NICLOSAMIDE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC P02DA01
UNII 8KK8CQ2K8G
EPA CompTox DTXSID7040362

Structure

InChI Key RJMUSRYZPJIFPJ-UHFFFAOYSA-N
Smiles O=C(Nc1ccc([N+](=O)[O-])cc1Cl)c1cc(Cl)ccc1O
InChI
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C13H8Cl2N2O4
Molecular Weight 327.12
AlogP 3.86
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 3.0
Polar Surface Area 92.47
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 21.0

Bioactivity

Mechanism of Action Action Reference
DNA inhibitor INHIBITOR PubMed Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase AKT family
- 59400 - - -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PDK1 subfamily
- 83900 - - -
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase GSK family
- 77500 - - -
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase AUR family
- 54100 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase EGFR family
- 10500 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase FGFR family
- 13100 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakA family
- 10000 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakB family
- 10000 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase PDGFR family
- 27800 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Src family
- 10000-10500 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Tie family
- 67800 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase VEGFR family
- 23100 - - -
Enzyme
- 10000-10500 - - -
Transcription factor
- 250 - - -
Assay Description Organism Bioactivity Reference
Inhibition of SARS coronavirus-induced cytopathogenicity in Vero E6 cells at 20 uM SARS coronavirus 25.0 %
Inhibition of SARS coronavirus-induced cytopathogenicity in Vero E6 cells at 10 uM SARS coronavirus 25.0 %
Inhibition of SARS virus-induced cytopathogenicity in Vero E6 cells at 3.3 uM SARS coronavirus 25.0 %
Inhibition of SARS virus-induced cytopathogenicity in Vero E6 cells at 1 uM SARS coronavirus 50.0 %
Antiviral activity against SARS coronavirus in Vero E6 cells assessed as inhibition of viral replication by ELISA SARS coronavirus 100.0 nM
Antiproliferative activity against human PC3 cells after 120 hrs by MTT assay Homo sapiens 400.0 nM
Antiproliferative activity against human A549 cells after 120 hrs by MTT assay Homo sapiens 400.0 nM
Antiproliferative activity against human LoVo cells after 120 hrs by MTT assay Homo sapiens 700.0 nM
Antiproliferative activity against human U87MG cells after 120 hrs by MTT assay Homo sapiens 400.0 nM
Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR green assay Plasmodium falciparum 0.89 nM Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR green assay Plasmodium falciparum 794.33 nM
Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR green assay Plasmodium falciparum 7G8 0.89 nM Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR green assay Plasmodium falciparum 7G8 794.33 nM
Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR green assay Plasmodium falciparum D10 1.0 nM
Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR green assay Plasmodium falciparum 1.48 nM
Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR green assay Plasmodium falciparum 0.74 nM Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR green assay Plasmodium falciparum 794.33 nM
Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR green assay Plasmodium falciparum HB3 0.89 nM Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR green assay Plasmodium falciparum HB3 794.33 nM
Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR green assay Plasmodium falciparum 0.56 nM Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR green assay Plasmodium falciparum 501.19 nM
Inhibition of STAT3 in human HeLa cells after 24 hrs by luciferase reporter gene assay Homo sapiens 250.0 nM
Antiproliferative activity against human DU145 cells after 72 hrs by MTT assay Homo sapiens 700.0 nM
Growth inhibition of human DU145 cells assessed as inhibition of colony formation after 11 to 12 days by crystal violet staining based microscopic analysis Homo sapiens 700.0 nM
Antiviral activity against HCV genotype 1b infected in Ava5 cells assessed as inhibition of viral replication after 3 days by blot hybridization analysis Hepatitis C virus subtype 1b 160.0 nM
