niclosamide chemical structure1. DESCRIPTION: is a STAT3 signaling pathway inhibitor. Displays selectivity for STAT3 over STAT1, STAT5, JAK1, JAK2 and Src kinases.

2. Niclosamide potently inhibits the activation and transcriptional function of STAT3 and induces cell growth inhibition, apoptosis, and cell cycle arrest of cancer cells with constitutively active STAT3.

3. Niclosamide also reversibly inhibits mTORC1 signaling and stimulates autophagy in vitro; displays antineoplastic effects in acute myelogenous leukemia (AML) stem cells.

4. Niclosamide (trade name Niclocide) is a teniacide ("tenia-" referring to tapeworm) in the anthelmintic family especially effective against cestodes that infect humans. It is also used as a piscicide.

5. It is stressed that while antihelmintics are a drug family used to treat worm infections, Niclosamide is used specifically to treat tapeworms and is not effective against worms such as pinworms or roundworms. It is a chewable tablet taken orally, dosage depending on type of worm and patient's age and/or weight. Niclosamide molecules are lethal to tapeworms upon contact. Source: Wikipedia.

6. APPEARANCE:Light Yellow/Greyish Solid

7. CHEMICAL NAME: 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide

8. Physical characteristics: Niclosamide is a yellowish grey odorless crystalline solid which melts between 224-229 °C. The piperazine salt melts above 240 °C with decomposition.  The ethanolamine salt form is a yellow solid melting at minimum 191 °C.

9. CHEMICAL FORMULA: C13H8Cl2N2O4

10. MOLECULAR WEIGHT: M.W. 325.99

11. CAS#: CAS#[50-65-7]

12. SOURCE: SYNTHETIC

13. STABILITY: Stability: In tablets niclosamide undergoes a biodegradation in moist environments but niclosamide itself is stable in an aqueous solution for several months.  The ethanolamine salt is stable to heat, hydrolyzed by concentrated acid or alkali, and stable in aquatic environments

14. MINIMUM PURITY: 99%

15. TOXICITY:Acute toxicity, Oral (Category 5) & Acute aquatic toxicity (Category 1)

16. Hazard statement(s): H303 May be harmful if swallowed. & H400 Very toxic to aquatic life.

17. Toxicity, single dose:

i. Oral LD50:

ii. Niclosamide:

i. Rat  (M,F)  5 000  mg/kg  b.w.

ii. Mouse  (F)  >1 500  mg/kg  b.w.

iii. Rabbit  5 000  mg/kg  b.w.

iv. Cat  >1 000  mg/kg  b.w.

18. Precautionary statement(s): P273 Avoid release to the environment.

19. MDL#: MFCD00057597

20. Applications: Colon cancer cell lines: Colon cancer cell lines (HCT116, SW620, LS174T, SW480, and DLD-1. Niclosamide inhibits S100A4-induced metastasis formation in a mouse model of colon cancer and has therapeutic potential4.

21. Wnt pathway Signaling: Niclosamide Development of small molecules targeting the Wnt pathway for the treatment of colon cancer: a high-throughput screening approach5.

22. Autophagy: NICLOSAMIDE is an m-TOR DEPENDENT, small molecule AUTOPHAGY INDUCER.

23. Ubquitinin/Proteasome research: Niclosamide Prevents the Formation of Large Ubiquitin-Containing Aggregates Caused by Proteasome Inhibition6.

24. Acute Myelogenous Leukemia Stem Cells.Antineoplastic mechanisms of niclosamide in acute myelogenous leukemia stem cells: inactivation of the NF-kappaB pathway and generation of reactive oxygen species2.

