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Thermodynamic analysis of celecoxib in amphiprotic and amphiprotic-aprotic solvent mixtures at several temperatures
Análisis termodinámico del celecoxib en mezclas disolventes anfipróticas y anfipróticas-apróticas a varias temperaturas
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https://doi.org/10.15446/rcciquifa.v48n3.84957Palabras clave:
celecoxib, solubility, solvent mixtures, thermodynamic quantities, characterization (en)celecoxib, solubilidad, mezcla disolvente, parámetros termodinámicos, caracterización (es)
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The solubilities of celecoxib (CLX), a COX-2 selective nonsteroidal anti-inflammatory drug, were determined in water-ethanol and ethanol-ethyl acetate mixtures at several temperatures (288.15-308.15 K). The solubility curves as a function of ethanol ratio were studied at five temperatures, they showed a single maximum located at 50% ethanol-ethyl acetate (δ1 = 22.50 MPa1/2). The measurements of the variation of inherent drug solubility with temperature were used to estimate different thermodynamic parameters, enthalpy, entropy and Gibbs free energy of solution (ΔHS,ΔSS and ΔGShm, respectively). The apparent enthalpies of the solution were a nonlinear function of the ethanol ratio in aqueous mixture. Non-linear enthalpy-entropy compensation analysis was observed indicating different dissolution mechanism with the variation in mixtures composition. The solubility enhancement is entropy driven at water-rich region (0-40% v/v ethanol) and enthalpy controlled at ethanol-rich region (40–100% v/v ethanol), likely due to water-structure loss around nonpolar moieties of the drug and for the ethanol-rich mixtures it is the enthalpy, probably due to the drug better solvation.
Se determinó la solubilidad del celecoxib (CLX), un fármaco antiinflamatorio no esteroide selectivo de COX-2, en agua-etanol y etanol-acetato de etilo a varias temperaturas (288,15-308,15 K). Los perfiles de solubilidad obtenidos fueron estudiados en función de la proporción de etanol en las cinco temperaturas de estudio. Los resultados muestran solamente un máximo en el 50% de etanol-acetato de etilo (δ1 = 22,50 MPa1/2). La variación de la solubilidad con la temperatura se utilizó para calcular diferentes parámetros termodinámicos, entalpía, entropía y energía de disolución libre de Gibbs (ΔHS, ΔSS y ΔGShm, respectivamente). Las entalpías aparentes de disolución fueron no lineales en la mezcla acuosa. Además, se observó un análisis de compensación de entalpía-entropía no lineal, lo que indica un mecanismo de disolución que varía con la composición de cada mezcla. El aumento de la solubilidad es impulsado por la entropía en la región rica en agua (0-40% v/v de etanol) y la entalpía en la región rica en etanol (40–100% v/v de etanol), probablemente debido a la pérdida de la estructura del agua alrededor de los residuos no polares del fármaco y para las mezclas ricas en etanol es la entalpía, probablemente debido a la mejor solvatación del fármaco.
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1. Vivek Verma, Rodrigo Soto, Shayon Bhattacharya, Damien Thompson, Kevin M. Ryan, Luis Padrela. (2022). Thermodynamic solubility of celecoxib in organic solvents. CrystEngComm, 24(3), p.698. https://doi.org/10.1039/D1CE01415C.
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