Determination and prediction of solubilities of active pharmaceutical ingredients in selected organic solvents

Matsuda, Hiroyuki; Mori, Takehiko; Tomioka, Mariko; Kariyasu, Nozomi; Fukami, Toshiro; Kurihara, Kiyofumi; Tochigi, Katsumi; Tomono, Kazuo

doi:10.1016/j.fluid.2015.07.032

Cited by 33 publications

(9 citation statements)

References 34 publications

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“…Aspirin (acetylsalicylic acid) is a widely available over the counter drug as it is an analgesic (pain reliever) and antipyretic (fever reducer) that also has anti-inflammatory properties. The solubility of aspirin has been collected in pure and mixed solvent systems across multiple cases in the literature. − The objective of this study is to investigate further the effect of temperature on the solubility in a wider range of pure solvents covering the alcohol, acetate, and ketone functional groups. The chemical structures of benzoic acid and aspirin are shown in Figure .…”

Section: Introductionmentioning

confidence: 99%

Solubility of Benzoic Acid and Aspirin in Pure Solvents Using Focused Beam Reflective Measurement

2015

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The solubility of benzoic acid and acetylsalicylic acid is reported in varied pure solvents over a range of 275.39–327.03 K and 275.12–327.91 K for benzoic acid and aspirin, respectively, using the polythermal method with a heating rate of 0.1 K/min that was combined with the Lasentec focused beam reflective measurement to determine the saturation point of the solutions. The results were correlated using a modified van’t Hoff equation that fitted the solubility with a 2 K interval over a temperature range of 278.15–323.15 K. The results from the fitting equation were in good agreement with the experimental data.

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Section: Introductionmentioning

confidence: 99%

Solubility of Benzoic Acid and Aspirin in Pure Solvents Using Focused Beam Reflective Measurement

2015

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“…The melting temperature of form A was higher than that of form B. Sulfathiazole form I also showed a melting peak, whereas forms II and IV exhibit an additional endothermic signal at a lower temperature due to the polymorphic transition into form I. The transition temperatures T tr and the corresponding molar enthalpy changes Δ h tr are listed in Table in comparison with the literature data. ,,,− …”

Section: Resultsmentioning

confidence: 81%

Polymorphic Solubility Ratio of Famotidine and Sulfathiazole in Various Solvents

Takebayashi

Sue

Furuya

et al. 2021

Crystal Growth & Design

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Solubilities of two polymorphs of famotidine (A, B) and three polymorphs of sulfathiazole (I, II, and IV) were measured in various solvents at 298.15 K to clarify how the solubility ratios B/A, I/IV, and II/IV depend on the solvent. The famotidine solubility increased in the order of ethyl acetate < water < 2-propanol < acetonitrile < 1-propanol < ethanol < acetone < methanol for both polymorphs. The solubility ratio B/A varied from 1.09 to 1.32, having a positive correlation with the solvent polarity. In contrast, the sulfathiazole solubility increased in the order of water < ethyl acetate < 2-propanol < 1-propanol < ethanol < methanol. The solubility ratios I/IV and II/IV changed little within 1.62 ± 0.04 and 1.00 ± 0.03, respectively. The negligible solvent dependence indicates that the solubility ratios are determined only by the free energy difference between the polymorphs in the solid state. This enabled us to estimate the solubilities of metastable form I in water, methanol, and ethanol, which could not be measured due to solvent-mediated transformation. The solubility ratios were compared with those calculated using three types of thermodynamic equations from the transition temperature and enthalpy change measured by differential scanning calorimetry. The equation proposed by Hoffmann gave the values closest to the experimental results.

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“…In PC-SAFT, pure components can be described using five pure-component parameters: (i) m , number of segments per chain; (ii) σ , diameter of each segment in Angstrom (Å); (iii) ε , energy parameter for each segment in Joules (J); (iv) κ AiBi , effective volume of the association (Å 3 ); (v) ε AiBi , energy parameter of the association (bar.l/mol); (vi) NumAss , number of association sites ( ). The parameters of each component are reported in Table I ( 43 , 45 ). The interaction parameters for binary systems (ethanol + water), (acetylsalicylic acid + water) and (acetylsalicylic acid + ethanol), k ij , for the purely predictive model were set to zero.…”

Section: Methodsmentioning

confidence: 99%

Solubility Study of Acetylsalicylic Acid in Ethanol + Water Mixtures: Measurement, Mathematical Modeling, and Stability Discussion

et al. 2021

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Solubility determination of poorly water-soluble drugs is pivotal for formulation scientists when they want to develop a liquid formulation. Performing such a test with different ratios of cosolvents with water is time-consuming and costly. The scarcity of solubility data for poorly water-soluble drugs increases the importance of developing correlation and prediction equations for these mixtures. Therefore, the aim of the current research is to determine the solubility of acetylsalicylic acid in binary mixtures of ethanol+water at 25 and 37°C. Acetylsalicylic acid is non-stable in aqueous solutions and readily hydrolyze to salicylic acid. So, the solubility of acetylsalicylic acid is measured in ethanolic mixtures by HPLC to follow the concentration of produced salicylic acid as well. Moreover, the solubility of acetylsalicylic acid is modeled using different cosolvency equations. The measured solubility data were also predicted using PC-SAFT EOS model. DSC results ruled out any changes in the polymorphic form of acetylsalicylic acid after the solubility test, whereas XRPD results showed some changes in crystallinity of the precipitated acetylsalicylic acid after the solubility test. Fitting the solubility data to the different cosolvency models showed that the mean relative deviation percentage for the Jouyban-Acree model was less than 10.0% showing that this equation is able to obtain accurate solubility data for acetylsalicylic acid in mixtures of ethanol and water. Also, the predicted data with an average mean relative deviation percentage (MRD%) of less than 29.65% show the capability of the PC-SAFT model for predicting solubility data. A brief comparison of the solubilities of structurally related solutes to acetylsalicylic acid was also provided.

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Determination and prediction of solubilities of active pharmaceutical ingredients in selected organic solvents

Cited by 33 publications

References 34 publications

Solubility of Benzoic Acid and Aspirin in Pure Solvents Using Focused Beam Reflective Measurement

Solubility of Benzoic Acid and Aspirin in Pure Solvents Using Focused Beam Reflective Measurement

Polymorphic Solubility Ratio of Famotidine and Sulfathiazole in Various Solvents

Solubility Study of Acetylsalicylic Acid in Ethanol + Water Mixtures: Measurement, Mathematical Modeling, and Stability Discussion

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