1-benzylimidazole

Identification

Name
1-benzylimidazole
Accession Number
DB04581
Type
Small Molecule
Groups
Experimental
Description

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

Structure
Thumb
Synonyms
  • 1-Benzyl-1H-imidazole
  • N-Benzylimidazole
Categories
UNII
Not Available
CAS number
4238-71-5
Weight
Average: 158.1998
Monoisotopic: 158.08439833
Chemical Formula
C10H10N2
InChI Key
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutaminyl-peptide cyclotransferaseNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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
PubChem Compound
77918
PubChem Substance
46506844
ChemSpider
70309
BindingDB
7887
ChEMBL
CHEMBL14192
HET
1BN
PDB Entries
2afx / 3pb9
MSDS
Download (69.7 KB)

Clinical Trials

Clinical Trials
Not Available

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)68-70 °CPhysProp
boiling point (°C)310 °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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Download (7.94 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-9500000021-54b882fcb3841d682e6b

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-substituted imidazoles. These are heterocyclic compounds containing an imidazole ring substituted at position 1.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Imidazoles
Direct Parent
N-substituted imidazoles
Alternative Parents
Benzene and substituted derivatives / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
Benzenoid / N-substituted imidazole / Monocyclic benzene moiety / Heteroaromatic compound / Azacycle / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound / Aromatic heteromonocyclic compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not 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 a...
Gene Name
QPCT
Uniprot ID
Q16769
Uniprot Name
Glutaminyl-peptide cyclotransferase
Molecular Weight
40876.14 Da

Drug created on September 11, 2007 11:48 / Updated on December 01, 2017 15:29