MEBENDAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H13N3O3
Molecular Weight	295.2927
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)NC1=NC2=CC=C(C=C2N1)C(=O)C3=CC=CC=C3

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

Description
Sources: https://www.drugs.com/pro/mebendazole.html

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tubulin 69 Target ID: CHEMBL2364705 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8139621	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Enterobius vermicularis (pinworm) infection 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=13631e94-269d-45db-a433-2aa4f8d465c6	Curative	Approved 8429	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 1995
Trichuriasis infection 6 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=13631e94-269d-45db-a433-2aa4f8d465c6	Curative	Approved 8429	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 1995
Ascaris lumbricoides infection 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=13631e94-269d-45db-a433-2aa4f8d465c6	Curative	Approved 8429	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 1995
Necator americanus infection 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=13631e94-269d-45db-a433-2aa4f8d465c6	Curative	Approved 8429	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 1995

C_max

Value	Dose	Co-administered	Analyte	Population
14 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf	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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7094986	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

Value	Dose	Co-administered	Analyte	Population
175 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf	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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7094986	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.6 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7094986	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
7.5% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/32400117 Page: p.4681	unhealthy, 25-68 n = 4 Health Status: unhealthy Condition: Glioblastoma Age Group: 25-68 Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/32400117 Page: p.4681	DLT: Neutropenia, Thrombocytopenia... Dose limiting toxicities: Neutropenia (grade 4, 25%) Thrombocytopenia (grade 3, 25%) Sources: https://pubmed.ncbi.nlm.nih.gov/32400117 Page: p.4681
500 mg single, oral Recommended Dose: 500 mg Route: oral Route: single Dose: 500 mg Co-administed with:: Metronidazole Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Gastrointestinal infections caused by Ascaris lumbricoides and Trichuris trichiura Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf Page: p.1
500 mg single, oral Recommended Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Gastrointestinal infections caused by Ascaris lumbricoides and Trichuris trichiura Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf Page: p.1	Disc. AE: Convulsions, Neutropenia... AEs leading to discontinuation/dose reduction: Convulsions Neutropenia Agranulocytosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf Page: p.1

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/32400117 Page: p.4681	unhealthy, 25-68 n = 4 Health Status: unhealthy Condition: Glioblastoma Age Group: 25-68 Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/32400117 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: https://pubmed.ncbi.nlm.nih.gov/32400117 Page: p.4681	unhealthy, 25-68 n = 4 Health Status: unhealthy Condition: Glioblastoma Age Group: 25-68 Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/32400117 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Gastrointestinal infections caused by Ascaris lumbricoides and Trichuris trichiura Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Gastrointestinal infections caused by Ascaris lumbricoides and Trichuris trichiura Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf Page: p.1
Agranulocytosis	Disc. AE	500 mg single, oral Recommended Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Gastrointestinal infections caused by Ascaris lumbricoides and Trichuris trichiura Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf Page: p.1
Convulsions	Disc. AE	500 mg single, oral Recommended Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Gastrointestinal infections caused by Ascaris lumbricoides and Trichuris trichiura Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf Page: p.1
Neutropenia	Disc. AE	500 mg single, oral Recommended Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Gastrointestinal infections caused by Ascaris lumbricoides and Trichuris trichiura Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208398s000lbl.pdf Page: p.1

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461 CYP3A 214 UGT 35 CYP 111 FMO 7	P-gp 1537 CYP450 65	CYP1A1 108 CYP3A 129 CYP1A 56

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A1 218	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208398Orig1s000ClinPharmR.pdf Page: 12.0	likely	yes (co-administration study) Comment: ritonavir decreased mebendazole auc 43% and cmax 41% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208398Orig1s000ClinPharmR.pdf Page: 12.0
UGT 59	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0034528806001974 Page: 23.0	minor
CYP 147	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0034528806001974 Page: 23.0	no
CYP1A 121	inducer 1573 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1365-2885.2004.00557.x Page: abstract	no
CYP3A 298	inducer 1573 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1365-2885.2004.00557.x Page: abstract	no
FMO 7	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0034528806001974 Page: 23.0	no
P-gp 1650	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/pii/S088723331730156X Page: 89.0	no
CYP3A 298	inhibitor 3277 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1365-2885.2004.00557.x Page: abstract	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP450 65	substrate 3367 Sources: https://link.springer.com/article/10.1007/s00228-009-0683-y Page: 1000.0	likely
P-gp 1537	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S088723331730156X Page: 89.0	likely

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208398Orig1s000SumR.pdf Page: 11.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6704	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6704
ChemicalBook	CB8700094	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8700094
MolPort	MolPort-000-765-625	https://www.molport.com/shop/molecule-link/MolPort-000-765-625
MolPort	MolPort-001-889-615	https://www.molport.com/shop/molecule-link/MolPort-001-889-615
ZINC	ZINC000000121541	http://zinc15.docking.org/substances/ZINC000000121541
eMolecules	511302	https://www.emolecules.com/cgi-bin/more?vid=511302
eMolecules	740153	https://www.emolecules.com/cgi-bin/more?vid=740153

