Identification
- Summary
Mebendazole is a benzimidazole anthelmintic used to treat helminth infections.
- Brand Names
- Emverm, Vermox
- Generic Name
- Mebendazole
- DrugBank Accession Number
- DB00643
- Background
A benzimidazole that acts by interfering with carbohydrate metabolism and inhibiting polymerization of microtubules. [PubChem]
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Mebendazole (DB00643)
- Weight
- Average: 295.2927
Monoisotopic: 295.095691297 - Chemical Formula
- C16H13N3O3
- Synonyms
- (5-benzoyl-1H-benzimidazol-2-yl)-carbamic acid methyl ester
- MBDZ
- Mebendazol
- Mébendazole
- Mebendazole
- Mebendazolum
- External IDs
- NSC-184849
- R 17,635
- R 17635
- R-17635
Pharmacology
- Indication
For the treatment of Enterobius vermicularis (pinworm), Trichuris trichiura (whipworm), Ascaris lumbricoides (common roundworm), Ancylostoma duodenale (common hookworm), Necator americanus (American hookworm) in single or mixed infections.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Ancylostoma caninum infection ••• ••••• Treatment of Ancylostoma duodenale infection •••••••••••• Treatment of Ascaris lumbricoides infection •••••••••••• Treatment of Capillariasis ••• ••••• Treatment of Enterobius vermicularis infection •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Mebendazole is a (synthetic) broad-spectrum anthelmintic. The principal mode of action for Mebendazole is by its inhibitory effect on tubulin polymerization which results in the loss of cytoplasmic microtubules.
- Mechanism of action
Mebendazole causes degenerative alterations in the tegument and intestinal cells of the worm by binding to the colchicine-sensitive site of tubulin, thus inhibiting its polymerization or assembly into microtubules. The loss of the cytoplasmic microtubules leads to impaired uptake of glucose by the larval and adult stages of the susceptible parasites, and depletes their glycogen stores. Degenerative changes in the endoplasmic reticulum, the mitochondria of the germinal layer, and the subsequent release of lysosomes result in decreased production of adenosine triphosphate (ATP), which is the energy required for the survival of the helminth. Due to diminished energy production, the parasite is immobilized and eventually dies.
Target Actions Organism ATubulin alpha-1A chain inhibitorHumans ATubulin beta-4B chain inhibitorHumans - Absorption
Poorly absorbed (approximately 5 to 10%) from gastrointestinal tract. Fatty food increases absorption.
- Volume of distribution
Not Available
- Protein binding
90-95%
- Metabolism
Primarily hepatic. Primary metabolite is 2-amino-5-benzoylbenzimidazole, but also metabolized to inactive hydroxy and hydroxyamino metabolites. All metabolites are devoid of anthelmintic activity.
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- Route of elimination
In man, approximately 2% of administered mebendazole is excreted in urine and the remainder in the feces as unchanged drug or a primary metabolite.
- Half-life
2.5 to 5.5 hours (range 2.5 to 9 hours) in patients with normal hepatic function. Approximately 35 hours in patients with impaired hepatic function (cholestasis).
