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)

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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
Determination of benzimidazole anthelmintics in animal-derived biological matrices.	2002 Apr	12073891
Effect of simultaneous and/or consecutive administration of the broad spectrum anthelmintic flubendazole together with praziquantel in experimental Schistosoma mansoni infection.	2003	12918221
Cystatin capture-dot-enzyme-linked immunosorbent assay for immunodiagnosis and assessment of cure of experimental trichinellosis in mice.	2003 Apr	12739817
Quantitative chromatographic determination of several benzimidazole anthelmintic molecules in parasite material.	2003 Dec 5	14630366
In vitro studies on the effects of flubendazole against Toxocara canis and Ascaris suum.	2003 Jan	12474046
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
Adverse drug reactions to anthelmintics.	2004 Mar	14749518
Anaphylaxis to povidone in a child.	2005 Jun	15943602
In vitro and in vivo effects of flubendazole on Echinococcus granulosus metacestodes.	2007 Apr	17171566
Activities of biotransformation enzymes in pheasant (Phasianus colchicus) and their modulation by in vivo administration of mebendazole and flubendazole.	2007 Aug	17316720
Achiral and chiral high-performance liquid chromatographic determination of flubendazole and its metabolites in biomatrices using UV photodiode-array and mass spectrometric detection.	2007 May 11	17258754
Influence of Ascaridia galli infections and anthelmintic treatments on the behaviour and social ranks of laying hens (Gallus gallus domesticus).	2007 May 31	17434676
Validation of a solid-phase extraction and liquid chromatography-electrospray tandem mass spectrometric method for the determination of nine basic pharmaceuticals in wastewater and surface water samples.	2008 Feb 29	18237738
Flubendazole in cystic echinococcosis therapy: pharmaco-parasitological evaluation in mice.	2009 Dec	19628054
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
Flubendazole metabolism and biotransformation enzymes activities in healthy sheep and sheep with haemonchosis.	2010 Feb	20444026
A field study on 8 pharmaceuticals and 1 pesticide in Belgium: removal rates in waste water treatment plants and occurrence in surface water.	2010 Jul 15	20471061
Sorption of benzimidazole anthelmintics to dissolved organic matter surrogates and sewage sludge.	2010 Jun	20452640
Activities of biotransformation enzymes and flubendazole metabolism in lambs (Ovis aries): effect of gender and flubendazole therapy.	2010 Mar-Apr	20508292
In vitro Effects of Albendazole on Raillietina echinobothrida, the Cestode of Chicken, Gallus domesticus.	2010 Oct	21264097

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