CHEBI:6704 - mebendazole

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ChEBI Name mebendazole
ChEBI ID CHEBI:6704
Definition A carbamate ester that is methyl 1H-benzimidazol-2-ylcarbamate substituted by a benzoyl group at position 5.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB8700094, eMolecules:511302, eMolecules:740153, ZINC000000121541
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Mebendazole (MBZ), sold under the brand name Vermox among others, is a medication used to treat a number of parasitic worm infestations. This includes ascariasis, pinworm infection, hookworm infections, guinea worm infections and hydatid disease, among others. It has been used for treatment of giardiasis but is not a preferred agent. It is taken by mouth. Mebendazole is usually well tolerated. Common side effects include headache, vomiting, and ringing in the ears. If used at large doses it may cause bone marrow suppression. It is unclear if it is safe in pregnancy. Mebendazole is a broad-spectrum antihelminthic agent of the benzimidazole type. Mebendazole came into use in 1971, after it was developed by Janssen Pharmaceutica in Belgium. It is on the World Health Organization's List of Essential Medicines. Mebendazole is available as a generic medication.
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Formula C16H13N3O3
Net Charge 0
Average Mass 295.29284
Monoisotopic Mass 295.09569
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)
InChIKey OPXLLQIJSORQAM-UHFFFAOYSA-N
SMILES COC(=O)Nc1nc2cc(ccc2[nH]1)C(=O)c1ccccc1
Roles Classification
Biological Role(s): tubulin modulator
Any substance that interacts with tubulin to inhibit or promote polymerisation of microtubules.
microtubule-destabilising agent
Any substance that interacts with tubulin to inhibit polymerisation of microtubules.
Application(s): antinematodal drug
A substance used in the treatment or control of nematode infestations.
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ChEBI Ontology
Outgoing mebendazole (CHEBI:6704) has parent hydride 1H-benzimidazole (CHEBI:41275)
mebendazole (CHEBI:6704) has role antinematodal drug (CHEBI:35444)
mebendazole (CHEBI:6704) has role microtubule-destabilising agent (CHEBI:61951)
mebendazole (CHEBI:6704) has role tubulin modulator (CHEBI:60832)
mebendazole (CHEBI:6704) is a aromatic ketone (CHEBI:76224)
mebendazole (CHEBI:6704) is a benzimidazoles (CHEBI:22715)
mebendazole (CHEBI:6704) is a carbamate ester (CHEBI:23003)
IUPAC Name
methyl (5-benzoyl-1H-benzimidazol-2-yl)carbamate
Synonyms Sources
(5-benzoyl-1H-benzimidazol-2-yl)-carbamic acid methyl ester ChemIDplus
MBDZ ChemIDplus
Mebendazole KEGG COMPOUND
Vermox ChemIDplus
Manual Xrefs Databases
1641 DrugCentral
D00368 KEGG DRUG
DB00643 DrugBank
LSM-3749 LINCS
Mebendazole Wikipedia
View more database links
Registry Numbers Types Sources
31431-39-7 CAS Registry Number ChemIDplus
759809 Reaxys Registry Number Reaxys
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Last Modified
22 February 2017