Cytotoxicity against human ER negative MDA-MB-231 cells after 72 hrs by MTS assay Homo sapiens 790.0 nM
CYtotoxicity against ER-negative human MDA-MB-231 cells by MTS assay Homo sapiens 790.0 nM
Inhibition of Wnt3A/beta-casein signaling in HEK293 cells after 8 hrs by TOPflash reporter assay Homo sapiens 400.0 nM
DNDI: Leish (axenic) in Vitro, 72 hour Leishmania donovani 150.0 nM
DNDI: Leish (macro) in Vitro, 96 hour Leishmania donovani 310.0 nM
PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 1.0 nM
PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 1.0 nM
PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmatory) None 144.0 nM
PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 1.44 nM
PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 472.85 nM
PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area decrease-IC50. (Class of assay: confirmatory) None 112.0 nM
PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 8.26 nM
PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 3.49 nM
PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 2.95 nM
Inhibition of Wnt/beta-catenin in HEK293 cells assessed as inhibition of Wnt3A-stimulated TOPFlash activity after 8 hrs Homo sapiens 340.0 nM
Cytotoxicity against human HCT116 cells assessed as growth inhibition after 72 hrs by MTS assay Homo sapiens 450.0 nM
Cytotoxicity against human breast cancer cells assessed as growth inhibition after 72 hrs by Cell Titer Glo Assay Homo sapiens 130.0 nM
Cytotoxicity against human colon cancer cells assessed as growth inhibition after 72 hrs by Cell Titer Glo Assay Homo sapiens 130.0 nM
Cytotoxicity against human lung cancer cells assessed as growth inhibition after 72 hrs by Cell Titer Glo Assay Homo sapiens 130.0 nM
Cytotoxicity against human prostate cancer cells assessed as growth inhibition after 72 hrs by Cell Titer Glo Assay Homo sapiens 130.0 nM
Cytotoxicity against human ovarian cancer cells assessed as growth inhibition after 72 hrs by Cell Titer Glo Assay Homo sapiens 130.0 nM
Cytotoxicity against human blood cancer cells assessed as growth inhibition after 72 hrs by Cell Titer Glo Assay Homo sapiens 130.0 nM
Cytotoxicity against human pancreatic cancer cells assessed as growth inhibition after 72 hrs by Cell Titer Glo Assay Homo sapiens 130.0 nM
Inhibition of Wnt/beta-catenin signaling (unknown origin) expressed in HEK293 cells assessed as inhibition of Wnt3A-stimulated beta-catenin response transcription after 6 hrs by TOPflash dual luciferase reporter gene assay Homo sapiens 120.0 nM
Effect on ATP homeostasis in human HCT116 cells assessed as reduction in ATP level after 3 hrs in absence of glucose by ATP bioluminescent assay Homo sapiens 56.0 nM Effect on ATP homeostasis in human HCT116 cells assessed as reduction in ATP level after 3 hrs in absence of glucose by ATP bioluminescent assay Homo sapiens 250.0 nM
Inhibition of Wnt/beta-catenin signaling (unknown origin) expressed in HEK293 cells assessed as inhibition of Wnt3A-stimulated beta-catenin response transcription at 0.16 uM after 6 hrs by TOPflash dual luciferase reporter gene assay relative to control Homo sapiens 40.0 %
Antiviral activity against Chikungunya virus infected in BHK-21 cells by RT-qPCR analysis Chikungunya virus 950.0 nM
Antiviral activity against Chikungunya virus 0611aTw infected in BHK-21 cells by RT-qPCR analysis Chikungunya virus 850.0 nM
Antiviral activity against Chikungunya virus 0810bTw infected in BHK-21 cells by RT-qPCR analysis Chikungunya virus 900.0 nM
Antiviral activity against Chikungunya virus infected in human U2OS cells by RT-qPCR analysis Chikungunya virus 360.0 nM
Inhibition of Wnt3A-stimulated Wnt/beta-catenin pathway in HEK293 cells transfected with p8xTOPFlash, Renilla luciferase plasmid pRL-TK and pLKO.1 after 6 hrs by Dual topflash luciferase reporter assay Homo sapiens 450.0 nM
Antiproliferative activity against human SW948 cells after 72 hrs by colorimetric MTS assay Homo sapiens 110.0 nM
Antiproliferative activity against human HT-29 cells after 72 hrs by colorimetric MTS assay Homo sapiens 130.0 nM
Antiproliferative activity against human HCT116 cells after 72 hrs by colorimetric MTS assay Homo sapiens 410.0 nM
