NITAZOXANIDE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC P01AX11
UNII SOA12P041N
EPA CompTox DTXSID5033757

Structure

InChI Key YQNQNVDNTFHQSW-UHFFFAOYSA-N
Smiles CC(=O)Oc1ccccc1C(=O)Nc1ncc([N+](=O)[O-])s1
InChI
InChI=1S/C12H9N3O5S/c1-7(16)20-9-5-3-2-4-8(9)11(17)14-12-13-6-10(21-12)15(18)19/h2-6H,1H3,(H,13,14,17)

Physicochemical Descriptors

Property Name Value
Molecular Formula C12H9N3O5S
Molecular Weight 307.29
AlogP 2.23
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 111.43
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 21.0

Bioactivity

Mechanism of Action Action Reference
Pyruvate:ferredoxin oxidoreductase inhibitor INHIBITOR DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 8220 - 10500 -
Transcription factor
- 9800-9980 - - 55
Assay Description Organism Bioactivity Reference
Growth inhibition of Escherichia coli CC104 expressing rdxA gene after 16 hrs Escherichia coli 35.0 %
Growth inhibition of Escherichia coli pBSK after 16 hrs Escherichia coli 35.0 %
Inhibition of Escherichia coli JVQ2 PDH at 20 uM Escherichia coli 22.0 %
Inhibition of Giardia lamblia recombinant nitroreductase 1 (EAA43030.1) expressed in Escherichia coli Giardia intestinalis 300.0 nM
Inhibition of Giardia lamblia recombinant nitroreductase 1 (EAA43030.1) expressed in Escherichia coli at 5 uM Giardia intestinalis 75.0 %
Antimicrobial activity against Giardia Giardia 2.5 ug.mL-1
Inhibition of Helicobacter pyroli PFOR expressed in Escherichia coli at 40 uM Helicobacter pylori 54.0 %
Antiparasitic activity against Cryptosporidium parvum infected in human HTC8 cells after 46 hrs by immunofluorescence method Cryptosporidium parvum 1.2 ug.mL-1 Antiparasitic activity against Cryptosporidium parvum infected in human HTC8 cells after 46 hrs by immunofluorescence method Cryptosporidium parvum 10.0 ug.mL-1
Antiviral activity against HCV genotype 1a in replicon system Hepatitis C virus subtype 1a 130.0 nM
Antiviral activity against HCV genotype 1b in RP7 replicon cell after 4 days by blot hybridization analysis Hepatitis C virus subtype 1b 160.0 nM
Antimicrobial activity against biofilm-positive Staphylococcus epidermidis clinical isolate ICS1 by microdilution method Staphylococcus epidermidis 1.0 ug.mL-1
Antimicrobial activity against biofilm-positive Staphylococcus epidermidis clinical isolate ICS2 by microdilution method Staphylococcus epidermidis 1.0 ug.mL-1
Antimicrobial activity against biofilm-positive Staphylococcus epidermidis clinical isolate ICS3 by microdilution method Staphylococcus epidermidis 1.0 ug.mL-1
Antimicrobial activity against biofilm-positive Staphylococcus epidermidis clinical isolate ICS4 by microdilution method Staphylococcus epidermidis 1.0 ug.mL-1
Antimicrobial activity against biofilm-positive Staphylococcus epidermidis clinical isolate ICS5 by microdilution method Staphylococcus epidermidis 1.0 ug.mL-1
Antimicrobial activity against Staphylococcus epidermidis clinical isolate 5179-R1 derived from PNAG negative, icaA::IS257 mutant 5179 strain produces a proteinaceous biofilm dependent on a truncated 140-kDa isoform of Aap by microdilution method Staphylococcus epidermidis 1.0 ug.mL-1
Antiprotozoan activity against Trichomonas vaginalis GT3 trophozoites after 48 hrs Trichomonas vaginalis 68.0 nM
Antiprotozoan activity against Entamoeba histolytica HM1-IMSS trophozoites after 48 hrs Entamoeba histolytica 504.0 nM
Antiviral activity against Hepatitis B virus infected in human HepG2(2.2.15) cells assessed as decrease in extracellular viral DNA measured 24 hrs after last dose Hepatitis B virus 120.0 nM
Antiviral activity against Hepatitis B virus infected in human HepG2(2.2.15) cells assessed as decrease in intracellular viral DNA measured 24 hrs after last dose Hepatitis B virus 590.0 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 210.0 nM
