Preparation and Physicochemical Characterization of Amoxicillin β-cyclodextrin Complexes
| Autor: | Francine Kedzierewicz, Chantal Finance, Stéphane Fontanay, Catherine Bisson-Boutelliez |
|---|---|
| Přispěvatelé: | Stress, Immunité, Pathogènes (SIMPA), Université de Lorraine (UL), Structure et Réactivité des Systèmes Moléculaires Complexes (SRSMC), Institut de Chimie du CNRS (INC)-Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2010 |
| Předmět: |
Drug Compounding
[SDV]Life Sciences [q-bio] Pharmaceutical Science Infrared spectroscopy Beta-Cyclodextrins 02 engineering and technology Aquatic Science 010402 general chemistry 01 natural sciences High-performance liquid chromatography Excipients chemistry.chemical_compound Drug Stability Drug Discovery Phenyl group Ecology Evolution Behavior and Systematics chemistry.chemical_classification amoxicillin Chromatography Ecology Cyclodextrin Hydrogen bond beta-Cyclodextrins General Medicine 021001 nanoscience & nanotechnology NMR Anti-Bacterial Agents 0104 chemical sciences FT-IR HPLC stability constant chemistry β-cyclodextrin Stability constants of complexes Food Additives DSC-TG-SM 0210 nano-technology Penam Agronomy and Crop Science complex Research Article Nuclear chemistry |
| Zdroj: | AAPS PharmSciTech AAPS PharmSciTech, American Association of Pharmaceutical Scientists, 2010, 11, pp.574-581. ⟨10.1208/s12249-010-9412-1⟩ |
| ISSN: | 1530-9932 |
| DOI: | 10.1208/s12249-010-9412-1 |
| Popis: | Amoxicillin (AMOX), a penicillin A, belongs to the beta-lactam family It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other beta-lactam antibiotics. Its beta-lactamase degradation might be prevented by using a molecular [AMOX:beta-CD] complex. The aim of this work was to prepare complexes using two methods and then characterize interactions between AMOX and the native beta-CD. The extent of complexation in solution has been evaluated by high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR), and 2D rotating-frame Overhauser enhancement spectroscopy (2D ROESY). Mass changes (TG), calorimetric effects (DSC), and mass spectrometry (MS) were determined on the same sample under identical conditions using the Skimmer coupling system. Skimmer and infrared spectroscopy (FT-IR) were used to characterize the solid state of the binary system. Complexation of AMOX with beta-CD was proven by FT-IR, NMR, DSC, and HPLC. The 2D ROESY spectra did not show any dipolar proton interaction of the AMOX with cyclodextrin. The 1:1 stoichiometry of the complex was obtained by HPLC. The stability constant for AMOX with beta-CD was determined to be 1,878 M(-1). In the [AMOX:beta-CD] complex, the phenyl group is included inside the beta-CD, and the ionized carboxyl group on the penam ring forms hydrogen bonds with the secondary hydroxyl groups of another beta-CD to keep the complex stable. Preparation methods allowed exactly the same complex. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full text from SpringerLink