Cocrystals of fenamic acids with nicotinamide

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Accepted Version
Fábián, László
Hamill, Noel
Eccles, Kevin S.
Moynihan, Humphrey A.
Maguire, Anita R.
McCausland, Linda
Lawrence, Simon E.
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American Chemical Society
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Cocrystal formation between nicotinamide and five fenamic acid derivative drugs (flufenamic acid, niflumic tolfenamic acid, mefenamic acid and meclofenamic acid) was investigated using solution-based and solid-state preparation methods. It was anticipated that the well-known acid-aromatic nitrogen heterosynthon would provide a sufficient driving force for cocrystallization. The experiments yielded cocrystals with four of the five acids. Although the structures of these molecules are similar, they showed marked differences in both the stability and the stoichiometry of the cocrystals. A detailed analysis of the structures and properties of both the starting materials and the cocrystals allows a tentative explanation of these differences, but it also shows that even though all four cocrystals utilize one of the most predictable supramolecular synthons (COOH center dot center dot center dot N), their structures and properties remain elusive to design.
Swiss light-source , Tolfenamic acid , Mefenamic acid , Powder diffraction , Co-crystals , Solubility , Complexes , Challenge , 1-octanol , Ethanol
Fabian, L., Hamill, N., Eccles, K.S., Moynihan, H.A., Maguire, A.R., McCausland, L., Lawrence, S.E. (2011) 'Cocrystals of Fenamic Acids with Nicotinamide'. Crystal Growth & Design, 11 (8):3522-3528.
© 2011, American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Crystal Growth & Design, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see