 15 times higher than the pure drug.

Authors+Show Affiliations

Dipartimento di Scienze Farmaceutiche, Facoltà di Farmacia, Università di Firenze, Florence, Italy. mura@farmfi.scifarth.unifi.itNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Comparative Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

12191690

Citation

Mura, Paola, et al. "Comparative Study of Ibuproxam Complexation With Amorphous Beta-cyclodextrin Derivatives in Solution and in the Solid State." European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Fur Pharmazeutische Verfahrenstechnik E.V, vol. 54, no. 2, 2002, pp. 181-91.
Mura P, Zerrouk N, Faucci M, et al. Comparative study of ibuproxam complexation with amorphous beta-cyclodextrin derivatives in solution and in the solid state. Eur J Pharm Biopharm. 2002;54(2):181-91.
Mura, P., Zerrouk, N., Faucci, M., Maestrelli, F., & Chemtob, C. (2002). Comparative study of ibuproxam complexation with amorphous beta-cyclodextrin derivatives in solution and in the solid state. European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Fur Pharmazeutische Verfahrenstechnik E.V, 54(2), 181-91.
Mura P, et al. Comparative Study of Ibuproxam Complexation With Amorphous Beta-cyclodextrin Derivatives in Solution and in the Solid State. Eur J Pharm Biopharm. 2002;54(2):181-91. PubMed PMID: 12191690.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Comparative study of ibuproxam complexation with amorphous beta-cyclodextrin derivatives in solution and in the solid state. AU - Mura,Paola, AU - Zerrouk,Naima, AU - Faucci,M, AU - Maestrelli,Francesca, AU - Chemtob,Chantal, PY - 2002/8/23/pubmed PY - 2003/4/29/medline PY - 2002/8/23/entrez SP - 181 EP - 91 JF - European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V JO - Eur J Pharm Biopharm VL - 54 IS - 2 N2 - The complexing, solubilizing and amorphizing abilities toward ibuproxam (a poorly water-soluble anti-inflammatory agent) of some randomly substituted amorphous beta-cyclodextrin derivatives (i.e. methyl- (MebetaCd), hydroxyethyl- (HEbetaCd), and hydroxypropyl- (HPbetaCd) beta-cyclodextrins) were investigated and compared with those of the parent beta-cyclodextrin. Equimolar drug-cyclodextrin solid systems were prepared by blending, cogrinding, coevaporation, and colyophilization. Drug-carrier interactions were studied in both the liquid and solid state by phase solubility analysis, supported by molecular modelling, differential scanning calorimetry, X-ray powder diffractometry, Fourier transform infrared spectroscopy and scanning electron microscopy. All the betaCd derivatives showed greater solubilizing efficacies toward ibuproxam than the parent one, due to their higher water solubility. On the contrary, a clear reduction of complexing ability was observed, indicative of some steric interferences to drug inclusion due to the presence of substituents, as confirmed by molecular modelling studies. However, this negative effect was not reflected in the dissolution behaviour (evaluated according to the dispersed amount method) of their solid binary systems, probably thanks to the greater amorphizing properties shown (DSC and X-ray analyses) by betaCd derivatives. In fact their dissolution efficiencies were not significantly different (MebetaCd) or only slightly lower (HEbetaCd and HPbetaCd) than those of the corresponding products with beta-cyclodextrin. Colyophilized products were in all cases the most effective, followed by coground and coevaporated systems, whose dissolution efficiencies were over four times higher than the corresponding physical mixtures and about 15 times higher than the pure drug. SN - 0939-6411 UR - https://www.unboundmedicine.com/medline/citation/12191690/Comparative_study_of_ibuproxam_complexation_with_amorphous_beta_cyclodextrin_derivatives_in_solution_and_in_the_solid_state_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0939641102000759 DB - PRIME DP - Unbound Medicine ER -