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Interaction of naproxen with ionic cyclodextrins in aqueous solution and in the solid state
P Mura1, S Furlanetto, M Cirri
1Dipartimento di Scienze Farmaceutiche, Università di Firenze, Polo Scientifico di Sesto Fiorentino, 50019 Sesto Fiorentino, Firenze, Italy. mura@unifi.it
Summary
Anionic sulfobutylether-beta-cyclodextrin (SBE-betaCyd) effectively solubilized naproxen, outperforming neutral beta-cyclodextrin. Cationic trimethylammonium-beta-cyclodextrin (TMA-betaCyd) showed limited efficacy, indicating charge is less critical than other factors for drug complexation.
Area of Science:
- Pharmaceutical Sciences
- Supramolecular Chemistry
- Drug Delivery
Background:
- Cyclodextrins (Cyds) are widely used to enhance drug solubility and bioavailability.
- The charge of cyclodextrin derivatives can influence their interaction with charged drug molecules.
- Naproxen, an acidic non-steroidal anti-inflammatory drug, presents challenges in formulation due to its limited aqueous solubility.
Purpose of the Study:
- To evaluate the role of cyclodextrin charge in complexation and solubilization of naproxen.
- To compare the performance of anionic (SBE-betaCyd) and cationic (TMA-betaCyd) cyclodextrins with neutral beta-cyclodextrin and its methyl derivative.
- To investigate the impact of preparation methods on the dissolution properties of naproxen-cyclodextrin solid systems.
Main Methods:
- Solution studies: phase-solubility, fluorescence, and circular dichroism analyses.
- Solid-state characterization: differential scanning calorimetry (DSC) and X-ray powder diffractometry (XRPD).
- Drug dissolution testing of prepared drug-carrier products.
Main Results:
- Anionic SBE-betaCyd demonstrated superior solubilizing and complexing properties for naproxen compared to native beta-cyclodextrin.
- Cationic TMA-betaCyd showed less efficacy than native beta-cyclodextrin, despite partial ionization of naproxen.
- Colyophilization yielded the most effective naproxen-SBE-betaCyd product, significantly enhancing dissolution efficiency and reducing dissolution time.
Conclusions:
- Cyclodextrin charge plays a less significant role in naproxen complexation than steric and hydrophobic interactions.
- Anionic SBE-betaCyd is a highly effective carrier for naproxen, improving its dissolution properties.
- Preparation method critically influences the performance of solid drug-cyclodextrin systems, with colyophilization being the most advantageous technique.