Growth, characterization and crystal structure analysis of rifapentine

Zhou, Kun; Li, J.; Zheng, Dechao

doi:10.1016/j.molstruc.2010.08.023

Cited by 6 publications

(7 citation statements)

References 9 publications

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“…It should be emphasized that these periodic rods were not found when rifampicin crystallized in the phenolic form (polymorph I and 1,1,1-trichoroethane solvate). Moreover, we have noticed that rifapentine (CSD refcode MAFLAI), reported to exist in its crystal in a phenolic form, actually has the phenolate form what is confirmed by molecular geometry and hydrogen bonding interactions. These observations suggest that electrostatic interactions between zwitterionic rifamycins may dominate in a hierarchy of intermolecular interactions over hydrogen bonding, being an important structure-determining factor.…”

Section: Resultsmentioning

confidence: 70%

Solvates of Zwitterionic Rifampicin: Recurring Packing Motifs via Nonspecific Interactions

Wicher

Pyta

Przybylski

et al. 2018

Crystal Growth & Design

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Antibiotic rifampicin was recrystallized from solutions containing aliphatic alcohols, ketones, or dimethyl sulfoxide. Thirteen new solvates were obtained that were studied by X-ray crystallography. In these solvates rifampicin exists in a zwitterionic form. The reported solvates are classified into eight different structural types. Whereas rifampicin molecules in the solvates form diverse assemblies via hydrogen bonds, the recurring structural motif in these crystals is generated by nonspecific intermolecular interactions. This motif has the form of a periodic one-dimensional (1D) rod, and similar 1D motifs were found in the structures of other zwitterionic or ionic rifamycins. In rifampicin solvates, these rods form a basis for the construction of two types of two-dimensional (2D) periodic modules: monolayers found in six structural types of rifampicin solvates and bilayers observed in two types of solvates. Diverse mutual arrangements of these 2D modules lead to the formation of channels with accommodated solvent molecules that consist of 10–40% of the crystal volume. Differential thermal analysis/thermogravimetric analyses and powder X-ray diffraction show that desolvation of the rifampicin 2-propanol solvate results in polymorph II of rifampicin. We show here that solvate decomposition may be a route to transformation of a thermodynamically stable polymorphic form into a metastable one.

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Section: Resultsmentioning

confidence: 70%

Solvates of Zwitterionic Rifampicin: Recurring Packing Motifs via Nonspecific Interactions

Wicher

Pyta

Przybylski

et al. 2018

Crystal Growth & Design

View full text Add to dashboard Cite

show abstract

“…The crystallization of rifapentine from organic solvents results in the formation of a solvate unsuitable for pharmaceutical use. For example, in crystals recovered from a methanol solution, the solvent integrates in the intermolecular hydrogen bonds thereby forming crystals of a rifapentine–methanol solvate rather than pure rifapentine . In our acetone–water cosolvent system, rifapentine was crystallized into a primarily aqueous environment, using heat to strip away the acetone.…”

Section: Discussionmentioning

confidence: 99%

“…For example, in crystals recovered from a methanol solution, the solvent integrates in the intermolecular hydrogen bonds thereby forming crystals of a rifapentine-methanol solvate rather than pure rifapentine. 18,19 In our acetone-water cosolvent system, rifapentine was crystallized into a primarily aqueous environment, using heat to strip away the acetone. A rifapentine-acetone solvate was ruled out by the lack of a significant acetone chemical shift in the NMR spectra or variations in the FTIR spectra ( Figs.…”

Section: Discussionmentioning

confidence: 99%

“…However, because of the differences in chemical structure between the two rifamycins, a crystalline dihydrate form of rifapentine could not be similarly generated by this method (unpublished data). In addition, published crystalline forms of rifapentine are limited to its methanol solvate, which are unsuitable for pharmaceutical use . Hence, if efficacious pulmonary levels of rifapentine are to be achieved, there is a need to identify a suitable synthesis method for a pure form of crystalline rifapentine that is readily tailored to an inhalable size.…”

Section: Introductionmentioning

confidence: 99%

“…In addition, published crystalline forms of rifapentine are limited to its methanol solvate, which are unsuitable for pharmaceutical use. 18,19 Hence, if efficacious pulmonary levels of rifapentine are to be achieved, there is a need to identify a suitable synthesis method for a pure form of crystalline rifapentine that is readily tailored to an inhalable size.…”

Section: Introductionmentioning

confidence: 99%

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