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Acute oral toxicity (LD50): 620 mg/kg [Mouse]. Symptoms of overdose include elevated liver enzymes, headaches, hair loss, low levels of white blood cells (neutropenia), fever, and itching.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareCimetidine The serum concentration of Mebendazole can be increased when it is combined with Cimetidine. Fosphenytoin The serum concentration of Mebendazole can be decreased when it is combined with Fosphenytoin. Methotrexate The excretion of Methotrexate can be decreased when combined with Mebendazole. Metronidazole The risk or severity of adverse effects can be increased when Mebendazole is combined with Metronidazole. Phenytoin The serum concentration of Mebendazole can be decreased when it is combined with Phenytoin. - Food Interactions
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- International/Other Brands
- Lomper (Esteve) / Meberix (Aversi) / Mebex (Cipla) / Mebezol (Johnson) / Mebfil (Fourrts Laboratories) / Mebutar (Andromaco) / Mebzol (Julphar) / Mendazole (GlaxoSmithKline) / Mezole (Yuan Chou) / Minyoozole (Emil) / Mopen (Li Taka Pharmaceuticals) / Multielmin (Osorio de Moraes) / Necamin (Aché) / Ovex (McNeil) / Panamox (Jayson) / Pantelmin (Janssen) / Tesical (Sintesina) / Thelmox (Remedica) / Ticoquer (Root)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Vermox Tablet, chewable 500 mg/1 Oral Janssen Pharmaceuticals, Inc. 2016-10-20 Not applicable US 
Vermox Tablet, chewable 100 mg/1 Oral Johnson & Johnson Consumer Inc, McNeil Consumer Healthcare Division 1975-01-14 Not applicable US Vermox Tablet 100 mg Oral Janssen Pharmaceuticals 1982-12-31 Not applicable Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Emverm Tablet, chewable 100 mg/1 Oral Amneal Pharmaceuticals LLC 2016-02-15 Not applicable US Emverm Tablet, chewable 100 mg/1 Oral Amedra Pharmaceuticals LLC 2016-02-15 2018-11-30 US Mebendazole Tablet, chewable 100 mg/1 Oral bryant ranch prepack 2000-06-23 2017-12-31 US 
Mebendazole Tablet, chewable 100 mg/1 Oral Teva 2000-06-23 2014-05-31 US 
Mebendazole Tablet, chewable 100 mg/1 Oral Physicians Total Care, Inc. 1996-04-04 Not applicable US 
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image CALPO SUSPENSION Suspension Oral WINWA MEDICAL SDN. BHD. 2020-09-08 Not applicable Malaysia 
M-zole Chewable Tablet Tablet, chewable Oral WINWA MEDICAL SDN. BHD. 2020-09-08 Not applicable Malaysia M-zole Suspension Suspension 500 mg Oral WINWA MEDICAL SDN. BHD. 2020-09-08 Not applicable Malaysia MEBENDAZOLE TABLET 100 mg Tablet 100 mg Oral BEACONS PHARMACEUTICALS PTE. LTD. 1988-04-05 Not applicable Singapore 
Medidazole Chewable Tablet 500mg Tablet, chewable 500 mg Oral World Medicare Supplies Sdn Bhd 2021-12-02 Not applicable Malaysia
Categories
- ATC Codes
- P02CA51 — Mebendazole, combinations
- P02CA — Benzimidazole derivatives
- P02C — ANTINEMATODAL AGENTS
- P02 — ANTHELMINTICS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- Drug Categories
- Acids, Acyclic
- Anthelmintics
- Anti-Infective Agents
- Antihelminthic
- Antimitotic Agents
- Antinematodal Agents
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Benzimidazole Derivatives
- Benzimidazoles
- Carbamates
- Heterocyclic Compounds, Fused-Ring
- Mitosis Modulators
- Tubulin Modulators
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzophenones
- Direct Parent
- Benzophenones
- Alternative Parents
- 2-benzimidazolylcarbamic acid esters / Aryl-phenylketones / Benzoyl derivatives / Imidazoles / Heteroaromatic compounds / Carbamate esters / Organic carbonic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds show 2 more
- Substituents
- 2-benzimidazolylcarbamic acid ester / Aromatic heteropolycyclic compound / Aryl ketone / Aryl-phenylketone / Azacycle / Azole / Benzimidazole / Benzophenone / Benzoyl / Carbamic acid ester show 13 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- carbamate ester, aromatic ketone, benzimidazoles (CHEBI:6704)
- Affected organisms
- Helminthic Microorganisms
Chemical Identifiers
- UNII
- 81G6I5V05I
- CAS number
- 31431-39-7
- InChI Key
- OPXLLQIJSORQAM-UHFFFAOYSA-N
- 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)
- IUPAC Name
- methyl N-(6-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate
- SMILES
- COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C1=CC=CC=C1
References
- Synthesis Reference
U.S. Patent 3,657,267.
