U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C16H13N3O3
Molecular Weight 295.2933
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEBENDAZOLE

SMILES

COC(=Nc1nc2ccc(cc2[nH]1)C(=O)c3ccccc3)O

InChI

InChIKey=OPXLLQIJSORQAM-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Mebendazole, known as Emverm is a (synthetic) broad-spectrum anthelmintic that acts by interfering with carbohydrate metabolism and inhibiting polymerization of 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. Emverm tablets are used 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. All metabolites are devoid of anthelmintic activity. In man, approximately 2% of administered mebendazole is excreted in urine and the remainder in the feces as unchanged drug or a primary metabolite. Preliminary evidence suggests that cimetidine inhibits mebendazole metabolism and may result in an increase in plasma concentrations drug. Mebendazole sometimes causes diarrhea, abdominal pain, and elevated liver enzymes. In rare cases, it has been associated with a dangerously low white blood cell count, low platelet count, and hair loss, with a risk of agranulocytosis in rare cases

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2364705
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
EMVERM

Approved Use

Emverm™ (mebendazole) chewable tablet, USP is indicated 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.

Launch Date

7.8917763E11
Curative
EMVERM

Approved Use

Emverm™ (mebendazole) chewable tablet, USP is indicated 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.

Launch Date

7.8917763E11
Curative
EMVERM

Approved Use

Emverm™ (mebendazole) chewable tablet, USP is indicated 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.

Launch Date

7.8917763E11
Curative
EMVERM

Approved Use

Emverm™ (mebendazole) chewable tablet, USP is indicated 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.

Launch Date

7.8917763E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
14 ng/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEBENDAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
69.5 ng/mL
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEBENDAZOLE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
175 ng × h/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEBENDAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
280.2 ng × h/mL
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEBENDAZOLE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.6 h
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEBENDAZOLE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
7.5%
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEBENDAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
1600 mg 3 times / day multiple, oral
MTD
Dose: 1600 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 3 times / day
Co-administed with::
CCNU, p.o(110 mg/m2; Day 1 for a 42 days cycle)
Sources: Page: p.4681
unhealthy, 25-68
n = 4
Health Status: unhealthy
Condition: Glioblastoma
Age Group: 25-68
Sex: M+F
Population Size: 4
Sources: Page: p.4681
DLT: Neutropenia, Thrombocytopenia...
Dose limiting toxicities:
Neutropenia (grade 4, 25%)
Thrombocytopenia (grade 3, 25%)
Sources: Page: p.4681
500 mg single, oral
Recommended
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Co-administed with::
Metronidazole
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal infections caused by Ascaris lumbricoides and Trichuris trichiura
Sources: Page: p.1
Disc. AE: Stevens-Johnson syndrome, Toxic epidermal necrolysis...
AEs leading to
discontinuation/dose reduction:
Stevens-Johnson syndrome (serious)
Toxic epidermal necrolysis (serious)
Sources: Page: p.1
500 mg single, oral
Recommended
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal infections caused by Ascaris lumbricoides and Trichuris trichiura
Sources: Page: p.1
Disc. AE: Convulsions, Neutropenia...
AEs leading to
discontinuation/dose reduction:
Convulsions
Neutropenia
Agranulocytosis
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Thrombocytopenia grade 3, 25%
DLT
1600 mg 3 times / day multiple, oral
MTD
Dose: 1600 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 3 times / day
Co-administed with::
CCNU, p.o(110 mg/m2; Day 1 for a 42 days cycle)
Sources: Page: p.4681
unhealthy, 25-68
n = 4
Health Status: unhealthy
Condition: Glioblastoma
Age Group: 25-68
Sex: M+F
Population Size: 4
Sources: Page: p.4681
Neutropenia grade 4, 25%
DLT
1600 mg 3 times / day multiple, oral
MTD
Dose: 1600 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 3 times / day
Co-administed with::
CCNU, p.o(110 mg/m2; Day 1 for a 42 days cycle)
Sources: Page: p.4681
unhealthy, 25-68
n = 4
Health Status: unhealthy
Condition: Glioblastoma
Age Group: 25-68
Sex: M+F
Population Size: 4
Sources: Page: p.4681
Stevens-Johnson syndrome serious
Disc. AE
500 mg single, oral
Recommended
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Co-administed with::
Metronidazole
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal infections caused by Ascaris lumbricoides and Trichuris trichiura
Sources: Page: p.1
Toxic epidermal necrolysis serious
Disc. AE
500 mg single, oral
Recommended
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Co-administed with::
Metronidazole
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal infections caused by Ascaris lumbricoides and Trichuris trichiura
Sources: Page: p.1
Agranulocytosis Disc. AE
500 mg single, oral
Recommended
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal infections caused by Ascaris lumbricoides and Trichuris trichiura
Sources: Page: p.1
Convulsions Disc. AE
500 mg single, oral
Recommended
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal infections caused by Ascaris lumbricoides and Trichuris trichiura
Sources: Page: p.1
Neutropenia Disc. AE
500 mg single, oral
Recommended
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Gastrointestinal infections caused by Ascaris lumbricoides and Trichuris trichiura
Sources: Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer










Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
[Mass chemotherapy for intestinal helminth infections in primary and secondary school students in Maoming city].
2001
[Efficacy of ablendazole emulsion in treatment of 212 patients with cystic echinococcosis].
2001
[Vomiting in an immigrant during early pregnancy].
2001
Primary echinococcal disease of the kidney: the case for a more conservative approach.
2001
Ecchymoses: an unusual manifestation of toxocariasis in children.
2001 Dec
[Toxocariasis].
2001 Dec
Echinococcal cysts of the liver: epidemiology, imaging classification, diagnosis and management.
2001 May-Jun
Anthelmintics: a review.
2001 Oct-Dec
[Neurotrichinosis].
2001 Sep-Oct
[Target chemotherapy of intestinal nematode infection in area with low endemicity].
2002
Musculoskeletal hydatid disease: a report of 13 cases.
2002 Apr
Maxillofacial hydatid cyst.
2002 Apr
Soil transmitted nematodes in children in Buea Health District of Cameroon.
2002 Aug
Two cases of imported gnathostomiasis in Spanish women.
2002 Aug
Opinion on the diagnosis and treatment of human trichinellosis.
2002 Aug
One-stage operation for hydatid disease of lung and liver: principles of treatment.
2002 Dec
Oxidative, heat and anthelminthic stress responses in four species of Trichinella: comparative study.
2002 Dec 1
Pulmonary hydatidosis--a surgical experience.
2002 Jan
Clinicopathological conference: a simple case of abdominal pain.
2002 Jul
Strongyloides stercoralis infection with bloody pericardial effusion in a non-immunosuppressed patient.
2002 Jun
Nitazoxanide compared with quinfamide and mebendazole in the treatment of helminthic infections and intestinal protozoa in children.
2002 Mar
Chemotherapeutic approaches to nematodes: current knowledge and outlook.
2002 Mar
Clinical manifestations of strongyloidiasis in southern Taiwan.
2002 Mar
Effect of a single dose (600 mg) of albendazole on Loa loa microfilaraemia.
2002 Mar
Is the exclusion of children under 24 months from anthelmintic treatment justifiable?
2002 Mar-Apr
Surgery and postoperative mebendazole in the treatment of hydatid disease.
2002 May
Infectious diseases of refugees and immigrants: hookworm.
2002 May
Surgery and postoperative mebendazole in the treatment of hydatid disease.
2002 Nov
The anthelmintic drug mebendazole induces mitotic arrest and apoptosis by depolymerizing tubulin in non-small cell lung cancer cells.
2002 Nov
[Adult ascaris in the intrahepatic bile ducts].
2002 Nov 9
Evaluation of the efficacy of pyrantel-oxantel for the treatment of soil-transmitted nematode infections.
2002 Nov-Dec
Case report: intraocular localization of Mansonella perstans in a patient from south Chad.
2002 Nov-Dec
Efficacy of alebendazole and mebendazole in the treatment of Ascaris and Trichuris infections.
2002 Oct
Soil-transmitted nematode infections and mebendazole treatment in Mafia Island schoolchildren.
2002 Oct
A randomized placebo-controlled trial of mebendazole for halitosis.
2002 Oct
[An outbreak of trichinosis in the Kaliningrad region].
2002 Oct-Dec
Laparoscopic treatment of hepatic hydatid cysts with a liposuction device.
2002 Oct-Dec
New policies for using anthelmintics in high risk groups.
2002 Sep
Mebendazole elicits a potent antitumor effect on human cancer cell lines both in vitro and in vivo.
2002 Sep
Evaluation of the Integrated Management of Childhood Illness guidelines for treatment of intestinal helminth infections among sick children aged 2-4 years in western Kenya.
2002 Sep-Oct
Developing a discriminating dissolution test for three mebendazole polymorphs based on solubility differences.
2003 Feb
Benzimidazole treatment of cystic echinococcosis.
2003 Feb
Hydatid cyst of the liver-criteria for the selection of appropriate treatment.
2003 Feb
Pharmacokinetic evaluation of guar gum-based colon-targeted drug delivery systems of mebendazole in healthy volunteers.
2003 Feb 14
Ascaris lumbricoides?
2003 Jan
Pregnancy outcome after gestational exposure to mebendazole: a prospective controlled cohort study.
2003 Jan
Use of anthelminthic drugs during pregnancy.
2003 Jan
In vitro studies on the effects of flubendazole against Toxocara canis and Ascaris suum.
2003 Jan
European echinococcosis registry: human alveolar echinococcosis, Europe, 1982-2000.
2003 Mar
Outbreak of Stevens-Johnson syndrome/toxic epidermal necrolysis associated with mebendazole and metronidazole use among Filipino laborers in Taiwan.
2003 Mar
Patents