Antiviral activity against HCV genotype 1a infected in Huh7.5 cells assessed as inhibition of viral replication after 3 days by blot hybridization analysis Hepatitis C virus subtype 1a 330.0 nM
Antimicrobial activity against Trichomonas vaginalis GT3 incubated for 48 hrs followed by compound washout measured after 48 hrs Trichomonas vaginalis 79.43 nM Antimicrobial activity against Trichomonas vaginalis GT3 incubated for 48 hrs followed by compound washout measured after 48 hrs Trichomonas vaginalis 68.0 nM
Antiviral activity against Hepatitis B virus Hepatitis B virus 120.0 nM
Trichomonicidal activity against Trichomonas vaginalis GT3 compound treated for 48 hrs followed by incubation for 48 hrs in compound-free medium by cell counting Trichomonas vaginalis 68.0 nM
Inhibition of Giardia intestinalis fructose 1,6-bisphosphate aldolase at 400 nM after 2 hrs by spectrophotometry Giardia intestinalis 31.0 %
Inhibition of HBV DNA replication Hepatitis B virus 120.0 nM
Antiviral activity against HBV infected in human HepG2(2.2.15) cells assessed as inhibition of extracellular viral DNA level Hepatitis B virus 120.0 nM
Antiprolferative activity against human Caco2 cells assessed as inhibition of cell proliferation by measuring [3H]-thymidine incorporation at 1 mM incubated for 48 hrs by liquid scintillometry Homo sapiens 80.0 %
Antiprotozoal activity against Trichomonas vaginalis GT3 trophozoites incubated for 48 hrs Trichomonas vaginalis 68.0 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 50.75 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -2.79 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 13.55 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 19.1 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 9.65 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 26.69 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 17.15 %
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 43.61 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.0 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 100.65 %
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 -0.07 % 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 0.78 % 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 0.78 % 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 -0.07 %
Growth inhibiting activity of Naegleria gruberi in vitro Naegleria gruberi 62.7 %
Inhibition of IL-6 induced STAT3 transcriptional activity in human HEK-Blue IL-6 cells assessed as secreted embryonic alkaline phosphatase reporter gene expression at 10 uM by microplate reader Homo sapiens 54.6 %
Cytotoxicity against human HeLa cells assessed as inhibition of cell viability at 10 uM measured after 48 hrs by MTT assay Homo sapiens 19.4 %
Cytotoxicity against human HEK 293T cells assessed as cell growth inhibition at 50 uM measured after 48 hrs by MTT assay Homo sapiens 24.4 %
Cytotoxicity against human HEK 293T cells assessed as cell growth inhibition at 10 uM measured after 48 hrs by MTT assay Homo sapiens -3.3 %
Giardicidal activity against Giardia intestinalis WB ATCC 30957 incubated for 48 hrs by hemocytometric counting method Giardia intestinalis 18.0 nM
Giardicidal activity against metronidazole-resistant Giardia intestinalis incubated for 48 hrs by hemocytometric counting method Giardia intestinalis 17.0 nM
Giardicidal activity against Giardia intestinalis IMSS isolate incubated for 48 hrs by hemocytometric counting method Giardia intestinalis 15.0 nM
Giardicidal activity against albendazole-resistant Giardia intestinalis incubated for 48 hrs by hemocytometric counting method Giardia intestinalis 21.0 nM

Cross References

Resources Reference
ChEBI 94807
ChEMBL CHEMBL1401
DrugBank DB00507
DrugCentral 1943
FDA SRS SOA12P041N
Human Metabolome Database HMDB0014649
PDB NTI
PharmGKB PA164754874
PubChem 41684
SureChEMBL SCHEMBL40981
ZINC ZINC000003956788
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