benzimidazole

General Material Information

Preferred name	benzimidazole
Trivial Name	Benzimidazole
Short Description	1H-benzo[d]imidazole
Formula	C7 H6 N2
CAS Number	51-17-2
Deleted CAS Number	116421-27-3
ECHA Number	200-081-4
FDA UNII	E24GX49LD8
Nikkaji Number	J2.303E
Beilstein Number	0109682
MDL	MFCD00005585
Bio Activity Summary	External link
NMR Predictor	External link
Synonyms	benzimidazol 1H- benzimidazol 1,3-benzimidazole 1H- benzimidazole 1H- benzimidazole (9CI) 1H- benzo[d]imidazole 1,3-benzodiazole benzoglyoxaline 1,3-diazaindene 1H-Benzimidazole 3-Azaindole Azindole o-Benzimidazole 1,3-Benzodiazole 1,3-Diazaindene N,N′-Methenyl-o-phenylenediamine Benziminazole BZI NSC 759 1H-Benzo[d]imidazole 1H-1,3-Benzodiazole

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Literature & References

	1H-benzimidazole
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	5798
Pubchem (sid):	134972101

Publications by PubMed
Determination of benzimidazole anthelmintics in milk and honey by monolithic fiber-based solid-phase microextraction combined with high-performance liquid chromatography-diode array detection.
Molecular characterization, fitness and mycotoxin production of benzimidazole-resistant isolates of Penicillium expansum.
[Benzimidazole and its derivatives--from fungicides to designer drugs. A new occupational and environmental hazards].
Factors affecting pharmacokinetics of benzimidazole anthelmintics in food-producing animals: the consequences and potential risks.
Selective ALDH3A1 inhibition by benzimidazole analogues increase mafosfamide sensitivity in cancer cells.
Synthesis and antifungal activity of 2-chloromethyl-1H-benzimidazole derivatives against phytopathogenic fungi in vitro.
Identification of a novel benzimidazole derivative as a highly potent NPY Y5 receptor antagonist with an anti-obesity profile.
Detection of benzimidazole carbamates and amino metabolites in liver by surface plasmon resonance-biosensor.
Determination of benzimidazole residues in animal tissue samples by combination of magnetic solid-phase extraction with capillary zone electrophoresis.
Determination of benzimidazole residues in edible animal food by polymer monolith microextraction combined with liquid chromatography-mass spectrometry.
Comparisons of metabolic and physiological changes in rats following short term oral dosing with pesticides commonly found in food.
Development of a liquid chromatography-tandem mass spectrometry with pressurized liquid extraction method for the determination of benzimidazole residues in edible tissues.
Discovery of benzimidazole pyrrolidinyl amides as prolylcarboxypeptidase inhibitors.
Mutations in a beta-tubulin confer resistance of Gibberella zeae to benzimidazole fungicides.
Benzimidazole carbamate residues in milk: Detection by Surface Plasmon Resonance-biosensor, using a modified QuEChERS (Quick, Easy, Cheap, Effective, Rugged and Safe) method for extraction.
Simultaneous direct analysis of benzimidazole fungicides and relevant metabolites in agricultural products based on multifunction dispersive solid-phase extraction and liquid chromatography-mass spectrometry.
Fasciola hepatica: histological changes in the reproductive structures of triclabendazole (TCBZ)-sensitive and TCBZ-resistant flukes after treatment in vivo with TCBZ and the related benzimidazole derivative, Compound Alpha.
Assessing quality of raw milk in southern Greece in the aspect of certain benzimidazole residues.
The transcriptional response of Caenorhabditis elegans to Ivermectin exposure identifies novel genes involved in the response to reduced food intake.
Discovery of a Potent and Selective DGAT1 Inhibitor with a Piperidinyl-oxy-cyclohexanecarboxylic Acid Moiety.
Induction of chromosome loss in Saccharomyces cerevisiae strain D61.M by selected benzimidazole compounds.
Structure-activity relationships of nitro and methyl-nitro derivatives of indoline, indole, indazole and benzimidazole in Salmonella typhimurium.
Determination of imidacloprid and benzimidazole residues in fruits and vegetables by liquid chromatography-mass spectrometry after ethyl acetate multiresidue extraction.
Matrix solid phase dispersion isolation and liquid chromatographic determination of five benzimidazole anthelmintics in fortified beef liver.
Pharmacokinetic properties of a novel gastric proton pump inhibitor, (+/-)-2-[(4-methoxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9- yl)sulfinyl]-1H-benzimidazole sodium salt, in healthy subjects.
Prevalence of benzimidazole resistant nematodes in sheep flocks in Yucatan, Mexico.
Determination of benzimidazole anthelmintics in animal-derived biological matrices.
Review of methodology for the determination of benzimidazole residues in biological matrices.
Benzimidazole drugs and modulation of biotransformation enzymes.
Kuwait's total diet study: dietary intake of organochlorine, carbamate, benzimidazole and phenylurea pesticide residues.
Ion-pairing liquid chromatographic determination of benzimidazole fungicides in foods.
