Evaluation of solubility and partition properties of ampicillin-based ionic liquids

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abstract

In order to overcome the problems associated with low water solubility, and consequently low bioavailability of active pharmaceutical ingredients (APIs), herein we explore a modular ionic liquid synthetic strategy for improved APIs. Ionic liquids containing L-ampicillin as active pharmaceutical ingredient anion were prepared using the methodology developed in our previous work, using organic cations selected from substituted ammonium, phosphonium, pyridinium and methylimidazolium salts, with the intent of enhancing the solubility and bioavailability of L-ampicillin forms. In order to evaluate important properties of the synthesized API-ILs, the water solubility at 25 degrees C and 37 degrees C (body temperature) as well as octanol-water partition coefficients (K-ow's) and HDPC micelles partition at 25 degrees C were measured. Critical micelle concentrations (CMC's) in water at 25 degrees C and 37 degrees C of the pharmaceutical ionic liquids bearing cations with surfactant properties were also determined from ionic conductivity measurements. (C) 2013 Elsevier B.V. All rights reserved.

keywords

ACTIVE PHARMACEUTICAL INGREDIENTS; BIOLOGICAL-ACTIVITY; COEFFICIENTS; WATER; BEHAVIOR; DRUGS

subject category

Pharmacology & Pharmacy

authors

Florindo, C; Araujo, JMM; Alves, F; Matos, C; Ferraz, R; Prudencio, C; Noronha, JP; Petrovski, Z; Branco, L; Rebelo, LPN; Marrucho, IM

our authors

foto Isabel Maria Delgado Jana Marrucho Ferreira

Isabel Maria Delgado Jana Marrucho Ferreira

Full professor

Groups

Projects

The best of two worlds: Ionic liquids as Active Pharmaceutical Ingredients (PTDC/EQU-EPR/104554/2008)

acknowledgements

The financial support from Fundacao para a Ciencia e Tecnologia - FCT (Portugal), through grant SFRH/BPD/65981/2009 (J.M.M. Araujo) and two contracts under Programa Ciencia 2007 (I.M. Marrucho and L.C. Branco). Project PTDC/EQU-EPR/104554/2008 and PTDC/EQU-FTT/116015/2009 is gratefully acknowledged. The NMR spectrometers are part of the National NMR Network (RNRMN) and are funded by FCT. The authors gratefully Cytec Industries Research for supplying trihexyl(tetradecyl)phosphonium chloride and Solchemar for supplying 1-ethyl-3-methylimidazolium bromide and 1-hydroxy-ethyl-3-methylimidazolium chloride.

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Publication Details

type
Journal Article
year
2013
journal
INTERNATIONAL JOURNAL OF PHARMACEUTICS
volume
456
publisher
ELSEVIER SCIENCE BV
issn
0378-5173
issue
2
digital object identifier
10.1016/j.ijpharm.2013.08.010
web of science article identifier
WOS:000325644600035

Journal Metrics (JCR 2019)

Journal Impact Factor
4.845
Journal Impact Factor (5 yrs)
4.442
category normalized journal percentile
88.704

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