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Merck
CN

N0290

Sigma-Aldrich

Nitazoxanide

≥98% (HPLC), pyruvate-ferredoxin oxidoreductase (PFOR) inhibitor, powder

Synonym(s):

NTZ; 2-(Acetyloxy)-N-(5-nitro-2-thiazolyl)benzamide

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About This Item

Empirical Formula (Hill Notation):
C12H9N3O5S
CAS Number:
55981-09-4
Molecular Weight:
307.28
EC Number:
259-931-8
MDL number:
MFCD00416599
UNSPSC Code:
12352200
PubChem Substance ID:
329818424
NACRES:
NA.77

Key Documents

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Product Name

Nitazoxanide, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

powder

originator

Romark

storage temp.

2-8°C

SMILES string

CC(=O)Oc1ccccc1C(=O)Nc2ncc(s2)[N+]([O-])=O

InChI

1S/C12H9N3O5S/c1-7(16)20-9-5-3-2-4-8(9)11(17)14-12-13-6-10(21-12)15(18)19/h2-6H,1H3,(H,13,14,17)

InChI key

YQNQNVDNTFHQSW-UHFFFAOYSA-N

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General description

Nitazoxanide (NTZ), a thiazolide compound is a antiparasitic drug with structure similar to niclosamide.

Application

Nitazoxanide has been used:
  • to test its anti-viral activity against chikungunya virus
  • as an antiprotozoal agent to test its effect on cell viability in various cancer cell lines
  • to test its effect on human cytomegalovirus (HCMV) infected human fibroblast HFF cells

Biochem/physiol Actions

Nitazoxanide (NTZ) promotes autophagy by acting on kinase based signaling pathways and acts on mammalian target of rapamycin complex 1 (mTORC1) in Mycobacteria. It has anti-viral property and effectively halts entry and release of chikungunya virus in in vitro studies. NTZ also inhibits Japanese encephalitis virus (JEV) infection in early stages and has the potential to treat other viral infections including dengue, hepatitis B (HBV), coronavirus and human immunodeficiency virus (HIV). It has antineoplastic functionality and may induce apoptosis by promoting proto-oncogene c-Myc inhibition resulting in tumor suppression.
Nitazoxanide is an inhibitor of pyruvate-ferredoxin oxidoreductase (PFOR); Antimicrobial recently found to kill both non-replicating and replicating mycobacteria.
Nitazoxanide is an inhibitor of pyruvate-ferredoxin oxidoreductase (PFOR); FDA approved anti-parasitic drug (2002). Recent work (C & EN Sept. 14, 2009, p. 28) highlights that NTZ kills non-replicating and replicating TB bacteria and no apparent resistance is detected.

Features and Benefits

This compound was developed by Romark. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

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
0000296365
0000296365
0000160660
0000114613

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Pathway-based drug repositioning for cancers: Computational prediction and experimental validation
Iwata M, et al.
Journal of Medicinal Chemistry, 61(21), 9583-9595 (2018)
Antiviral activities of niclosamide and nitazoxanide against chikungunya virus entry and transmission
Wang YM, et al.
Antiviral Research, 135, 81-90 (2016)
A c-Myc activation sensor-based high-throughput drug screening identifies an antineoplastic effect of nitazoxanide
Fan-Minogue H, et al.
Molecular Cancer Therapeutics, 12(9), 1896-1905 (2013)
Benjamin Speich et al.
PLoS neglected tropical diseases, 6(6), e1685-e1685 (2012-06-09)
The currently used anthelmintic drugs, in single oral application, have low efficacy against Trichuris trichiura infection, and hence novel anthelmintic drugs are needed. Nitazoxanide has been suggested as potential drug candidate. The efficacy and safety of a single oral dose
Karim Debache et al.
Experimental parasitology, 129(2), 95-100 (2011-08-02)
The cationic arylimidamide DB750 and the thiazolide nitazoxanide had been shown earlier to be effective against Neospora caninum tachyzoites in vitro with an IC(50) of 160nM and 4.23μM, respectively. In this study, we have investigated the effects of DB750 and
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