Determination of benzimidazole anthelmintics in meat samples.
Multiresidue assay for benzimidazole anthelmintics by liquid chromatography and confirmation by gas chromatography/selected-ion monitoring electron impact mass spectrometry.
Anthelmintic resistance and multidrug resistance in sheep gastro-intestinal nematodes in France, Greece and Italy.
Complexation of several benzimidazole-type fungicides with alpha- and beta-cyclodextrins.
A field evaluation of benzimidazole and nonbenzimidazole drugs in a herd of dairy goats.
Effect of sodium 2-n-pentadecyl-benzimidazole-5-carboxylate (M & B 35347B), an inhibitor of acetyl-CoA carboxylase, on lipogenesis and fat deposition in obese hyperglycaemic (ob/ob) and lean mice.
Hookworm infection among school age children in Kintampo north municipality, Ghana: nutritional risk factors and response to albendazole treatment.
Inhibitory action of benzimidazole fungicides on the in vivo incorporation of [3H]thymidine in various organs of the mouse.
Adsorption of benzimidazole fungicides on montmorillonite and kaolinite clay surfaces.
Investigation of the fate of trifluralin in shrimp.
Adsorption behavior of Hg2+ in aqueous solutions on a novel chelating cross-linked chitosan microsphere.
Activation of lateral hypothalamic mGlu1 and mGlu5 receptors elicits feeding in rats.
Current Status of Parasite Control at the Feed Yard.
A fast and reliable method for the quantitative determination of benzimidazoles and metabolites in milk by LC-MS/MS with on-line sample treatment.
TNFR1/TNF-α and mitochondria interrelated signaling pathway mediates quinocetone-induced apoptosis in HepG2 cells.
Food intake in laboratory rats provided standard and fenbendazole-supplemented diets.
Recent advances in candidate-gene and whole-genome approaches to the discovery of anthelmintic resistance markers and the description of drug/receptor interactions.
Reactive carbonyl-scavenging ability of 2-aminoimidazoles: 2-amino-1-methylbenzimidazole and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).
Bioassays for the detection of growth-promoting agents, veterinary drugs and environmental contaminants in food.
Fungicide Sensitivity and Characterization of Cobweb Disease on a Pleurotus eryngii Mushroom Crop Caused by Cladobotryum mycophilum.
High level of treatment failure with commonly used anthelmintics on Irish sheep farms.
The chemotherapy of onchocerciasis XVII. A clinical evaluation of albendazole in patients with onchocerciasis; effects of food and pretreatment with ivermectin on drug response and pharmacokinetics.
Antiparasitic mebendazole shows survival benefit in 2 preclinical models of glioblastoma multiforme.
In vitro aneugenic effects of the fungicide thiabendazole evaluated in human lymphocytes by the micronucleus assay.
In vitro effect of seven antiparasitics on Acolpenteron ureteroecetes (Dactylogyridae) from largemouth bass Micropterus salmoides (Centrarchidae).
Residual concentrations of the flukicidal compound triclabendazole in dairy cows' milk and cheese.
Design, synthesis and SAR of a novel series of benzimidazoles as potent NPY Y5 antagonists.
Oral maribavir for treatment of refractory or resistant cytomegalovirus infections in transplant recipients.
Bendamustine for the treatment of chronic lymphocytic leukemia and rituximab-refractory, indolent B-cell non-Hodgkin lymphoma.
Giardiasis in the post genomic era: treatment, drug resistance and novel therapeutic perspectives.
Genotoxical, teratological and biochemical effects of anthelmintic drug oxfendazole Maximum Residue Limit (MRL) in male and female mice.
4-[1-(4-Hy-droxy-3-meth-oxy-benz-yl)-1H-benzimidazol-2-yl]-2-meth-oxy-phenol.
Biological control of infective larvae of a gastro-intestinal nematode (Teladorsagia circumcincta) and a small lungworm (Muellerius capillaris) by Duddingtonia flagrans in goat faeces.
Pharmacokinetic properties of E3810, a new proton pump inhibitor, in healthy male volunteers.
Bendamustine: a new treatment option for chronic lymphocytic leukemia.
Treatment of mice with fenbendazole attenuates allergic airways inflammation and Th2 cytokine production in a model of asthma.
Effect of anilinopyrimidine resistance on aflatoxin production and fitness parameters in Aspergillus parasiticus Speare.
Dietary intake of pesticides: State of Kuwait total diet study.
Determination of carbendazim, thiophanate, thiophanate-methyl and benomyl residues in agricultural products by liquid chromatography-tandem mass spectrometry.
Triclabendazole for the treatment of fascioliasis and paragonimiasis.
A dual validation approach to detect anthelmintic residues in bovine liver over an extended concentration range.
Development of a high-performance liquid chromatography method to monitor the residues of benzimidazoles in bovine milk.
Towards a rational treatment of duodenal ulcer.
Therapeutic strategies for human microsporidia infections.
The identification of a new heterocyclic amine mutagen from a heated mixture of creatine, glutamic acid and glucose.
