Niclosamide
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MedKoo CAT#: 205940

CAS#: 50-65-7

Description: Niclosamide is an oral antihelminthic drug, which 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 active against cancer cells. Evidence supports that niclosamide targets multiple signaling pathways (NF-κB, Wnt/β-catenin, Notch, ROS, mTORC1, and Stat3), most of which are closely involved with cancer stem cells. Given its potential antitumor activity, clinical trials for niclosamide and its derivatives are warranted for cancer treatment.


Chemical Structure

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Niclosamide
CAS# 50-65-7

Theoretical Analysis

MedKoo Cat#: 205940
Name: Niclosamide
CAS#: 50-65-7
Chemical Formula: C13H8Cl2N2O4
Exact Mass: 325.99
Molecular Weight: 327.120
Elemental Analysis: C, 47.73; H, 2.47; Cl, 21.68; N, 8.56; O, 19.56

Price and Availability

Size Price Availability Quantity
500mg USD 150 Ready to ship
1g USD 250 Ready to ship
5g USD 450 Ready to ship
25g USD 850 2 weeks
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Synonym: Clonitralide, Fenasal, BAY 2353, BAY-2353, BAY2353, NSC 178296, NSC178296, NSC-178296, WR-46234, WR46234, WR 46234,

IUPAC/Chemical Name: 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide

InChi Key: RJMUSRYZPJIFPJ-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(NC1=CC=C([N+]([O-])=O)C=C1Cl)C2=CC(Cl)=CC=C2O

Appearance: Off-white to yellow solid powder.

Purity: >96% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: 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. 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 other 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. Niclosamide has been shown to inhibit the spread of colon cancer in animal studies. The drug works by blocking the expression of gene called S100A4/metastasin, which can prompt colon cancer metastasis. (source: http://en.wikipedia.org/wiki/Niclosamide).         

Product Data:
Safety Data Sheet (SDS):
Biological target: Niclosamide (BAY2353) is a chlorinated salicylanilide, with anthelmintic and potential antineoplastic activity that inhibits STAT3 with IC50 of 0.25 μM in HeLa cells.
In vitro activity: To further explore the potential mechanism of enhancement of PD-L1 antibody by niclosamide, it was evaluated whether niclosamide could have an impact on PD-L1 expression. The maximum niclosamide concentration tested (2 μM) was added to these NSCLC cell lines, which was lower than the IC30. Applying flow cytometry analysis, downregulation of PD-L1 expression after niclosamide treatment for 24 h (Fig. 3a) was observed. The inhibitory effect of niclosamide on PD-L1 expression was futher evaluated. After treatment with differing concentrations of niclosamide, it was observed that niclosamide decreased PD-L1 expression as well as STAT3 phosphorylation in a concentration-dependent manner in NSCLC cell lines (Fig.3b-d,3b-d, h-i). Moreover, cells treated with 2 μM niclosamide at different time points showed a time-dependent suppression of PD-L1 and p-STAT3 levels (Fig.3e-g,3e-g, k-m). J Immunother Cancer. 2019; 7: 245. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6739982/
In vivo activity: As early embryonic development in zebrafish is dependent, in part, on uptake of maternally deposited nutrients in the yolk as well as metabolism of cellular lipid droplets, the metabolomic profiles of zebrafish embryos following niclosamide exposure were investigated. The abundance and distribution of non-polar metabolites and lipids were not significantly affected within embryos exposed to 0.313 μM niclosamide from 2–5 hpf (Figures 2A and 2B; Supplementary Data S1). However, niclosamide exposure resulted in significant alterations on polar metabolites, where the majority of significantly affected metabolites were amino acids involved in the aminoacyl-tRNA biosynthesis pathway (Figures 3A and 3B; Figure 4; Supplementary Data S1). These results suggest that, within embryos exposed from 2–5 hpf, niclosamide affected the abundance and distribution of amino acids in the absence of effects of non-polar metabolites and lipids. Toxicol Appl Pharmacol. 2019 Oct 1; 380: 114699. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6717554/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 4.0 12.20
Ethanol 0.5 1.50

Preparing Stock Solutions

The following data is based on the product molecular weight 327.12 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Luo F, Luo M, Rong QX, Zhang H, Chen Z, Wang F, Zhao HY, Fu LW. Niclosamide, an antihelmintic drug, enhances efficacy of PD-1/PD-L1 immune checkpoint blockade in non-small cell lung cancer. J Immunother Cancer. 2019 Sep 11;7(1):245. doi: 10.1186/s40425-019-0733-7. PMID: 31511071; PMCID: PMC6739982. 2. Park SY, Kim JY, Choi JH, Kim JH, Lee CJ, Singh P, Sarkar S, Baek JH, Nam JS. Inhibition of LEF1-Mediated DCLK1 by Niclosamide Attenuates Colorectal Cancer Stemness. Clin Cancer Res. 2019 Feb 15;25(4):1415-1429. doi: 10.1158/1078-0432.CCR18-1232. Epub 2018 Nov 16. PMID: 30446587. 3.Vliet SMF, Dasgupta S, Sparks NRL, Kirkwood JS, Vollaro A, Hur M, Zur Nieden NI, Volz DC. Maternal-to-zygotic transition as a potential target for niclosamide during early embryogenesis. Toxicol Appl Pharmacol. 2019 Oct 1;380:114699. doi: 10.1016/j.taap.2019.114699. Epub 2019 Aug 6. PMID: 31398420; PMCID: PMC6717554.
In vitro protocol: 1. Luo F, Luo M, Rong QX, Zhang H, Chen Z, Wang F, Zhao HY, Fu LW. Niclosamide, an antihelmintic drug, enhances efficacy of PD-1/PD-L1 immune checkpoint blockade in non-small cell lung cancer. J Immunother Cancer. 2019 Sep 11;7(1):245. doi: 10.1186/s40425-019-0733-7. PMID: 31511071; PMCID: PMC6739982. 2. Park SY, Kim JY, Choi JH, Kim JH, Lee CJ, Singh P, Sarkar S, Baek JH, Nam JS. Inhibition of LEF1-Mediated DCLK1 by Niclosamide Attenuates Colorectal Cancer Stemness. Clin Cancer Res. 2019 Feb 15;25(4):1415-1429. doi: 10.1158/1078-0432.CCR18-1232. Epub 2018 Nov 16. PMID: 30446587.
In vivo protocol: 1.Vliet SMF, Dasgupta S, Sparks NRL, Kirkwood JS, Vollaro A, Hur M, Zur Nieden NI, Volz DC. Maternal-to-zygotic transition as a potential target for niclosamide during early embryogenesis. Toxicol Appl Pharmacol. 2019 Oct 1;380:114699. doi: 10.1016/j.taap.2019.114699. Epub 2019 Aug 6. PMID: 31398420; PMCID: PMC6717554. 2. Luo F, Luo M, Rong QX, Zhang H, Chen Z, Wang F, Zhao HY, Fu LW. Niclosamide, an antihelmintic drug, enhances efficacy of PD-1/PD-L1 immune checkpoint blockade in non-small cell lung cancer. J Immunother Cancer. 2019 Sep 11;7(1):245. doi: 10.1186/s40425-019-0733-7. PMID: 31511071; PMCID: PMC6739982.