Antiproliferative activity against human CRC240 cells after 72 hrs by colorimetric MTS assay Homo sapiens 890.0 nM
Antiproliferative activity against human SW480 cells after 72 hrs by colorimetric MTS assay Homo sapiens 980.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -35.91 %
Antiviral activity against SARS-CoV-2 (viral titer) measured by plaque assay in Vero cells at MOI 0.0125 after 24 hr Chlorocebus sabaeus 280.0 nM
Inhibition of Wnt3A-stimulated Wnt/beta-catenin pathway in HEK293 cells transfected with p8xTOPFlash, Renilla luciferase plasmid pRL-TK and pLKO.1 after 8 hrs by Dual topflash luciferase reporter gene assay Homo sapiens 340.0 nM
Inhibition of Wnt/beta-catenin signaling pathway in human HCT116 cells cytosol lysate harboring beta-catenin mutation assessed as reduction in Axin2 protein expression at 5 uM after 18 hrs by Western blot analysis relative to control Homo sapiens 35.0 %
Inhibition of Wnt/beta-catenin signaling pathway in human HCT116 cells cytosol lysate harboring beta-catenin mutation assessed as reduction in beta-catenin protein expression at 5 uM after 18 hrs by Western blot analysis relative to control Homo sapiens 46.0 %
Inhibition of Wnt/beta-catenin signaling pathway in human HCT116 whole cell lysate harboring beta-catenin mutation assessed as reduction in c-Myc protein expression at 5 uM after 18 hrs by Western blot analysis relative to control Homo sapiens 1.0 %
Inhibition of Wnt/beta-catenin signaling pathway in human HCT116 whole cell lysate harboring beta-catenin mutation assessed as reduction in survivin protein expression at 5 uM after 18 hrs by Western blot analysis relative to control Homo sapiens 44.0 %
Inhibition of Wnt/beta-catenin signaling pathway in human HCT116 whole cell lysate harboring beta-catenin mutation assessed as reduction in cyclin D1 protein expression at 5 uM after 18 hrs by Western blot analysis relative to control Homo sapiens 28.0 %
Inhibition of Wnt/beta-catenin signaling pathway in human SW480 cells cytosol lysate harboring APC mutation assessed as reduction in Axin2 protein expression at 5 uM after 18 hrs by Western blot analysis relative to control Homo sapiens 29.0 %
Inhibition of Wnt/beta-catenin signaling pathway in human SW480 cells cytosol lysate harboring APC mutation assessed as reduction in beta-catenin protein expression at 5 uM after 18 hrs by Western blot analysis relative to control Homo sapiens 74.0 %
Inhibition of Wnt/beta-catenin signaling pathway in human SW480 whole cell lysate harboring APC mutation assessed as reduction in c-Myc protein expression at 5 uM after 18 hrs by Western blot analysis relative to control Homo sapiens 3.0 %
Inhibition of Wnt/beta-catenin signaling pathway in human SW480 whole cell lysate harboring APC mutation assessed as reduction in survivin protein expression at 5 uM after 18 hrs by Western blot analysis relative to control Homo sapiens 41.0 %
Inhibition of Wnt/beta-catenin signaling pathway in human SW480 whole cell lysate harboring APC mutation assessed as reduction in cyclin D1 protein expression at 5 uM after 18 hrs by Western blot analysis relative to control Homo sapiens 45.0 %
Cytotoxicity against human HL60 cells incubated for 3 days by CellTiter-Glo luminescent assay Homo sapiens 300.0 nM
Cytotoxicity against human KG1 cells incubated for 3 days by CellTiter-Glo luminescent assay Homo sapiens 360.0 nM
Cytotoxicity against human Jurkat cells incubated for 3 days by CellTiter-Glo luminescent assay Homo sapiens 400.0 nM
Cytotoxicity against human NALM6 cells incubated for 3 days by CellTiter-Glo luminescent assay Homo sapiens 620.0 nM
Antiparasitic activity against Toxoplasma gondii Toxoplasma gondii 0.0453 ug.mL-1
Antiviral activity against Human adenovirus 5 infected in 293beta5 cells assessed as inhibition of plaque formation at 10 uM incubated for 7 days by GFP reporter gene assay relative to control Human adenovirus 5 100.0 %
Antiviral activity against Human adenovirus 5 infected in 293beta5 cells assessed as inhibition of plaque formation incubated for 7 days by GFP reporter gene assay Human adenovirus 5 600.0 nM
Antiviral activity against Human adenovirus 5 infected in human A549 cells assessed as inhibition of viral entry at 50 uM after 48 hrs by GFP reporter gene based assay relative to control Human adenovirus 5 100.0 %
