Benzimidazole

Identification

Generic Name
Benzimidazole
DrugBank Accession Number
DB02962
Background

Not Available

Type
Small Molecule
Groups
Experimental, Investigational
Structure
Weight
Average: 118.1359
Monoisotopic: 118.053098202
Chemical Formula
C7H6N2
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferaseNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
Not Available
Direct Parent
Benzimidazoles
Alternative Parents
Benzenoids / Imidazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzimidazole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Organic nitrogen compound / Organonitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
benzimidazole, polycyclic heteroarene (CHEBI:41275) / a small molecule (BENZIMIDAZOLE)
Affected organisms
Not Available

Chemical Identifiers

UNII
E24GX49LD8
CAS number
51-17-2
InChI Key
HYZJCKYKOHLVJF-UHFFFAOYSA-N
InChI
InChI=1S/C7H6N2/c1-2-4-7-6(3-1)8-5-9-7/h1-5H,(H,8,9)
IUPAC Name
1H-1,3-benzodiazole
SMILES
N1C=NC2=CC=CC=C12

References

Synthesis Reference

Aime Joseph Arsac, Pierre Frank, "Process for making 2-(4'-aminophenyl) 5-amino benzimidazole." U.S. Patent US4109093, issued 1893.

US4109093
General References
Not Available
KEGG Compound
C02009
PubChem Compound
5798
PubChem Substance
46508614
ChemSpider
5593
BindingDB
7939
RxNav
1362885
ChEBI
41275
ChEMBL
CHEMBL306226
ZINC
ZINC000000331902
PDBe Ligand
BZI
Wikipedia
Benzimidazole
PDB Entries
1kxm / 1l5f / 1ryc / 4dsu / 4hpx / 4nve / 4xv5 / 4xva / 5k1l / 5phk
show 5 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentDrug Resistance / Helminths Infection1
Not AvailableCompletedSupportive CareAlveolar Echinococcosis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)170.5 °CPhysProp
boiling point (°C)>360 °CPhysProp
water solubility2010 mg/L (at 20 °C)PEARLMAN,RS ET AL. (1984)
logP1.32HANSCH,C ET AL. (1995)
pKa5.3 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility17.0 mg/mLALOGPS
logP1.67ALOGPS
logP1.26Chemaxon
logS-0.84ALOGPS
pKa (Strongest Acidic)12.25Chemaxon
pKa (Strongest Basic)5.79Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area28.68 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity34.97 m3·mol-1Chemaxon
Polarizability12.21 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9967
Blood Brain Barrier+0.9786
Caco-2 permeable-0.7338
P-glycoprotein substrateNon-substrate0.7182
P-glycoprotein inhibitor INon-inhibitor0.9582
P-glycoprotein inhibitor IINon-inhibitor0.9557
Renal organic cation transporterNon-inhibitor0.7847
CYP450 2C9 substrateNon-substrate0.8587
CYP450 2D6 substrateNon-substrate0.9037
CYP450 3A4 substrateNon-substrate0.8284
CYP450 1A2 substrateInhibitor0.6295
CYP450 2C9 inhibitorNon-inhibitor0.7881
CYP450 2D6 inhibitorNon-inhibitor0.7732
CYP450 2C19 inhibitorNon-inhibitor0.6999
CYP450 3A4 inhibitorNon-inhibitor0.7951
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6663
Ames testNon AMES toxic0.7738
CarcinogenicityNon-carcinogens0.9529
BiodegradationNot ready biodegradable0.8487
Rat acute toxicity2.3190 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9459
hERG inhibition (predictor II)Non-inhibitor0.952
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-a748760e317519d35edb
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-237aaedc281a7c6869af
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-d19bf07c42eb46d0bdc2
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-3900000000-ec0018fe194a581ffd72
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00kf-9300000000-4dbba5feb460aad64125
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0900000000-ad44ad5a59274045d611
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0900000000-e13078ed71220f011c2d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-4900000000-aaf85c7703530656ac3b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014l-9200000000-db09859cc86d414cc704
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-ec3b4c31062d629a0e89
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-c202fec2faf3ae48abc5
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-52d1a9a5355bc378ce3a
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-16431851c6c511b8d416
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-966741cba5b2d1aca700
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-617c630f2de78c87d130
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-4ca0c3738d04b209f461
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-2900000000-3fd0f394d6fe39aaae0a
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-5900000000-82aeab4fa1e6b14e1abd
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014l-9500000000-4db723cb3bf3c8c453d9
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-014i-9200000000-2f1f1f2bd0631421dc22
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-7da2d3e52636ea8c8bf1
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-b8c5326e8d974f5bf6ff
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-b8c5326e8d974f5bf6ff
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-b8c5326e8d974f5bf6ff
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-b8c5326e8d974f5bf6ff
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-762607d8f21784e4109a
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-65cf4c18e545ae77303a
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-b4ae6114cabd67f948e8
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-0e56e36335a479aee5de
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-ceb364cfb6bf981d96cd
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-2900000000-d41b37ced0ce9ccaecf0
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014i-4900000000-48d04c98a03ef812bcad
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-014l-8900000000-125a3354549e1a353c49
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-00kf-9400000000-e66ec268c94c020163a5
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-bd88b80667e7579ea2d2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-285bdd446d18b97b82f6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-71703b0a894ead0ffed5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-1315874f582e807f48e3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-1900000000-9ba01b0d14ded4a9e582
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-1900000000-24295fbd7ac1feedece8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-0f33aeec091742b9b487
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-117.3302436
predicted
DarkChem Lite v0.1.0
[M-H]-117.1948436
predicted
DarkChem Lite v0.1.0
[M-H]-118.78081
predicted
DeepCCS 1.0 (2019)
[M+H]+118.5293436
predicted
DarkChem Lite v0.1.0
[M+H]+118.5655436
predicted
DarkChem Lite v0.1.0
[M+H]+121.58701
predicted
DeepCCS 1.0 (2019)
[M+Na]+117.8110436
predicted
DarkChem Lite v0.1.0
[M+Na]+130.12584
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Nicotinate-nucleotide-dimethylbenzimidazole phosphoribosyltransferase activity
Specific Function
Catalyzes the synthesis of alpha-ribazole-5'-phosphate from nicotinate mononucleotide (NAMN) and 5,6-dimethylbenzimidazole (DMB).
Gene Name
cobT
Uniprot ID
Q05603
Uniprot Name
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase
Molecular Weight
36612.305 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52