25. Inhibiting the Wnt/beta-Catenin Pathway:The Wnt/beta-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/beta-catenin signaling and represents a promising anticancer target. Recently, the antihelminthic drug, niclosamide was found to inhibit Wnt/beta-catenin signaling, although the mechanism was not well defined. We found that niclosamide was able to suppress LRP6 expression and phosphorylation, block Wnt3A-induced beta-catenin accumulation, and inhibit Wnt/beta-catenin signaling in HEK293 cells. Furthermore, the inhibitory effects of niclosamide on LRP6 expression/phosphorylation and Wnt/beta-catenin signaling were conformed in human prostate PC-3 and DU145 and breast MDA-MB-231 and T-47D cancer cells.

26. SOLUBILITY & STORAGE INFORMATION: Niclosamide is not very water soluble, 5-8 mg/L at 20 °C, sparingly soluble in ether, ethanol (22 mM), chloroform, acetone and DMSO ( to 10 mM). The ethanolamine salt dissolves in distilled water 180-280 mg/L at 20 °C.

a.Solutions can be difficult to obtain and can be aided by rapid stirring, sonication or gentle warming in water bath at 45-60ºC.

b. General guidelines

c. Solid: Protect from light & moisture. Store at +4ºC. Use within 6 months of receipt of product

d. Solutions: Once stock solutions are prepared, utilize fresh if possible. Otherwise store tightly at -20ºC and utilize within the month.

27. MINIMUM PURITY: 99%

28. TOXICITY:Acute toxicity, Oral (Category 5) & Acute aquatic toxicity (Category)  i.

29. Hazard statement(s): H303 May be harmful if swallowed. & H400 Very toxic to aquatic life.

30. Precautionary statement(s): P273 Avoid release to the environment.

31. What is RTECS# and what does it tell us?: (Registry of Toxic effects of Chemical substances) RTECS is a compendium of data extracted from the open scientific literature. The data are recorded in the format developed by the RTECS staff and arranged in alphabetical order by prime chemical name. Six types of toxicity data are included in the file: (1) primary irritation; (2) mutagenic effects; (3) reproductive effects; (4) tumorigenic effects; (5) acute toxicity; and (6) other multiple dose toxicity. Specific numeric toxicity values such as LD50, LC50, TDLo, and TCLo are noted as well as species studied and route of administration used. For each citation, the bibliographic source is listed thereby enabling the user to access the actual studies cited. No attempt has been made to evaluate the studies cited in RTECS. The user has the responsibility of making such assessments.

 

REFERENCES:

1. Balgi et al (2009) Screen for chemical modulators of autophagy reveals novel therapeutic inhibitors of mTORC1 signaling. PLoS One 4 e7124. PMID: 19771169.

2. Jin et al (2010) Antineoplastic mechanisms of niclosamide in acute myelogenous leukemia stem cells: inactivation of the NF-B pathway and generation of reactive oxygen species. Cancer Res. 70 2516. PMID: 20215516.

3. Ren et al (2010) Identification of niclosamide as a new small-molecule inhibitor of the STAT3 signaling pathway. ACS Med.Chem.Lett. 1 454.

4. Ulrike Sack, et al (2011) Niclosamide: An Established Antihelminthic Drug as a Potential Therapy Against S100A4-Mediated Metastatic Colon Tumors JNCI J Natl Cancer Inst 103(13): 991-992.

5. Wei Chen, et al. Development of small molecules targeting the Wnt pathway for the treatment of colon cancer: a high-throughput screening approach Am J Physiol Gastrointest Liver Physiol 299: G293–G300, 2010. First published May 27, 2010.

6. Gies E, Wilde I, Winget JM, Brack M, Rotblat B, et al. (2010) Niclosamide Prevents the Formation of Large Ubiquitin-Containing Aggregates Caused by Proteasome Inhibition. PLoS ONE 5(12): e14410. doi:10.1371/journal.pone.0014410.

7. Lu W, Lin C, Roberts MJ, Waud WR, Piazza GA, et al. (2011) Niclosamide Suppresses Cancer Cell Growth By Inducing Wnt Co-Receptor LRP6 Degradation and Inhibiting the Wnt/beta-Catenin Pathway. PLoS ONE 6(12): e29290. doi:10.1371/journal.pone.0029290.

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