Thermodynamic solubility and density of sildenafil citrate in ethanol and water mixtures: Measurement and correlation at various temperatures

Pirhayati, Faezeh H.; Shayanfar, Ali; Azarbayjani, Anahita Fathi; Martínez, Fleming; Sajedi-Amin, Sanaz; Jouyban, Abolghasem

doi:10.1016/j.molliq.2016.11.055

Cited by 13 publications

(4 citation statements)

References 26 publications

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“…It was later grouped here, as it shared certain structural characteristics with dimethyl sulfoxide (DMSO) and acetonitrile. The three solvents, DMSO, acetonitrile, and acetone, are all considered to be polar aprotic solvents, the strength of which was determined by the dielectric constant for the solvent (Table 1) [61]. From the | g lum | data shown in Table 5, acetone is the solvent, with which the perturbation is greatest in the higher ratios of 70:30 (−0.01616), 60:40 (−0.02274), and 50:50 (−0.02697).…”

Section: Resultsmentioning

confidence: 99%

“…It is possible that the most significant difference between the solvents in this group was the strength of their respective hydrogen bond acceptor strengths. DMSO is classified as a stronger hydrogen bond donor compared to both acetone and acetonitrile [61]. This is due to the presence of the sulfur atom, which is much more polarizable than carbon and less electronegative than oxygen or nitrogen.…”

Section: Resultsmentioning

confidence: 99%

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The Importance of Solvent Effects on the Mechanism of the Pfeiffer Effect

et al. 2018

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The Pfeiffer effect is observed when an optically active compound such as an amino acid is introduced to a solution containing a labile racemic metal complex, and an equilibrium shift is obtained. The “perturbation” results in an excess of one enantiomer over the other. The shift is a result of a preferential outer sphere interaction between the introduced chiral species and one enantiomeric form (Λ or ∆) of a labile metal complex. Speculations regarding the mechanism of the Pfeiffer effect have attributed observations to a singular factor such as pH, solvent polarity, or numerous other intermolecular interactions. Through the use of the lanthanide(III) complexes [Tb(DPA)3]3− and [Eu(DPA)3]3− (where DPA = 2,6-pyridinedicarboxylate) and the amino acids l-serine and l-proline; it is becoming clear that the mechanism is not so simply described as per the preliminary findings that are discussed in this study. It appears that the true mechanism is far more complicated than the attribute just a singular factor. This work attempts to shine light on the fact that understanding the behavior of the solvent environment may hypothetically be the key to offering a more detailed description of the mechanism.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

The Importance of Solvent Effects on the Mechanism of the Pfeiffer Effect

et al. 2018

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“…Sildenafil citrate, the active pharmaceutical ingredient in medications like Viagra®, exhibits variable solubility dependent on factors such as temperature and pH of the solvent. At room temperature, its solubility in water is moderately at around 4.1 ± 1.3 mg/mL, but slightly increases with higher temperatures ( Pirhayati et al, 2017 ). Aldawsari et al have prepared solid dispersions of sildenafil using hydrophilic polymers such as Kollidon® 30, Kolliphor® P188, and Kollidon and demonstrated enhanced dissolution rate, and significant improvement in inter-copulatory efficiency and copulatory efficiency in male rat models ( Aldawsari et al, 2021 ).…”

Section: Introductionmentioning

confidence: 99%

Development and evaluation of sildenafil/glycyrrhizin-loaded nanofibers as a potential novel buccal delivery system for erectile dysfunction

Alamer,

Alshehri,

Aodah

et al. 2024

Saudi Pharmaceutical Journal

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“…Because of to a low concentration of drugs in aqueous medium, it might be preferable to place three methods, that is, i.e. cosolvents, multiple cosolvents containing hydrotropy and (cosolvents + buffer). − Co-solvency is an optional and effective solubilization strategy considered as an alternative to the solubility, as anhydrous liquid mixtures are a crucial impact factor for medicinal industries in that they could be available for reaction medium or recrystallization solvents in the synthesis and purification process of numerous pharmaceuticals. − …”

Section: Introductionmentioning

confidence: 99%

Cosolvency and Mathematical Modeling Analysis of Chloroxine in Some Binary Solvent System

Shi¹,

Xie²,

Xu³

et al. 2018

J. Chem. Eng. Data

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Equilibrium solubilities of chloroxine in binary solvent mixtures of ethyl acetate plus methanol, ethanol, n-propanol, and isopropanol were measured by the static equilibrium method in the temperature range of 283.15−333.15 K at pressure of 1 atm. The solubility data is positively increased with increasing temperature at different solvent composition ranging from 0 to 1 and decreased with the increasing mass fraction of alcohol in each binary system, and the maximum solubility of 7.819 × 10 −3 at 333.15 K was found in neat ethyl acetate. Under the same composition of ethyl acetate and temperature conditions, the solubility of chloroxine was greater in (methanol + ethyl acetate) than in the other three solution mixtures. Several mathematical models, that is, the Jouyban−Acree model, Van't Hoff−Jouyban−Acree model and Apelblat−Jouyban−Acree model were adopted to correlate the measured solubility values. As a result, the calculated data are in alignment to measured values at evaluated temperatures and RAD (× 10 −2 ) and RMSD (× 10 −4 ) data were no more than 3.49 and 0.94, respectively. X-ray powder diffraction serves to analyze the equilibrium solid phase crystal of chloroxine and results turns out that no polymorphic transformation, solvate formation or crystal transition in the whole solvent crystallization process.

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Thermodynamic solubility and density of sildenafil citrate in ethanol and water mixtures: Measurement and correlation at various temperatures

Cited by 13 publications

References 26 publications

The Importance of Solvent Effects on the Mechanism of the Pfeiffer Effect

The Importance of Solvent Effects on the Mechanism of the Pfeiffer Effect

Development and evaluation of sildenafil/glycyrrhizin-loaded nanofibers as a potential novel buccal delivery system for erectile dysfunction

Cosolvency and Mathematical Modeling Analysis of Chloroxine in Some Binary Solvent System

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