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Fenbendazole

HCID 3334
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Basic information

CAS
43210-67-9
Standard SMILES
COC(=O)Nc1nc2ccc(Sc3ccccc3)cc2[nH]1
InChIKey
HDDSHPAODJUKPD-UHFFFAOYSA-N
Molecular formula
C15H13N3O2S
Average molar mass
299.3 g/mol
Monoisotopic mass
299.07284766

Overview

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.

Names & identifiers

Preferred name
Fenbendazole
IUPAC
methyl N-(6-phenylsulfanyl-1H-benzimidazol-2-yl)carbamate
English name
Fenbendazole
Molecular formula
C15H13N3O2S
Molecular weight
299.35

Names & synonyms

fenbendazole43210-67-9PanacurFenbendazolPhenbendasolFenbendazolumHoe 881vSafe-quardSafe-GuardMethyl 5-(phenylthio)-2-benzimidazolecarbamatePanacur aquasolHOE-881v
Show more names
FebendazoleFenbedazole5-(phenylthio)-2-benzimidazolecarbamic acid methyl esterMethyl (6-(phenylthio)-1H-benzo[d]iMidazol-2-yl)carbaMate[5-(Phenylthio)-1H-benzimidazol-2-yl]carbonic acid, Methyl esterhoe881AxilurFenbion
2-(Methoxycarbonylamino)-5-(phenylthio)benzimidazoleDTXSID0040672NSC-757824Fenbendazole for veterinary useHOE-881YCarbamic acid, (5-(phenylthio)-1H-benzimidazol-2-yl)-, methyl esterMethyl (5-(phenylthio)-1H-benzimidazol-2-yl)carbamate621BVT9M36

Database identifiers

CAS
43210-67-9

Properties

Computed structural properties

XLogP
3.6
Topological polar surface area
92.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
4
Heavy atoms
21
Formal charge
0
Complexity
363

Experimental & physicochemical properties

DrugsDrug
Solubility0.9 [ug/mL] (The mean of the results at pH 7.4)
Animal Drugs · 4 items

EMA approved medicines: Veterinary medicine

FDA approved animal drugs -> Active ingredient

Pharmaceuticals -> UK Veterinary Medicines Directorate List

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Melting Point233 °C
Physical DescriptionSolid
Collision Cross Section · 4 items

174.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID0040672]

170.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

186.5 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

169.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
233 °C · 233°C

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1.3% (2 of 157) of reports.

Warning

H361 (66.2%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P203, P260, P273, P280, P318, P319, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 157 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationFenbendazole: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Carbamic acid, [5-(phenylthio)-1H-benzimidazol-2-yl]-, methyl ester: Environment tier I assessment
Hazard Classes and CategoriesRepr. 2 (66.2%)

Toxicology

Hepatotoxicity · 1 item

The side effects of fenbendazole therapy in humans have not been well described, but other benzimidazoles are associated with transient and asymptomatic elevations in serum aminotransferase levels in up to 50% of patients treated for more than a few weeks. These abnormalities rapidly improve with stopping therapy. Fenbendazole taken by patients without prescription for its purported antineoplastic activity has been associated with several instances of clinically apparent liver injury. The onset of injury has been within a few days to as long as a year after starting therapy or more rapidly with multiple courses of treatment. The pattern of serum enzyme elevations is typically hepatocellular or mixed. Allergic features (rash, fever, eosinophilia) may be present but are not prominent. Most cases have been mild to moderate in severity, and recovery is rapid once the drug is stopped. However, some cases have been severe and potentially life-threatening. Rapid recurrence with rechallenge has been reported with other benzimidazoles but with similar severity.

Chemistry & industry

Pharmacology

ATC Code · 2 items

P - Antiparasitic products, insecticides and repellents

QP - Antiparasitic products, insecticides and repellents

Mechanism of Action · 1 item

Due to its poor absorption by oral administration, fenbendazole is particularly effective for targeting intestinal parasites. It exerts its antiparasitic effects primarily in the anterior intestine by depolymerizing microtubules, inhibiting intestinal secretory vesicle transport. When fenbendazole binds to beta-tubulin in parasites, it causes microtubule destabilization and hinders tubulin polymerization. This destabilization disrupts cellular function, such as glucose uptake, and thus affects the energy management of parasites.

MeSH Pharmacological ClassificationSubstances used in the treatment or control of nematode infestations. They are used also in veterinary practice.
Cellular LocationsMembrane

Uses & manufacturing

Uses · 1 item

Fenbendazole is a benzimidazole anthelmintic agent commonly used to treat animal parasitic infections. In humans, other benzimidazoles, such as mebendazole and albendazole, are used as antiparasitic agents. Fenbendazole is not currently approved by the FDA or EMA and its pharmacokinetics and safety in humans are not well-documented.

Use Classification · 6 items

Veterinary Drug -> ANTHELMINTHIC_AGENT -> JECFA Functional Classes

Veterinary Drug -> ANTHELMINTHIC_AGENT -> JECFA Functional Classes

Veterinary Drug -> ANTHELMINTHIC_AGENT -> JECFA Functional Classes

Veterinary Drug -> ANTHELMINTHIC_AGENT -> JECFA Functional Classes

Veterinary Drug -> ANTHELMINTHIC_AGENT -> JECFA Functional Classes

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Applications

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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PubChem CID
3334
DTXSID
DTXSID0040672
ChEMBL
CHEMBL37161
ChEBI
CHEBI:77092
UNII
621BVT9M36
EC Number
256-145-7
Nikkaji
J15.833J
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.
Toxicity Summary · 2 items

Fenbendazole has a high safety margin and low toxicity in animals. A study of fenbendazole administered to cattle found that it was well-tolerated, even when administered at six times the prescribed dose and three times the recommended duration. The lethal dose (LD50) in rodents is greater than 10 g/kg, which is 1,000 times the therapeutic level. Lifetime studies in rats indicated no maternal or reproductive toxicity and no carcinogenesis.

Fenbendazole (FBZ) is used to treat or prevent pinworm outbreaks in laboratory rodents. At therapeutic levels, FBZ does not alter the total content of cytochromes P450 but does induce certain hepatic cytochrome P450 isoforms known for bioactivating a number of procarcinogens. Lifetime studies in rats have shown that FBZ is not a carcinogen but that it may behave as a tumor promoter when given after certain initiators. FBZ treatment-associated myelosuppression has not been reported to occur in rodents.

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
· 5 items

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

Cyanamide Methyl5-Chloro-2-nitroanilineAcetonitrile5-Phenylthio-2-nitroanilineThiophenolFerrousChloroformIron3-Chloroanilineo-Phenylenediamine2-Methyl-2-thiopseudourea sulfateMethyl chloroformate5-Phenylthio-1,2-diaminobenzene2-Nitro-5-(phenylthio)aniline

Downstream products

Oxfendazole
Additional notes · 1 item

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.