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Interaction of naproxen with noncrystalline acetyl beta- and acetyl gamma-cyclodextrins in the solid and liquid state.
Eur J Pharm Sci. 2002 Feb; 15(1):21-9.EJ

Abstract

Randomly acetylated, amorphous beta-cyclodextrin (AcbetaCd) and gamma-cyclodextrin (AcgammaCd), having an average substitution degree per anhydroglucose unit, respectively, of 1.1 and 0.95 (approximately 7.7 acetyl residues per macrocycle), were investigated for their interactions in the solid and liquid state with naproxen (NAP). Differential scanning calorimetry (DSC), supported by X-ray powder diffractometry (XRD), of NAP-AcbetaCd and NAP-AcgammaCd blends revealed an apparent decrease in drug crystallinity which was related to a heating-induced solid-state interaction between the drug and each carrier. A solubility of approximately 0.40 NAP mass fraction in amorphous AcbetaCd and amorphous AcgammaCd at room temperature was determined. Phase-solubility analysis at 25, 37, and 45 degrees C accounted for A(L)-type inclusion complexation of NAP with AcbetaCd (K(1:1,25 degrees C)=4.5(4) x 10(3) l mol(-1)) and AcgammaCd (K(1:1,25 degrees C)=0.80(7) x 10(3) l mol(-1)) and revealed a solubilizing efficiency of AcbetaCd toward NAP approximately 4 times that of AcgammaCd. Equimolar drug-carrier combinations prepared from the respective blends by grinding, kneading, coevaporation and freeze-drying were characterized by DSC and XRD and tested for dissolution rate of NAP using the dispersed amount and continuous flow through methods. The best performance in terms of dissolution rate enhancement (approximately 23 times and approximately 10 times the dissolution efficiency of pure drug in the dispersed amount and continuous flow through tests, respectively) was displayed by the NAP-AcbetaCd colyophilized product.

Authors+Show Affiliations

Dipartimento di Chimica Farmaceutica, Università di Pavia, Viale Taramelli 12, I-27100 Pavia, Italy.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

11803128

Citation

Bettinetti, Giampiero, et al. "Interaction of Naproxen With Noncrystalline Acetyl Beta- and Acetyl Gamma-cyclodextrins in the Solid and Liquid State." European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences, vol. 15, no. 1, 2002, pp. 21-9.
Bettinetti G, Mura P, Faucci MT, et al. Interaction of naproxen with noncrystalline acetyl beta- and acetyl gamma-cyclodextrins in the solid and liquid state. Eur J Pharm Sci. 2002;15(1):21-9.
Bettinetti, G., Mura, P., Faucci, M. T., Sorrenti, M., & Setti, M. (2002). Interaction of naproxen with noncrystalline acetyl beta- and acetyl gamma-cyclodextrins in the solid and liquid state. European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences, 15(1), 21-9.
Bettinetti G, et al. Interaction of Naproxen With Noncrystalline Acetyl Beta- and Acetyl Gamma-cyclodextrins in the Solid and Liquid State. Eur J Pharm Sci. 2002;15(1):21-9. PubMed PMID: 11803128.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Interaction of naproxen with noncrystalline acetyl beta- and acetyl gamma-cyclodextrins in the solid and liquid state. AU - Bettinetti,Giampiero, AU - Mura,Paola, AU - Faucci,Maria Teresa, AU - Sorrenti,Milena, AU - Setti,Massimo, PY - 2002/1/23/pubmed PY - 2002/5/1/medline PY - 2002/1/23/entrez SP - 21 EP - 9 JF - European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences JO - Eur J Pharm Sci VL - 15 IS - 1 N2 - Randomly acetylated, amorphous beta-cyclodextrin (AcbetaCd) and gamma-cyclodextrin (AcgammaCd), having an average substitution degree per anhydroglucose unit, respectively, of 1.1 and 0.95 (approximately 7.7 acetyl residues per macrocycle), were investigated for their interactions in the solid and liquid state with naproxen (NAP). Differential scanning calorimetry (DSC), supported by X-ray powder diffractometry (XRD), of NAP-AcbetaCd and NAP-AcgammaCd blends revealed an apparent decrease in drug crystallinity which was related to a heating-induced solid-state interaction between the drug and each carrier. A solubility of approximately 0.40 NAP mass fraction in amorphous AcbetaCd and amorphous AcgammaCd at room temperature was determined. Phase-solubility analysis at 25, 37, and 45 degrees C accounted for A(L)-type inclusion complexation of NAP with AcbetaCd (K(1:1,25 degrees C)=4.5(4) x 10(3) l mol(-1)) and AcgammaCd (K(1:1,25 degrees C)=0.80(7) x 10(3) l mol(-1)) and revealed a solubilizing efficiency of AcbetaCd toward NAP approximately 4 times that of AcgammaCd. Equimolar drug-carrier combinations prepared from the respective blends by grinding, kneading, coevaporation and freeze-drying were characterized by DSC and XRD and tested for dissolution rate of NAP using the dispersed amount and continuous flow through methods. The best performance in terms of dissolution rate enhancement (approximately 23 times and approximately 10 times the dissolution efficiency of pure drug in the dispersed amount and continuous flow through tests, respectively) was displayed by the NAP-AcbetaCd colyophilized product. SN - 0928-0987 UR - https://www.unboundmedicine.com/medline/citation/11803128/Interaction_of_naproxen_with_noncrystalline_acetyl_beta__and_acetyl_gamma_cyclodextrins_in_the_solid_and_liquid_state_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0928098701001993 DB - PRIME DP - Unbound Medicine ER -