FLUBENDAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H12FN3O3
Molecular Weight	313.2832
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=C(F)C=C3

InChI

InChIKey=CPEUVMUXAHMANV-UHFFFAOYSA-N

InChI=1S/C16H12FN3O3/c1-23-16(22)20-15-18-12-7-4-10(8-13(12)19-15)14(21)9-2-5-11(17)6-3-9/h2-8H,1H3,(H2,18,19,20,22)

HIDE SMILES / InChI

Description
Sources: http://www.dolf.wustl.edu/wp-content/uploads/A-review-of-flubendazole-Report.pdf

Flubendazole is an anthelmintic that is used to treat worm infection in humans. It is available OTC in Europe. Flubendazole is registered and sold in Europe (EMEA) as Fluvermal (Johnson and Johnson, Sante Bea). A 100mg dose of Fluvermal is most commonly proscribed for treating pinwoms (Enterobius vermiculus)). This is followed by a second dose of 100mg 15-21 days later to ensure reinfection is avoided, as flubendazole does not kill pinworm eggs. 100mg taken 3 times a day for 3 days is effective against larger nematodes, but only marginally effective against tapeworms. Flubendazole was validated for its anti-proliferative efficacy in MDA-MB-231 cells. Moreover, Flubendazole induced autophagy and increased ROS production. In silico analysis and experimental validation together demonstrate that Flubendazole can target autophagy-related protein 4B (Atg4B) in MDA-MB-231 cells and induce autophagy, which may shed light on the exploration of this compound as a potential new Atg4B targeted drug for future triple-negative breast cancer (TNBC) therapy.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
tegument of the parasite 1 Target ID: tegument of the parasite Sources: https://www.ncbi.nlm.nih.gov/pubmed/16374619	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Intestinal nematodes 1 Sources: http://www.dolf.wustl.edu/wp-content/uploads/A-review-of-flubendazole-Report.pdf	Curative		Approved 8429	Fluvermal Approved Use Unknown

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
[Toxocariasis].	2001 Dec	11908154
The efficacy of flubendazole against Trichinella spiralis in swine.	2001 Jun	11484353
Determination of benzimidazole anthelmintics in animal-derived biological matrices.	2002 Apr	12073891
Prevalence of levamisole and benzimidazole resistance in oesophagostomum populations of pig-breeding farms in North Rhine-Westphalia, Germany.	2002 Jan	11822739
In vitro studies on the effects of flubendazole against Toxocara canis and Ascaris suum.	2003 Jan	12474046
Effect of oral dosing vehicles on the developmental toxicity of flubendazole in rats.	2003 Jul-Aug	12849847
Comparative efficacy of flubendazole chewable tablets and a tablet combination of febantel, pyrantel embonate and praziquantel against Trichuris vulpis in experimentally infected dogs.	2003 Oct	14650738
Anaphylaxis to povidone in a child.	2005 Jun	15943602
Modulation of porcine biotransformation enzymes by anthelmintic therapy with fenbendazole and flubendazole.	2006 Jun	16125742
Biotransformation of flubendazole and selected model xenobiotics in Haemonchus contortus.	2008 Feb 14	18054171
LC-MS-MS identification of albendazole and flubendazole metabolites formed ex vivo by Haemonchus contortus.	2008 May	18344069
Pharmacokinetics of flubendazole and its metabolites in lambs and adult sheep (Ovis aries).	2009 Dec	20444016
Comparative assessment of albendazole and triclabendazole ovicidal activity on Fasciola hepatica eggs.	2009 Oct 14	19560276
Liquid chromatography/mass spectrometric identification of benzimidazole anthelminthics metabolites formed ex vivo by Dicrocoelium dendriticum.	2009 Sep	19630029
Chemoprophylactic activity of flubendazole in cystic echinococcosis.	2010	20948209

Patents

Sample Use Guides

In Vivo Use Guide

A 100mg dose of Fluvermal (FLUBENDAZOLE) is most commonly proscribed for treating pinwoms (Enterobius vermiculus)). This is followed by a second dose of 100 mg 15-21 days later to ensure reinfection is avoided, as flubendazole does not kill pinworm eggs. 100mg taken 3 times a day for 3 days is effective against larger nematodes, but only marginally effective against tapeworms.

Route of Administration: Oral

In Vitro Use Guide

Protoscoleces of E. granulosus were incubated with flubendazole (FLBZ) at concentrations of 10, 5 and 1 uM. The first signs of FLBZ-induced damage were observed 3 days post-incubation. A clear protoscolicidal effect, reducing the vitality of protoscoleces to 35.6+/-0.7%, was observed after 18 days of incubation. After 25 days of FLBZ incubation (5 uM), the percentage of vital protoscoleces was 13.9+/-5.9%. Protoscolex mortality was 100% (10 and 1 ug/L) and 0.7+/-0.7% (5 ug/ml) after FLBZ incubation for 30 days.

Name

Type

Language

FLUBENDAZOLE

Official Name

English

Flubendazole [WHO-DD]

Common Name

English

flubendazole [INN]

Common Name

English

FLUBENDAZOLE [MART.]

Common Name

English

NSC-313680

Code

English

R-17,889

Code

English

METHYL 5-(P-FLUOROBENZOYL)-2-BENZIMIDAZOLECARBAMATE

Common Name

English

FLUBENDAZOLE [MI]

Common Name

English

CARBAMIC ACID, (5-(4-FLUOROBENZOYL)-1H-BENZIMIDAZOL-2-YL)-, METHYL ESTER

Common Name

English

FLUBENDAZOLE [USAN]

Common Name

English

FLUBENDAZOLE [EP MONOGRAPH]

Common Name

English

R 17,889

Code

English

R-17889

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C250