NAV

1-benzylimidazole

Identification

Generic Name
1-benzylimidazole
DrugBank Accession Number
DB04581
Background

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

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 158.1998
Monoisotopic: 158.08439833
Chemical Formula
C10H10N2
Synonyms
  • 1-benzyl-1H-imidazole
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlutaminyl-peptide cyclotransferaseNot AvailableHumans
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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

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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.
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Acebutolol1-benzylimidazole may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with 1-benzylimidazole.
AlclofenacThe risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Alclofenac.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Monocyclic benzene moiety / N-substituted imidazole / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
W4C9Z5BCV7
CAS number
4238-71-5
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

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. [Article]
  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. [Article]
  3. Tuttle RS, Garcia-Minor C, Simon M: Cardiovascular effects of 1-benzylimidazole. J Pharmacol Exp Ther. 1975 Sep;194(3):624-32. [Article]
PubChem Compound
77918
PubChem Substance
46506844
ChemSpider
70309
BindingDB
7887
ChEMBL
CHEMBL14192
ZINC
ZINC000000169811
PDBe Ligand
1BN
PDB Entries
2afx / 3pb9 / 5s8m / 7d1d
MSDS
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Clinical Trials

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PhaseStatusPurposeConditionsCount

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)6.47Chemaxon
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)
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Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9300000000-e99503ac6cf14b4847f2
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0a59-2941000000-3faff0ef96c1702ba849
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-9500000021-54b882fcb3841d682e6b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-8550329fa4790ad2b722
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-da02d453c707d386640a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-0a33d5c4021ace3da0c6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pb9-0900000000-f4de72bcdbc9f24ca3ec
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-9000000000-a4b1ce55b369b4fd1207
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gb9-3900000000-c4fdfd8c84a6f2a8adf1
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]-136.6402567
predicted
DarkChem Lite v0.1.0
[M-H]-128.94899
predicted
DeepCCS 1.0 (2019)
[M+H]+137.7244567
predicted
DarkChem Lite v0.1.0
[M+H]+131.73573
predicted
DeepCCS 1.0 (2019)
[M+Na]+136.6474567
predicted
DarkChem Lite v0.1.0
[M+Na]+140.38078
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Glutaminyl-peptide cyclotransferase
Kind
Protein
Organism
Humans
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 at September 11, 2007 17:48 / Updated at June 12, 2020 16:52