Crystal structure and solid-state properties of 3,4-diaminopyridine dihydrogen phosphate and their comparison with other diaminopyridine salts
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Document typeArticle
Defense date2013-02
Rights accessRestricted access - publisher's policy
Abstract
3,4-Diaminopyridine is an active pharmaceutical ingredient for the treatment of Lambert−Eaton myasthenic
syndrome (LEMS). It is 3,4-diaminopyridine dihydrogen phosphate that has become the active ingredient of choice. As part of a
larger study for the development of this drug, solid-state studies have been carried out. At room temperature, the crystals are
monoclinic (C2/c). Dihydrogen phosphate anions H2PO4
− form infinite chains parallel to the b axis, and these chains can be
considered as macroanions (H2PO4)∞. The organic cations form hydrogen bonds with the macroanions bridging them together.
A negative thermal expansion is observed along the [103] direction in the crystal, which coincides with the direction of chains of
interchanging anions and cations. The crystal packing shows similarities with the hydrogen tartrate salt as illustrated by a
Hirshfeld surface analysis. This phosphate and this tartrate salt are also the two diaminopyridine salts that have been selected for
therapeutic use because of their appropriate physical properties.
CitationMahe, N. [et al.]. Crystal structure and solid-state properties of 3,4-diaminopyridine dihydrogen phosphate and their comparison with other diaminopyridine salts. "Crystal growth and design", Febrer 2013, vol. 13, núm. 2, p. 708-715.
ISSN1528-7483
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