Niclosamide monohydrate - CAS 73360-56-2
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Not Intended for Therapeutic Use. For research use only.
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Niclosamide Monohydrate is used for the treatment of most tapeworm infections by inhibiting DNA replication. It inhibits the TNF-induced NF-κB reporter activity in a dose- and time-dependent manner in U2OS cells. It also inhibits TNF-induced degradation of IκBα and relocation of p65 in a dose- and time-dependent manner in HL-60, Molm13, or AML primary cells.
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Niclocide monohydrate; BAY2353 monohydrate; Cestocid monohydrate; Sagimid monohydrate; Yomesan monohydrate
1.Physical transformation of niclosamide solvates in pharmaceutical suspensions determined by DSC and TG analysis.
de Villiers MM1, Mahlatji MD, Malan SF, van Tonder EC, Liebenberg W. Pharmazie. 2004 Jul;59(7):534-40.
This study reports the preparation of four niclosamide solvates and the determination of the stability of the crystal forms in different suspension vehicles by DSC and TG analysis. Thermal analysis showed that the niclosamide solvates were extremely unstable in a PVP-vehicle and rapidly changed to monohydrated crystals. A suspension in propylene glycol was more stable and TG analysis showed that crystal transformation was less rapid. In this vehicle, the crystals transformed to the anhydrate, rather than the monohydrate, since the vehicle was non-aqueous. The TEG-hemisolvate was the most stable in suspension and offered the best possibility of commercial exploitation.
2.Niclosamide methanol solvate and niclosamide hydrate: structure, solvent inclusion mode and implications for properties.
Harriss BI1, Wilson C2, Radosavljevic Evans I1. Acta Crystallogr C Struct Chem. 2014 Aug;70(Pt 8):758-63. doi: 10.1107/S2053229614015496. Epub 2014 Jul 10.
Structural studies have been carried out of two solid forms of niclosamide [5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide, NCL], a widely used anthelmintic drug, namely niclosamide methanol monosolvate, C13H8Cl2N2O4·CH3OH or NCL·MeOH, and niclosamide monohydrate, denoted HA. The structure of the methanol solvate obtained from single-crystal X-ray diffraction is reported for the first time, elucidating the key host-guest hydrogen-bonding interactions which lead to solvate formation. The essentially planar NCL host molecules interact via π-stacking and pack in a herringbone-type arrangement, giving rise to channels along the crystallographic a axis in which the methanol guest molecules are located. The methanol and NCL molecules interact via short O-H...O hydrogen bonds. Laboratory powder X-ray diffraction (PXRD) measurements reveal that the initially phase-pure NCL·MeOH solvate readily transforms into NCL monohydrate within hours under ambient conditions.
3.Preparation and physicochemical properties of niclosamide anhydrate and two monohydrates.
van Tonder EC1, Maleka TS, Liebenberg W, Song M, Wurster DE, de Villiers MM. Int J Pharm. 2004 Jan 28;269(2):417-32.
The intent of the study was to prepare and characterize three crystal forms of niclosamide namely the anhydrate and the two monohydrates and to investigate the moisture adsorption and desorption behavior of these crystal forms. The crystal forms were prepared by recrystallization and were characterized by differential scanning calorimetry, thermogravimetric analysis, isoperibol solution calorimetry, Karl Fischer titration, and X-ray powder diffractometry. Moisture adsorption by the anhydrate at increased relative humidities and two temperatures, 30 and 40 degrees C, was measured while the desorption from the monohydrates was determined at 45, 55, and 65 degrees C for monohydrate H(A) and 75, 90, and 100 degrees C for monohydrate H(B). Thermal analysis and solution calorimetry showed that monohydrate H(B) is more stable than monohydrate H(A) and solubility measurements showed the solubility of the crystal forms decreased in the order: anhydrate>>monohydrate H(A)>monohydrate H(B).
4.Influence of moisture on the crystal forms of niclosamide obtained from acetone and ethyl acetate.
Manek RV1, Kolling WM. AAPS PharmSciTech. 2004 Mar 4;5(1):E14.
The purpose of this study was to elucidate the formation of crystal hydrates of niclosamide and to delineate the effect of relative humidity on the crystal forms obtained from acetone and ethyl acetate. Recrystallization of niclosamide was performed in the presence and absence of moisture. Two hydrates and their corresponding anhydrates were isolated. The hydrates obtained by the process of recrystallization from acetone (Form I) and that obtained from ethyl acetate (Form II) were classified based on differences in their dehydration profile, crystal structure, shape, and morphology. Crystals obtained in the absence of moisture were unstable, and when exposed to the laboratory atmosphere transformed to their corresponding hydrates. Differential scanning calorimetry thermograms indicate that Form I changes to an anhydrate at temperatures below 100 degrees C, while Form II dehydrates in a stepwise manner above 140 degrees C. This finding was further confirmed by thermogravimetric analysis.
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CAS 73360-56-2 Niclosamide monohydrate

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