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N0290

Sigma-Aldrich

Nitazoxanide

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C12H9N3O5S
Numéro CAS:
55981-09-4
Poids moléculaire :
307.28
Numéro CE :
259-931-8
Numéro MDL:
MFCD00416599
Code UNSPSC :
12352200
ID de substance PubChem :
329818424
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Auteur

Romark

Température de stockage

2-8°C

Chaîne SMILES 

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)

Clé InChI

YQNQNVDNTFHQSW-UHFFFAOYSA-N

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Description générale

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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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)
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
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
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
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
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