Electrochemically induced co-crystallization for product removal

Urbanus, J.; Roelands, C.P.M.; Mazurek, Jarosław; Verdoes, D.; Horst, Joop H. ter

doi:10.1039/c0ce00284d

Cited by 21 publications

(15 citation statements)

References 17 publications

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“…Electrochemically induced cocrystallization can create a potential cocrystallization of ionizable compounds. While preparing a cocrystal of cinnamic acid and 3-nitrobenzamide, the electrochemical application can shift the pH to get neutral carboxylic acids and thus act as a driving tool for the cocrystallization ( Urbanus et al, 2011 ).…”

Section: Cocrystallization Techniquesmentioning

confidence: 99%

Recent Advances in Pharmaceutical Cocrystals: From Bench to Market

Bandaru¹,

Rout²,

Kenguva³

et al. 2021

Front. Pharmacol.

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The pharmacokinetics profile of active pharmaceutical ingredients (APIs) in the solid pharmaceutical dosage forms is largely dependent on the solid-state characteristics of the chemicals to understand the physicochemical properties by particle size, size distribution, surface area, solubility, stability, porosity, thermal properties, etc. The formation of salts, solvates, and polymorphs are the conventional strategies for altering the solid characteristics of pharmaceutical compounds, but they have their own limitations. Cocrystallization approach was established as an alternative method for tuning the solubility, permeability, and processability of APIs by introducing another compatible molecule/s into the crystal structure without affecting its therapeutic efficacy to successfully develop the formulation with the desired pharmacokinetic profile. In the present review, we have grossly focused on cocrystallization, particularly at different stages of development, from design to production. Furthermore, we have also discussed regulatory guidelines for pharmaceutical industries and challenges associated with the design, development and production of pharmaceutical cocrystals with commercially available cocrystal-based products.

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Section: Cocrystallization Techniquesmentioning

confidence: 99%

Recent Advances in Pharmaceutical Cocrystals: From Bench to Market

Bandaru¹,

Rout²,

Kenguva³

et al. 2021

Front. Pharmacol.

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“…Searching for amide-containing co-formers gave only two entries, both contain nitrogen in the cycle. In the group of carboxyl-containing compounds, the most studied co-formers were oxalic, maleic, tartaric, and mandelic acids (23,14,11, and 9 entries, respectively). All of the compounds with oxalic and maleic acids were salts, whereas among the rest of compound, both salts and cocrystals existed.…”

Section: S-naproxen/d-tyrosinementioning

confidence: 99%

“…22 They furthermore extended this work by showing how electrochemistry can be combined with cocrystallization for the in situ product removal of carboxyl acids. 23 Although cocrystals of chiral APIs are common, chirality in cocrystals is a relatively unexplored area. Motherwell et al showed how caffeine and theophylline behave differently with respect to DL-and D-tartaric acid.…”

Section: Introductionmentioning

confidence: 99%

Structural insight into cocrystallization with zwitterionic co-formers: cocrystals of S-naproxen

et al. 2014

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The screening of S-naproxen, S-oxiracetam, S-diprophylline, and levetiracetam with a series of essential and nonessential amino acid co-formers has yielded cocrystals only for S-naproxen, thus showing that amino acids seem to have a preference for forming cocrystals with compounds containing a carboxyl group. Herein, we report the crystal structures of four S-naproxen cocrystals: S-naproxen/L-alanine, S-naproxen/D-alanine, S-naproxen/D-tyrosine, and S-naproxen/D-tryptophan monohydrate. All of the described cocrystals show similar structural motifs, i.e., amino acids form head-to-tail chains with strong charge-assisted hydrogen bonding, which are similar to those found in the individual amino acids, with S-naproxen molecules grafted on them. According to the systematic search of the Cambridge Structural Database for other cocrystals that involve zwitterionic co-formers, charge-assisted hydrogen bonds between amino acid molecules play an essential role, being present in the majority of structures. The results of this work provide an insight into structural aspects of cocrystallization with zwitterionic co-formers, offer new possibilities for S-naproxen pharmaceutical formulations, and can serve as guidelines when developing new cocrystals involving zwitterionic co-formers.

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“…Even if the primary focus of cocrystal research remains oriented toward the ability to control pharmaceutical properties, recent contributions also investigate novel applications based on the specific properties of these systems. 5,6 Amongst these, the interesting behavior of cocrystal systems comprising two chiral partners has been highlighted by several research groups, 7,8 reviving the idea of using cocrystallization as a chiral resolution tool.…”

Section: Introductionmentioning

confidence: 99%