Development of novel ionic liquids based on ampicillin

Abstract

Novel ionic liquids containing ampicillin as an active pharmaceutical ingredient anion were prepared with good yields by using a new, efficient synthetic procedure based on the neutralization of a moderately basic ammonia solution of ampicillin with different organic cation hydroxides. The relevant physical and thermal properties of these novel ionic liquids based on ampicillin were also evaluated.

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

“…More experimental details on the synthesis can be found in our previous work (Ferraz et al, 2012). The water content of all the API-ILs studied in this work was <500 ppm.…”

“…These API-ILs compounds offer improved properties, such as increased stability, solubility, permeability and drug delivery, as compared to the corresponding solid pharmaceutical forms (Ferraz et al, 2012). Also, the use of an active drug in the liquid form (at room temperature) can avoid some of the issues of polymorphism associated with crystalline solids and, thus, dramatically influence the drug's solubility and dosages Ferraz et al, 2011;Stoimenovski et al, 2010).…”

“…One of the most recent studies concerning API-ILs refers to the development of novel ionic liquids based on l-ampicillin (Ferraz et al, 2012), where ampicillin was used as anion combined with different organic cations. In that work, we reported a new and efficient method for the synthesis ofˇ-lactam antibiotics like ampicillin, which may prove useful for the development of new bioactive materials or to reduce drug resistance in microorganisms.…”

“…In that work, we reported a new and efficient method for the synthesis ofˇ-lactam antibiotics like ampicillin, which may prove useful for the development of new bioactive materials or to reduce drug resistance in microorganisms. This study is a continuation of our previous work (Ferraz et al, 2012), and it aims at evaluating the effect of the proposed methodology on two important parameters within drug absorption: water solubility and hydrophilic/lipophilic balance. This last parameter represents the delicate balance between the different thermophysical properties and influences the bioavailability of a drug, as well as its toxicity and half-life features.…”

Cholinium-based ionic liquids with pharmaceutically active anions

“…Several studies have been recently published on API-ILs by an increasing number of research groups. Our group reported novel ILs containing antibiotics, ampicillin as an API anion 5,7 and tetracycline as an API cation, 6 while Bica et al 17 reported ILs based on analgesic, anti-pyretic and anti-inammatory compounds (acetylsalicylic and salicylic acids). Hough et al 2 and MacFarlane and co-workers 3 addressed API-ILs containing various active cations and anions.…”