Rifampicin solvates - their structure and decomposition process
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2022-02-10 22:36
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WICHER, B., GDANIEC, Maria. Rifampicin solvates - their structure and decomposition process. In: Materials Science and Condensed Matter Physics, Ed. 7, 16-19 septembrie 2014, Chișinău. Chișinău, Republica Moldova: Institutul de Fizică Aplicată, 2014, Editia 7, p. 129.
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Materials Science and Condensed Matter Physics
Editia 7, 2014
Conferința "Materials Science and Condensed Matter Physics"
7, Chișinău, Moldova, 16-19 septembrie 2014

Rifampicin solvates - their structure and decomposition process


Pag. 129-129

Wicher B.12, Gdaniec Maria1
 
1 Adam Mickiewicz University in Poznan,
2 Poznan University of Medical Sciences
 
Disponibil în IBN: 4 martie 2019


Rezumat

Rifampicin (Scheme), an antibiotic from the group of rifamycins, is one of the key components of the first-line treatment against tuberculosis that is in use since 1968. In the solid state and in solution rifampicin can exist in two forms, neutral or zwitterionic, with the proton transferred from the phenolic group to the N-CH3 unit of the N-methylpiperazine group. This compound is also chemically unstable and poorly soluble in water. Scheme Rifampicin is known to exist in two polymorphic forms, I and II, and to easily form solvated crystals. There are only a few rifampicin solvates that have been structurally characterized. Generally, the crystals obtained from protic solvents, or a mixture of a protic and aprotic solvents, consist of rifampicin molecules in the phenolate form. We have been able to obtain a large number of new crystalline rifamipicin solvates and to determine their crystal structures. In prevailing number of cases these crystals contained both organic solvent and water molecules. Unfortunately, rifampicin did not form cocrystals with a variety of typical cocrystal formers. Despite the presence of numerous hydrogen-bond donor groups, the recurring structural motif of these crystals, polar 2D assembly of p1211 layer group symmetry, is not stabilized by conventional hydrogen bonds but by weak van der Waals interactions. The divers types of 3D structures of rifampicin solvates result from different orientation and relative position of the neighboring layers and these, in turn, are affected by the size of solvent molecules. Decomposition of the solvated forms in which rifampicin exist as a zwitterion results in polymorph II.