Polymorphic Cocrystals of Nutraceutical Compound <i>p</i>-Coumaric Acid with Nicotinamide: Characterization, Relative Solid-State Stability, and Conversion to Alternate Stoichiometries

Bevill, Melanie J.; Vlahova, Petinka I.; Smit, Jared P.

doi:10.1021/cg4019037

Cited by 49 publications

(47 citation statements)

References 42 publications

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“…With changes in the reacting molar ratio of the API and coformer, products such as salts or co-crystals that may exist in variable stoichiometric proportions due to the distinct arrangement of molecules can result in different physicochemical properties (Bruni et al, 2012;Zhang et al, 2013;Bevill et al, 2014). Moreover, the products of the different molar ratios of APIs and co-former can be used to apply for new patents.…”

Section: Introductionmentioning

confidence: 99%

Salt screening and characterization of ciprofloxacin

Zhang

Yang

et al. 2016

Acta Crystallogr Sect B

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With the aim of improving the solubility of ciprofloxacin, polybasic organic acids were utilized to react with ciprofloxacin in different stoichiometric proportions. The use of the solvent drop grinding (SDG) method, as well as the solvent evaporation method, resulted in the crystalline salts ciprofloxacin/fumaric acid (1:1, 2:1), ciprofloxacin/maleic acid (1:1) and ciprofloxacin/citric acid (2:1). The solubilities of these salts in pure water (pH 7.0) were determined using high-performance liquid chromatography (HPLC) at 310 K, with the salts showing considerably greater solubility than ciprofloxacin itself and, interestingly, ciprofloxacin/fumaric acid (2:1) being more soluble than ciprofloxacin/fumaric acid (1:1). Intrigued by this phenomenon, we undertook a comparison of the crystal structures of the salts: the three-dimensional sandwich-like structure observed in the 2:1 salt indicates that the preferred stacking may be a factor in increasing the solubility of ciprofloxacin.

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Section: Introductionmentioning

confidence: 99%

Salt screening and characterization of ciprofloxacin

Zhang

Yang

et al. 2016

Acta Crystallogr Sect B

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“…1,2,5,30) Many examples of cocrystals exhibiting polymorphism have been reported and include polymorphs of cocrystals which are in enantiotropic relationships. [31][32][33][34][35][36] The polymorphism of TFG-KOAc illustrates that salt cocrystals also exhibit polymorphism.…”

Section: Resultsmentioning

confidence: 99%

Tofogliflozin Salt Cocrystals with Sodium Acetate and Potassium Acetate

Takata

Tanida

Nakae

et al. 2018

CHEMICAL & PHARMACEUTICAL BULLETIN

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We investigated the salt cocrystals formed by tofogliflozin with sodium acetate and potassium acetate by determining the crystal structures of the salt cocrystals and characterizing the solid states. The salt cocrystal screening using the slurry method and the liquid-assisted grinding method resulted in the formation of tofogliflozin-sodium acetate 1 : 1 and tofogliflozin-potassium acetate 1 : 1 salt cocrystals. Single-crystal X-ray diffraction revealed that, although each salt cocrystal belongs to a different space group, both of the salt cocrystals have almost similar structural features, including the conformation of tofogliflozin molecules, the coordination to Na /K ions, and hydrogen bonds. The salt cocrystals exhibited extreme hygroscopicity with deliquescence, which is also a property of sodium acetate and potassium acetate. In addition, tofogliflozinpotassium acetate salt cocrystal had two polymorphs, which were enantiotropically related.

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“…Therefore, the combining rules derived by Wolbach and Sandler 54 were required for calculation of the association-energy parameter ߝ ݇ ⁄ in Eq. (21) and the association-volume parameter ߢ in Eq. (22).…”

Section: Pc-saftmentioning

confidence: 99%

Predicting the Effect of pH on Stability and Solubility of Polymorphs, Hydrates, and Cocrystals

Lange

Schleinitz

Sadowski

2016

Crystal Growth & Design

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Cocrystal-formation processes from aqueous solutions are often affected by pH-dependent dissociation, polymorphic transitions, as well as by formation of hydrates and salts. To enhance the efficiency of those processes, the aqueous stability and solubility of pharmaceutical cocrystals were predicted in this study using the Perturbed-Chain Statistical Associating Fluid Theory (PC-SAFT). The solubilities in the binary systems caffeine/water and oxalic acid/water were modeled including hydrate formation and polymorphic transitions between the corresponding anhydrate forms I and II. Moreover, pH-dependent solubilities of these hydrate-forming components, their 2:1 cocrystal as well as for all appearing salts were measured and modeled at 298.15 K. It was found, that the pH-dependent acid-base equilibria of caffeine and oxalic acid directly influence the stability and solubility of their cocrystal, their hydrates and salts. In consideration of the thermodynamic non-ideality of the components in the cocrystal system, PC-SAFT enables the solubility predictions of the before-mentioned components as well as if any cocrystal is formed at given conditions of pH and temperature.

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Polymorphic Cocrystals of Nutraceutical Compound p-Coumaric Acid with Nicotinamide: Characterization, Relative Solid-State Stability, and Conversion to Alternate Stoichiometries

Cited by 49 publications

References 42 publications

Salt screening and characterization of ciprofloxacin

Salt screening and characterization of ciprofloxacin

Tofogliflozin Salt Cocrystals with Sodium Acetate and Potassium Acetate

Predicting the Effect of pH on Stability and Solubility of Polymorphs, Hydrates, and Cocrystals

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