From unexpected reactions to a new family of ionic co-crystals: the case of barbituric acid with alkali bromides and caesium iodide

Braga, Dario; Grepioni, Fabrizia; Maini, Lucia; Prosperi, Susanna; Gobetto, Roberto; Chierotti, Michele R.

doi:10.1039/c0cc02701d

Cited by 166 publications

(161 citation statements)

References 35 publications

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“…Recently, pharmaceutical co-crystals have gained a lot of attention due to their ability to tailor physiochemical properties, particularly solubility, dissolution, stability and bioavailability. With increasing popularity, the technique of co-crystallization offers the ability to design new supramolecular scaffolds with desired functional properties [7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Studies on the synthesis, structural characterization, Hirshfeld analysis and stability of apovincamine (API) and its co-crystal (terephthalic acid: Apovincamine=1:2)

Wang

et al. 2015

Journal of Molecular Structure

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Section: Introductionmentioning

confidence: 99%

Studies on the synthesis, structural characterization, Hirshfeld analysis and stability of apovincamine (API) and its co-crystal (terephthalic acid: Apovincamine=1:2)

Wang

et al. 2015

Journal of Molecular Structure

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“…17 Subsequently, sodium chloride-mannitol was reported in 1976, 18 sodium chloride-glucose hydrate in 1991, 19 and the term ionic cocrystal (ICC) was coined by Braga for the sodium bromide-barbituric acid cocrystal in 2010. 20 However, even today ICCs are not that well explored and studied compared to molecular cocrystals and it is reasonable to assert that ICCs are a long known but underexplored class of compounds. A schematic of an ICC is given in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Physical Stability Enhancement and Pharmacokinetics of a Lithium Ionic Cocrystal with Glucose

Duggirala

Smith

Wojtas

et al. 2014

Crystal Growth & Design

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Current lithium drugs are plagued with a narrow therapeutic window and tend to be hygroscopic. However, they remain the gold standard for treating manic episodes in bipolar disorder. In this contribution, we report a crystal engineering study aimed at the preparation and characterization of ionic cocrystals (ICCs) of lithium chloride (LIC) and lithium bromide (LIB) with glucose (GLU). The structure of LIBGLU was studied by single crystal X-ray diffraction and found to be isostructural with related sodium chloride-glucose ICCs. The physical stability of LICGLU was compared to LIC at 50% RH and 25°C and through dynamic vapor sorption analysis. The blood and brain pharmacokinetics of LICGLU was compared to LIC in rat models and revealed little change in performance. This study reveals that ICCs can modestly improve solid form stability of lithium salts without impacting in vivo performance, a step towards enabling development of the next generation of lithium therapeutics.

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“…NaTA·0.5H 2 O, prepared in a pure form by kneading 5 stoichiometric amounts of HTA and NaOH, shows the splitting of almost all resonances in the 13 C CPMAS spectrum (Figure 2c), indicating the presence of two independent molecules in the unit cell. The splitting is especially marked for atoms C3, C8 and C14.…”

Section: Figmentioning

confidence: 99%

“…4 The use of inorganic salts as co-formers has already been explored, by our group, as an effective method for producing ionic co-crystals and salt co-crystals of barbituric 35 acid. 5 The difference between ionic co-crystals and salt cocrystals is found in the type of co-former. Ionic co-crystals are formed of an organic molecule and an ionic salt (i.e.…”

mentioning

confidence: 99%

Improvement of the water solubility of tolfenamic acid by new multiple-component crystals produced by mechanochemical methods

Gaglioti¹,

Chierotti²,

Grifasi³

et al. 2014

CrystEngComm

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Tolfenamic acid (HTA) is a drug characterized by very poor water solubility (13.6 nM under acidic\ud conditions) and moderate solubility in ethanol (0.17 M). A series of new multicomponent crystals have been\ud obtained by applying mechanochemical methods (i.e. kneading) to mixtures of HTA with sodium acetate,\ud sodium carbonate, sodium hydroxide and imidazole. These reactions resulted in two salts (NaTA·0.5H2O\ud and NaTA HT Form), a co-crystal of salts (NaTA·HTA·0.5NaAc·2H2O) and two salt co-crystals\ud (NaTA·HTA·H2O/NaHCO3 and IMH-TA·HTA). Due to the lack of suitable crystals for single-crystal X-ray\ud diffraction analysis, the structural features of the samples have been characterized by solid-state NMR\ud (1H MAS, 13C CPMAS, 1H-13C FSLG LG-CP HETCOR and 15N CPMAS), IR(ATR) and Raman spectroscopy,\ud VT-XRPD and elemental analysis. The evaluation of thermal stability and dissolution behavior was\ud performed using thermogravimetry, differential scanning calorimetry and dissolution kinetic tests. The new\ud solid-state forms show better thermal stability than pure HTA and an improved dissolution rate, which is\ud most pronounced in NaTA·HTA·H2O/NaHCO3, NaTA HT Form and NaTA·0.5H2O

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From unexpected reactions to a new family of ionic co-crystals: the case of barbituric acid with alkali bromides and caesium iodide

Cited by 166 publications

References 35 publications

Studies on the synthesis, structural characterization, Hirshfeld analysis and stability of apovincamine (API) and its co-crystal (terephthalic acid: Apovincamine=1:2)

Studies on the synthesis, structural characterization, Hirshfeld analysis and stability of apovincamine (API) and its co-crystal (terephthalic acid: Apovincamine=1:2)

Physical Stability Enhancement and Pharmacokinetics of a Lithium Ionic Cocrystal with Glucose

Improvement of the water solubility of tolfenamic acid by new multiple-component crystals produced by mechanochemical methods

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