Sample Use Guides

Pinworm (enterobiasis): 1 tablet, once; Whipworm (trichuriasis): 1 tablet morning and evening for 3 consecutive days; Common Roundworm (ascariasis): 1 tablet morning and evening for 3 consecutive days; Hookworm: 1 tablet morning and evening for 3 consecutive days
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment:: The release of interleukin (IL)-8 and tumor necrosis factor (TNF) α from human monocytic THP-1 cells was significantly increased by treatment with mebendazole (MBZ). MBZ also significantly increased the phosphorylation of extracellular signal-regulated kinase (ERK) 1/2 and c-Jun N-terminal kinase (JNK) 1/2 in THP-1 cells.
Unknown
Name Type Language
MEBENDAZOLE
EP   GREEN BOOK   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
MEBENDAZOLE [INN]
Common Name English
MEBENDAZOLE [GREEN BOOK]
Common Name English
MEBENDAZOLE [USP MONOGRAPH]
Common Name English
MEBENDAZOLE [JAN]
Common Name English
NSC-184849
Code English
MEBENDAZOLE [EP MONOGRAPH]
Common Name English
MEBENDAZOLE [HSDB]
Common Name English
CARBAMIC ACID, (5-BENZOYL-1H-BENZIMIDAZOL-2-YL)-, METHYL ESTER
Common Name English
R-17635
Code English
MEBENDAZOLE [USP]
Common Name English
MEBENDAZOLE [WHO-IP]
Common Name English
MEBENDAZOLE [WHO-DD]
Common Name English
VERMICIDIN
Common Name English
MEBENDAZOLE [ORANGE BOOK]
Common Name English
MEBENDAZOLE POLYMORPH C
USP-RS  
Common Name English
ZHIHUANQING
Common Name English
VERMOX
Brand Name English
R 17,635
Code English
MEBENDAZOLE [USP-RS]
Common Name English
OVITELMIN
Common Name English
PANTELMIN
Common Name English
MEBENDAZOLE [VANDF]
Common Name English
MEBENDAZOLE [USAN]
Common Name English
MEBENDAZOLE [MART.]
Common Name English
METHYL 5-BENZOYL-2-BENZIMIDAZOLECARBAMATE
Common Name English
MEBENDAZOLE POLYMORPH C [USP-RS]
Common Name English
MEBENDAZOLUM [WHO-IP]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 520.1320
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
LIVERTOX 584
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
WHO-ATC P02CA01
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
CFR 21 CFR 520.1326A
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
WHO-VATC QP52AC09
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.1.1
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
NCI_THESAURUS C250
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
CFR 21 CFR 520.1326B
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
WHO-ATC P02CA51
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
EPA PESTICIDE CODE 600073
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
FDA ORPHAN DRUG 397013
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
CFR 21 CFR 520.1326
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
NDF-RT N0000175481
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
WHO-VATC QP52AC59
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C47595
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY
CAS
31431-39-7
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY
DRUG CENTRAL
1641
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY
MESH
D008463
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY
INN
2942
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY
HSDB
3232
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY
LACTMED
Mebendazole
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY
WIKIPEDIA
MEBENDAZOLE
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY
ChEMBL
CHEMBL685
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY
DRUG BANK
DB00643
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY
FDA UNII
81G6I5V05I
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY
ECHA (EC/EINECS)
250-635-4
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
MEBENDAZOLE
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY Description: A white to slightly yellow powder. Solubility: Practically insoluble in water, dilute mineral acids, ethanol (~750 g/l) TS and ether R ; freely soluble in formic acid(~1080 g/l) TS. Category: Anthelmintic drug. Storage: Mebendazole should be kept in a well-closed container, protected from light. Additional information: Mebendazole exhibits polymorphism. Definition: Mebendazole is polymorph C, the crystal form of mebendazole RS. Mebendazole contains not less than 98.0% andnot more than 102.0% of mebendazole (C16H13N3O3), calculated with reference to the dried substance.
PUBCHEM
4030
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY
USP_CATALOG
1375502
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY USP-RS
RXCUI
6672
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY RxNorm
EVMPD
SUB08660MIG
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY
MERCK INDEX
M7107
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY Merck Index
EPA CompTox
31431-39-7
Created by admin on Fri Jun 25 20:56:31 UTC 2021 , Edited by admin on Fri Jun 25 20:56:31 UTC 2021
PRIMARY