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      Improved Stability and Smart-Material Functionality Realized in an Energetic Cocrystal

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      Angewandte Chemie International Edition
      Wiley-Blackwell

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          The role of cocrystals in pharmaceutical science.

          Pharmaceutical cocrystals, a subset of a long known but little-studied class of compounds, represent an emerging class of crystal forms in the context of pharmaceutical science. They are attractive to pharmaceutical scientists because they can significantly diversify the number of crystal forms that exist for a particular active pharmaceutical ingredient (API), and they can lead to improvements in physical properties of clinical relevance. In this article we address pharmaceutical cocrystals from the perspective of design (crystal engineering) and present a series of case studies that demonstrate how they can enhance the solubility, bioavailability, and/or stability of API crystal forms.
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            Supramolekulare Synthone für das Kristall-Engineering - eine neue organische Synthese

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              Crystal engineering of novel cocrystals of a triazole drug with 1,4-dicarboxylic acids.

              Cocrystals of the poorly soluble antifungal drug cis-itraconazole (1) with 1,4-dicarboxylic acids have been prepared. The crystal structure of the succinic acid cocrystal with 1 was determined to be a trimer by single-crystal X-ray. The trimer is comprised of two molecules of 1 oriented in antiparallel fashion to form a pocket with a triazole at either end. The extended succinic acid molecule fills the pocket, bridging the triazole groups through hydrogen-bonding interactions rather than interacting with the more basic piperazine nitrogens. The solubility and dissolution rate of some of the cocrystals are approximately the same as those of the amorphous drug in the commercial formulation and are much higher than those for the crystalline free base. The results suggest that cocrystals of drug molecules have the possibility of achieving the higher oral bioavailability common for amorphous forms of water-insoluble drugs while maintaining the long-term chemical and physical stability that crystal forms provide.
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                Author and article information

                Journal
                Angewandte Chemie International Edition
                Angew. Chem. Int. Ed.
                Wiley-Blackwell
                14337851
                September 12 2011
                September 12 2011
                : 50
                : 38
                : 8960-8963
                Article
                10.1002/anie.201104164
                99f608eb-fa9c-4ca9-8e9c-379eaf3de063
                © 2011

                http://doi.wiley.com/10.1002/tdm_license_1.1

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