Flubendazole

Base Information

• Chemical Name: Flubendazole
• CAS No.: 31430-15-6
• Molecular Formula: C16H12FN3O3
• Molecular Weight: 313.288
• Hs Code.: 29339900
• European Community (EC) Number: 250-624-4
• NSC Number: 313680
• UNII: R8M46911LR
• DSSTox Substance ID: DTXSID8023058
• Nikkaji Number: J20.325D
• Wikipedia: Flubendazole
• Wikidata: Q241992
• NCI Thesaurus Code: C75219
• Metabolomics Workbench ID: 152049
• ChEMBL ID: CHEMBL1454946
• Mol file: 31430-15-6.mol

Synonyms:carbamic acid, (5-(4-fluorobenzoyl)-1H-benzimidazol-2-yl)-, methyl ester;flubendazole;fluoromebendazole;methyl(5-(4-fluorobenzoyl)-1H-benzimidazol- 2-yl)carbamate;R 17,889;R 17889;R-17,889;R-17889

Chemical Property of Flubendazole

Chemical Property:

• Appearance/Colour: almost white powder
• Melting Point: 290 °C
• Refractive Index: 1.685
• PKA: 10.66±0.10(Predicted)
• PSA: 84.08000
• Density: 1.444 g/cm³
• LogP: 3.18430
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, in alcohol and in methylene chloride
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 313.08626942
• Heavy Atom Count: 23
• Complexity: 454

Purity/Quality:

99% ^*data from raw suppliers

Flubendazole ^*data from reagent suppliers

Safty Information:

• Statements: 22
• Safety Statements: 44

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C3=CC=C(C=C3)F
• Description: Flubendazole 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.
• Uses: An anthelmintic. An insectocidal agent. 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.
• Therapeutic Function: Anthelmintic

Technology Process of Flubendazole

There total 8 articles about Flubendazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.8%

reduced flubendazole → methyl N-[6-(4-fluorobenzoyl)-1H-benzimidazol-2-yl]carbamate (31430-15-6)

Guidance literature:

With dihydrogen peroxide; In methanol; water; at 25 - 30 ℃; for 2.5h; Large scale;

Reference yield: 87.6%

(3,4-diaminophenyl)(4-fluorophenyl)ketone (66938-86-1) + O-methyl-N-(methoxycarbonyl)-isourea (40943-37-1) → flubendazole (31430-15-6)

Guidance literature:

With formic acid; at 80 ℃; for 3h;

Reference yield:

C16H15FN4O3 → flubendazole (31430-15-6)

Guidance literature:

With formic acid;

upstream raw materials:

(3,4-diaminophenyl)(4-fluorophenyl)ketone

O-methyl-N-(methoxycarbonyl)-isourea

4-chloro-3-nitrobenzoate

4-chloro-3-nitro-benzoyl chloride

Downstream raw materials:

6-(4-fluorobenzoyl)-1H-benzimidazol-2-amine

Refernces

• 1、 -. "Preparation method of flubendazole". Paragraph 0040; 0041. . Retrieved 2018/03/26.
• 2、 Raeymackers,Van Gelder,Roevens,Janssen. "Synthesis and anthelminthic acitivity of alkyl-(5-acyl-1-benzimidazol-2-yl) carbamates". . p. 586 - 594. Retrieved 2007/10/05.