| Identification | More | [Name]
Fenbendazole | [CAS]
43210-67-9 | [Synonyms]
[5-(PHENYLTHIO)-1H-BENZIMIDAZOL-2-YL]CARBAMIC ACID, METHYL ESTER
FENBENDAZOLE
HOE-881V
METHYL 5-(PHENYLTHIO)-2-BENZIMIDAZOLECARBAMATE
PANACUR
SAFEGARD
(5-(phenylthio)-1h-benzimidazol-2-yl)-carbamicacimethylester
5-(phenylthio)-2-benzimidazolecarbamicacimethylester
fenbendazol
hoe881
Fenbedazole
Fenbendazole CPV2000 EP2000
FENBENDAZOLE VETRANAL
FENBENDAZOLE EP STANDARD
FENBENDAZOLE BP STANDARD
FENBENDAZOLE IMPURITY BMETHYL[5(6)-CHLOROBENZIMIDAZOL-2-YL]CARBAMATE EP STANDARD
FENBENDAZOLE USP STANDARD
FENBENDAZOLE IMPURITY AMETHYL(1H-BENZIMIDAZOL-2-YL)CARBAMATE EP STANDARD
FENBENDAZOLE RELATED COMPOUND BMETHYL [5(6)CHLOROBENZIMIDAZOLE-2-YL) CARBAMATE USP STANDARD
FENBENDAZOLE RELATED COMPOUND AMETHYL (1H-BENZIMIDAZOLE-2-YL) CARBAMATE USP STANDARD | [EINECS(EC#)]
256-145-7 | [Molecular Formula]
C15H13N3O2S | [MDL Number]
MFCD00144301 | [Molecular Weight]
299.35 | [MOL File]
43210-67-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [Melting point ]
233°C | [density ]
1.2767 (rough estimate) | [refractive index ]
1.6740 (estimate) | [storage temp. ]
0-6°C | [solubility ]
DMSO:16.67(Max Conc. mg/mL);55.69(Max Conc. mM)
DMF:10.0(Max Conc. mg/mL);33.41(Max Conc. mM) | [Water Solubility ]
Insoluble in water | [form ]
neat | [pka]
10.80±0.10(Predicted) | [color ]
White to Light yellow | [Usage]
An anthelmintic (Nematodes) | [Merck ]
14,3960 | [BRN ]
759077 | [InChI]
InChI=1S/C15H13N3O2S/c1-20-15(19)18-14-16-12-8-7-11(9-13(12)17-14)21-10-5-3-2-4-6-10/h2-9H,1H3,(H2,16,17,18,19) | [InChIKey]
HDDSHPAODJUKPD-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)NC1NC2=CC(SC3=CC=CC=C3)=CC=C2N=1 | [CAS DataBase Reference]
43210-67-9(CAS DataBase Reference) | [EPA Substance Registry System]
Carbamic acid, N-[6-(phenylthio)-1H-benzimidazol-2-yl]-, methyl ester (43210-67-9) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
2
| [RTECS ]
DD6520500
| [HS Code ]
29339900 | [Toxicity]
dog,LD50,oral,> 500mg/kg (500mg/kg),Pesticide Science. Vol. 8, Pg. 550, 1977. |
| Hazard Information | Back Directory | [Description]
Fenbendazole(43210-67-9) is a benzimidazole anthelmintic.1 It is active against Giardia in vitro (IC50 = 0.3 μM). Fenbendazole (20 mg/kg) prevents infiltration of parasites into the brain in a rabbit model of E. cuniculi infection.2 Fenbendazole also activates HIF-1α and prevents oxidative stress-induced death in primary neurons in vitro.3
| [Originator]
Panacur,Hoechst,W. Germany,1980 | [Definition]
ChEBI: A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted at positons 2 and 5 by (methoxycarbonyl)amino and phenylsulfanediyl groups, respectively. A broad-spectrum anthelmintic, it is used, particularly in v
terinary medicine, for the treatment of nematodal infections. | [Manufacturing Process]
20.9 g of S-methyl-thiourea were dissolved in 27 ml of water with 13.5 ml of
chloroformic acid methyl ester. Then, 45.7 ml of 25% sodium hydroxide
solution were added dropwise, while stirring, at a temperature of 5°C to 10°C.
After having stirred for 20 minutes, the reaction mixture was combined with 27 ml of glacial acetic acid, 100 ml of water and 29 g of 3,4-diaminodiphenyl-
thioether. Stirring was continued for 90 minutes at a temperature of
85°C, during which time methyl-mercaptan was separated. After having
allowed the whole to cool and stand overnight, the 5-phenylmercaptobenzimidazole-
2-methyl-carbamate that had formed was filtered off with
suction. After recrystallization from a mixture of glacial acetic acid and
methanol, 14 g of 4-phenylmercapto-benzimidazole-2-methyl-carbamate
melting at 233°C were obtained. | [Brand name]
Panacur (Hoechst-Roussel). | [Therapeutic Function]
Anthelmintic | [General Description]
Fenbendazole is a thio substituted benzimidazole, which belongs to the group of anthelmintics. It can be widely used in veterinary medicine particularly, in the treatment of helminth infections. | [Side effects]
According to the results of toxicological studies, fenbendazole appears to be a safe drug, but up to 5% of people may experience stomach pain or diarrhea if taken in large amounts without interruption. People with severe renal failure or liver failure have a reduced level of drug excretion, and since fenbendazole powder is metabolized mainly in the liver, long-term heavy use can cause an asymptomatic increase in liver enzymes. | [Veterinary Drugs and Treatments]
Fenbendazole(43210-67-9) is indicated (labeled) for the removal of the following
parasites in dogs: ascarids (Toxocara canis, T. leonina), Hookworms
(Ancylostoma caninum, Uncinaria stenocephala),
whipworms
(Trichuris vulpis), and tapeworms (Taenia pisiformis). It is not effective
against Dipylidium caninum. Fenbendazole has also been
used clinically to treat Capillaria aerophilia, Filaroides
hirthi, and
Paragonimus kellicotti infections in dogs.
