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Basic information
- Standard SMILES
COC(=O)Nc1nc2ccc(Sc3ccccc3)cc2[nH]1- InChIKey
HDDSHPAODJUKPD-UHFFFAOYSA-N- Molecular formula
- C15H13N3O2S
- Average molar mass
- 299.355 g/mol
- Monoisotopic mass
- 299.07284766
Names & identifiers
- Preferred name
- Fenbendazole
- IUPAC
- Methyl [5-(phenylsulfanyl)-1H-benzimidazol-2-yl]carbamate
- English name
- Fenbendazole
- Molecular formula
- C15H13N3O2S
- Molecular weight
- 299.35
Names & synonyms
Database identifiers
- CAS
43210-67-9- PubChem CID
- 3334
- DTXSID
DTXSID0040672- ChEMBL
CHEMBL37161- ChEBI
CHEBI:77092- UNII
- 621BVT9M36
- EC Number
- 256-145-7
- Nikkaji
- J15.833J
Properties
Physicochemical properties
- Melting point
- 233 °C · 233°C
- Density
- 1.2767 · 1.2767 (rough estimate)
- refractive index
- 1.674 · 1.6740 (estimate)
- storage temp.
- 2 · 2-8°C
- Water Solubility
- Insoluble in water
- solubility
- 16.67 · DMSO:16.67(Max Conc. mg/mL);55.69(Max Conc. mM)DMF:10.0(Max Conc. mg/mL);33.41(Max Conc. mM)
- pka
- 10.8 · 10.80±0.10(Predicted)
- form
- Solid
- color
- White to Light yellow
- Merck
- 14 · 14,3960
- BRN
- 759077 · 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 · 43210-67-9(CAS DataBase Reference)
- FDA 21 CFR
- 556.275 · 556.275; 558.258; 558.4
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 621 BVT9M36 · 621BVT9M36
- ATC code
- 2 CA06 · P02CA06
- EPA Substance Registry System
- 6 · Carbamic acid, N-[6-(phenylthio)-1H-benzimidazol-2-yl]-, methyl ester (43210-67-9)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 8 · GHS08,GHS09
- Signal word
- Warning
- Hazard statements
- 361 fd-H373-H410 · H361fd-H373-H410
- Precautionary statements
- 201 · P201-P202-P260-P273-P280-P308+P313
- target organs
- Liver,lymph node,Stomach,Nervous system
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-24/25
- WGK Germany
- 2 · 2
- RTECS
- 6520500 · DD6520500
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Repr. 2STOT RE 2
- Toxicity
- 50 · dog,LD50,oral,> 500mg/kg (500mg/kg),Pesticide Science. Vol. 8, Pg. 550, 1977.
Safety & regulation
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- DD6520500
- hs_code
- 29339900
- Toxicity
- dog,LD50,oral,> 500mg/kg (500mg/kg),Pesticide Science. Vol. 8, Pg. 550, 1977.
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS08,GHS09
- hazard_code
- Xi
- safety_code
- 26-36-24/25
- Storage Class
- 11 - Combustible Solids
- target organs
- Liver,lymph node,Stomach,Nervous system
- Hazard statements
- H361fd-H373-H410
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Repr. 2STOT RE 2
- Precautionary statements
- P201-P202-P260-P273-P280-P308+P313
Chemistry & industry
Applications
UsesAnthelmintic. 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.
DescriptionFenbendazole is a benzimidazole anthelmintic. 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. Fenbendazole also activates HIF-1α and prevents oxidative stress-induced death in primary neurons in vitro.
UsesFenbendazole is a benzimidazole anthelmintic that is metabolised in mammals to a series of other benzimidazoles including oxfendazole. It is used for the control of gastrointestinal roundworms, lung worms, Nematodes and tape worms. It is the only benzimidazole approved for use in organic livestock production.
UsesFenbendazole is a medication used to treat parasites, mainly in dogs. However, studies have found that in a group of mice treated with a combination of fenbendazole and vitamins, tumor growth inhibition was unexpected It may be because it interferes with the uptake of glucose by cancer cells, which is essential for tumor growth and proliferation. It prevents cancer cells from obtaining the glucose needed to grow and divide to inhibit the growth of cancer cells. Studies have found that fenbendazole can kill cancer cells and promote tumor regression in patients with metastatic large B-cell lymphoma, and also plays a role in other metastatic malignant tumors such as bladder cancer and renal cell carcinoma. It is currently being treated in combination with other anti-cancer drugs to study its anti-cancer potential[1-3].
General DescriptionFenbendazole 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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: Fenbendazole is 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 veterinary medicine, for the treatment of nematodal infections. It has a role as an antinematodal drug. It is a member of benzimidazoles, a carbamate ester and an aryl sulfide.
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