Abstract Tizoxanide [2-(hydroxy)- N -(5-nitro-2-thiazolyl)benzamide, TIZ] is a new potent anti-infective agent which may enhance current therapies for leishmaniasis, Chagas disease and viral hepatitis. The aim of this study was to identify the conformational preferences that may be related to the biological activity of TIZ by resolving its crystal structure and characterizing various physicochemical properties, including its experimental vibrational and 13 C nuclear magnetic resonance properties, behavior on heating and solubility in several solvents at 25 °C. TIZ crystallizes from dimethylformamide as the carboxamide tautomer in the triclinic system, space group P (−1) (No. 2) with the following unit cell parameters at 173(2) K: a = 5.4110(3) A, b = 7.3315(6) A, c = 13.5293(9) A, α = 97.528(3), β = 95.390(4), γ = 97.316(5), V = 524.41(6) A 3 , Z = 2, D c = 1.680 g/cm 3 , R 1 = 0.0482 and wR 2 = 0.0911 for 2374 reflections. This modification of TIZ has a ‘graphitic’ structure and is composed of tightly packed layers of extensively hydrogen-bonded molecules. The various spectroscopic data [Diffuse Fourier transform infrared (DRIFT) and FT-Raman, recorded in the range 3600–500 and 4000–200 cm −1 respectively, and solid-state 13 C NMR] were consistent with the structure determined by X-ray crystallography. From DSC, TG and thermomicroscopy, it was concluded that TIZ is thermally stable as a solid and that melting is not an isolated event from the one-step thermal decomposition that it undergoes above 270 °C. This modification of TIZ is practically insoluble in water and slightly soluble in polar aprotic solvents such as dimethylsulfoxide, dimethylformamide and dioxane.
Characterization and structural analysis of the potent antiparasitic and antiviral agent tizoxanide
F. Bruno,M. Caira,E. C. Martin,G. Monti,N. Sperandeo
Published 2013 in Journal of Molecular Structure
ABSTRACT
PUBLICATION RECORD
- Publication year
2013
- Venue
Journal of Molecular Structure
- Publication date
2013-03-27
- Fields of study
Medicine, Chemistry
- Identifiers
- External record
- Source metadata
Semantic Scholar
CITATION MAP
EXTRACTION MAP
CLAIMS
CONCEPTS
- carboxamide tautomer
The amide tautomeric form assigned to tizoxanide in the crystal.
- dimethylformamide
A polar aprotic solvent used to crystallize tizoxanide and included in the solubility discussion.
Aliases: DMF
- graphitic structure
A layered crystal-packing motif described for the tizoxanide solid form.
- hydrogen-bonded layers
Intermolecularly linked molecular layers that make up the crystal packing.
- solubility in solvents
The reported room-temperature solubility profile in water and several polar aprotic solvents.
Aliases: solubility at 25 C
- thermal decomposition
The high-temperature solid-state behavior analyzed with DSC, TG, and thermomicroscopy.
Aliases: one-step thermal decomposition
- tizoxanide
The antiparasitic and antiviral compound characterized by crystal structure, spectroscopy, thermal behavior, and solubility.
Aliases: TIZ
- triclinic system
The low-symmetry crystal system reported for the unit cell.
- vibrational and nmr spectroscopy
The DRIFT, FT-Raman, and solid-state 13C NMR measurements used to characterize the compound.
Aliases: DRIFT, FT-Raman, solid-state 13C NMR
- x-ray crystallography
The diffraction-based structure-determination method used to resolve the crystal structure.
Aliases: X-ray crystal structure
REFERENCES
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