Fenbendazole is indicated (labeled) for the removal of the following
parasites in cattle: Adult forms of: Haemonchus contortus,
Ostertagia ostertagi, Trichostrongylus axei, Bunostomum phlebotomum,
Nematodirus helvetianus, Cooperia spp., Trichostrongylus
colubriformis, Oesophagostomum radiatum,
and Dictyocaulus vivaparus.
It is also effective against most immature stages of the above
listed parasites. Although not approved, it has good activity against
Moniezia spp., and arrested 4th stage forms of Ostertagia ostertagi.
Fenbendazole is indicated (labeled) for the removal of the following
parasites in horses: large strongyles (S. edentatus, S. equinus,
S. vulgaris), small strongyles (Cyathostomum spp., Cylicocylus
spp., Cylicostephanus spp., Triodontophorus spp.), and pinworms
(Oxyuris equi).
Fenbendazole is indicated (labeled) for the removal of the following
parasites in swine: large roundworms
(Ascaris suum), lungworms
(Metastrongylus pair), nodular worms (Oesphagostomum dentatum,
O. quadrispinolatum), small stomach worms (Hyostrongylus rubidus),
whipworms (Trichuris suis), and kidney worms (Stephanurus
dentatus; both mature and immature).
Although not approved, fenbendazole has been used in cats,
sheep, goats, pet birds, and llamas.
See Dosage section for more information.
| [Mode of action]
Fenbendazole is a benzimidazole antiparasitic drug that works at the sub-cellular level preventing cell division. Benzimidazoles bind to the β-tubulin, inhibiting the cell’s microtubule assembly responsible for intracellular transport and required for mitotic cellular division. In effect, it starves the parasite by causing intestinal cell disruption. | [References]
[1] Gao P, et al. Unexpected antitumorigenic effect of fenbendazole when combined with supplementary vitamins. Journal of the American Association for Laboratory Animal Science : JAALAS, 2008.
[2] Park D, et al. Anti-cancer effects of fenbendazole on 5-fluorouracil-resistant colorectal cancer cells. The Korean Journal of Physiology Pharmacology, 2022; 26: 377-387.[3] Shin Y, et al. Anticancer Evaluation of Methoxy Poly(Ethylene Glycol)-b-Poly(Caprolactone) Polymeric Micelles Encapsulating Fenbendazole and Rapamycin in Ovarian Cancer. International Journal of Nanomedicine, 2023; 2023: 2209—2223. |
| Questions And Answer | Back Directory | [Benzimidazole anthelmintics]
Fenbendazole is a benzimidazole anthelmintic with a broad spectrum,high efficiency and low toxicity ,in the structure,it has a strong affinity with the parasite tubulin ,by influencing cell transport and energy metabolism,it plays a role in preventing the polymerization of micro tubes, which ultimately destroys the integrity of parasite cells and energy transmission.
Fenbendazole is used to drive and to kill the animal gastrointestinal parasites, it not only has a highly anthelmintic activity on animal gastrointestinal roundworms, hookworms, whipworms, some tapeworms and nematodes , but also has a preferred effect on the part of the bronchial tree and lung parasites (Aelurostrongylus abstrutus and lung fluke) .
| [Aofendazuo]
Aofendazuo is a benzimidazole anthelmintic, also known as the Austrian phenol metronidazole, oxfendazole, benzene etomidate sulfoxide, benzene sulfur oxygen imidazole ,it is the sulfoxide form of Fenbendazole , white or off-white powder at room temperature, slight special smell, it can damage the microtubules of the worms epithelial cells of the gastrointestinal tract, and inhibit the worms uptake of glucose from the intestine.
Aofendazuo is used for the treatment and control of gastrointestinal adults and larvae, it has a good effect on the treatment of in vivo roundworms and lung worms in pigs and sheep , including Oster nematodes (Ostertagia), Haemonchus , Trichostrongylus, Nematodirus , Cooper nematode (Cooperia), capillary nematodes (Capillaria), toothed Oesophagostomum (Oesophagostomum), Chabertia, Trichuris nematodes form (Trichuris) and dictyocaulasis ( Dictyocaulus) and so on.
The above information is edited by the chemicalbook of Tian Ye.
| [Chemical Properties]
Gray light brown crystalline powder. Melting point 233 ℃ (decomposition). Soluble in dimethyl sulfoxide (DMSO), slightly soluble in common organic solvents, insoluble in water. Odorless, tasteless.
| [Uses]
Anthelmintic. Broad-spectrum, high efficiency, low toxicity, antiparasitic. It has a strong killing effect on Roundworm, nematodes, tapeworms, cysticercosis , Fasciola and other parasites, not only killing worms, especially having a great effect on Transitional larvae ehich are hazardous to the liver, lungs and intestines .Fenbendazole is a benzimidazole anthelmintic, not only having a highly anthelmintic activity for gastrointestinal nematodes adults and larvae , but also having a good effect on dictyocaulasis, flukes and tapeworms, in addition,it has a strong killing eggs effect.
| [Production method]
5-chloro-2-nitroaniline reacts with benzene thiol, to thereby obtain 5-phenylthio-2-nitroaniline in 91% yield.Generate 3-phenylthio-o-phenylenediamine by ferrous sulfate-iron reduction in 90% yield. Finally, cyclize it with the S-methyl-melamine Methyl to obtain fenbendazole.
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