Synergistic effect of fungicides on resistant strains of Penicillium italicum and Penicillium digitatum.
Enzyme-linked immunosorbent assay of benomyl and thiabendazole in some foods.
Benomyl induction of brain aromatase and toxic effects in the zebrafish embryo.
Determination of the maximum tolerated dose and the safety index of an experimental fasciolicide in cattle.
Proton pump inhibitors in GORD An overview of their pharmacology, efficacy and safety.
The role of multigeneration studies in safety assessment of residues of veterinary drugs and additives.
Modifying the formulation or delivery mechanism to increase the activity of anthelmintic compounds.
Antifungal characteristics of N,N'-hexamethylenebis (4-carbamoyl-1-decylpyridinium bromide).
The effect of ZIMET 3164 and ZIMET 3393 on phagocytosis in Tetrahymena pyriformis GL.
[Neurocysticercosis--pathogenesis and clinical aspects].
Validation of a histamine H3 receptor model through structure-activity relationships for classical H3 antagonists.
Microsporidiosis: an emerging and opportunistic infection in humans and animals.
Methods for generation of monoclonal antibodies to the very small drug hapten, 5-benzimidazolecarboxylic acid.
Physiology, pharmacology and parasitology.
Acute, subacute and chronic oral toxicity studies of the new serotonin (5-HT)3-receptor antagonist ramosetron in beagle dogs.
Clinical pharmacokinetics of lansoprazole.
The clinical significance of gastrointestinal helminths--a review.
Maribavir: a novel antiviral agent with activity against cytomegalovirus.
Pharmacokinetics of pantoprazole in man.
Pharmacokinetics of pantoprazole in man.
Albendazole inhibits Pneumocystis carinii proliferation in inoculated immunosuppressed mice.
Therapeutic evaluation of omeprazole.
Influence of chronic omeprazole treatment on gastric endocrine function.
Radioimmunoassay of oxfendazole in sheep fat.
WAY 100635 produces discriminative stimulus effects in rats mediated by dopamine D(4) receptor activation.
Fenbendazole pharmacokinetics, metabolism, and potentiation in horses.
Effect of pesticide mixtures on in vitro nervous cells: comparison with single pesticides.
Prenatal risks deriving from environmental chemicals.
Formation of acids, lactones and esters through the Maillard reaction.
Increased visualization of antral gastrin-producing G-cells after acute stimulation of gastrin release in the rat.
Anthelmintic resistance in Australian sheep nematode populations.
Nephrotoxicity of thiazoles structurally related to thiabendazole in mice depleted of glutathione by treatment with buthionine sulfoximine.
Insulin in aging and cancer: antidiabetic drug Diabenol as geroprotector and anticarcinogen.
[Effect of antidiabetic drug diabenol on parameters of biological age, life span and tumor development in NMRI and HER-2/neu mice].
Nephrotoxicity of thiabendazole in mice depleted of glutathione by treatment with DL-buthionine sulphoximine.
Benomyl resistance of Colletotrichum acutatum is caused by enhanced expression of beta-tubulin 1 gene regulated by putative leucine zipper protein CaBEN1.
Assessing N,N'-Dibutylurea (DBU) formation in soils after application of n-butylisocyanate and benlate fungicides.
Transcriptional and posttranscriptional roles for p38 mitogen-activated protein kinase in upregulation of TNF-alpha expression by deoxynivalenol (vomitoxin).
Analysis of fenbendazole residues in bovine milk by ELISA.
Developmental toxicity of orally administered thiabendazole in ICR mice.
Comparative Metabolism of Thiabendazole in Cultured Hepatocytes from Rats, Rabbits, Calves, Pigs, and Sheep, Including the Formation of Protein-Bound Residues.
Effect of temperature and humidity on the formation of dibutylurea in benlate fungicide.
Developmental toxicity of carbendazim: comparison of no-observed-adverse-effect level and benchmark dose approach.
Superinduction of IL-2 gene expression by vomitoxin (deoxynivalenol) involves increased mRNA stability.
Formation of toxic metabolites from thiabendazole and other thiazoles in mice. Identification of thioamides as ring cleavage products.
Acute renal toxicity of thiabendazole (TBZ) in ICR mice.
New metabolites of thiabendazole and the metabolism of thiabendazole by mouse embryo in vivo and in vitro.
Utilization of Folin-Ciocalteu phenol reagent for the detection of certain nitrogen compounds.
Superinduction of TNF-alpha and IL-6 in macrophages by vomitoxin (deoxynivalenol) modulated by mRNA stabilization.
Determination of flubendazole and its metabolites in eggs and poultry muscle with liquid chromatography-tandem mass spectrometry.
Determination of benomyl, diphenyl, o-phenylphenol, thiabendazole, chlorpyrifos, methidathion, and methyl parathion in oranges by solid-phase extraction, liquid chromatography, and gas chromatography.
Effects of alternation of drug classes on the development of oxibendazole resistance in a herd of horses.
The feasibility of using Chinese hamsters as an animal model for aneuploidy.
In vitro metabolism of teratogens by differentiating rat embryo cells.

