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Identification
Name1-benzylimidazole
Accession NumberDB04581
TypeSmall Molecule
GroupsExperimental
Description

1-benzylimidazole, an N-imidazole derivative, has been shown to have strong cardiotonic activity.

Structure
Thumb
Synonyms
1-Benzyl-1H-imidazole
N-Benzylimidazole
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIINot Available
CAS number4238-71-5
WeightAverage: 158.1998
Monoisotopic: 158.08439833
Chemical FormulaC10H10N2
InChI KeyInChIKey=KKKDZZRICRFGSD-UHFFFAOYSA-N
InChI
InChI=1S/C10H10N2/c1-2-4-10(5-3-1)8-12-7-6-11-9-12/h1-7,9H,8H2
IUPAC Name
1-benzyl-1H-imidazole
SMILES
C(N1C=CN=C1)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
Direct ParentPhenylmethylamines
Alternative Parents
Substituents
  • Phenylmethylamine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9565
Blood Brain Barrier+0.983
Caco-2 permeable+0.6674
P-glycoprotein substrateNon-substrate0.7264
P-glycoprotein inhibitor INon-inhibitor0.9772
P-glycoprotein inhibitor IINon-inhibitor0.9044
Renal organic cation transporterInhibitor0.5285
CYP450 2C9 substrateNon-substrate0.8583
CYP450 2D6 substrateNon-substrate0.8724
CYP450 3A4 substrateNon-substrate0.8169
CYP450 1A2 substrateInhibitor0.7491
CYP450 2C9 inhibitorNon-inhibitor0.7615
CYP450 2D6 inhibitorInhibitor0.5463
CYP450 2C19 inhibitorNon-inhibitor0.5434
CYP450 3A4 inhibitorNon-inhibitor0.6991
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8173
Ames testAMES toxic0.836
CarcinogenicityNon-carcinogens0.9052
BiodegradationNot ready biodegradable0.7719
Rat acute toxicity2.4931 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8224
hERG inhibition (predictor II)Non-inhibitor0.8281
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point68-70 °CPhysProp
boiling point310 °CPhysProp
logP1.60AVDEEF,A (1993)
pKa6.7AVDEEF,A (1993)
Predicted Properties
PropertyValueSource
Water Solubility1.47 mg/mLALOGPS
logP1.58ALOGPS
logP1.8ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)6.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.82 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.52 m3·mol-1ChemAxon
Polarizability17.07 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.94 KB)
SpectraNot Available
References
Synthesis Reference

Natsuo Sawa, Takeshi Masuda, Shozo Miura, Naoki Kano, Kazuo Kamagata, Masayuki Ito, “Process for preparation of 1-benzylimidazole compound.” U.S. Patent US5021584, issued June 04, 1991.

US5021584
General References
  1. Mori Y, Iimura K, Hirano K: N-benzylimidazole, a potent inducer of rat liver enzymes involved in mutagenic activation of various carcinogens. Mutat Res. 1993 Jun;302(2):129-33. [PubMed:7684507 ]
  2. Lucas J, Chan PS, Mateja N, Cervoni P, Ronsberg MA, Lipchuck LM: 1-Benzylimidazole, a thromboxane synthetase inhibitor acutely lowers blood pressure mainly by alpha-adrenoceptor blockade in spontaneously hypertensive rats (SHR). Prostaglandins Leukot Med. 1983 Dec;12(4):409-21. [PubMed:6142461 ]
  3. Tuttle RS, Garcia-Minor C, Simon M: Cardiovascular effects of 1-benzylimidazole. J Pharmacol Exp Ther. 1975 Sep;194(3):624-32. [PubMed:1159635 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (69.7 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Responsible for the biosynthesis of pyroglutamyl peptides. Has a bias against acidic and tryptophan residues adjacent to the N-terminal glutaminyl residue and a lack of importance of chain length after the second residue. Also catalyzes N-terminal pyroglutamate formation. In vitro, catalyzes pyroglutamate formation of N-terminally truncated form of APP amyloid-beta peptides [Glu-3]-beta-amyloid...
Gene Name:
QPCT
Uniprot ID:
Q16769
Molecular Weight:
40876.14 Da
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Drug created on September 11, 2007 11:48 / Updated on August 17, 2016 12:24