31430-15-6 Usage
Description
Flubendazole is a benzimidazole carbamate anthelmintic, belonging to the class of mebendazole derivatives with a p-fluorobenzoyl group replacing the benzoyl group. It is a white solid that exhibits broad-spectrum anthelmintic properties and is used in both veterinary and human medicine for the treatment of nematodal infections.
Uses
Used in Veterinary Medicine:
Flubendazole is used as an anthelmintic for deworming poultry, swine, dogs, and cats. It effectively eliminates larvae in various infection models and inhibits tubulin polymerization, contributing to its deworming capabilities.
Used in Human Medicine:
Flubendazole is used as an anthelmintic in human medicine, targeting nematodal infections and providing a broad-spectrum treatment option.
Used in Insecticidal Applications:
Flubendazole also serves as an insectocidal agent, offering a means to control insect populations in various settings.
Used in Pharmaceutical Analysis:
VETRANAL? analytical standard can be utilized in the liquid chromatography coupled to mass spectrometry (LC-MS/MS) procedure for the analysis of macrocyclic lactones in milk, ensuring the accurate detection and measurement of these compounds in dairy products.
Used in Cancer Research:
Flubendazole has demonstrated the ability to inhibit the proliferation of various breast cancer cells and reduce tumor growth in mouse xenograft models, indicating its potential use in cancer research and treatment development.
Originator
Fluvermal,Janssen-Le Brun,France,1980
Manufacturing Process
To a stirred and cooled (ice bath) suspension of 25 parts of aluminum chloride
in 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 is
poured onto water and the product is extracted with methylene chloride. The
extract is washed successively with sodium hydrogen carbonate solution and
water, dried, filtered and evaporated in vacuo. The solid residue is crystallized
from 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 of
methanol, 13 parts of sulfolane and 3.12 parts of ammonia is heated in a
sealed tube for 20 hours at 120°C. To the reaction mixture is added
successively 50 parts of water and 25 parts of a diluted hydrochloric acid
solution and the whole is stirred and refluxed for 5 minutes. The reaction
mixture 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 parts
of methanol, 6 parts of concentrated hydrochloric acid solution and 0.5 part of
platinum oxide is hydrogenated at normal pressure and at room temperature.
After the calculated amount of hydrogen is taken up, hydrogenation is
stopped. The catalyst is filtered off and the filtrate is evaporated. The residue
is 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 methyl
chloroformate in 7 parts of water is cooled, and at a temperature of 5°C to
10°C, sodium hydroxide solution 25% is added until pH equals 8. Then there
are added successively 6.4 parts of acetic acid, 2.6 parts of sodium acetate
and 8.9 parts of 3,4-diamino-4'-fluorobenzophenone hydrochloride and the
whole is stirred while heating at 85°C for 45 minutes (during this reaction
time, water and 2-propanol is added). The precipitated product is filtered off,
washed with methanol and recrystallized from a mixture of 200 parts of acetic
acid and 80 parts of methanol, yielding methyl N-[5(6)-p-fluorobenzoyl-2-
benzimidazolyl] carbamate; MP > 260°C.
Therapeutic Function
Anthelmintic
Biochem/physiol Actions
Flubendazole, an antithelmintic, has been widely used in treating intestinal parasites. Additionally, Flubendazole has been reported to exert anticancer activities.
Check Digit Verification of cas no
The CAS Registry Mumber 31430-15-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,1,4,3 and 0 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 31430-15:
(7*3)+(6*1)+(5*4)+(4*3)+(3*0)+(2*1)+(1*5)=66
66 % 10 = 6
So 31430-15-6 is a valid CAS Registry Number.
InChI:InChI=1/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)
31430-15-6Relevant articles and documents
Synthesis method of flubendazole
-
Paragraph 0002; 0008, (2020/12/30)
The invention relates to a synthesis method of flubendazole, which comprises the following steps of 1) adding a reductant and a methyl ester reactant into a reaction flask, adding formic acid, heatingto 80 DEG C, and keeping the temperature for 2.5-3 hours, wherein the molar ratio of the reductant to the methyl ester to the formic acid is 1: 1.2: 16-20, and the reaction equation is shown in the specification, and 2) injecting the solution in the reaction bottle into methanol, cooling to room temperature, and filtering to obtain the flubendazole. The step of acetic acid condensation is omitted, excessive formic acid is directly added to synthesize the flubendazole in one step, the reaction steps are simple, the operation rate is high, and the yield is high and is about 86.9-87.6%.
1,5-diphenyl-3-formazancarbonitril parasiticides
-
, (2008/06/13)
The present invention is directed to the use of 1,5-diaryl-3 -formazancarbonitrile compounds for the control of parasites in vertebrate animals.
