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SML2837

Sigma-Aldrich

Tizoxanide

≥98% (HPLC)

Synonym(s):

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

Empirical Formula (Hill Notation):
C10H7N3O4S
CAS Number:
173903-47-4
Molecular Weight:
265.25
MDL number:
MFCD07484970
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

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)

InChI key

FDTZUTSGGSRHQF-UHFFFAOYSA-N

Biochem/physiol Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (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
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)
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
G Gargala et al.
The Journal of antimicrobial chemotherapy, 46(1), 57-60 (2000-07-07)
The effects of nitazoxanide and its metabolites, tizoxanide and tizoxanide glucuronide, on the development of the asexual and sexual stages of Cryptosporidium parvum in differentiated human enterocytic HCT-8 cells were evaluated in a quantitative alkaline phosphatase immunoassay. Nitazoxanide, tizoxanide and
Jinqiu Liu et al.
Biomedical chromatography : BMC, 30(11), 1744-1749 (2016-04-24)
Nitazoxanide (NTZ) is a broad-spectrum antimicrobial agent. Tizoxanide (T) and tizoxanide glucuronide (TG) are the major circulating metabolites after oral administration of NTZ. A rapid and specific LC-MS/MS method for the simultaneous quantification of T and TG in mouse plasma
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