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New cocrystals of ezetimibe with L-proline and imidazole
Umeå University, Faculty of Science and Technology, Department of Applied Physics and Electronics.
2014 (English)In: CrysteEngComm, ISSN 1466-8033, Vol. 16, no 38, 8984-8993 p.Article in journal (Refereed) Published
Abstract [en]

The objectives of the study were to screen and prepare cocrystals of anti-cholesterol drug ezetimibe (EZT) with the aim of increasing its solubility and dissolution rate. Thermodynamic phase diagram based high throughput screening was performed using wet milling/grinding or solution crystallization methods. A large number of coformers were tested and the resulting solids were preliminarily characterized using X-ray powder diffraction (PXRD) and Raman spectroscopy. Potential cocrystals of EZT with L-proline and imidazole and a solvate formamide were identified in the screening experiments. The cocrystal hits were further characterized by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), solution Proton nuclear magnetic resonance spectroscopy (H-1-NMR) and single crystal XRD. The dissolution properties and stability of cocrystals were determined. Single-crystal X-ray diffraction data were obtained for EZT, EZT-IMI cocrystal and formamide solvate of ezetimibe. All three systems were crystallized in non-centrosymmetric orthorhombic space group P2(1)2(1)2(1) with Z = 4. Robust O-H center dot center dot center dot O, O-H center dot center dot center dot N, N-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds played an important role in all these crystal structures. EZT-PRO cocrystal showed improved apparent solubility and solid state stability.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2014. Vol. 16, no 38, 8984-8993 p.
National Category
Engineering and Technology
URN: urn:nbn:se:umu:diva-94945DOI: 10.1039/c4ce01127aISI: 000342070400009OAI: diva2:762705
Available from: 2014-11-12 Created: 2014-10-20 Last updated: 2014-11-12Bibliographically approved

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Boström, Dan
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