Solubility and preferential solvation of some non-steroidal anti-inflammatory drugs in methanol + water mixtures at 298.15 K

Jiménez, Daniel M.; Muñoz, María M.; Rodríguez, Carlos J.; Cárdenas, Zaira J.; Martínez, Fleming

doi:10.1080/00319104.2016.1140763

Cited by 17 publications

(8 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The concentration of the impurity (IBF) remains constant at 0.062 mg/g (standard deviation of 0.04 mg/g, n = 13) across the entire V p range and is equal to its solubility. The reported solubility of pure IBF in 10 wt % MeOH in H 2 O at 25 °C is 0.096 mg/g according to Jimenez et al, 2016 . The concentration of salicylic acid is equal to its solubility up to 350–400 L/kg, in this study at 2.95 mg/g (standard deviation of 0.067 mg/g, n = 7).…”

Section: Resultssupporting

confidence: 50%

“…The reported solubility of pure IBF in 10 wt % MeOH in H 2 O at 25 °C is 0.096 mg/g according to Jimenez et al, 2016. 18 The concentration of salicylic acid is equal to its solubility up to 350−400 L/kg, in this study at 2.95 mg/g (standard deviation of 0.067 mg/g, n = 7). This is within the range for pure salicylic acid reported by Matsuda et al 17 Case Study 3.…”

Section: Acetaminophenmentioning

confidence: 76%

“…All the components were fully dissolved in pure MeOH prior to crystallization through the addition of water. The experimental solubilities of the pure APAP, SA, and IBF in MeOH/H 2 O have been reported in the literature. − Each isolated material contained different amounts of impurity levels. These materials were then subjected to the so-called SLIP test, explained above.…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Solubility-Limited Impurity Purge in Crystallization

Nordström

Linehan

Teerakapibal

et al. 2019

Crystal Growth & Design

View full text Add to dashboard Cite

Crystallization from solution is a key unit operation utilized across the synthetic scheme to remove impurities. However, little is still known of the underlying impurity purge mechanisms that are responsible for controlling the final purity of the product. Reported herein is the solubility-limited impurity purge mechanism in which the impurity exists as a separate solid phase with its own solubility. A mathematical framework is presented that describes the separation of the impurity in the solid and liquid phases based on the relative solubilities of the product and impurity, and initial impurity level. Three theoretical solubility-limited impurity purge mechanisms are derived that are confirmed experimentally using salicylic acid, ibuprofen, and acetaminophen as model compounds. A practical experimental test is introduced that is used to identify if the impurity is rejected by solubility-limitation and its corresponding type. Finally, development strategies are presented to remove impurities that are purged based on their solubilities.

show abstract

Section: Resultssupporting

confidence: 50%

Section: Acetaminophenmentioning

confidence: 76%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Solubility-Limited Impurity Purge in Crystallization

Nordström

Linehan

Teerakapibal

et al. 2019

Crystal Growth & Design

View full text Add to dashboard Cite

show abstract

“…In the case of IP, such data are available for 18 neat solvents, including methanol [94], ethanol [94,[97][98][99][100], 1-propanol [97], 2-Propanol [94,97,101,102], 1-butanol [97], isobutanol [97], 1-pentanol [97], 3-methyl-1-butanol [97], 1-octanol [95,100], propylene glycol [98], ethyl acetate [94,97], isopropyl acetate [51], isopropyl myristate [51], acetone [94,103], 2-butanone [51], 4-methyl-2-pentanone [94], 3-methyl-2-butanone [51], acetonitrile [51], cyclohexane [95], toluene [94], heptane [51], dichloromethane [103], chloroform [94,95], and water [99,104]. Additionally, there are four reports documenting the solubility of IP in binary mixtures such as water-methanol [105], water-ethanol [99], waterpropylene glycol [104], and ethanol-propylene glycol [98]. The solubility of S-enantiomer, (S)-(+)-ibuprofen, was measured [106] in methanol, 1-butylanol, isobutanol, 1-pentanol, and 1-octanol.…”

Section: Solubility Datasetmentioning

confidence: 99%

Experimental and Machine-Learning-Assisted Design of Pharmaceutically Acceptable Deep Eutectic Solvents for the Solubility Improvement of Non-Selective COX Inhibitors Ibuprofen and Ketoprofen

Cysewski,

Jeliński,

Przybyłek

et al. 2024

Molecules

View full text Add to dashboard Cite

Deep eutectic solvents (DESs) are commonly used in pharmaceutical applications as excellent solubilizers of active substances. This study investigated the tuning of ibuprofen and ketoprofen solubility utilizing DESs containing choline chloride or betaine as hydrogen bond acceptors and various polyols (ethylene glycol, diethylene glycol, triethylene glycol, glycerol, 1,2-propanediol, 1,3-butanediol) as hydrogen bond donors. Experimental solubility data were collected for all DES systems. A machine learning model was developed using COSMO-RS molecular descriptors to predict solubility. All studied DESs exhibited a cosolvency effect, increasing drug solubility at modest concentrations of water. The model accurately predicted solubility for ibuprofen, ketoprofen, and related analogs (flurbiprofen, felbinac, phenylacetic acid, diphenylacetic acid). A machine learning approach utilizing COSMO-RS descriptors enables the rational design and solubility prediction of DES formulations for improved pharmaceutical applications.

show abstract

“…The preferential solvation parameters of several anti-inflamatory drugs: naproxen, ketoprofen, and ibuprofen in methanol+water binary mixtures were derived by means of the IKBI method from their solubilities at 25°C [38]. These drugs are very sensitive to specific solvation effects.…”

Section: Pharmmentioning

confidence: 99%

Preferential Solvation of Drugs in Binary Solvent Mixtures

Marcus¹

2017

Pharm Anal Acta

View full text Add to dashboard Cite

The preferential solvation of many drugs in binary solvent mixtures, as derived by means of the quasi-lattice quasi-chemical and the inverse Kirkwood-Buff integrals methods from solubility and other thermodynamic data, is reviewed. The preferences were described in terms of the local mole fractions of the solvent components in the solvation sphere of the drug molecule and their differences with respect to these mole fractions in the bulk: the preferential solvation parameters. When data were available at several temperatures these preferences were described in terms of the enthalpic and entropic contributions.

show abstract

Solubility and preferential solvation of some non-steroidal anti-inflammatory drugs in methanol + water mixtures at 298.15 K

Cited by 17 publications

References 45 publications

Solubility-Limited Impurity Purge in Crystallization

Solubility-Limited Impurity Purge in Crystallization

Experimental and Machine-Learning-Assisted Design of Pharmaceutically Acceptable Deep Eutectic Solvents for the Solubility Improvement of Non-Selective COX Inhibitors Ibuprofen and Ketoprofen

Preferential Solvation of Drugs in Binary Solvent Mixtures

Contact Info

Product

Resources

About