THIABENDAZOLE

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Trade Names
Synonyms
Status
Molecule Category Free-form
UNII N1Q45E87DT
EPA CompTox DTXSID0021337

Structure

InChI Key WJCNZQLZVWNLKY-UHFFFAOYSA-N
Smiles c1ccc2[nH]c(-c3cscn3)nc2c1
InChI
InChI=1S/C10H7N3S/c1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9/h1-6H,(H,12,13)

Physicochemical Descriptors

Property Name Value
Molecular Formula C10H7N3S
Molecular Weight 201.25
AlogP 2.69
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 1.0
Polar Surface Area 41.57
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 14.0

Bioactivity

Mechanism of Action Action Reference
Tubulin inhibitor INHIBITOR ISBN ISBN PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 14600 - - -
Enzyme Isomerase
- - 60000 - -
Enzyme Protease Metallo protease Metallo protease MG clan Metallo protease M24A subfamily
3400 44700 - - 28
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 77
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- - - - 55
Assay Description Organism Bioactivity Reference
Effective concentration (anti-HIV activity) required to reduce HIV-1 induced cytopathic effect by 50% in MT-4 cells Human immunodeficiency virus 1 352.0 nM
Inhibition of Co2+ loaded MetAP expressed in Escherichia coli Escherichia coli 472.0 nM
Antifungal activity against Sclerotina sclerotiorum assessed as growth inhibition at 0.10 mM after 48 hrs Sclerotinia sclerotiorum 86.0 %
Antifungal activity against Sclerotina sclerotiorum assessed as growth inhibition at 0.50 mM after 48 hrs Sclerotinia sclerotiorum 93.0 %
Inhibition of Escherichia coli MetAP at 25 uM Escherichia coli 86.3 %
Inhibition of Escherichia coli MetAP Escherichia coli 470.0 nM
Inhibition of Staphylococcus aureus MetAP at 25 uM Staphylococcus aureus 28.0 %
Inhibition of human MetAP1 at 25 uM Homo sapiens 28.0 %
Inhibition of human MetAP2 expressed in baculovirus infected Sf9 cells at 25 uM Homo sapiens 32.0 %
DRUGMATRIX: CYP450, 1A2 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) None 800.0 nM
Fungicidal activity against Rhizoctonia solani AG-1 IA assessed as inhibition of mycelial radial growth Rhizoctonia solani AG-1 IA 0.22 ug.mL-1
Inhibition of Leptosphaeria maculans brassinin oxidase activity at 0.30 mM relative to control Leptosphaeria maculans 25.0 %
Antifungal activity against Leptosphaeria maculans assessed as inhibition of mycelial growth at 0.10 mM relative to control Leptosphaeria maculans 100.0 %
Inhibition of Leptosphaeria maculans brassinin oxidase activity at 0.10 mM relative to control Leptosphaeria maculans 16.0 %
Fungicidal activity against Fusarium graminearum E198Q harboring mutation at codon 198 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 4.52 ug.mL-1
Fungicidal activity against Fusarium graminearum ZJ80 harboring mutation at codon 198 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 4.52 ug.mL-1
Fungicidal activity against Fusarium graminearum E198K harboring mutation at codon 198 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 3.56 ug.mL-1
Fungicidal activity against Fusarium graminearum F200Y harboring mutation at codon 200 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 5.85 ug.mL-1
Fungicidal activity against Fusarium graminearum J2 harboring mutation at codon 198 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 3.86 ug.mL-1
Fungicidal activity against Fusarium graminearum NT7 harboring mutation at codon 200 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 6.76 ug.mL-1
Fungicidal activity against Fusarium graminearum F167Y harboring mutation at codon 167 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 14.63 ug.mL-1
Fungicidal activity against Fusarium graminearum 2052 harboring mutation at codon 167 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 10.75 ug.mL-1
Fungicidal activity against Fusarium graminearum Y50C harboring mutation at codon 50 of beta2 tubulin assessed as mycelial growth inhibition after 3 days Fusarium graminearum 3.74 ug.mL-1
Fungicidal activity against Fusarium graminearum 2021 assessed as mycelial growth inhibition after 3 days Fusarium graminearum 1.13 ug.mL-1
Inhibition of human MATE1-mediated ASP+ uptake expressed in HEK293 cells at 20 uM after 1.5 mins by fluorescence assay Homo sapiens 55.0 %
Inhibition of Escherichia coli methionine aminopeptidase Escherichia coli 400.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 76.75 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 94.36 %
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 9.35 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 1.68 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 17.05 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 16.13 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 17.74 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 1.43 %
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 -4.52 %
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 7.81 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.08 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 31.55 %
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 0.17 % 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 -0.12 % 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 -0.12 % 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 0.17 %

Environmental Exposure

Environmental Exposure Map
Countries
USA

Cross References

Resources Reference
ChEBI 45979
ChEMBL CHEMBL625
DrugBank DB00730
DrugCentral 2621
FDA SRS N1Q45E87DT
Human Metabolome Database HMDB0014868
Guide to Pharmacology 7304
KEGG C07131
PDB TMG
PharmGKB PA164746466
PubChem 5430
SureChEMBL SCHEMBL19842
ZINC ZINC000000073711
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