- General References
- Vermox (Mebendazole) FDA Label [Link]
- External Links
- Human Metabolome Database
- HMDB0014781
- KEGG Drug
- D00368
- PubChem Compound
- 4030
- PubChem Substance
- 46508807
- ChemSpider
- 3890
- BindingDB
- 50180753
- 6672
- ChEBI
- 6704
- ChEMBL
- CHEMBL685
- ZINC
- ZINC000000121541
- Therapeutic Targets Database
- DAP000950
- PharmGKB
- PA164776669
- PDBe Ligand
- V95
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Mebendazole
- PDB Entries
- 7odn / 7ogn
- MSDS
- Download (72.8 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Amebiasis / Helminthiasis 1 4 Completed Treatment Ancylostoma Caninum / Ancylostoma Ceylanicum / Ancylostoma Duodenal / Ascaris Lumbricoides / Ascaris Suum / Necator Americanus / Trichuris Trichiura / Trichuris Vulpis 1 4 Completed Treatment Drug Resistance / Helminths Infection 1 4 Completed Treatment Hook Worm 1 4 Completed Treatment Hookworm Infections 1
Pharmacoeconomics
- Manufacturers
- Teva pharmaceuticals usa
- Mcneil pediatrics
- Packagers
- Advanced Pharmaceutical Services Inc.
- Apotheca Inc.
- AQ Pharmaceuticals Inc.
- A-S Medication Solutions LLC
- Dept Health Central Pharmacy
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- H.J. Harkins Co. Inc.
- Janssen-Ortho Inc.
- McNeil Laboratories
- Novopharm Ltd.
- Nucare Pharmaceuticals Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmedix
- Physicians Total Care Inc.
- Spectrum Pharmaceuticals
- Teva Pharmaceutical Industries Ltd.
- USAN
- Dosage Forms
Form Route Strength Suspension Oral 60.000 mg Suspension Oral 200000 g Tablet Oral 100.00 mg Suspension Oral 2.00 g Tablet, chewable Oral 500 mg Suspension Oral 500 mg Tablet Oral Suspension Oral 2 g Suspension Oral 2000 mg Tablet, chewable Oral 100 mg/1 Tablet Oral 100 mg Tablet Oral 100.000 mg Tablet Oral 300.000 mg Tablet, chewable Oral Tablet Oral Tablet Oral 500.000 mg Suspension Oral Granule Oral Suspension Oral 2.000 g Suspension Oral 20 MG/ML Tablet Oral 500 MG Tablet, chewable Oral 500 mg/1 Suspension Oral Tablet Buccal; Oral 100 mg Tablet, coated Oral 300 mg Suspension Oral 100 mg/5mL Tablet, chewable Oral 100 mg Tablet 500 mg Tablet 100 mg Tablet, coated Oral 100 mg Tablet, coated Oral 500 mg Syrup 100 mg/5ml - Prices
Unit description Cost Unit Mebendazole 100 mg Chew Tabs 16.42USD tab Mebendazole 100 mg tablet chew 5.32USD tablet Mebendazole powder 5.03USD g Vermox 100 mg Chewable Tablet 4.14USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 288.5 °C PhysProp water solubility 71.3 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 2.83 SANGSTER (1994) logS -3.88 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.0387 mg/mL ALOGPS logP 2.95 ALOGPS logP 3.26 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 8.44 Chemaxon pKa (Strongest Basic) 3.93 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 84.08 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 81.5 m3·mol-1 Chemaxon Polarizability 31.1 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9932 Blood Brain Barrier + 0.9261 Caco-2 permeable + 0.7261 P-glycoprotein substrate Non-substrate 0.6073 P-glycoprotein inhibitor I Inhibitor 0.5844 P-glycoprotein inhibitor II Inhibitor 0.7534 Renal organic cation transporter Non-inhibitor 0.8464 CYP450 2C9 substrate Non-substrate 0.749 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.6532 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8308 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6779 Ames test AMES toxic 0.7212 Carcinogenicity Non-carcinogens 0.9102 Biodegradation Not ready biodegradable 0.994 Rat acute toxicity 2.5855 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9515 hERG inhibition (predictor II) Non-inhibitor 0.8028
