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=C(N1)C=C(C=C2)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
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.35 ng/mL |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLUBENDAZOLE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FASTED |
|
0.74 ng/mL |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLUBENDAZOLE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FASTED |
|
4.06 ng/mL |
2000 mg single, oral dose: 2000 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLUBENDAZOLE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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. | 2010-10-20 |
|
| In vitro Effects of Albendazole on Raillietina echinobothrida, the Cestode of Chicken, Gallus domesticus. | 2010-10 |
|
| Effect of Ascaris suum infection on performance of fattening pigs. | 2010-09-20 |
|
| A field study on 8 pharmaceuticals and 1 pesticide in Belgium: removal rates in waste water treatment plants and occurrence in surface water. | 2010-07-15 |
|
| The antihelmintic flubendazole inhibits microtubule function through a mechanism distinct from Vinca alkaloids and displays preclinical activity in leukemia and myeloma. | 2010-06-10 |
|
| Sorption of benzimidazole anthelmintics to dissolved organic matter surrogates and sewage sludge. | 2010-06 |
|
| Anthelmintic effects of phytogenic feed additives in Ascaris suum inoculated pigs. | 2010-03-25 |
|
| Flubendazole metabolism and biotransformation enzymes activities in healthy sheep and sheep with haemonchosis. | 2010-02 |
|
| Chemoprophylactic activity of flubendazole in cystic echinococcosis. | 2010 |
|
| Pharmacokinetics of flubendazole and its metabolites in lambs and adult sheep (Ovis aries). | 2009-12 |
|
| Flubendazole in cystic echinococcosis therapy: pharmaco-parasitological evaluation in mice. | 2009-12 |
|
| Comparative assessment of albendazole and triclabendazole ovicidal activity on Fasciola hepatica eggs. | 2009-10-14 |
|
| Liquid chromatography/mass spectrometric identification of benzimidazole anthelminthics metabolites formed ex vivo by Dicrocoelium dendriticum. | 2009-09 |
|
| Flubendazole and ivermectin in vitro combination therapy produces a marked effect on Echinococcus granulosus protoscoleces and metacestodes. | 2009-09 |
|
| Flubendazole interferes with a wide spectrum of cell homeostatic mechanisms in Echinococcus granulosus protoscoleces. | 2009-09 |
|
| Supply of Flubenvet 2.5% 240 g medicated premixture. | 2009-08-29 |
|
| Molecularly imprinted polymers: an analytical tool for the determination of benzimidazole compounds in water samples. | 2009-05-15 |
|
| Partial sequence of the beta-tubulin of Histomonas meleagridis and the activity of benzimidazoles against H. meleagridis in vitro. | 2009-04 |
|
| Activities of biotransformation enzymes and flubendazole metabolism in lambs (Ovis aries): effect of gender and flubendazole therapy. | 2009-02-19 |
|
| 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. | 2008-12-01 |
|
| 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. | 2008-10 |
|
| Hepatic and extra-hepatic metabolic pathways involved in flubendazole biotransformation in sheep. | 2008-09-15 |
|
| Sulfamethazine and flubendazole in seepage water after the sprinkling of manured areas. | 2008-07 |
|
| UMF-078: A modified flubendazole with potent macrofilaricidal activity against Onchocerca ochengi in African cattle. | 2008-06-20 |
|
| High-performance liquid chromatography-tandem mass spectrometry in the identification and determination of phase I and phase II drug metabolites. | 2008-05 |
|
| LC-MS-MS identification of albendazole and flubendazole metabolites formed ex vivo by Haemonchus contortus. | 2008-05 |
|
| Comparison of matrix effects in HPLC-MS/MS and UPLC-MS/MS analysis of nine basic pharmaceuticals in surface waters. | 2008-05 |
|
| 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. | 2008-02-29 |
|
| Biotransformation of flubendazole and selected model xenobiotics in Haemonchus contortus. | 2008-02-14 |
|
| Modulation of porcine (Sus scrofa domestica) and pheasant (Phasianus colchicus) carbonyl reducing enzymes by anthelmintic therapy with flubendazole. | 2008-01 |
|
| Activities of biotransformation enzymes in pheasant (Phasianus colchicus) and their modulation by in vivo administration of mebendazole and flubendazole. | 2007-08 |
|
