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
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)
| Molecular Formula | C16H12FN3O3 |
| Molecular Weight | 313.2832 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
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 |
|
| [Toxocariasis]. | 2001 Dec |
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| Determination of benzimidazole anthelmintics in animal-derived biological matrices. | 2002 Apr |
|
| Prevalence of levamisole and benzimidazole resistance in oesophagostomum populations of pig-breeding farms in North Rhine-Westphalia, Germany. | 2002 Jan |
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| Characteristics of a flubendazole resistant isolate of Oesophagostomum dentatum from Germany. | 2002 Jan 3 |
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| Cystatin capture-dot-enzyme-linked immunosorbent assay for immunodiagnosis and assessment of cure of experimental trichinellosis in mice. | 2003 Apr |
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| Polarographic determination of flubendazole in spiked human urine and plasma. | 2003 Aug |
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| Effect of oral dosing vehicles on the developmental toxicity of flubendazole in rats. | 2003 Jul-Aug |
|
| [Effect of anthelmintic therapy supplemented with glucan in experimental toxocarosis]. | 2004 |
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| Distribution and depletion of flubendazole and its metabolites in edible tissues of guinea fowl. | 2004 Aug |
|
| Integrated pharmacological assessment of flubendazole potential for use in sheep: disposition kinetics, liver metabolism and parasite diffusion ability. | 2004 Oct |
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| Anaphylaxis to povidone in a child. | 2005 Jun |
|
| The effects of flubendazole and mebendazole on cytochromes P4501A in pheasant hepatocytes. | 2005 Oct |
|
| Tackling matrix effects during development of a liquid chromatographic-electrospray ionisation tandem mass spectrometric analysis of nine basic pharmaceuticals in aqueous environmental samples. | 2006 Aug 4 |
|
| In vitro and in vivo effects of flubendazole on Echinococcus granulosus metacestodes. | 2007 Apr |
|
| 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 |
|
| Influence of Ascaridia galli infections and anthelmintic treatments on the behaviour and social ranks of laying hens (Gallus gallus domesticus). | 2007 May 31 |
|
| Sensitive chiral high-performance liquid chromatographic determination of anthelmintic flubendazole and its phase I metabolites in blood plasma using UV photodiode-array and fluorescence detection Application to pharmacokinetic studies in sheep. | 2008 Dec 1 |
|
| Biotransformation of flubendazole and selected model xenobiotics in Haemonchus contortus. | 2008 Feb 14 |
|
| 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 |
|
| Modulation of porcine (Sus scrofa domestica) and pheasant (Phasianus colchicus) carbonyl reducing enzymes by anthelmintic therapy with flubendazole. | 2008 Jan |
|
| UMF-078: A modified flubendazole with potent macrofilaricidal activity against Onchocerca ochengi in African cattle. | 2008 Jun 20 |
|
| LC-MS-MS identification of albendazole and flubendazole metabolites formed ex vivo by Haemonchus contortus. | 2008 May |
|
| Effect of chemotherapeutic treatment on cytokine (IFN-gamma, IL-2, IL-4, IL-5, IL-10) gene transcription in response to specific antigens in Brugia malayi-infected Mastomys coucha. | 2008 Oct |
|
| Partial sequence of the beta-tubulin of Histomonas meleagridis and the activity of benzimidazoles against H. meleagridis in vitro. | 2009 Apr |
|
| Supply of Flubenvet 2.5% 240 g medicated premixture. | 2009 Aug 29 |
|
| Pharmacokinetics of flubendazole and its metabolites in lambs and adult sheep (Ovis aries). | 2009 Dec |
|
| Molecularly imprinted polymers: an analytical tool for the determination of benzimidazole compounds in water samples. | 2009 May 15 |
|
| Comparative assessment of albendazole and triclabendazole ovicidal activity on Fasciola hepatica eggs. | 2009 Oct 14 |
|
| Flubendazole interferes with a wide spectrum of cell homeostatic mechanisms in Echinococcus granulosus protoscoleces. | 2009 Sep |
|
| Chemoprophylactic activity of flubendazole in cystic echinococcosis. | 2010 |
|
| Flubendazole metabolism and biotransformation enzymes activities in healthy sheep and sheep with haemonchosis. | 2010 Feb |
|
| Sorption of benzimidazole anthelmintics to dissolved organic matter surrogates and sewage sludge. | 2010 Jun |
|
| The antihelmintic flubendazole inhibits microtubule function through a mechanism distinct from Vinca alkaloids and displays preclinical activity in leukemia and myeloma. | 2010 Jun 10 |
|
| Anthelmintic effects of phytogenic feed additives in Ascaris suum inoculated pigs. | 2010 Mar 25 |
|
| Activities of biotransformation enzymes and flubendazole metabolism in lambs (Ovis aries): effect of gender and flubendazole therapy. | 2010 Mar-Apr |
|
| In vitro Effects of Albendazole on Raillietina echinobothrida, the Cestode of Chicken, Gallus domesticus. | 2010 Oct |
|
| The 6th Meeting of the Global Alliance to Eliminate Lymphatic Filariasis: A half-time review of lymphatic filariasis elimination and its integration with the control of other neglected tropical diseases. | 2010 Oct 20 |
|
| Effect of Ascaris suum infection on performance of fattening pigs. | 2010 Sep 20 |
Patents
Sample Use Guides
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
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:24:31 UTC 2023
by
admin
on
Fri Dec 15 15:24:31 UTC 2023
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| Record UNII |
R8M46911LR
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C250
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FDA ORPHAN DRUG |
396713
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WHO-VATC |
QP52AC12
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WHO-ATC |
P02CA05
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FDA ORPHAN DRUG |
399813
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250-624-4
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R8M46911LR
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Flubendazole
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SUB07666MIG
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C018945
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1186
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CHEMBL1454946
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77095
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m5419
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DB08974
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C75219
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25096
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100000092259
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313680
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3904
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