Antiproliferative activity against human LN229 cells after 5 days by AlamarBlue assay Homo sapiens 300.0 nM
Antiproliferative activity against human T98G cells after 5 days by AlamarBlue assay Homo sapiens 300.0 nM
Antiproliferative activity against human U87 cells after 5 days by AlamarBlue assay Homo sapiens 300.0 nM
Antiproliferative activity against human U138MG cells after 5 days by AlamarBlue assay Homo sapiens 300.0 nM
Antiproliferative activity against human U373 cells after 5 days by AlamarBlue assay Homo sapiens 300.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 28.67 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 5.92 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 10.92 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 32.08 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 14.78 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 14.57 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 32.08 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 14.78 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 14.57 %
Antiviral activity against GFP-fused Human adenovirus 5 infected in 293beta5 cells assessed as inhibition of plaque formation incubated for 7 days by GFP reporter gene assay Human adenovirus 5 600.0 nM
Antiviral activity against Human adenovirus 5 infected in 293beta5 cells assessed as inhibition of plaque formation at 10 uM incubated for 7 days by GFP reporter gene assay relative to control Human adenovirus 5 100.0 %
Antiviral activity against wild-type Human adenovirus 5 infected in human A549 cells assessed as inhibition of virus entry at 50 uM incubated for 48 hrs by fluorescence assay relative to control Human adenovirus 5 100.0 %
Antiviral activity against Human adenovirus 5 infected in 293beta5 cells assessed as inhibition of virus infection at 10 fold IC50 measured after 60 mins by GFP reporter gene assay relative to control Human adenovirus 5 50.0 %
Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition of cell viability at 10 uM after 48 hrs by MTT assay relative to control Homo sapiens 91.54 %
Antiproliferative activity against human HCT116 cells assessed as inhibition of cell viability at 10 uM after 48 hrs by MTT assay relative to control Homo sapiens 73.77 %
Antiproliferative activity against human SW480 cells assessed as inhibition of cell viability at 10 uM after 48 hrs by MTT assay relative to control Homo sapiens 76.81 %
Antiproliferative activity against human L3.6 cells assessed as inhibition of cell viability at 10 uM after 48 hrs by MTT assay relative to control Homo sapiens 66.16 %
Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition of cell viability after 48 hrs by MTT assay Homo sapiens 800.0 nM
Antiproliferative activity against human HCT-116 cells assessed as inhibition of cell viability after 48 hrs by MTT assay Homo sapiens 450.0 nM
Inhibition of STAT3 phosphorylation in human MDA-MB-231 cells by sandwich ELISA Homo sapiens 210.0 nM
Inhibition of STAT3 promoter activity in human MDA-MB-231 cells at 1 uM incubated for 24 hrs by dual luciferase reporter assay Homo sapiens 88.2 %
Inhibition of NS-1in Zika virus Zika virus 570.0 nM
Inhibition of envelope protein in Zika virus Zika virus 880.0 nM
Antiviral activity against Zika virus infected in SNB-19 cells assessed as reduction in viral titer Homo sapiens 120.0 nM
Antiviral activity against SARS Cov-2 infected in Vero cells assessed as inhibition of viral cytopathic effect measured after 72 hrs by CellTiter-Glo luminescent cell viability assay Severe acute respiratory syndrome coronavirus 2 280.0 nM
Antiviral activity against SARS Cov-2 USA_WA1/2020 infected in Vero E6 cells assessed as inhibition of viral cytopathic effect measured after 72 hrs by CellTiter-Glo luminescent cell viability assay Severe acute respiratory syndrome coronavirus 2 112.0 nM

Cross References

Resources Reference
ChEBI 7553
ChEMBL CHEMBL1448
DrugBank DB06803
DrugCentral 1912
FDA SRS 8KK8CQ2K8G
Human Metabolome Database HMDB0015679
Guide to Pharmacology 8494
KEGG D00436
PharmGKB PA165958408
PubChem 4477
SureChEMBL SCHEMBL67182
ZINC ZINC000003874496
CONTENTS