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

Abstract

a b s t r a c tIn 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 (K ow '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.

Primaquine-based ionic liquids as a novel class of antimalarial hits

“…In fact, most ionic antimalarial APIs are administered as salts (e.g., primaquine bisphosphate, proguanil hydrochloride, sodium artesunate), and the formulation and formation of these salts are considered essential steps in the preclinical phase of modern drug development. 1,7 This type of combination showed that ILs-APIs physicochemical descriptors like solubility and lipophilicity could be tuned by choice of the adequate cation. 3,8 Recently, we have developed a method termed neutralization with buffer, 1 which avoids contamination problems associated to the metathesis approach, 1 where anionic ampicillin was combined with six different organic cations.…”

Evolution of Choice of Solubility and Dissolution Media After Two Decades of Biopharmaceutical Classification System

“…The reviewed publications showed that different grades of water were used as media to determine the solubility of drug substance: double-distilled water (6)(7)(8); double deionized water (9), Milli-Q® purified water (10), 18.2 MΩ.cm/ 0.22 μm (11); Milli-Q®ultrapure water, conductivity less than 0.1 μS cm (12,13); ultrapure water Elix® Millipore (14); distilled water (5,15-21) deionized water (22)(23)(24)(25)(26); distilled, deionized, and filtered water (27); purified water (28)(29)(30)(31)(32)(33)(34)(35)(36); demineralized water (37). The type of water was not specified in 19 of 51 studies (37%) (38)(39)(40)(41)(42)(43)(44)(45)(46)(47)(48)(49)(50)(51)(52)(53)(54)(55)(56).…”

The effects of bronchodilator drugs and antibiotics used for respiratory infection on human erythrocyte carbonic anhydrase I and II isozymes

“…Penicillin is a highlight antibiotic and preferable by modern medicine. Ampicillin, a group of synthetic penicillin, was used as anion combined with different organic cautions (Florindo et al, 2013).…”