Flubendazole
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| Category | Bioactive by-products |
| Catalog number | BBF-04011 |
| CAS | 31430-15-6 |
| Molecular Weight | 313.28 |
| Molecular Formula | C16H12FN3O3 |
| Purity | >98% |
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Description
Flubendazole is an anthelmintic agent for MDAY-D2 cells with IC50 of 3 nM. Its brand name is Flutelmium which is a paste manufactured by Janssen Pharmaceutica N.V. used by veterinarians for protection against internal parasites and worms in dogs and cats. Other brand names are Flubenol, Biovermin, and Flumoxal.
Specification
| Synonyms | NSC 313680; NSC313680; NSC-313680; R 17899; R17899; R-17899 |
| Storage | Store at -20°C |
| IUPAC Name | methyl N-[6-(4-fluorobenzoyl)-1H-benzimidazol-2-yl]carbamate |
| Canonical SMILES | COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C3=CC=C(C=C3)F |
| InChI | 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) |
| InChI Key | CPEUVMUXAHMANV-UHFFFAOYSA-N |
Properties
| Appearance | White to Light Yellow Powder |
| Application | Antinematodal Agents |
| Antibiotic Activity Spectrum | parasites |
| Melting Point | 290°C |
| Density | 1.444 g/cm3 |
| Solubility | Soluble in DMSO, Acetic Acid |
Reference Reading
1.Systems biology-based discovery of a potential Atg4B agonist (Flubendazole) that induces autophagy in breast cancer.
Zhang L1, Guo M, Li J, Zheng Y, Zhang S, Xie T, Liu B. Mol Biosyst. 2015 Nov;11(11):2860-6. doi: 10.1039/c5mb00466g.
The aim of this study was to explore the autophagy-related protein 4B(ATG4B) and its targeted candidate agonist in triple-negative breast cancer (TNBC) therapy. In this study, the identification of Atg4B as a novel breast cancer target for screening candidate small molecular agonists was performed by phylogenetic analysis, network construction, molecular modelling, molecular docking and molecular dynamics (MD) simulation. In vitro, MTT assay, electron microscopy, western blot and ROS measurement were used for validating the efficacy of the candidate compounds. We used the phylogenetic analysis of Atg4B and constructed their protein-protein interaction (PPI) network. Also, we screened target compounds of Atg4 proteins from Drugbank and ZINC. Flubendazole was validated for its anti-proliferative efficacy in MDA-MB-231 cells. Further MD simulation results supported the stable interaction between Flubendazole and Atg4B. Moreover, Flubendazole induced autophagy and increased ROS production.
2.Genotoxicity of flubendazole and its metabolites in vitro and the impact of a new formulation on in vivo aneugenicity.
Tweats DJ, Johnson GE, Scandale I1, Whitwell J2, Evans DB1. Mutagenesis. 2015 Oct 6. pii: gev070. [Epub ahead of print]
The anti-parasitic benzimidazole flubendazole has been used for many years to treat intestinal infections in humans and animals. Previous genotoxicity studies have shown that the compound is not a bacterial mutagen and a bone marrow micronucleus test, using a formulation that limited systemic absorption, was negative. The purpose of this study is to explore the genotoxicity of flubendazole and its main metabolites in in vitro micronucleus studies and to test a new oral formulation that improves systemic absorption in an in vivo micronucleus test. The isolated metabolites were also screened using the Ames test for bacterial mutagenicity. It was found that flubendazole, like other chemically related benzimidazoles used in anti-parasitic therapies, is a potent aneugen in vitro. The hydrolysed metabolite of flubendazole is negative in these tests, but the reduced metabolite (R- and S-forms) shows both aneugenic and clastogenic activity. However, in vitro micronucleus tests of flubendazole in the presence of rat liver S9 gave almost identical signals for aneugenicity as they did in the absence of S9, suggesting that any clastogenicity from the reduced metabolite is not sufficient to change the overall profile.
3.Flubendazole induces mitotic catastrophe and senescence in colon cancer cells in vitro.
Králová V1, Hanušová V1, Rudolf E1, Čáňová K1, Skálová L2. J Pharm Pharmacol. 2016 Feb;68(2):208-18. doi: 10.1111/jphp.12503. Epub 2016 Jan 4.
OBJECTIVES: Flubendazole (FLU), a member of benzimidazole family of anthelmintic drugs, is able to inhibit proliferation of various cancer cells. The aim of present study was to elucidate the mechanisms of antiproliferative effect of FLU on colorectal cancer cells in vitro.
4.Pharmaceutical screen identifies novel target processes for activation of autophagy with a broad translational potential.
Chauhan S1, Ahmed Z2, Bradfute SB1, Arko-Mensah J1, Mandell MA1, Won Choi S1, Kimura T1, Blanchet F2, Waller A3, Mudd MH1, Jiang S1, Sklar L3, Timmins GS4, Maphis N1, Bhaskar K1,5, Piguet V2, Deretic V1,5. Nat Commun. 2015 Oct 27;6:8620. doi: 10.1038/ncomms9620.
Autophagy is a conserved homeostatic process active in all human cells and affecting a spectrum of diseases. Here we use a pharmaceutical screen to discover new mechanisms for activation of autophagy. We identify a subset of pharmaceuticals inducing autophagic flux with effects in diverse cellular systems modelling specific stages of several human diseases such as HIV transmission and hyperphosphorylated tau accumulation in Alzheimer's disease. One drug, flubendazole, is a potent inducer of autophagy initiation and flux by affecting acetylated and dynamic microtubules in a reciprocal way. Disruption of dynamic microtubules by flubendazole results in mTOR deactivation and dissociation from lysosomes leading to TFEB (transcription factor EB) nuclear translocation and activation of autophagy. By inducing microtubule acetylation, flubendazole activates JNK1 leading to Bcl-2 phosphorylation, causing release of Beclin1 from Bcl-2-Beclin1 complexes for autophagy induction, thus uncovering a new approach to inducing autophagic flux that may be applicable in disease treatment.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
