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N3510

Sigma-Aldrich

Niclosamide

Synonym(s):

2′,5-Dichloro-4′-nitrosalicylanilide

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About This Item

Empirical Formula (Hill Notation):
C13H8Cl2N2O4
CAS Number:
50-65-7
Molecular Weight:
327.12
Beilstein:
2820605
EC Number:
200-056-8
MDL number:
MFCD00057597
UNSPSC Code:
51102829
PubChem Substance ID:
24278585
NACRES:
NA.85

form

powder

Quality Level

200

antibiotic activity spectrum

parasites

Mode of action

enzyme | inhibits

SMILES string

Oc1ccc(Cl)cc1C(=O)Nc2ccc(cc2Cl)[N+]([O-])=O

InChI

1S/C13H8Cl2N2O4/c14-7-1-4-12(18)9(5-7)13(19)16-11-3-2-8(17(20)21)6-10(11)15/h1-6,18H,(H,16,19)

InChI key

RJMUSRYZPJIFPJ-UHFFFAOYSA-N

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Application

Niclosamide is a teniacide in the anthelmintic family. It is effective against cestodes that infect humans. Niclosamide is used to study the Wnt/Frizzled-1 signaling pathway. It is used to inhibit transcription and DNA binding of the NF-?B pathway and it increases ROS levels to induce apoptosis in acute myelogenous leukemia (AML) cells.

Biochem/physiol Actions

Niclosamide uncouples oxidative phosphorylation in the tapeworm and inhibits mitochondrial oxidative phosphorylation of parasitic helminths. It blocks tumor necrosis factor-induced IκBα phosphorylation, translocation of p65, and expression of NF-κΒ– regulated genes in AML cells.

Other Notes

50g,250g
Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Mechanism of action of reagents that uncouple oxidative phosphorylation.
E C Weinbach et al.
Nature, 221(5185), 1016-1018 (1969-03-15)
Masanori Ono et al.
Fertility and sterility, 101(5), 1441-1449 (2014-02-19)
To assess the effect of three WNT/β-catenin pathway inhibitors-inhibitor of β-catenin and TCF4 (ICAT), niclosamide, and XAV939-on the proliferation of primary cultures of human uterine leiomyoma cells. Prospective study of human leiomyoma cells obtained from myomectomy or hysterectomy. University research
Wenyan Lu et al.
PloS one, 6(12), e29290-e29290 (2011-12-24)
The Wnt/β-catenin signaling pathway is important for tumor initiation and progression. The low density lipoprotein receptor-related protein-6 (LRP6) is an essential Wnt co-receptor for Wnt/β-catenin signaling and represents a promising anticancer target. Recently, the antihelminthic drug, niclosamide was found to
K Ketola et al.
British journal of cancer, 106(1), 99-106 (2012-01-05)
We have shown that a sodium ionophore monensin inhibits prostate cancer cell growth. A structurally related compound to monensin, salinomycin, was recently identified as a putative cancer stem cell inhibitor. The growth inhibitory potential of salinomycin was studied in a
Jing-Xuan Pan et al.
Chinese journal of cancer, 31(4), 178-184 (2012-01-13)
Niclosamide, an oral antihelminthic drug, has been used to treat tapeworm infection for about 50 years. Niclosamide is also used as a molluscicide for water treatment in schistosomiasis control programs. Recently, several groups have independently discovered that niclosamide is also
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