Crystallization Tendency of Active Pharmaceutical Ingredients Following Rapid Solvent Evaporation—Classification and Comparison with Crystallization Tendency from Under cooled Melts

Eerdenbrugh, Bernard Van; Baird, Jared A.; Taylor, Lynne S.

doi:10.1002/jps.22214

Cited by 156 publications

(136 citation statements)

References 32 publications

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“…44 A model drug-polymer blend system composed of felodipine and poly(acrylic acid) (PAA) was examined with AFM-IR. 44 When prepared as an amorphous solid by solvent evaporation, felodipine has relatively low crystallization tendency; 47,48 therefore, it serves as a good model compound to evaluate drugpolymer miscibility, because it can be assumed that the drug will remain amorphous. PAA is an amorphous polymer that does not crystallize.…”

Section: Miscibility In Pharmaceutical Blend Formulationsmentioning

confidence: 99%

AFM–IR: Combining Atomic Force Microscopy and Infrared Spectroscopy for Nanoscale Chemical Characterization

Dazzi

Prater²,

Hu³

et al. 2012

Appl Spectrosc

468

444

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Polymer and life science applications of a technique that combines atomic force microscopy (AFM) and infrared (IR) spectroscopy to obtain nanoscale IR spectra and images are reviewed. The AFM–IR spectra generated from this technique contain the same information with respect to molecular structure as conventional IR spectroscopy measurements, allowing significant leverage of existing expertise in IR spectroscopy. The AFM–IR technique can be used to acquire IR absorption spectra and absorption images with spatial resolution on the 50 to 100 nm scale, versus the scale of many micrometers or more for conventional IR spectroscopy. In the life sciences, experiments have demonstrated the capacity to perform chemical spectroscopy at the sub-cellular level. Specifically, the AFM–IR technique provides a label-free method for mapping IR-absorbing species in biological materials. On the polymer side, AFM–IR was used to map the IR absorption properties of polymer blends, multilayer films, thin films for active devices such as organic photovoltaics, microdomains in a semicrystalline polyhydroxyalkanoate copolymer, as well as model pharmaceutical blend systems. The ability to obtain spatially resolved IR spectra as well as high-resolution chemical images collected at specific IR wavenumbers was demonstrated. Complementary measurements mapping variations in sample stiffness were also obtained by tracking changes in the cantilever contact resonance frequency. Finally, it was shown that by taking advantage of the ability to arbitrarily control the polarization direction of the IR excitation laser, it is possible to obtain important information regarding molecular orientation in electrospun nanofibers.

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Section: Miscibility In Pharmaceutical Blend Formulationsmentioning

confidence: 99%

AFM–IR: Combining Atomic Force Microscopy and Infrared Spectroscopy for Nanoscale Chemical Characterization

Dazzi

Prater²,

Hu³

et al. 2012

Appl Spectrosc

468

444

View full text Add to dashboard Cite

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“…The vast majority of literature dealing with this compound concerns its clinical action, bioavailability, and formulation [1][2][3][4][5]. In addition there is some limited literature concerning its physico-chemical properties [6][7][8][9][10][11], including spectroscopic and analytical data [12][13][14][15], and the crystal structures of its two known polymorphs [16][17][18]. Some rough solubility data for a number of solvents are reported, with no mention of temperature [7].…”

Section: Introductionmentioning

confidence: 99%

Thermodynamics of fenofibrate and solubility in pure organic solvents

Watterson

Hudson

Svärd

et al. 2014

Fluid Phase Equilibria

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Highlights! ! Solubility data of fenofibrate FI was collected between 5-45°C in seven pure solvents.! ! Melting data and heat capacity of the solid and the melt were measured with DSC.! ! Fusion thermodynamics and ideal solubility were calculated using experimental data.! ! The heat capacity component of the enthalpy of fusion is shown to be important.! ! In some solvents the activity coefficient term controls the shape of van't Hoff plots. AbstractCalorimetric data on the melting of 1-methylethyl 2-[4-(4-chlorobenzoyl)-phenoxy]-2-methylpropanoate (fenofibrate) and the heat capacity of the solid and the melt have been determined, from which the Gibbs energy, enthalpy and entropy of fusion are calculated. Solid-liquid solubility data have been collected by a gravimetric method in seven pure solvents (methanol, ethanol, 1-propanol, 2-propanol, ethyl acetate, acetonitrile, and acetone) across a range of temperatures. Fenofibrate is much more soluble in ethyl acetate, acetonitrile and acetone compared to alcohols. In the alcohols the solubility increases with aliphatic chain length. The Gibbs energy of fusion is used to estimate the activity of the solid within a Raoult's law framework. Except for ethyl acetate solutions which are almost ideal, solutions in all evaluated solvents exhibit positive deviation from Raoult's law, and in the alcohols the activity coefficient ranges up to 25. It is shown that the heat capacity component of the enthalpy of fusion is not negligible at room temperature, in spite of the proximity to the melting point, and furthermore that the temperature dependence of the activity coefficient in the saturated solution has a governing influence on the van't Hoff enthalpy of solution in acetonitrile and the alcohols. Crystals obtained by two different methods from a range of solvents have been analysed by PXRD, FTIR and NMR spectroscopy, TGA and DSC, and have in all cases been shown to consist of the stable polymorph (form I).

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“…At storage temperatures near to and above glass transition, the rates of crystallization increased. On the other hand, the temperature dependence of molecular motions below the glass transition temperature is highly dependent upon conditions under which the glass was formed [27,[34][35][36][37][38]. Those molecular motions are consequences of relaxation of a sample.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and thermal study of new N-substituted 1H-pyrrolo[3,4-c]pyridine-1,3(2H)diones of Mannich base type

Krzyżak

Szczęśniak-Sięga

Szkatuła

et al. 2011

J Therm Anal Calorim

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The new derivatives of 3,4-pyridinedicarboximide were synthesised. Experimental measurements were carried out using 1 H NMR spectra, IR spectra, elemental analyses and differential scanning calorimetry. The purpose of this study was to study the thermal stability of these four new compounds and to establish a solid-state polymorphism. Measurements were carried out for samples obtained from ethanol and n-hexane and after a long-time storage.

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Crystallization Tendency of Active Pharmaceutical Ingredients Following Rapid Solvent Evaporation—Classification and Comparison with Crystallization Tendency from Under cooled Melts

Cited by 156 publications

References 32 publications

AFM–IR: Combining Atomic Force Microscopy and Infrared Spectroscopy for Nanoscale Chemical Characterization

AFM–IR: Combining Atomic Force Microscopy and Infrared Spectroscopy for Nanoscale Chemical Characterization

Thermodynamics of fenofibrate and solubility in pure organic solvents

Synthesis and thermal study of new N-substituted 1H-pyrrolo[3,4-c]pyridine-1,3(2H)diones of Mannich base type

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