mebendazole   Click here for help

GtoPdb Ligand ID: 13427

Synonyms: Emverm® | Vermox®
Approved drug PDB Ligand
mebendazole is an approved drug (FDA (1974))
Compound class: Synthetic organic
Comment: Mebendazole is a long-established broad spectrum anthelmintic drug that is used in human and veterinary medicine. Benzimidazole class compounds like mebendazole interact with the colchicine-binding site of β tubulin and thereby disrupt polymerisation of microtubules. Repurposing of mebendazole for oncological indications has been proposed [1,5-6,8,11], with mechanism of action focussing on tubulin depolymerisation [3,10].

In 2024 mebendazole was identified as a repurposing candidate with potential to treat the rare genetic disorder autosomal dominant polycystic kidney disease (ADPKD) [2]. Transcriptomic and computational drug discovery tools were used to predict mebendazole's ADPKD potential, and this was validated in vitro (using patient-derived 3D kidney cyst cultures) and in mouse models of the disease.

mebendazole is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 79.79
Molecular weight 295.29
XLogP 1.92
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COC(=O)NC1=NC2=C(C=C(C=C2)C(=O)C3=CC=CC=C3)N1
Isomeric SMILES COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C3=CC=CC=C3
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)
InChI Key OPXLLQIJSORQAM-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (1974)
IUPAC Name Click here for help
methyl N-(6-benzoyl-1H-benzimidazol-2-yl)carbamate
International Nonproprietary Names Click here for help
INN number INN
2942 mebendazole
Synonyms Click here for help
Emverm® | Vermox®
Database Links Click here for help
CAS Registry No. 31431-39-7 (source: WHO INN record)
ChEBI CHEBI:6704
ChEMBL Ligand CHEMBL685
DrugBank Ligand DB00643
GtoPdb PubChem SID 496703397
PubChem CID 4030
RCSB PDB Ligand V95
Search Google for chemical match using the InChIKey OPXLLQIJSORQAM-UHFFFAOYSA-N
Search Google for chemicals with the same backbone OPXLLQIJSORQAM
Search PubMed clinical trials mebendazole
Search PubMed titles mebendazole
Search PubMed titles/abstracts mebendazole
UniChem Compound Search for chemical match using the InChIKey OPXLLQIJSORQAM-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey OPXLLQIJSORQAM-UHFFFAOYSA-N

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MedChemExpress
Mebendazole (links to external site)
Cat. No. HY-17595