Pressure-temperature phase diagram of the dimorphism of the anti-inflammatory drug nimesulide

Huguet, J.; Robert, Benoit; Rietveld, Ivo B.; Céolin, R.; Tamarit, J. Ll.

doi:10.1016/j.ijpharm.2017.04.016

Cited by 10 publications

(9 citation statements)

References 24 publications

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“…As when comparing the relative thermodynamic stabilities of glycine polymorphs at ambient pressure, a reliable answer on the relative stabilities at high pressures could be given by high-pressure calorimetry. Examples of such studies for several compounds are known, [117][118][119][120][121][122][123][124][125][126] but not for glycine (yet? ).…”

Section: Relative Stabilities and Transformation At High Pressuresmentioning

confidence: 99%

Glycine: The Gift that Keeps on Giving

Boldyreva

2021

Israel Journal of Chemistry

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Glycine is a small molecule. It cannot change its conformation and is achiral. Despite the apparent simplicity, glycine shows endless diversity in its behavior over many phenomena. It was the first amino acid for which polymorphism was reported, first on crystallization and then on hydrostatic compression. The polymorphs differ in their physical properties and their biological activity. Glycine clusters persist in solution, leading to "solution memory". Phenomena at interfaces are critically important for crystal growth, dissolution, and for physical properties, which can be at times unexpected, like polarity in centrosymmetric αpolymorph. It is a great pleasure to remind of these remarkable phenomena in a special issue honoring professors Meir Lahav and Leslie Leiserowitz, who pioneered the study of the behavior of this unique molecule in many respects, and showed how complex and non-trivial phenomena can be at interfaces: between phases and between research fields.

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Section: Relative Stabilities and Transformation At High Pressuresmentioning

confidence: 99%

Glycine: The Gift that Keeps on Giving

Boldyreva

2021

Israel Journal of Chemistry

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“…Finally, we applied the FH theory to the data generated under elevated pressure (50 MPa). The melting point of NMS under such a condition is 435 K, 65 while the enthalpy of drug melting and density of the components were taken to be comparable to those obtained when no pressure was applied. Using the approach (I), the χ parameter was determined to be −1.3 ± 0.2, implying the miscibility of the drug and polymer; however, it was clear that the fit is not precise.…”

Section: Resultsmentioning

confidence: 99%

“…Next, we decided to shift vertically the experimental data corresponding to the solubility limits obtained at elevated pressures. As a reference point, we used the melting temperature of neat NMS at 50 65 and 0.1 MPa. 47 As can be seen in panel (a) of Figure 13 , this procedure provides an interesting result (gray pentagons, empty and filled, respectively).…”

Section: Resultsmentioning

confidence: 99%

“… (a,b) Glass-transition temperatures of NMS + KVA mixtures. Circles correspond to the experimentally determined T g at 0.1 MPa, while filled and empty stars correspond to the solubility limit values determined at ambient and elevated pressures (50 MPa), respectively, and filled and empty pentagons (NMS) represent data taken from the literature at ambient 47 and elevated pressure, 65 respectively. Panel (a) serves as a visual aid to illustrate the vertical transfer of the experimental data corresponding to the solubility limits obtained at elevated pressures.…”

Section: Resultsmentioning

confidence: 99%

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High-Pressure Dielectric Studies—a Way to Experimentally Determine the Solubility of a Drug in the Polymer Matrix at Low Temperatures

et al. 2021

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In this work, we employed broad-band dielectric spectroscopy to determine the solubility limits of nimesulide in the Kollidon VA64 matrix at ambient and elevated pressure conditions. Our studies confirmed that the solubility of the drug in the polymer matrix decreases with increasing pressure, and molecular dynamics controls the process of recrystallization of the excess of amorphous nimesulide from the supersaturated drug–polymer solution. More precisely, recrystallization initiated at a certain structural relaxation time of the sample stops when a molecular mobility different from the initial one is reached, regardless of the temperature and pressure conditions. Finally, based on the presented results, one can conclude that by transposing vertically the results obtained at elevated pressures, one can obtain the solubility limit values corresponding to low temperatures. This approach was validated by the comparison of the experimentally determined points with the theoretically obtained values based on the Flory–Huggins theory.

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“…Nimesulide is a potent and selective inhibitor of cyclooxygenase-2, very effective in the treatment of various forms of pain and inflammatory conditions with minimal side effects and low toxicity [13,14] and is a potential drug for future treatment strategies against the SARS-CoV-2 virus, as it appears to completely eliminate, indirectly, the B0AT1 protein transport function [15]. Two polymorphic forms of nimesulide have been reported in the literature: form I [16] and form II [17,18]. In order to have good bioavailability, the drugs must be soluble in the gastric juice, in the case of oral administration or in appropriate solvents to improve transdermal permeability [19].…”

Section: Introductionmentioning

confidence: 99%

Thermal Behavior of the Nimesulide-Salicylic Acid Eutectic Mixtures Prepared by Mechanosynthesis and Recrystallization

et al. 2021

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Nimesulide, salicylic acid and their binary mixtures were studied by differential scanning calorimetry (DSC) and Fourier Transform Infrared spectroscopy (FTIR). The study of such systems is a promising and viable approach for solving the problem of poor solubility of materials in general and drug systems in particular. All areas of human activity are inextricably linked to materials, and thus, the study presented in the paper and not reported in the literature is very important and provides useful data for those working in various fields. The eutectic mixtures were obtained by mechanosynthesis and by recrystallization from ethanol over the entire 0–1 range of molar fractions. For both situations at the molar fraction of nimesulide 0.5, the mixture has a eutectic that suggests an increase in solubility at this composition. The interactions that take place between the components were determined with the help of the excess thermodynamic functions (GE, SE, µE), which highlight the deviation from the ideality of the considered binary systems.

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Pressure-temperature phase diagram of the dimorphism of the anti-inflammatory drug nimesulide

Cited by 10 publications

References 24 publications

Glycine: The Gift that Keeps on Giving

Glycine: The Gift that Keeps on Giving

High-Pressure Dielectric Studies—a Way to Experimentally Determine the Solubility of a Drug in the Polymer Matrix at Low Temperatures

Thermal Behavior of the Nimesulide-Salicylic Acid Eutectic Mixtures Prepared by Mechanosynthesis and Recrystallization

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