The Role of l-arginine in Inclusion Complexes of Omeprazole with Cyclodextrins
- 5 February 2010
- journal article
- Published by Springer Science and Business Media LLC in AAPS PharmSciTech
- Vol. 11 (1), 233-240
- https://doi.org/10.1208/s12249-009-9375-2
Abstract
In this study, we investigate how the effect of l-arginine (ARG) and cyclodextrins upon omeprazole (OME) stability and solubility. The effect of the presence of ARG on the apparent stability constants (K1:1) of the inclusion complexes formed between OME and each cyclodextrin, β-cyclodextrin (βCD), and methyl-β-cyclodextrin (MβCD) is studied by phase solubility diagrams and nuclear magnetic resonance (NMR) spectroscopy. The interaction of OME with those cyclodextrins, in the presence of ARG, is characterized using NMR spectroscopy and molecular dynamics simulations. ARG significantly increases the drug solubility and complex stability, in comparison to inclusion complexes formed in its absence. The effect is more pronounced for the OME:βCD complex. ARG also contributes to a larger stability of OME when free in aqueous solution. The combination of ARG with cyclodextrins can represent an important tool to develop stable drug formulations.Keywords
This publication has 39 references indexed in Scilit:
- Effect of PVP K30 and/orl-Arginine on Stability Constant of Etoricoxib–HPβCD Inclusion Complex: Preparation and Characterization of Etoricoxib–HPβCD Binary SystemDrug Development and Industrial Pharmacy, 2009
- Study of ascorbic acid interaction with hydroxypropyl-β-cyclodextrin and triethanolamine, separately and in combinationJournal of Pharmaceutical and Biomedical Analysis, 2007
- Host–guest interactions in cyclodextrin inclusion complexes with solvatochromic dyesJournal of Physical Organic Chemistry, 2006
- Physical and thermal characterisation of chiral omeprazole sodium saltsJournal of Pharmaceutical and Biomedical Analysis, 2006
- Determination of omeprazole, hydroxyomeprazole and omeprazole sulfone using automated solid phase extraction and micellar electrokinetic capillary chromatographyJournal of Pharmaceutical and Biomedical Analysis, 2006
- Solid state interactions between the proton pump inhibitor omeprazole and various enteric coating polymersJournal of Pharmaceutical Sciences, 2006
- Validation of the spectrophotometric determination of omeprazole and pantoprazole sodium via their metal chelatesJournal of Pharmaceutical and Biomedical Analysis, 2003
- Acid–base chemistry of omeprazole in aqueous solutionsAnalytica Chimica Acta, 2003
- GROMACS: A message-passing parallel molecular dynamics implementationComputer Physics Communications, 1995
- Molecular dynamics with coupling to an external bathThe Journal of Chemical Physics, 1984