Imidazole

Details

Stereochemistry	ACHIRAL
Molecular Formula	C3H4N2
Molecular Weight	68.0773
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N1C=CN=C1

InChI

InChIKey=RAXXELZNTBOGNW-UHFFFAOYSA-N

InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)

HIDE SMILES / InChI

Molecular Formula	C3H4N2
Molecular Weight	68.0773
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.imedpub.com/articles/imidazole-and-its-biological-activities-a-review.pdf
Curator's Comment: Description was created based on several sources, including https://www.hindawi.com/journals/jchem/2013/329412/ | http://www.inchem.org/documents/sids/sids/288324.pdf

Imidazole is a planer five-member heterocyclic ring with 3C and 2N atom and in ring N is present in 1st and 3rd positions. The imidazole ring is a constituent of several important natural products, including purine, histamine, histidine and nucleic acid. Being a polar and ionisable aromatic compound, it improves pharmacokinetic characteristics of lead molecules and thus used as a remedy to optimize solubility and bioavailability parameters of proposed poorly soluble lead molecules. The imidazole derivatives possess extensive spectrum of biological activities such as antibacterial, anticancer, antitubercular, antifungal, analgesic, and anti-HIV activities. The organic compound is used in the chemical industry as an intermediate in the production of pharmaceuticals, pesticides, dye intermediates, auxiliaries for textile dyeing and finishing, photographic chemicals and corrosion inhibitors. The chemical possesses properties (corrosivity to skin, irreversible damage to eyes, teratogenic effects) indicating a hazard for human health. Humans are exposed by consumer products (chemical concentrations up to 10%) and at the workplace. Therefore, the chemical is a candidate for further work. An exposure assessment and if indicated a risk assessment is recommended.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
cell migration 3 Target ID: GO:0016477 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20604839	Inhibitor 8504
execution phase of apoptosis 3 Target ID: GO:0097194 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12370494 \| https://www.ncbi.nlm.nih.gov/pubmed/25422052	Activator 1447
autophagy 17 Target ID: GO:0006914 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25422052	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9679284	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Mutational and kinetic evaluation of conserved His-123 in dual specificity protein-tyrosine phosphatase vaccinia H1-related phosphatase: participation of Tyr-78 and Thr-73 residues in tuning the orientation of His-123.	2001-07-20	11346639
A quantum chemical survey of metalloporphyrin-nitrosyl linkage isomers: insights into the observation of multiple FeNO conformations in a recent crystallographic determination of nitrophorin 4.	2001-06-20	11403599
Synthesis of primary aromatic amides by aminocarbonylation of aryl halides using formamide as an ammonia synthon.	2001-06-15	11397169
Sequence-specific recognition of DNA in the nucleosome by pyrrole-imidazole polyamides.	2001-06-08	11397084
Investigations of new lead structures for the design of selective estrogen receptor modulators.	2001-06-07	11384241
Effect of zinc ion on the inhibition of carboxypeptidase A by imidazole-bearing substrate analogues.	2001-06-04	11378369
Molecular modeling study of beta- and gamma-cyclodextrin complexes with miconazole.	2001-06	11384849
Influence of imidazole replacement in different structural classes of histamine H(3)-receptor antagonists.	2001-06	11384847
High efficiency of 5-aminolevulinate-photodynamic treatment using UVA irradiation.	2001-06	11375893
Pharmacological enhancement of synaptic efficacy, spatial learning, and memory through carbonic anhydrase activation in rats.	2001-06	11356917
Protonation of histidine and histidine-tryptophan interaction in the activation of the M2 ion channel from influenza a virus.	2001-05-22	11352741
Inner-sphere reorganization energy of iron-sulfur clusters studied with theoretical methods.	2001-05-21	11350228
Short, strong hydrogen bonds at the active site of human acetylcholinesterase: proton NMR studies.	2001-05-15	11341833
Selective adenosine A2A receptor antagonists.	2001-05-12	11347973
Phenoxypyrimidine inhibitors of p38alpha kinase: synthesis and statistical evaluation of the p38 inhibitory potencies of a series of 1-(piperidin-4-yl)-4-(4-fluorophenyl)-5-(2-phenoxypyrimidin-4-yl) imidazoles.	2001-05-07	11354358
Coordination chemistry of the heme in cystathionine beta-synthase: formation of iron(II)-isonitrile complexes.	2001-05-04	11327727
Flash vacuum pyrolysis over solid catalysts. 1. Pyrazoles over zeolites.	2001-05-04	11325258
A theoretical prediction of potentially observable lithium compounds with planar tetracoordinate carbons.	2001-05-03	11348206
Thermodynamic and multinuclear magnetic resonance study of dimethyltin (IV) complexes with some imidazoles in aqueous solutions.	2001-05-02	11329772
