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N0290

Sigma-Aldrich

Nitazoxanide

≥98% (HPLC)

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

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); 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Andrew Hemphill et al.
Expert opinion on pharmacotherapy, 7(7), 953-964 (2006-04-26)
Colonisation of the gastrointestinal tract by anaerobic bacteria, protozoa, trematodes, cestodes and/or nematodes and other infectious pathogens, including viruses, represents a major cause of morbidity and mortality in Africa, South America and southeast Asia, as well as other parts of
Cirle A Warren et al.
Antimicrobial agents and chemotherapy, 56(8), 4103-4111 (2012-05-16)
Clostridium difficile infection (CDI) is a serious diarrheal disease that often develops following prior antibiotic usage. One of the major problems with current therapies (oral vancomycin and metronidazole) is the high rate of recurrence. Nitazoxanide (NTZ), an inhibitor of pyruvate:ferredoxin
G Esmat et al.
Liver international : official journal of the International Association for the Study of the Liver, 32 Suppl 1, 146-150 (2012-01-11)
Hepatitis C virus genotype 4 (HCV-4) is the most common type of hepatitis C virus (HCV) in the Middle East and Africa, in particular Egypt. Since the development of new protease inhibitors, the response of HCV-4 to the standard regimen
Drug repurposing approach identifies inhibitors of the prototypic viral transcription factor IE2 that block human cytomegalovirus replication
Mercorelli B, et al.
Cell Chemical Biology, 23(3), 340-351 (2016)
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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