ChemicalBook CAS DataBase List 40321-86-6

40321-86-6

Name	NiclosaMide (sodiuM salt)
CAS	40321-86-6
Molecular Formula	C13H9Cl2N2NaO4
MDL Number	MFCD28386656
Molecular Weight	351.11
MOL File	40321-86-6.mol

Hazard Information

Description

Niclosamide sodium is an antihelmintic that is active against most tapeworms.

Uses

Niclosamide (BAY2353) sodium is an orally active antihelminthic agent used in parasitic infection research[1]. Niclosamide sodium is a STAT3 inhibitor with an IC50 of 0.25 μM in HeLa cells[4]. Niclosamide sodium has biological activities against cancer, and inhibits DNA replication in Vero E6 cells[2][3][5].

Production Methods

The production of niclosamide-olamine begins with the synthesis of niclosamide, typically via a condensation reaction between 5-chlorosalicylic acid and 2-chloro-4-nitroaniline in the presence of a chlorinating agent such as phosphorus trichloride, often carried out in a solvent like chlorobenzene at elevated temperatures. The resulting niclosamide is then purified through recrystallisation. To form the sodium salt, niclosamide is then reacted with sodium hydroxide in aqueous or alcoholic solution, converting the phenolic hydroxyl group into its sodium salt form.

Mechanism of action

Respiratory & stomach action. Acts by uncoupling oxidative phosphorylation in the tapeworm

in vivo

Niclosamide sodium (oral gavage; 100 mg/kg, 200 mg/kg; once a week; 8 weeks) treatment inhibits adrenocortical carcinoma tumor growth in vivo^[3].

Animal Model:	Nu⁺/Nu⁺ mice injected with NCI-H295R cells^[3]
Dosage:	100 mg/kg, 200 mg/kg
Administration:	Oral gavage; 100 mg/kg, 200 mg/kg; once a week; 8 weeks
Result:	Showed a 60%-80% inhibition in tumor growth, as compared to the control group.

References

[1] P Andrews, et al. The biology and toxicology of molluscicides, Bayluscide. Pharmacol Ther. 1982;19(2):245-95. DOI:10.1016/0163-7258(82)90064-x
[2] Wei Chen, et al. Niclosamide: Beyond an antihelminthic drug. Cell Signal. 2018 Jan;41:89-96. DOI:10.1016/j.cellsig.2017.04.001
[3] Kei Satoh, et al. Identification of Niclosamide as a Novel Anticancer Agent for Adrenocortical Carcinoma. Clin Cancer Res. 2016 Jul 15;22(14):3458-66. DOI:10.1158/1078-0432.CCR-15-2256
[4] Xiaomei Ren, et al. Identification of Niclosamide as a New Small-Molecule Inhibitor of the STAT3 Signaling Pathway. ACS Med Chem Lett. 2010 Sep 7;1(9):454-9. DOI:10.1021/ml100146z
[5] Chang-Jer Wu, et al. Inhibition of severe acute respiratory syndrome coronavirus replication by niclosamide. Antimicrob Agents Chemother. 2004 Jul;48(7):2693-6. DOI:10.1128/AAC.48.7.2693-2696.2004