Solubility and thermodynamic analysis of ketoprofen in organic solvents

Svärd, Michael; Verma, Vivek; Padrela, Luís; Ryan, Kevin M.; Rasmuson, Åke C.

doi:10.1016/j.ijpharm.2020.119686

Cited by 17 publications

(15 citation statements)

References 37 publications

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“…All of the solventsmethanol (CAS: 67-56-1, ≥99.9% GC), ethanol (CAS: 64-17-5, ≥99.9% GC), isopropanol (CAS: 67-63-0, ≥99.9% GC), n -butanol (CAS: 71-36-3, ≥99.9% GC), acetonitrile (ACN, CAS: 75-05-8, ≥99.9% GC), 1,4-dioxane (CAS: 123-91-1, ≥99.9% GC), ethyl acetate (CAS: 141-78-6, ≥99.9% GC), and toluene (CAS: 108-88-3, ≥99.9% GC)were acquired from Fisher Scientific Ltd. (Ireland). A detailed analysis of the solid-phase characterization and further details on the properties of the solvents can be found elsewhere …”

Section: Methodsmentioning

confidence: 99%

“…Principal component analysis (PCA) and multiple regression analysis are used as the chemometric tools to refine the spectroscopic information collected and to correlate absorbance with solution concentration. The solubility curves obtained by the two approaches are compared using for data validation the solubility values obtained by a gravimetric method reported in our previous study . The second aim is to increase the understanding of the thermodynamic behavior of the particular compound by calorimetric determination of enthalpies of solution in the different solvents.…”

Section: Introductionmentioning

confidence: 99%

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Ketoprofen Solubility in Pure Organic Solvents Using In Situ FTIR and UV–Vis and Analysis of Solution Thermodynamics

Verma

Sadeghi

Rasmuson

2021

Org. Process Res. Dev.

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This work investigates the use of in situ process analytical technologies, namely, attenuated total reflectance Fourier transform infrared spectroscopy (ATR FTIR) and ATR UV−vis, coupled with a robust chemometric multivariate analysis approach for the determination of the solubility of ketoprofen in organic solvents within the temperature range of 273.15−303.15 K. Principal component analysis of the raw spectral data is applied along with multiple regression analysis and a stepwise regression procedure as the chemometric approach to build inferential models able to predict solubility data. For each solvent, the constructed models are used for solubility determinations and the results are compared with those previously determined by a gravimetric method. Both in situ FTIR and UV−vis render an accurate prediction of solubility data, with a notably high number of data points enabling the subsequent thermodynamic analysis. However, the accuracy of the solubility rendered from the spectroscopic analysis is not as accurate as by the gravimetric method at low temperatures. In addition, the experimental enthalpies of solution are determined by solution calorimetry and are found to be in a range of 18.6−32.4 kJ/mol in the different solvents. The order of solubility data obtained in the solvents studied is discussed in terms of the strength of the interactions with the ketoprofen carbonyl groups analyzed by the CO frequency of the FTIR data and based on the solution thermodynamic data obtained. All solutions of the work are relatively nonideal, with activity coefficients deviating from unity and enthalpies of mixing deviating from zero. The thermodynamic analysis and results clearly show that calorimetric enthalpies of solution are theoretically and quantitatively different from the corresponding van't Hoff enthalpies of solution, and a detailed explanation is provided.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ketoprofen Solubility in Pure Organic Solvents Using In Situ FTIR and UV–Vis and Analysis of Solution Thermodynamics

Verma

Sadeghi

Rasmuson

2021

Org. Process Res. Dev.

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“…The model drug employed in this study is ketoprofen (KET), a highly potent nonsteroidal anti-inflammatory drug which is widely prescribed due to its analgesic, antipyretic and anti-inflammatory properties in the treatment of numerous acute and chronic conditions, but mostly in the management of pain and rheumatic disorders. In conformity with the Biopharmaceutics Classification System (BCS), KET is assigned to Class II by presenting poor water solubility and high permeability [ 28 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

Polyvinyl Alcohol-Based 3D Printed Tablets: Novel Insight into the Influence of Polymer Particle Size on Filament Preparation and Drug Release Performance

et al. 2021

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Three-dimensional printing (3DP) by fused deposition modeling (FDM) has gained momentum as a promising pharmaceutical manufacturing method due to encouraging forward-looking perspectives in personalized medicine preparation. The current challenges the technology has for applicability in the fabrication of solid dosage forms include the limited range of suitable pharmaceutical grade thermoplastic materials. Hence, it is important to investigate the implications of variable properties of the polymeric carrier on the preparation steps and the final output, as versatile products could be obtained by using the same material. In this study, we highlighted the influence of polyvinyl alcohol (PVA) particle size on the residence time of the mixtures in the extruder during the drug-loaded filament preparation step and the consequent impact on drug release from the 3D printed dosage form. We enhanced filament printability by exploiting the plasticizing potential of the active pharmaceutical ingredient (API) and we explored a channeled tablet model as a design strategy for dissolution facilitating purposes. Our findings disclosed a new perspective regarding material considerations for the preparation of PVA-based solid dosage forms by coupling hot melt extrusion (HME) and FDM-3DP.

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“…It is soluble in acetone, ethanol, methylene chloride and strongly alkaline solutions [12]. It is slightly soluble in water and acidic solutions [13]. There are several methods employed to determine ketoprofen in pharmaceutical preparations such as: electrophoresis [14], spectrophotometry [13] high-performance liquid chromatography (HPLC) [15][16][17][18], electrochemical methods [19,20] and FT-IR spectrometry [21].…”

Section: Introductionmentioning

confidence: 99%

“…It is slightly soluble in water and acidic solutions [13]. There are several methods employed to determine ketoprofen in pharmaceutical preparations such as: electrophoresis [14], spectrophotometry [13] high-performance liquid chromatography (HPLC) [15][16][17][18], electrochemical methods [19,20] and FT-IR spectrometry [21]. This paper aims to highlight the in vitro stability of ketoprofen embedded in solid pharmaceutical forms (coated tablets) as a function of time under stress conditions such as temperature and high humidity.…”

Section: Introductionmentioning

confidence: 99%

In Vitro Studies of the Stability of Ketoprofen Tablets based on the European Pharmacopoeia Guideline (ICHQ1A)

Ganea¹,

Miere²,

Vicaş³

et al. 2021

Pharmacophore

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Solubility and thermodynamic analysis of ketoprofen in organic solvents

Cited by 17 publications

References 37 publications

Ketoprofen Solubility in Pure Organic Solvents Using In Situ FTIR and UV–Vis and Analysis of Solution Thermodynamics

Ketoprofen Solubility in Pure Organic Solvents Using In Situ FTIR and UV–Vis and Analysis of Solution Thermodynamics

Polyvinyl Alcohol-Based 3D Printed Tablets: Novel Insight into the Influence of Polymer Particle Size on Filament Preparation and Drug Release Performance

In Vitro Studies of the Stability of Ketoprofen Tablets based on the European Pharmacopoeia Guideline (ICHQ1A)

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