Cocrystal screening of hydroxybenzamides with benzoic acid derivatives: A comparative study of thermal and solution-based methods

Manin, Alex N.; Voronin, Alexander P.; Drozd, Ksenia V.; Manin, N. G.; Bauer‐Brandl, Annette; Perlovich, German L.

doi:10.1016/j.ejps.2014.09.003

Cited by 62 publications

(52 citation statements)

References 31 publications

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“…42,50) Several cocrystals melt at temperatures different from their API and conformer components. Thermal scans using temperature-controlled PXRD or simultaneous DSC-PXRD systems directly detect physical changes occurring during measurements.…”

Section: Physical Properties Of Pharmaceutical Cocrystalsmentioning

confidence: 99%

Characterization and Quality Control of Pharmaceutical Cocrystals

Izutsu¹,

Koide²,

Takata

et al. 2016

Chem. Pharm. Bull.

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Recent active research and new regulatory guidance on pharmaceutical cocrystals have increased the rate of their development as promising approaches to improve handling, storage stability, and bioavailability of poorly soluble active pharmaceutical ingredients (APIs). However, their complex structure and the limited amount of available information related to their performance may require development strategies that differ from those of single-component crystals to ensure their clinical safety and efficacy. This article highlights current methods of characterizing pharmaceutical cocrystals and approaches to controlling their quality. Different cocrystal regulatory approaches between regions are also discussed. The physical characterization of cocrystals should include elucidating the structure of their objective crystal form as well as their possible variations (e.g., polymorphs, hydrates). Some solids may also contain crystals of individual components. Multiple processes to prepare pharmaceutical cocrystals (e.g., crystallization from solutions, grinding) vary in their applicable ingredients, scalability, and characteristics of resulting solids. The choice of the manufacturing method affects the quality control of particular cocrystals and their formulations. In vitro evaluation of the properties that govern clinical performance is attracting increasing attention in the development of pharmaceutical cocrystals. Understanding and mitigating possible factors perturbing the dissolution and/ or dissolved states, including solution-mediated phase transformation (SMPT) and precipitation from supersaturated solutions, are important to ensure the bioavailability of orally administrated lower-solubility APIs. The effect of polymer excipients on the performance of APIs emphasizes the relevance of formulation design for appropriate use.

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Section: Physical Properties Of Pharmaceutical Cocrystalsmentioning

confidence: 99%

Characterization and Quality Control of Pharmaceutical Cocrystals

Izutsu¹,

Koide²,

Takata

et al. 2016

Chem. Pharm. Bull.

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“…Also many other physicochemical properties can be modulated by cocrystallization including stability [21][22][23][24], hygroscopicity [25] and prolonged shelf life [26]. Among many drugs, aromatic amides acting either as APIs or as excipients attract nowadays substantial attention [27][28][29][30][31][32][33][34][35]. These compounds are known for their important roles in medical applications.…”

Section: Introductionmentioning

confidence: 99%

“…Although many pharmaceutical cocrystals containing amides have been studied [27][28][29][30][31][32][33][34][35], the data deposited in the Cambridge Structural Database (CSD) [41] are rather variable in the sense that many coformers were used for synthesis of diverse cocrystals. For example cocrystals of fumaric acid with benzamide, isonicotinamide or nicotinamide are known under refcodes YOPBUB, LUNNOX and EDAPOQ, respectively, but there is no information about solids of these coformers with temozolomide.…”

Section: Introductionmentioning

confidence: 99%

Transferability of cocrystallization propensities between aromatic and heteroaromatic amides

Cysewski

2016

Struct Chem

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New virtual cocrystal screening was proposed taking advantage of the similarities between cocrystallization landscapes of different compounds. Assuming that cocrystallization propensities can be modeled by miscibility affinities of liquid components under supercooled conditions, the quantitative rules of likeness were formulated and validated for 45 aromatic and heteroaromatic amides interacting with a variety of coformers. The most important finding comes from the observed linear trends between the values of mixing enthalpies of amides with respect to a reference molecule. Particularly isonicotinamide was found as a very convenient comparative system since it constitutes 97 binary cocrystals. Many experimentally observed cocrystals were used for supporting the analogy hypothesis, which states that a properly selected reference molecule, for which cocrystals were experimentally documented, can provide practical information about cocrystallization propensities of another compound provided that two criterions are met, namely sufficiently high similarities and high enough affinities. Hence, it is not necessary to perform experimental cocrystallization of every pair of coformers since miscibility in the solid state of one compound can be transferred to another one at least in the case of aromatic or heteroaromatic amides.

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“…During dissolution, the functional groups in the drug and conformer interact with each other and form hydrogen bonds [89] . This is most commonly used method for the preparation of cocrystals by researchers [79,94] .…”

Section: Solution-based Methodsmentioning

confidence: 99%

“…Among different methods for cocrystal screening and saturation temperature method was found to be most effective than DSC and HSM. However, it requires the use of solvent and is most time-consuming method [79] .…”

Section: Thermal Analysismentioning

confidence: 99%