CAMBENDAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H14N4O2S
Molecular Weight	302.352
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)OC(=O)NC1=CC=C2N=C(NC2=C1)C3=CSC=N3

InChI

InChIKey=QZWHWHNCPFEXLL-UHFFFAOYSA-N

InChI=1S/C14H14N4O2S/c1-8(2)20-14(19)16-9-3-4-10-11(5-9)18-13(17-10)12-6-21-7-15-12/h3-8H,1-2H3,(H,16,19)(H,17,18)

HIDE SMILES / InChI

Description
Sources: https://www.gpo.gov/fdsys/pkg/CFR-2015-title21-vol6/pdf/CFR-2015-title21-vol6-sec520-300b.pdf | DOI: 10.1007/978-3-642-69527-8, Vanden Bossche H., Thienpont D., Janssens P.G., 'Chemotherapy of Gastrointestinal Helminths' (2012), p. 135, Retrieved from https://books.google.com/books?id=8u7xCAAAQBAJ&dq

Cambendazole is a veterinary anti-parasitic drug, which was approved by FDA for the treatment of worm infections in horses. The mode of action of cambendazole is the inhibition of glucose uptake, fumarate reductase and phosphoenolpyruvate carboxykinase. Due to its mechanism of action, cambendazole causes the paralysis of parasites.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Parasitic fumarate reductase 1 Target ID: Parasitic fumarate reductase Sources: DOI: 10.1007/978-3-642-69527-8, Vanden Bossche H., Thienpont D., Janssens P.G., "Chemotherapy of Gastrointestinal Helminths" (2012), p. 135, Retrieved from https://books.google.com/books?id=8u7xCAAAQBAJ&dq	Inhibitor 8297
glucose transport 1 Target ID: GO:0015758 Sources: DOI: 10.1007/978-3-642-69527-8, Vanden Bossche H., Thienpont D., Janssens P.G., 'Chemotherapy of Gastrointestinal Helminths' (2012), p. 134, Retrieved from https://books.google.com/books?id=8u7xCAAAQBAJ&dq	Inhibitor 8297
Parasitic phosphoenolpyruvate carboxykinase 1 Target ID: Parasitic phosphoenolpyruvate carboxykinase Sources: DOI: 10.1007/978-3-642-69527-8, Vanden Bossche H., Thienpont D., Janssens P.G., "Chemotherapy of Gastrointestinal Helminths" (2012), p. 135, Retrieved from https://books.google.com/books?id=8u7xCAAAQBAJ&dq	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parasitic worms 1 Sources: https://www.gpo.gov/fdsys/pkg/CFR-2015-title21-vol6/pdf/CFR-2015-title21-vol6-sec520-300b.pdf	Curative		Approved 8429	CAMVET Approved Use It is used in horses for the control of large strongyles (Strongylus vulgaris, S. edentatus, S. equinus); small strongyles (Trichonema, Poteriostomum, Cylicobrachytus, Craterostomum, Oesophagodontus); roundworms (Parascaris); pinworms (Oxyuris); and threadworms (Strongyloides).

PubMed

Title	Date	PubMed
In vitro susceptibilities of the AIDS-associated microsporidian Encephalitozoon intestinalis to albendazole, its sulfoxide metabolite, and 12 additional benzimidazole derivatives.	1997 Dec	9420047
Population-S benzimidazole- and tetrahydropyrimidine-resistant small strongyles in a pony herd in Kentucky (1977-1999): effects of anthelmintic treatment on the parasites as determined in critical tests.	2003 Nov	14530968
Comparison of multivariate calibration methods to determine simultaneously mebendazole-cambendazole and mebendazole-thiabendazole in pharmaceutical preparations by UV-visible spectrophotometry.	2003 Nov 24	14623591
Replacement of the essential Dictyostelium Arp2 gene by its Entamoeba homologue using parasexual genetics.	2007 Jun 6	17553170

Sample Use Guides

In Vivo Use Guide

It is administered by stomach tube or as a drench at a dose of 0.9 gram of cambendazole per 100 pounds of body weight (20 milligrams per kilogram).

Route of Administration: Oral

In Vitro Use Guide

Thirty-two small watch glasses were each set up with 100 ug aliquots of feces containing eggs of S.ratti. To each of these was added 400 uL PBS containing either no drug or 200 ug of cambendazole giving a final concentration of 400 ug drug/ml. There was a 52% reduction in the numbers of first-stage larvae in feces incubated with cambendazole for seven hours. After 24 hours incubation with drug (48 hours after feces were moistened) no viable infective larvae were seen in feces.

Name

Type

Language

CAMBENDAZOLE

Official Name

English

CAMBENDAZOLE [MART.]

Common Name

English

Cambendazole [WHO-DD]

Common Name

English

CAMBENDAZOLE [GREEN BOOK]

Common Name

English

CAMVET

Brand Name

English

CARBAMIC ACID, (2-(4-THIAZOLYL)-1H-BENZIMIDAZOL-5-YL)-, 1-METHYLETHYL ESTER

Common Name

English

CAMBENDAZOLE [USAN]

Common Name

English

Isopropyl 2-(4-triazolyl)-5-benzimidazolecarbamate

Common Name

English

CAMBENDAZOLE [MI]

Common Name

English

NSC-377071

Code

English

CAMDAN

Brand Name

English

cambendazole [INN]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 520.284B