Thermodynamic study and preferential solvation of sulfamerazine in acetonitrile + methanol cosolvent mixtures at different temperatures

Cárdenas, Rossember E.; Ortíz, Claudia Patricia; Acree, William E.; Jouyban, Abolghasem; Martínez, Fleming; Delgado, Daniel Ricardo

doi:10.1016/j.molliq.2021.118172

Cited by 11 publications

(6 citation statements)

References 41 publications

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“…When comparing the preferential solvation behavior of sulfadiazine (SD [45]), sulfamerazine (SMR [46]) and sulfamethazine (SMT) in MeCN + MeOH cosolvent mixtures, the influence of the methyl groups (-CH 3 ) can be seen (SD: 0 groups -CH 3 ; SMR: 1 -CH 3 groups; SMT: 2 -CH 3 groups) in the displacement of the maximum solvation point of the three sulfonamides by MeOH, the more polar SD tends to present the peak in more polar zones, while the SMT shows the peak of maximum solvation in less polar co-solvent mixtures. This tendency of the three sulfonamides to be preferentially solvated by MeOH in most of the mixtures, especially in SMT, which is practically solvated by MeOH in all cosolvent systems MeCN+MeOH, may be a consequence of a possible self-association of MeCN, which has been reported by Marcus [42] in different binary mixtures MeCN + organic solvents and by Hawlicka and Grabowski [47] for mixtures MeCN + MeOH.…”

Section: Preferential Solvationmentioning

confidence: 99%

Solubility of Sulfamethazine in the Binary Mixture of Acetonitrile + Methanol from 278.15 to 318.15 K: Measurement, Dissolution Thermodynamics, Preferential Solvation, and Correlation

et al. 2021

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Solubility of sulfamethazine (SMT) in acetonitrile (MeCN) + methanol (MeOH) cosolvents was determined at nine temperatures between 278.15 and 318.15 K. From the solubility data expressed in molar fraction, the thermodynamic functions of solution, transfer and mixing were calculated using the Gibbs and van ’t Hoff equations; on the other hand, the solubility data were modeled according to the Wilson models and NRTL. The solubility of SMT is thermo-dependent and is influenced by the solubility parameter of the cosolvent mixtures. In this case, the maximum solubility was achieved in the cosolvent mixture w0.40 at 318.15 K and the minimum in pure MeOH at 278.15 K. According to the thermodynamic functions, the SMT solution process is endothermic in addition to being favored by the entropic factor, and as for the preferential solvation parameter, SMT tends to be preferentially solvated by MeOH in all cosolvent systems; however, δx3,1<0.01, so the results are not conclusive. Finally, according to mean relative deviations (MRD%), the two models could be very useful tools for calculating the solubility of SMT in cosolvent mixtures and temperatures different from those reported in this research.

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Section: Preferential Solvationmentioning

confidence: 99%

Solubility of Sulfamethazine in the Binary Mixture of Acetonitrile + Methanol from 278.15 to 318.15 K: Measurement, Dissolution Thermodynamics, Preferential Solvation, and Correlation

et al. 2021

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“…Our recent efforts pertaining to solubility have focused on experimental measurements for crystalline nonelectrolyte solutes dissolved in select organic mono-solvents [14][15][16][17] and in binary aqueous-organic solvent mixtures [18][19][20][21][22]. The measured solubility data has been used in the calculation of the Abraham model solute descriptors [14][15][16][17] and in developing the Abraham model correlations for predicting the solubilities of pharmaceutical compounds in organic solvents used in recrystallization purifications and in co-solvency solubility enhancements [23][24][25][26][27].…”

Section: Introductionmentioning

confidence: 99%

Abraham Model Descriptors for Vitamin K4: Prediction of Solution, Biological and Thermodynamic Properties

