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  • Title: The methanol disolvate and the dihydrate of fexofenadine, an antihistamine drug.
    Author: Tessler L, Goldberg I.
    Journal: Acta Crystallogr C; 2005 Dec; 61(Pt 12):o707-10. PubMed ID: 16330854.
    Abstract:
    Fexofenadine [systematic name: (+/-)-(4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidinium-1-yl]-butyl]phenyl)-2-methylpropionate], crystallizes in two forms, viz. as the methanol disolvate, C32H39NO4.2CH4O, and as the dihydrate, C32H39NO4.2H2O. It exists in the two structures as a zwitterion, which self-assembles as dimers sustained by a pair of charged-assisted N-H...OOC hydrogen bonds. In the methanol disolvate, the supramolecular organization consists of discrete fexofenadine dimers solvated by four molecules of methanol. The dihydrate structure is sustained by a more extended hydrogen-bonding scheme, wherein the hydrated dimeric entities are interlinked by additional hydrogen bonds. The fexofenadine molecule adopts different and differently disordered conformations of the 1-hydroxybutyl residue in the two structures.
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