Other Information

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
CHEBI:	View
CHEMBL:	View
KEGG (GenomeNet):	C02009
HMDB (The Human Metabolome Database):	HMDB36258
Export Tariff Code:	2933.99.8290
ChemSpider:	View
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Sigma-Aldrich: Aldrich

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	118.1388168335
Flash Point TCC Value	208.4 °C TCC
logP (o/w)	1.32
Solubility
water, 2010 mg/L @ 20 °C (exp)	Yes
water, 7604 mg/L @ 25 °C (est)	Yes

Safety Information

Safety information

Preferred SDS: View

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 445 mg/kg Pharmaceutical Chemistry Journal Vol. 14, Pg. 130, 1980. intravenous-mouse LD50 280 mg/kg "Principles of Medicinal Chemistry," Foye, W.O., et al., eds., Philadelphia, Lea & Febiger, 1974Vol. -, Pg. 246, 1974. oral-mouse LD50 2910 mg/kg LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Journal of Pharmacology and Experimental Therapeutics. Vol. 105, Pg. 486, 1952. intraperitoneal-rat LD50 385 mg/kg PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Archives Internationales de Pharmacodynamie et de Therapie. Vol. 95, Pg. 123, 1953. oral-rat LDLo 500 mg/kg National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 22, 1953.
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
cosmetic agents
Recommendation for benzimidazole usage levels up to:
	not for fragrance use.

Recommendation for benzimidazole flavor usage levels up to:
	not for flavor use.

Safety references

European Food Safety Authority (EFSA) reference(s):

Reasoned opinion on the toxicological properties and maximum residue levels (MRLs) for the benzimidazole substances carbendazim and thiophanate-methyl
View page or View pdf

EPI System: View

ClinicalTrials.gov:search

Daily Med:search

Chemical Carcinogenesis Research Information System:Search

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA Substance Registry Services (TSCA):51-17-2

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :5798

National Institute of Allergy and Infectious Diseases:Data