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SML2837

Sigma-Aldrich

Tizoxanide

≥98% (HPLC)

Sinónimos:

2-Hydroxy-N-(5-nitro-2-thiazolyl)benzamide, 2-Hydroxy-N-(5-nitrothiazol-2-yl)benzamide, Desacetyl-NTZ, Desacetyl-nitazoxanide, NSC 697856, NTZ metabolite, Nitazoxanide metabolite, TIZ

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About This Item

Fórmula empírica (notación de Hill):
C10H7N3O4S
Número de CAS:
173903-47-4
Peso molecular:
265.25
Número MDL:
MFCD07484970
Código UNSPSC:
12352200
NACRES:
NA.77

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

powder

color

white to beige

solubilidad

DMSO: 2 mg/mL, clear

temp. de almacenamiento

2-8°C

cadena SMILES

OC1=C(C(NC2=NC=C([N+]([O-])=O)S2)=O)C=CC=C1

InChI

1S/C10H7N3O4S/c14-7-4-2-1-3-6(7)9(15)12-10-11-5-8(18-10)13(16)17/h1-5,14H,(H,11,12,15)

Clave InChI

FDTZUTSGGSRHQF-UHFFFAOYSA-N

Acciones bioquímicas o fisiológicas

Active metabolite of the antimicrobial nitazoxanide (NTZ) with antiparasitic, antiviral and broad-spectrum bacterial pyruvate-ferredoxin oxidoreductase (PFOR) inhibitory efficacy.
Tizoxanide (TIZ) is the active metabolite of the broad-spectrum parasiticidal drug nitazoxanide (NTZ), a noncompetitive inhibitor against bacterial pyruvate-ferredoxin oxidoreductase (PFOR Ki 2 to 10 μM). NTZ deacetylates rapidly to TIZ in plasma (t1/2 ~6 min at 37°C in human plasma) and in the presence of liver microsomes. NTZ is also reported to exhibit antiviral activity against Hepatitis C, Norovirus, Paramyxovirus, Influenza, Vaccinia, and Zika.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000104090
0000318269
0000318268
0000318269
0000318268

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A Stockis et al.
International journal of clinical pharmacology and therapeutics, 40(5), 213-220 (2002-06-08)
Nitazoxanide (N) is a new broad-spectrum intestinal antiparasitic agent. Deacetyl-N or tizoxanide (T) and its glucuronide (TG) are the major circulating species metabolites after oral administration of N. Bioavailability is substantially increased by food. The objectives of this phase IA
J Broekhuysen et al.
International journal of clinical pharmacology and therapeutics, 38(8), 387-394 (2000-09-13)
Nitazoxanide (N), a new broad-spectrum parasiticidal agent, is rapidly deacetylated to tizoxanide (T). The objective of the study was to determine if metabolites other than T are present in the plasma and excreted after single dose oral administration of radiocarbon-labelled
Z Zhao et al.
Journal of veterinary pharmacology and therapeutics, 33(2), 147-153 (2010-05-07)
The pharmacokinetics of tizoxanide (T), the active metabolite of nitazoxanide (NTZ), and its protein binding ability in goat plasma and in the solutions of albumin and alpha-1-acid-glycoprotein were investigated. The plasma and protein binding samples were analyzed using a high-performance
Paul S Hoffman et al.
Antimicrobial agents and chemotherapy, 51(3), 868-876 (2006-12-13)
Nitazoxanide (NTZ) exhibits broad-spectrum activity against anaerobic bacteria and parasites and the ulcer-causing pathogen Helicobacter pylori. Here we show that NTZ is a noncompetitive inhibitor (K(i), 2 to 10 microM) of the pyruvate:ferredoxin/flavodoxin oxidoreductases (PFORs) of Trichomonas vaginalis, Entamoeba histolytica
Elizabeth P Harausz et al.
Tuberculosis (Edinburgh, Scotland), 98, 92-96 (2016-05-10)
Nitazoxanide (NTZ) and its metabolite tizoxanide (TIZ) were studied as antimycobacterial agents in vitro (in mycobacterial growth indicator tube [MGIT] cultures) and in a whole blood bactericidal assay. Both NTZ and TIZ show high protein binding. In MGIT cultures (albumin concentration = 78 μM)
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