MEBENDAZOLE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC P02CA01
UNII 81G6I5V05I
EPA CompTox DTXSID4040682

Structure

InChI Key OPXLLQIJSORQAM-UHFFFAOYSA-N
Smiles COC(=O)Nc1nc2cc(C(=O)c3ccccc3)ccc2[nH]1
InChI
InChI=1S/C16H13N3O3/c1-22-16(21)19-15-17-12-8-7-11(9-13(12)18-15)14(20)10-5-3-2-4-6-10/h2-9H,1H3,(H2,17,18,19,21)

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H13N3O3
Molecular Weight 295.3
AlogP 2.97
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 3.0
Polar Surface Area 84.08
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 22.0

Bioactivity

Mechanism of Action Action Reference
Tubulin inhibitor INHIBITOR ISBN PubMed DailyMed Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Abl family
- 5000 - 4600 -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase VEGFR family
- 3600-8800 - - -
Enzyme Oxidoreductase
- - - - 15
Enzyme Protease Metallo protease Metallo protease MG clan Metallo protease M24A subfamily
- - - - 29
Enzyme
- 3600-8800 - 4600 15
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 160
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 15500 - - -
Assay Description Organism Bioactivity Reference
Inhibition of beta-lactamase at 100 uM None 5.0 %
Inhibition of chymotrypsin at 250 uM unidentified 5.0 %
Inhibition of malate dehydrogenase (MDH) at 400 uM None 15.0 %
Inhibition of Co2+ loaded MetAP expressed in Escherichia coli at 10 uM Escherichia coli 28.99 %
Anthelmintic activity against Caenorhabditis elegans Caenorhabditis elegans 10.0 ppm
Inhibition of Escherichia coli MetAP at 25 uM Escherichia coli 47.0 %
Antiparasitic activity against Giardia duodenalis IMSS:0989 after 48 hrs Giardia intestinalis 55.0 nM
Inhibition of N-terminal hexaHis-tagged Toxoplasma gondii CDPK1 expressed in Escherichia coli BL21* by nonradioactive Kinaseglo luciferase assay Toxoplasma gondii 340.0 nM
Inhibition of Cryptosporidium parvum CDPK1 by nonradioactive Kinaseglo luciferase assay Cryptosporidium parvum 440.0 nM
Inhibition of Cryptosporidium parvum CDPK1 Cryptosporidium parvum 920.0 nM
Inhibition of Toxoplasma gondii CDPK1 Toxoplasma gondii 670.0 nM
Inhibition of mouse Ido2 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation at 20 uM after 45 mins by spectrophotometric analysis relative to control Mus musculus 55.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 159.55 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 99.0 %
PubChem BioAssay. Increased HeLa cells with 2N DNA content-IC50. (Class of assay: confirmatory) None 76.1 nM
PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmatory) None 54.2 nM
PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area decrease-IC50. (Class of assay: confirmatory) None 369.9 nM
PubChem BioAssay. Increased HeLa cells with 4N DNA content-IC50. (Class of assay: confirmatory) None 80.0 nM
PubChem BioAssay. alkaline phosphatase stimulation in WNT3A conditioned C2C12 cells-IC50. (Class of assay: confirmatory) None 245.4 nM
PubChem BioAssay. Increased chromatin condensation in HeLa cells-IC50. (Class of assay: confirmatory) None 64.8 nM
Cytotoxicity against human PC3MLN4 cells assessed as reduction in cell viability after 48 hrs by cyquant reagent based fluorescence spectrometric assay Homo sapiens 700.0 nM
Cytotoxicity against human A549 cells assessed as reduction in cell viability after 72 hrs by MTT assay Homo sapiens 900.0 nM
Cytotoxicity against human PC3MLN4 cells assessed as reduction in cell viability after 72 hrs by MTT assay Homo sapiens 500.0 nM
Cytotoxicity against human SKOV3 cells assessed as reduction in cell viability after 72 hrs by MTT assay Homo sapiens 500.0 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 7.86 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 3.86 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 11.43 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 13.95 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 19.38 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 4.65 %
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 41.35 %
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 13.81 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 35.63 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 31.63 %
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 0.61 % 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 0.67 % 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 0.61 % 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 0.67 %
Growth inhibiting activity of Naegleria gruberi in vitro Naegleria gruberi 29.8 %
Antigiardial activity against Giardia lamblia P1 incubated for 48 hrs by haemocytometric counting method Giardia intestinalis 60.0 nM
Antigiardial activity against Giardia lamblia WB incubated for 48 hrs by microscopic method Giardia intestinalis 60.0 nM
Antigiardial activity against Giardia lamblia H/7 incubated for 48 hrs by microscopic method Giardia intestinalis 60.0 nM

Cross References

Resources Reference
ChEBI 6704
ChEMBL CHEMBL685
DrugBank DB00643
DrugCentral 1641
FDA SRS 81G6I5V05I
Human Metabolome Database HMDB0014781
KEGG D00368
PharmGKB PA164776669
PubChem 4030
SureChEMBL SCHEMBL15860
ZINC ZINC000000121541
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