PubMed

Title	Date	PubMed
Primary echinococcal disease of the kidney: the case for a more conservative approach.	2001	11989550
Optimising the benefits of anthelmintic treatment in children.	2001	11513281
Urinary ascariasis in a man with hematuria.	2001 Apr	11332920
A comparative study of different albendazole and mebendazole regimens for the treatment of intestinal infections in school children of Usigu Division, western Kenya.	2001 Apr	11318574
[Endoscopic treatment of cholestasis caused by Ascaris lumbricoides].	2001 Apr 1	11338572
[Ascaridiasis in a pregnant woman].	2001 Apr 20	11360456
Eosinophilic meningitis caused by Angiostrongylus cantonensis: report of 17 cases.	2001 Aug	11498063
Ecchymoses: an unusual manifestation of toxocariasis in children.	2001 Dec	12164030
[Toxocariasis].	2001 Dec	11908154
Hydatid cyst of the kidney.	2001 Dec	11805421
Effects of iron supplementation and anthelmintic treatment on motor and language development of preschool children in Zanzibar: double blind, placebo controlled study.	2001 Dec 15	11744561
Chemotherapy of enterobiasis (oxyuriasis).	2001 Feb	11336585
Pharmacotherapy of ascariasis.	2001 Feb	11336582
Increase in serum beta-carotene following dark green leafy vegetable supplementation in Mebendazole-treated school children in Bangladesh.	2001 Jan	11303489
Pulmonary sparganosis: a case report with five years follow-up.	2001 Jan	11281492
TLC determination of mebendazol and pentoxifylline as residues on pharmaceutical equipment surfaces.	2001 Jul-Aug	11501930
Treatment of Toxocara canis infections in mice with liposome-incorporated benzimidazole carbamates and immunomodulator glucan.	2001 Jun	11520437
Efficacy of flubendazole and albendazole against Trichinella spiralis in mice.	2001 Jun	11484354
The efficacy of flubendazole against Trichinella spiralis in swine.	2001 Jun	11484353
Congenital trichinellosis? Case report.	2001 Jun	11484349
Assessment of benzimidazole binding to individual recombinant tubulin isotypes from Haemonchus contortus.	2001 Jun	11444621
Anthelmintic resistance and parasite control in commercial eel farms: consequences for producers.	2001 Jun 23	11465267
Geo-helminth infections in a rural area of Sri Lanka.	2001 Mar	11485089
Hepatobiliary and pancreatic ascariasis.	2001 Mar	11293175
[Orthopedic aspects of osseous echinococcosis--radiologic diagnosis, current surgery and drug therapy aspects].	2001 May-Jun	11486632
Asymptomatic ascariasis infection in a child.	2001 Oct	11820520
Anthelmintics: a review.	2001 Oct-Dec	11963321
Management of hydatid disease of the lung.	2001 Sep-Dec	11805402
Prospects in medical management of Echinococcus granulosus.	2001 Sep-Oct	11677989
Musculoskeletal hydatid disease: a report of 13 cases.	2002 Apr	12079024
Soil transmitted nematodes in children in Buea Health District of Cameroon.	2002 Aug	12638847
Opinion on the diagnosis and treatment of human trichinellosis.	2002 Aug	12150691
Pulmonary hydatidosis--a surgical experience.	2002 Jan	12206337
Characteristics of a flubendazole resistant isolate of Oesophagostomum dentatum from Germany.	2002 Jan 3	11751004
Clinicopathological conference: a simple case of abdominal pain.	2002 Jul	12093711
Strongyloides stercoralis infection with bloody pericardial effusion in a non-immunosuppressed patient.	2002 Jun	12074284
Chemotherapeutic approaches to nematodes: current knowledge and outlook.	2002 Mar	11954915
Clinical manifestations of strongyloidiasis in southern Taiwan.	2002 Mar	11950117
Is the exclusion of children under 24 months from anthelmintic treatment justifiable?	2002 Mar-Apr	12055814
Surgery and postoperative mebendazole in the treatment of hydatid disease.	2002 May	12070583
Infectious diseases of refugees and immigrants: hookworm.	2002 May	12051141
Surgery and postoperative mebendazole in the treatment of hydatid disease.	2002 Nov	12506313
Soil-transmitted nematode infections and mebendazole treatment in Mafia Island schoolchildren.	2002 Oct	12537633
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	12474486
Developing a discriminating dissolution test for three mebendazole polymorphs based on solubility differences.	2003 Feb	12641328
Ascaris lumbricoides?	2003 Jan	12602732
Pregnancy outcome after gestational exposure to mebendazole: a prospective controlled cohort study.	2003 Jan	12548230
Use of anthelminthic drugs during pregnancy.	2003 Jan	12548188
In vitro studies on the effects of flubendazole against Toxocara canis and Ascaris suum.	2003 Jan	12474046
European echinococcosis registry: human alveolar echinococcosis, Europe, 1982-2000.	2003 Mar	12643830

Patents

Sample Use Guides

In Vivo Use Guide

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

Unknown

Name

Type

Language

MEBENDAZOLE

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 [WHO-IP]

Common Name

English

MEBENDAZOLE [USP IMPURITY]

Common Name

English

VERMICIDIN

Common Name

English

MEBENDAZOLE [ORANGE BOOK]

Common Name

English

MEBENDAZOLE POLYMORPH C

Common Name

English

Mebendazole [WHO-DD]

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