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 185.7056459 predictedDarkChem Lite v0.1.0 [M-H]- 186.3411459 predictedDarkChem Lite v0.1.0 [M-H]- 166.63223 predictedDeepCCS 1.0 (2019) [M+H]+ 185.8648459 predictedDarkChem Lite v0.1.0 [M+H]+ 185.9313459 predictedDarkChem Lite v0.1.0 [M+H]+ 168.99023 predictedDeepCCS 1.0 (2019) [M+Na]+ 185.4740459 predictedDarkChem Lite v0.1.0 [M+Na]+ 186.4872459 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.11368 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
- Specific Function
- Gtp binding
- Gene Name
- TUBA1A
- Uniprot ID
- Q71U36
- Uniprot Name
- Tubulin alpha-1A chain
- Molecular Weight
- 50135.25 Da
References
- Lubega GW, Geary TG, Klein RD, Prichard RK: Expression of cloned beta-tubulin genes of Haemonchus contortus in Escherichia coli: interaction of recombinant beta-tubulin with native tubulin and mebendazole. Mol Biochem Parasitol. 1993 Dec;62(2):281-92. [Article]
- MacDonald LM, Armson A, Thompson AR, Reynoldson JA: Characterisation of benzimidazole binding with recombinant tubulin from Giardia duodenalis, Encephalitozoon intestinalis, and Cryptosporidium parvum. Mol Biochem Parasitol. 2004 Nov;138(1):89-96. [Article]
- Oxberry ME, Gear TG, Prichard RK: Assessment of benzimidazole binding to individual recombinant tubulin isotypes from Haemonchus contortus. Parasitology. 2001 Jun;122(Pt 6):683-7. [Article]
- Ochola DO, Prichard RK, Lubega GW: Classical ligands bind tubulin of trypanosomes and inhibit their growth in vitro. J Parasitol. 2002 Jun;88(3):600-4. [Article]
- Wampande EM, Richard McIntosh J, Lubega GW: Classical ligands interact with native and recombinant tubulin from Onchocerca volvulus with similar rank order of magnitude. Protein Expr Purif. 2007 Oct;55(2):236-45. Epub 2007 Apr 25. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Unfolded protein binding
- Specific Function
- Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
- Gene Name
- TUBB4B
- Uniprot ID
- P68371
- Uniprot Name
- Tubulin beta-4B chain
- Molecular Weight
- 49830.72 Da
References
- Lubega GW, Geary TG, Klein RD, Prichard RK: Expression of cloned beta-tubulin genes of Haemonchus contortus in Escherichia coli: interaction of recombinant beta-tubulin with native tubulin and mebendazole. Mol Biochem Parasitol. 1993 Dec;62(2):281-92. [Article]
- MacDonald LM, Armson A, Thompson AR, Reynoldson JA: Characterisation of benzimidazole binding with recombinant tubulin from Giardia duodenalis, Encephalitozoon intestinalis, and Cryptosporidium parvum. Mol Biochem Parasitol. 2004 Nov;138(1):89-96. [Article]
- Oxberry ME, Gear TG, Prichard RK: Assessment of benzimidazole binding to individual recombinant tubulin isotypes from Haemonchus contortus. Parasitology. 2001 Jun;122(Pt 6):683-7. [Article]
- Ochola DO, Prichard RK, Lubega GW: Classical ligands bind tubulin of trypanosomes and inhibit their growth in vitro. J Parasitol. 2002 Jun;88(3):600-4. [Article]
- Wampande EM, Richard McIntosh J, Lubega GW: Classical ligands interact with native and recombinant tubulin from Onchocerca volvulus with similar rank order of magnitude. Protein Expr Purif. 2007 Oct;55(2):236-45. Epub 2007 Apr 25. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Vitamin d 24-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Baliharova V, Skalova L, Maas RF, De Vrieze G, Bull S, Fink-Gremmels J: The effects of mebendazole on P4501A activity in rat hepatocytes and HepG2 cells. Comparison with tiabendazole and omeprazole. J Pharm Pharmacol. 2003 Jun;55(6):773-81. doi: 10.1211/002235703765951375. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Components:
| Name | UniProt ID |
|---|---|
| Cytochrome P450 3A4 | P08684 |
| Cytochrome P450 3A43 | Q9HB55 |
| Cytochrome P450 3A5 | P20815 |
| Cytochrome P450 3A7 | P24462 |
References
- Baliharova V, Velik J, Savlik M, Szotakova B, Lamka J, Tahotna L, Skalova L: The effects of fenbendazole, flubendazole and mebendazole on activities of hepatic cytochromes P450 in pig. J Vet Pharmacol Ther. 2004 Apr;27(2):85-90. doi: 10.1111/j.1365-2885.2004.00557.x. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54