| Influence of Ascaridia galli infections and anthelmintic treatments on the behaviour and social ranks of laying hens (Gallus gallus domesticus). | 2007-05-31 |
|
| Achiral and chiral high-performance liquid chromatographic determination of flubendazole and its metabolites in biomatrices using UV photodiode-array and mass spectrometric detection. | 2007-05-11 |
|
| In vitro and in vivo effects of flubendazole on Echinococcus granulosus metacestodes. | 2007-04 |
|
| Tackling matrix effects during development of a liquid chromatographic-electrospray ionisation tandem mass spectrometric analysis of nine basic pharmaceuticals in aqueous environmental samples. | 2006-08-04 |
|
| Ecological hazard assessment of major veterinary benzimidazoles: acute and chronic toxicities to aquatic microbes and invertebrates. | 2006-08 |
|
| Modulation of porcine biotransformation enzymes by anthelmintic therapy with fenbendazole and flubendazole. | 2006-06 |
|
| In vitro effects of flubendazole on Echinococcus granulosus protoscoleces. | 2006-03 |
|
| The effects of flubendazole and mebendazole on cytochromes P4501A in pheasant hepatocytes. | 2005-10 |
|
| Rapid determination of the antiparasitic drugs flubendazole and febantel in feeds by HPLC with ultraviolet detection. | 2005-06-15 |
|
| Anaphylaxis to povidone in a child. | 2005-06 |
|
| Integrated pharmacological assessment of flubendazole potential for use in sheep: disposition kinetics, liver metabolism and parasite diffusion ability. | 2004-10 |
|
| Distribution and depletion of flubendazole and its metabolites in edible tissues of guinea fowl. | 2004-08 |
|
| The effects of fenbendazole, flubendazole and mebendazole on activities of hepatic cytochromes P450 in pig. | 2004-04 |
|
| Adverse drug reactions to anthelmintics. | 2004-03 |
|
| [Effect of anthelmintic therapy supplemented with glucan in experimental toxocarosis]. | 2004 |
|
| Quantitative chromatographic determination of several benzimidazole anthelmintic molecules in parasite material. | 2003-12-05 |
|
| Comparative efficacy of flubendazole chewable tablets and a tablet combination of febantel, pyrantel embonate and praziquantel against Trichuris vulpis in experimentally infected dogs. | 2003-10 |
|
| Effect of simultaneous and/or consecutive administration of the broad spectrum anthelmintic flubendazole together with praziquantel in experimental Schistosoma mansoni infection. | 2003 |
|
| In vitro susceptibilities of the AIDS-associated microsporidian Encephalitozoon intestinalis to albendazole, its sulfoxide metabolite, and 12 additional benzimidazole derivatives. | 1997-12 |
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
Mon Mar 31 17:56:42 GMT 2025
by
admin
on
Mon Mar 31 17:56:42 GMT 2025
|
| Record UNII |
R8M46911LR
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C250
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
||
|
FDA ORPHAN DRUG |
396713
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
||
|
WHO-VATC |
QP52AC12
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
||
|
WHO-ATC |
P02CA05
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
||
|
FDA ORPHAN DRUG |
399813
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
250-624-4
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
R8M46911LR
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
Flubendazole
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
SUB07666MIG
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
C018945
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
1186
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
CHEMBL1454946
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
DTXSID8023058
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
31430-15-6
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
35802
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
77095
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
R8M46911LR
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
m5419
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | Merck Index | ||
|
DB08974
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
C75219
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
25096
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | RxNorm | ||
|
100000092259
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
313680
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY | |||
|
3904
Created by
admin on Mon Mar 31 17:56:42 GMT 2025 , Edited by admin on Mon Mar 31 17:56:42 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
|
