Spectroscopic, thermal and X-ray structural study of the antiparasitic and antiviral drug nitazoxanide

ELSEVIER SCIENCE BV

Año: 2010 vol. 984 p. 51 - 51

Nitazoxanide [2-(acetyloxy)-N-(5-nitro-2-thiazolyl)benzamide, NTZ] is a potent antiparasitic and antiviralagent recently approved. The anti-protozoal activity of NTZ is believed to be due to interference withthe pyruvate:ferredoxin oxidoreductase (PFOR) enzyme dependent electron transfer reaction. As drug?enzyme interactions are governed by the three-dimensional stereochemistry of both participants, thecrystal structure of NTZ was determined for the first time to identify the conformational preferences thatmay be related to biological activity. NTZ crystallizes as the carboxamide tautomer in the orthorhombicsystem, space group Pna21 with the following parameters at 100(2) K: a = 14.302(2) Å, b = 5.2800(8) Å,c = 33.183(5) Å, V = 2505.8(6) Å3, Z = 8, Dx = 1.629 g cm3, R = 0.0319, wR2 = 0.0799 for 5121 reflections.In addition, the spectroscopic and thermal properties were determined and related to the molecularstructure. The 13C