Basic information
- CAS
31430-15-6- Standard SMILES
COC(=O)Nc1nc2ccc(C(=O)c3ccc(F)cc3)cc2[nH]1- InChIKey
CPEUVMUXAHMANV-UHFFFAOYSA-N- Molecular formula
- C16H12FN3O3
- Average molar mass
- 313.28 g/mol
- Monoisotopic mass
- 313.08626942
Overview
Flubendazole is a member of the class of mebendazole in which the benzoyl group is replaced by a p-fluorobenzoyl group. A broad-spectrum anthelmintic, it is used, particularly in veterinary medicine, for the treatment of nematodal infections. It has a role as an antinematodal drug and a teratogenic agent. It is a member of benzimidazoles, a carbamate ester, an organofluorine compound and an aromatic ketone.
Names & identifiers
- Preferred name
- Flubendazole
- IUPAC
- methyl N-[6-(4-fluorobenzoyl)-1H-benzimidazol-2-yl]carbamate
- English name
- Flubendazole
- Molecular formula
- C16H12FN3O3
- Molecular weight
- 313.28
Names & synonyms
Flubendazole31430-15-6FlubendazolFlubendazolumR 17,889Methyl 5-(p-fluorobenzoyl)-2-benzimidazolecarbamateDTXSID8023058R 17899NSC-313680(5-(4-Fluorobenzoyl)-1H-benzimidazole-2-yl)carbamic acid methyl esterR8M46911LRCarbamic acid, (5-(4-fluorobenzoyl)-1H-benzimidazol-2-yl)-, methyl ester
Show more names
Flubendazole Polymorph BR-17899R 17889FLUMOXALFLUBENOLFLUVERNALFLUMOXANEfluvermalFlubenvet
Methyl N-(5-(p-fluorobenzoyl)-2-benzimidazolyl)carbamateR-17889R-17,889CHEBI:77095fluoromebendazolemethyl N-[5-(4-fluorobenzoyl)-1H-1,3-benzodiazol-2-yl]carbamatemethyl N-(5-(4-fluorobenzoyl)-1H-1,3-benzodiazol-2-yl)carbamateZELCOM
Database identifiers
- CAS
31430-15-6- PubChem CID
- 35802
- DTXSID
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 84.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 454
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antiparasitic products, insecticides and repellents -> Antiprotozoals
Animal Drugs
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point> 260
Collision Cross Section177.36 Ų [M-H]-
Physicochemical properties
- Melting point
- 290 °C · 290°C
- Density
- 1.372 · 1.3720 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Practically insoluble in water, in alcohol and in methylene chloride
- pka
- 10.66 · 10.66±0.10(Predicted)
- form
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 23.8% (5 of 21) of reports.
Warning
H361 (66.7%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 21 reports by companies from 7 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationFlubendazole: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Carbamic acid, [5-(4-fluorobenzoyl)-1H-benzimidazol-2-yl]-,methyl ester: Environment tier I assessment
Hazard Classes and CategoriesRepr. 2 (66.7%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- DD6497500
- hs_code
- 29339900
- Toxicity
- LD50 in mice, rats, guinea pigs (mg/kg): >2560 orally (Thienpont)
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- safety_code
- 44
- Storage Class
- 10 - Combustible liquids
- Hazard statements
Chemistry & industry
Pharmacology
ATC Code
P - Antiparasitic products, insecticides and repellents
QP - Antiparasitic products, insecticides and repellents
Mechanism of Action
Flubendazole is a benzimidazole that inhibits microtubule function by binding tubulin and inhibiting tubulin polymerization. It binds to the colchicine-binding site of the tubulin protein, located at the interface of the alpha (α) and beta (β) tubulin heterodimer.
MeSH Pharmacological ClassificationSubstances used in the treatment or control of nematode infestations. They are used also in veterinary practice.
Uses & manufacturing
Use Classification
Veterinary Drug -> ANTHELMINTHIC_AGENT -> JECFA Functional Classes
Veterinary Drug -> ANTHELMINTHIC_AGENT -> JECFA Functional Classes
Veterinary Drug -> ANTHELMINTHIC_AGENT -> JECFA Functional Classes
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Applications
DescriptionFlubendazole is a benzimidazole carbamate anthelmintic. It completely eliminates larvae in a mouse model of A. cantonensis infection and exhibits a mean larval reduction of 100% in a T. spiralis infection model when administered at doses of 5 and 50 mg/kg per day, respectively. Flubendazole inhibits mammalian tubulin polymerization (IC50 = 2.5 μM) and inhibits binding of [3H]mebendazole to H. contortus L3 larval tubulin (IC50 = 0.17 μM). Flubendazole also inhibits the proliferation of BT-549, SK-BR-3, MDA-MB-231, and MCF-7 breast cancer cells (IC50s = 0.72, 1.51, 1.75, and 5.51 μM, respectively) and reduces tumor growth in an MDA-MB-231 mouse xenograft model when administered at a dose of 25 mg/kg.
UsesAn anthelmintic.
VETRANAL analytical standard can be used in the liquid chromatography coupled to mass spectrometry (LC-MS/MS) procedure, performed for the analysis of macrocyclic lactones in milk.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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