Motati,

Kandi

et al. 2023

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Spectrophotometric measurements were used to determine the mole fraction solubilities of vitamin K4 dissolved in cyclohexane, methylcyclohexane, 1-heptanol, 2-butanol, 2-pentanol, 2-methyl-1-butanol, 4-methyl-2-pentanol, and cyclopentanol at 298.15 K. Results from our experimental measurements, combined with the published solubility data, are used to calculate the solute descriptors of the vitamin K4 solute. The calculated solute descriptors describe the observed solubility data to within an overall standard deviation of 0.110 log units. The calculated solute descriptors were also used to estimate the several blood-to-rat tissue partition coefficients of vitamin K4, as well as the equilibrium vapor pressure above the solid vitamin at 298 K, and the vitamin’s enthalpy of solvation in both water and in 1,4-dioxane organic mono-solvent.

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“…Sulfamerazine (SMR; Figure 1) is used in the treatment of pathologies caused by bacteria, such as bronchitis, prostatitis, and urinary tract infections [11,12]. One of the major challenges when developing drug formulations whose active pharmaceutical ingredient (API) is SMR is the low solubility of the drug in aqueous systems; therefore, studies in cosolvent systems are highly relevant [13,14].…”

Section: Introductionmentioning

confidence: 99%

“…In addition, SMR is among the most widely used sulfonamides in the design of pharmaceutical forms (FPs) for veterinary use, and due to the increase in bacterial resistance to first-line antibiotics meant for humans, its use in the development of FP for human therapy has also increased. The solubility of SMR was studied in several cosolvent mixtures of pharmaceutical interest, such as water and methanol [15], water and ethanol [16], water and 1-propanol [17], acetonitrile and methanol [11], ethylene glycol and water [18], acetonitrile and water [12], and propylene glycol and water [19]. Nevertheless, it is important to conduct new studies in order to contribute to the understanding of the possible mechanisms of the SMR solution process.…”

Section: Introductionmentioning

confidence: 99%

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Numerical Analysis of Sulfamerazine Solubility in Acetonitrile + 1-Propanol Cosolvent Mixtures at Different Temperatures

et al. 2023

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The current challenges of the pharmaceutical industry regarding the environmental impact caused by its waste have led to the design and development of more efficient industrial processes. In this context, solubility studies are at the core of different processes, such as formulation, preformulation, synthesis, purification, recrystallization, quantification, and quality control. This research evaluates the solubility of sulfamerazine (SMR) in acetonitrile + 1-propanol cosolvent mixtures at nine temperature levels with UV/vis spectrophotometry using the vial-shake method. According to the analysis of the solid phase in equilibrium using differential scanning calorimetry, there were no polymorphic changes. The minimal solubility of SMR was reached in 1-propanol at 278.15 K, and the maximal solubility in acetonitrile at 313.15 K. In all cases, the process was endothermic and dependent on the cosolvent composition, and the solution enthalpy drove the solution process. The solubility data were well correlated with the van’t Hoff, Yalkowsky–Roseman–van’t Hoff, Apelblat, Buchowski–Ksiazczak λh, Yaws, NRTL, Wilson, and modified Wilson models, with the YR model being one of the most attractive because it presented an excellent prediction percentage from four sets of experimental data. The solution process of SMR in acetonitrile + 1-propanol cosolvent mixtures depends on the affinity of SMR for acetonitrile and temperature increase.

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Thermodynamic study and preferential solvation of sulfamerazine in acetonitrile + methanol cosolvent mixtures at different temperatures

Cited by 11 publications

References 41 publications

Solubility of Sulfamethazine in the Binary Mixture of Acetonitrile + Methanol from 278.15 to 318.15 K: Measurement, Dissolution Thermodynamics, Preferential Solvation, and Correlation

Solubility of Sulfamethazine in the Binary Mixture of Acetonitrile + Methanol from 278.15 to 318.15 K: Measurement, Dissolution Thermodynamics, Preferential Solvation, and Correlation

Abraham Model Descriptors for Vitamin K4: Prediction of Solution, Biological and Thermodynamic Properties

Numerical Analysis of Sulfamerazine Solubility in Acetonitrile + 1-Propanol Cosolvent Mixtures at Different Temperatures

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