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Merck

SML2837

Sigma-Aldrich

Tizoxanide

≥98% (HPLC)

Synonym(e):

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

Empirische Formel (Hill-System):
C10H7N3O4S
CAS-Nummer:
Molekulargewicht:
265.25
MDL-Nummer:
UNSPSC-Code:
12352200
NACRES:
NA.77

Qualitätsniveau

Assay

≥98% (HPLC)

Form

powder

Farbe

white to beige

Löslichkeit

DMSO: 2 mg/mL, clear

Lagertemp.

2-8°C

SMILES String

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)

InChIKey

FDTZUTSGGSRHQF-UHFFFAOYSA-N

Biochem./physiol. Wirkung

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


Analysenzertifikate (COA)

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L Dubreuil et al.
Antimicrobial agents and chemotherapy, 40(10), 2266-2270 (1996-10-01)
The antibacterial activities of nitazoxanide and its main metabolite, tizoxanide, were tested against a broad range of bacteria, including anaerobes. Metronidazole, amoxicillin, amoxicillin-clavulanic acid, piperacillin, cefoxitin, imipenem, and clindamycin were used as positive controls. MICs were determined by reference agar
Y Yamamoto et al.
Chemotherapy, 45(4), 303-312 (1999-07-08)
Nitazoxanide (NTZ), a synthesized drug of the nitrothiazolide class, was initially developed as an antiparasitic compound. This compound has recently been shown to have antibacterial activities against some bacterial pathogens. In the present study, NTZ and its main metabolite tizoxanide
F Mégraud et al.
Antimicrobial agents and chemotherapy, 42(11), 2836-2840 (1998-10-31)
Nitazoxanide, a thiazolide compound, and its desacetyl derivative, tizoxanide, have antimicrobial properties against anaerobic bacteria, as well as against helminths and protozoa. Because the treatment of Helicobacter pylori infection may be jeopardized by metronidazole resistance, nitazoxanide and tizoxanide were tested
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

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