title: Evaluation of solubility and partition properties of ampicillin-based ionic liquids.
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 °C and 37 °C (body temperature) as well as octanol-water partition coefficients (Kow's) and HDPC micelles partition at 25 °C were measured. Critical micelle concentrations (CMC's) in water at 25 °C and 37 °C of the pharmaceutical ionic liquids bearing cations with surfactant properties were also determined from ionic conductivity measurements.
authors: Instituto de Tecnologia Química e Biológica, Universidade Nova de Lisboa, Avenida da República, Estação Agronómica Nacional, 2780-157 Oeiras, Portugal(2).
authors: Catarina
authors: C
authors: Florindo
authors: João M M
authors: JM
authors: Araújo
authors: Filipa
authors: F
authors: Alves
authors: Carla
authors: C
authors: Matos
authors: Ricardo
authors: R
authors: Ferraz
authors: Cristina
authors: C
authors: Prudêncio
authors: João Paulo
authors: JP
authors: Noronha
authors: Željko
authors: Ž
authors: Petrovski
authors: Luís
authors: L
authors: Branco
authors: Luís Paulo N
authors: LP
authors: Rebelo
authors: Isabel M
authors: IM
authors: Marrucho
mesh_terms: D000667:Ampicillin / Q000737:chemistry* / Q000493:pharmacokinetics*; D004353:Drug Evaluation, Preclinical / Q000379:methods; D052578:Ionic Liquids / Q000737:chemistry* / Q000493:pharmacokinetics*; D008823:Micelles; D012995:Solubility
chemical_list: D052578:Ionic Liquids; D008823:Micelles; D000667:Ampicillin
keywords: Active pharmaceutical ionic liquids; Bioavailability; Critical micelle concentrations; Octanol–water partition coefficients; Solubility