Flubendazole CAS 31430-15-6
Introduction：Basic information about Flubendazole CAS 31430-15-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Flubendazole Basic information
| Product Name: | Flubendazole |
| Synonyms: | METHYL [5-(4-FLUOROBENZOYL)-1H-BENZIMIDAZOL-2-YL]CARBAMATE;CARBAMIC ACID, [5-(4-FLUOROBENZOYL)-1H-BENZIMIDAZOL-2-YL]-METHYL ESTER;FLUMOXAL;FLUMOXANAL;FLUMOXANE;FLUBENDAZOL;FLUBENDAZOLE;FLUBENOL |
| CAS: | 31430-15-6 |
| MF: | C16H12FN3O3 |
| MW: | 313.28 |
| EINECS: | 250-624-4 |
| Product Categories: | Fluorobenzene;Active Pharmaceutical Ingredients;31430-15-6 |
| Mol File: | 31430-15-6.mol |
Flubendazole Chemical Properties
| Melting point | 290°C |
| density | 1.3720 (estimate) |
| storage temp. | 2-8°C |
| solubility | Practically insoluble in water, in alcohol and in methylene chloride |
| pka | 10.66±0.10(Predicted) |
| form | Solid |
| color | White to Off-White |
| Merck | 14,4118 |
| Major Application | forensics and toxicology pharmaceutical (small molecule) |
| 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) |
| InChIKey | CPEUVMUXAHMANV-UHFFFAOYSA-N |
| SMILES | COC(=O)Nc1nc2cc(ccc2[nH]1)C(=O)c3ccc(F)cc3 |
| CAS DataBase Reference | 31430-15-6(CAS DataBase Reference) |
Safety Information
| Risk Statements | 22 |
| Safety Statements | 44 |
| WGK Germany | 2 |
| RTECS | DD6497500 |
| HS Code | 29339900 |
| Storage Class | 10 - Combustible liquids |
| Toxicity | LD50 in mice, rats, guinea pigs (mg/kg): >2560 orally (Thienpont) |
| 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. |
| Chemical Properties | White Solid |
| Originator | Fluvermal,Janssen-Le Brun,France,1980 |
| Uses | An anthelmintic. |
| Uses | An insectocidal agent. |
| Uses | 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. |
| Definition | ChEBI: 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. |
| Manufacturing Process | To a stirred and cooled (ice bath) suspension of 25 parts of aluminum chloridein 52 parts of fluorobenzene is added dropwise a solution of 27.5 parts of 4-chloro-3-nitrobenzoyl chloride in 52 parts of fluorobenzene. Upon completion,stirring is continued overnight at room temperature. The reaction mixture ispoured onto water and the product is extracted with methylene chloride. Theextract is washed successively with sodium hydrogen carbonate solution andwater, dried, filtered and evaporated in vacuo. The solid residue is crystallizedfrom 2-propanol, yielding 4-chloro-4'-fluoro-3-nitrobenzophenone; MP 97.9°C. A mixture of 24.5 parts of 4-chloro-4'-fluoro-3-nitrobenzophenone, 72 parts ofmethanol, 13 parts of sulfolane and 3.12 parts of ammonia is heated in asealed tube for 20 hours at 120°C. To the reaction mixture is addedsuccessively 50 parts of water and 25 parts of a diluted hydrochloric acidsolution and the whole is stirred and refluxed for 5 minutes. The reactionmixture is cooled and the precipitated product is filtered off. It is washed with 2-propanol and recrystallized from 640 parts of toluene, yielding 4-amino-4'-fluoro-3-nitrobenzophenone; MP 199°C. A mixture of 14.5 parts of 4-amino-4'-fluoro-3-nitrobenzophenone, 160 partsof methanol, 6 parts of concentrated hydrochloric acid solution and 0.5 part ofplatinum oxide is hydrogenated at normal pressure and at room temperature.After the calculated amount of hydrogen is taken up, hydrogenation isstopped. The catalyst is filtered off and the filtrate is evaporated. The residueis washed with 2-propanol and dried, yielding 3,4-diamino-4'-fluorobenzophenone hydrochloride; MP 226°C to 230.5°C. A mixture of 89 parts of S-methylisothiourea sulfate, 6.05 parts of methylchloroformate in 7 parts of water is cooled, and at a temperature of 5°C to10°C, sodium hydroxide solution 25% is added until pH equals 8. Then thereare added successively 6.4 parts of acetic acid, 2.6 parts of sodium acetateand 8.9 parts of 3,4-diamino-4'-fluorobenzophenone hydrochloride and thewhole is stirred while heating at 85°C for 45 minutes (during this reactiontime, water and 2-propanol is added). The precipitated product is filtered off,washed with methanol and recrystallized from a mixture of 200 parts of aceticacid and 80 parts of methanol, yielding methyl N-[5(6)-p-fluorobenzoyl-2-benzimidazolyl] carbamate; MP > 260°C. |
| Therapeutic Function | Anthelmintic |
| General Description | Flubendazol is a broad spectrum anthelmintic, which belongs to the class of compounds known as benzimidazoles. It can be widely used in veterinary and human medicine. It mainly finds applications in deworming poultry, swine, dogs and cats. |
| Biochem/physiol Actions | Flubendazole, an antithelmintic, has been widely used in treating intestinal parasites. Additionally, Flubendazole has been reported to exert anticancer activities. |
| References | [1] KRISTYNA ?á?OVá Emil R Lucie Rozkydalová. Anthelmintic Flubendazole and Its Potential Use in Anticancer Therapy.[J]. Acta medica (Hradec Kralove), 2017, 60 1: 5-11. DOI: 10.14712/18059694.2017.44 [2] J MAKI T Y. A comparison of the effects of flubendazole and thiabendazole on the larvae of Angiostrongylus cantonensis, Trichinella spiralis, Diphyllobothrium erinacei and Hymenolepis nana in mice.[J]. Parasitology, 1983, 87 (Pt 3): 525-531. DOI: 10.1017/s0031182000083049 [3] LACEY E. Mode of action of benzimidazoles[J]. Parasitology today (Personal ed.), 1990, 6 4: Pages 112-115. DOI: 10.1016/0169-4758(90)90227-u [4] ZHI-JIE HOU. Flubendazole, FDA-approved anthelmintic, targets breast cancer stem-like cells.[J]. Oncotarget, 2015, 6 8: 6326-6340. DOI: 10.18632/oncotarget.3436 |
Flubendazole Preparation Products And Raw materials
| Raw materials | Fluorobenzene-->Ammonia-->2-METHYL-2-THIOPSEUDOUREA,SULFATE-->Aluminum chloride-->4-Chloro-3-nitrobenzoyl chloride |
