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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

11 - Combustible Solids

wgk_germany

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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Vanessa R Anderson et al.
Drugs, 67(13), 1947-1967 (2007-08-29)
Nitazoxanide (Alinia, Daxon, Dexidex, Paramix, Kidonax, Colufase, Annita) has in vitro activity against a variety of microorganisms, including a broad range of protozoa and helminths. Nitazoxanide is effective in the treatment of protozoal and helminthic infections, including Cryptosporidium parvum or
Irit Krause et al.
The Pediatric infectious disease journal, 31(11), 1135-1138 (2012-07-20)
Cryptosporidium parvum is a common cause of diarrhea. In immunocompetent individuals, spontaneous recovery is the rule. In immunocompromised patients, it may cause a serious disease. Data on cryptosporidiosis in children after solid organ transplantation are few. We report on 6
Nitazoxanide stimulates autophagy and inhibits mTORC1 signaling and intracellular proliferation of Mycobacterium tuberculosis
Lam KYK
PLoS Pathogens, 8(5), 340-351 (2012)
P Patrick Basu et al.
The American journal of gastroenterology, 106(11), 1970-1975 (2011-10-13)
Resistance to standard Helicobacter pylori (HP) treatment regimens has led to unsatisfactory cure rates in HP-infected patients. This study was designed to evaluate a novel four-drug regimen (three antibiotics and a proton pump inhibitor (PPI)) for eradication of HP infection
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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