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1: Yo YT, Lin YW, Wang YC, Balch C, Huang RL, Chan MW, Sytwu HK, Chen CK, Chang CC, Nephew KP, Huang T, Yu MH, Lai HC. Growth inhibition of ovarian tumor-initiating cells by niclosamide. Mol Cancer Ther. 2012 Aug;11(8):1703-12. doi: 10.1158/1535-7163.MCT-12-0002. Epub 2012 May 10. PubMed PMID: 22576131.

2: Fonseca BD, Diering GH, Bidinosti MA, Dalal K, Alain T, Balgi AD, Forestieri R, Nodwell M, Rajadurai CV, Gunaratnam C, Tee AR, Duong F, Andersen RJ, Orlowski J, Numata M, Sonenberg N, Roberge M. Structure-activity analysis of niclosamide reveals potential role for cytoplasmic pH in control of mammalian target of rapamycin complex 1 (mTORC1) signaling. J Biol Chem. 2012 May 18;287(21):17530-45. doi: 10.1074/jbc.M112.359638. Epub 2012 Apr 2. PubMed PMID: 22474287; PubMed Central PMCID: PMC3366846.

3: Pan JX, Ding K, Wang CY. Niclosamide, an old antihelminthic agent, demonstrates antitumor activity by blocking multiple signaling pathways of cancer stem cells. Chin J Cancer. 2012 Apr;31(4):178-84. doi: 10.5732/cjc.011.10290. Epub 2012 Jan 9. PubMed PMID: 22237038.

4: Lu W, Lin C, Roberts MJ, Waud WR, Piazza GA, Li Y. Niclosamide suppresses cancer cell growth by inducing Wnt co-receptor LRP6 degradation and inhibiting the Wnt/β-catenin pathway. PLoS One. 2011;6(12):e29290. doi: 10.1371/journal.pone.0029290. Epub 2011 Dec 16. PubMed PMID: 22195040; PubMed Central PMCID: PMC3241710.

5: Helfman DM. Niclosamide: an established antihelminthic drug as a potential therapy against S100A4-mediated metastatic colon tumors. J Natl Cancer Inst. 2011 Jul 6;103(13):991-2. doi: 10.1093/jnci/djr221. Epub 2011 Jun 17. PubMed PMID: 21685360.

6: Sack U, Walther W, Scudiero D, Selby M, Kobelt D, Lemm M, Fichtner I, Schlag PM, Shoemaker RH, Stein U. Novel effect of antihelminthic Niclosamide on S100A4-mediated metastatic progression in colon cancer. J Natl Cancer Inst. 2011 Jul 6;103(13):1018-36. doi: 10.1093/jnci/djr190. Epub 2011 Jun 17. PubMed PMID: 21685359.

7: Osada T, Chen M, Yang XY, Spasojevic I, Vandeusen JB, Hsu D, Clary BM, Clay TM, Chen W, Morse MA, Lyerly HK. Antihelminth compound niclosamide downregulates Wnt signaling and elicits antitumor responses in tumors with activating APC mutations. Cancer Res. 2011 Jun 15;71(12):4172-82. doi: 10.1158/0008-5472.CAN-10-3978. Epub 2011 Apr 29. PubMed PMID: 21531761; PubMed Central PMCID: PMC3117125.

8: Jin Y, Lu Z, Ding K, Li J, Du X, Chen C, Sun X, Wu Y, Zhou J, Pan J. Antineoplastic mechanisms of niclosamide in acute myelogenous leukemia stem cells: inactivation of the NF-kappaB pathway and generation of reactive oxygen species. Cancer Res. 2010 Mar 15;70(6):2516-27. doi: 10.1158/0008-5472.CAN-09-3950. Epub 2010 Mar 9. PubMed PMID: 20215516.

9: Wang AM, Ku HH, Liang YC, Chen YC, Hwu YM, Yeh TS. The autonomous notch signal pathway is activated by baicalin and baicalein but is suppressed by niclosamide in K562 cells. J Cell Biochem. 2009 Mar 1;106(4):682-92. doi: 10.1002/jcb.22065. PubMed PMID: 19160421.