Effect of β- and γ-cyclodextrins and their methylated derivatives on the degradation rate of benzylpenicillin

Effect of β- and γ-cyclodextrins and their methylated derivatives on the degradation rate of... Benzylpenicillin is characterized by instability in aqueous media, low oral bioavailability, and short biological half-life. Since their degradation products can cause allergic reactions, β-lactam antibiotics are supplied as a powder for injection and require special precaution when stored and re-constituted in water. An efficient method for β-lactam stabilization in the aqueous environment could reduce allergic side effects and facilitate their handling. Previously we proposed that complexa- tion with cyclodextrins (CDs) is a way to achieve this goal. The purpose of the present study was to investigate the effect of methylation of CD on the chemical stability of benzylpenicillin. Kinetic studies revealed that degree of methylation of the CD molecule determines whether the CD has destabilizing or stabilizing effect on the β-lactam. The fully methylated βCD derivative Trimeb stabilizes benzylpenicillin while partial methylation of βCD only decreases to some extent the catalytic effect of native βCD. The complexes of all investigated CDs were also studied by DSC, FT-IR and NMR spectroscopy. Keywords Benzylpenicillin · Cyclodextrin · Degradation · Stabilization · Catalysis · Polyhydric alcohol Introduction maximum stability at pH around 7 [2, 3]. Due to its poor oral bioavailability and high susceptibility to acid-catalyzed Benzylpenicillin is a naturally occurring β-lactam antibi- hydrolysis, the preferred routes http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Inclusion Phenomena and Macrocyclic Chemistry Springer Journals

Effect of β- and γ-cyclodextrins and their methylated derivatives on the degradation rate of benzylpenicillin

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Publisher
Springer Netherlands
Copyright
Copyright © 2018 by Springer Science+Business Media B.V., part of Springer Nature
Subject
Chemistry; Organic Chemistry; Food Science; Crystallography and Scattering Methods
ISSN
1388-3127
eISSN
1573-1111
D.O.I.
10.1007/s10847-018-0816-y
Publisher site
See Article on Publisher Site

Abstract

Benzylpenicillin is characterized by instability in aqueous media, low oral bioavailability, and short biological half-life. Since their degradation products can cause allergic reactions, β-lactam antibiotics are supplied as a powder for injection and require special precaution when stored and re-constituted in water. An efficient method for β-lactam stabilization in the aqueous environment could reduce allergic side effects and facilitate their handling. Previously we proposed that complexa- tion with cyclodextrins (CDs) is a way to achieve this goal. The purpose of the present study was to investigate the effect of methylation of CD on the chemical stability of benzylpenicillin. Kinetic studies revealed that degree of methylation of the CD molecule determines whether the CD has destabilizing or stabilizing effect on the β-lactam. The fully methylated βCD derivative Trimeb stabilizes benzylpenicillin while partial methylation of βCD only decreases to some extent the catalytic effect of native βCD. The complexes of all investigated CDs were also studied by DSC, FT-IR and NMR spectroscopy. Keywords Benzylpenicillin · Cyclodextrin · Degradation · Stabilization · Catalysis · Polyhydric alcohol Introduction maximum stability at pH around 7 [2, 3]. Due to its poor oral bioavailability and high susceptibility to acid-catalyzed Benzylpenicillin is a naturally occurring β-lactam antibi- hydrolysis, the preferred routes

Journal

Journal of Inclusion Phenomena and Macrocyclic ChemistrySpringer Journals

Published: Jun 6, 2018

References

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