Experimental Study and Thermodynamic Modeling of Mesalamine and Azathioprine Solubility in Some Choline Chloride-Based Deep Eutectic Solvents

Abstract

The present study attempted to measure the solubility of mesalamine and azathioprine in the aqueous solution of some deep eutectic solvents (DESs) at various DES weight fractions (0–1) over the temperature range of 283.15–323.15 K. We prepared the DESs by combining choline chloride (ChCl, hydrogen bond acceptor, HBA) and ethylene glycol (EG) and 1,2-propanediol (PD) (hydrogen bond donors, HBDs) with molar ratios of 1:2 and 1:3, respectively. The results indicate that the solubility is significantly increased up to 30-fold for mesalamine and 75-fold for azathioprine compared to water. Besides, the solubility of both pharmaceuticals is enhanced by increasing the temperature and weight fraction of DESs. Also, DES1 (ChCl + EG) shows higher solubility for mesalamine than DES2 (ChCl + PD), which is the opposite for azathioprine. The experimental solubility data were accurately correlated using the local composition models such as Wilson, nonrandom two-liquid theory (NRTL), and universal quasi-chemical (UNIQUAC). On the other hand, we applied the nonrandom two-liquid-segment activity coefficient (NRTL-SAC) and universal quasi-chemical segment activity coefficient (UNIQUAC-SAC) models to correlate and predict the solubility of the mesalamine and azathioprine in DES1 and DES2. In addition, the calculated values of the thermodynamic functions of dissolution reveal that in the dissolution process of both drugs, enthalpy is the primary contribution term to the standard Gibbs free energy.

Novel hybrid QSPR-GPR approach for modeling of carbon dioxide capture using deep eutectic solvents

“…Currently, diverse thermodynamic models comprising UNIQUAC Functional-group Activity Coefficients (UNIFAC), 30 UNIversal QUAsi Chemical (UNIQUAC), 31 and Non-Random Two-Liquid (NRTL), 32 in conjunction with an equation of state techniques like Peng–Robinson state equation (PR-EoS), 33 Cubic-Plus Association (CPA), 34 soft-SAFT, 35 and perturbed chain statistical associating fluid theory (PC-SAFT), 36 have been effectively employed to estimated gas solubility in systems including DESs. These thermodynamic models offer valuable tools for estimating gas solubility in DES-containing systems.…”

“…The development of dependable computational models for predicting CO 2 solubilities in DESs stands as an increasing and highly coveted area of research, as these models expedite the discovery and optimization of DES-based solvent systems, propelling the development of efficient and sustainable solutions for CO 2 emissions mitigation. [27][28][29] Currently, diverse thermodynamic models comprising UNI-QUAC Functional-group Activity Coefficients (UNIFAC), 30 UNIversal QUAsi Chemical (UNIQUAC), 31 and Non-Random Two-Liquid (NRTL), 32 in conjunction with an equation of state techniques like Peng-Robinson state equation (PR-EoS), 33 Cubic-Plus Association (CPA), 34 so-SAFT, 35 and perturbed chain statistical associating uid theory (PC-SAFT), 36 have been effectively employed to estimated gas solubility in systems including DESs. These thermodynamic models offer valuable tools for estimating gas solubility in DES-containing systems.…”

Eutectic Mixtures to Enhance the Solubility of Active Pharmaceutical Ingredients: Density Functional Theory and Infrared Spectroscopy Approaches

“…[1,2] It is widely known that dissolving of drug is often the rate-limiting stage in the gastrointestinal absorption of the medication in solid dosage forms. [3][4][5] In recent years, there has been a lot of research in making or designing of eutectic mixtures of poorly soluble active pharmaceutical ingradients (APIs) to enhance the solubility as well as oral absorption. It is essential to keep in mind that most of the APIs are sparingly to poorly water-soluble.…”

“…[4] Many attempts have been made by employing techniques such as creating solid dispersions, generating cocrystals and salts, emulsions, or confinement in mesoporous silica to solve these problems. [5] Mostly the drugs belonging to classes II and IV are used in developing drugs but face solubility problems. In recent years, researchers have been focussing on green technology in the pharmaceutical and chemical industries.…”

“…Solid oral dose forms are among the most utilized and have various advantages [1,2] . It is widely known that dissolving of drug is often the rate‐limiting stage in the gastrointestinal absorption of the medication in solid dosage forms [3–5] . In recent years, there has been a lot of research in making or designing of eutectic mixtures of poorly soluble active pharmaceutical ingradients (APIs) to enhance the solubility as well as oral absorption.…”