Functionalized biopolymers as soluble macromolecular chelating agents.	2001-05-02	11329763
A novel series of thromboxane A2 synthetase inhibitors with free radical scavenging and anti-peroxidative activities.	2001-05	11383607
Probing the binding site of 800-nm bacteriochlorophyll in the membrane-linked LH2 protein of Rhodobacter capsulatus by local unfolding and chemical modification: evidence for the involvement of a betaHis20 residue.	2001-05	11358494
Contact imidazole activity against resistant bacteria and fungi.	2001-05	11337226
Affinity chromatography of polyhistidine tagged enzymes. New dextran-coated immobilized metal ion affinity chromatography matrices for prevention of undesired multipoint adsorptions.	2001-04-27	11358266
[Drug-induced taste disorders: analysis of the French Pharmacovigilance Database and literature review].	2001-04-27	11322016
Quantitation of rate enhancements attained by the binding of cobalamin to methionine synthase.	2001-04-24	11305922
Novel non-peptide ligands for the somatostatin sst3 receptor.	2001-04-23	11327607
The theory and application of transition state pK(a) values: the reaction of papain with a series of trimethylene disulphide reactivity probes.	2001-04-21	11319891
Fmoc solid phase synthesis of polyamides containing pyrrole and imidazole amino acids.	2001-04-19	11348194
Synthesis and characterization of polyamine-based biomimetic catalysts as artificial ribonuclease.	2001-04-17	11303558
Evaluation of immobilized metal affinity chromatography for purification of penicillin acylase.	2001-04-15	11318408
Syntheses of the first amine-dicarboxyboranes and their bis(methylester) and bis(N-ethylamide) derivatives.	2001-04-09	11312731
Polymer versus monomer as displacer in immobilized metal affinity chromatography.	2001-04-05	11334341
Enzymatic active site of caspase-activated DNase (CAD) and its inhibition by inhibitor of CAD.	2001-04-01	11361146
Biophysical analysis of natural, double-helical DNA modified by anticancer heterocyclic complexes of ruthenium(III) in cell-free media.	2001-04	11372202
Chemical and biological prerequisites for novel bisphosphonate molecules: results of comparative preclinical studies.	2001-04	11346859
The enhancement of riboflavin-mediated photo-oxidation of doxorubicin by histidine and urocanic acid.	2001-04	11345651
1:2 Complexes of chloranilic acid with pyrazole and imidazole, and the acetonitrile solvate of a 1:1 complex with imidazole.	2001-04	11313599
[Azole. 45(1). Uber 2,4-Dinitrophenylhydrazone von Morpholinonitroimidazolderivaten].	2001-04	11313595
Identification of catalytically active groups of Penicillium canescens F-436 beta-galactosidase.	2001-03	11333160
Detection of biomolecules in electrophoresis gels with salts of imidazole and zinc II: a decade of research.	2001-03	11332754
Formation of mu-oxo dimer by the reaction of (meso-tetraphenylporphyrinato)iron(III) with various imidazoles.	2001-03	11330473
Hydrolysis of the tumor-inhibiting ruthenium(III) complexes HIm trans-[RuCl4(im)2] and HInd trans-[RuCl4(ind)2] investigated by means of HPCE and HPLC-MS.	2001-03	11315565
Analysis of alcohols, as dimethylglycine esters, by electrospray ionization tandem mass spectrometry.	2001-03	11312519
Expanding the recognition of the minor groove of DNA by incorporation of beta-alanine in hairpin polyamides.	2001-03	11310600
An examination of the purported reverse anomeric effect beyond acetylated N-xylosyl- and N-glucosylimidazoles.	2001-02-23	11312934
Mechanistic features and structure of the nitrogenase alpha-Gln195 MoFe protein.	2001-02-13	11327812
An essential role of active site arginine residue in iodide binding and histidine residue in electron transfer for iodide oxidation by horseradish peroxidase.	2001-02	11330823
Synthesis of a set of ethyl 1-carbamoyl-3-oxoquinoxaline-2-carboxylates and of their constrained analogue imidazo.	2001-02	11311751
Inhibitors of leukotriene A4 (LTA4) hydrolase as potential anti-inflammatory agents.	2001-02	11311111

Patents

Sample Use Guides

In Vivo Use Guide

The pharmacokinetic parameters were determined in human studies with ITF 182 in single (248 mg of imidazole) and multiple dose (3 single doses per day) studies. The main pharmacokinetic parameters in humans after oral intake may be summarized as follows: maximum plasma levels were reached after approx. 3 hours, elimination half-life was approx. 1.8 to 3 hours. Bioavailability was complete. Protein binding was determined to range between 5 to 15 %. In contrast, no effects were noted in a pilot study after dermal application Imidazole is of moderate oral toxicity in a scientifically valid study. LD50 in rats was determined to be 960 - 970 mg/kg bw.

Route of Administration: Oral

In Vitro Use Guide

Imidazole did not exhibit cytotoxic effects on B16 cells at a concentration below 100 uM. Imidazole inhibits B16 cell migration through beta-catenin degradation.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:24:05 GMT 2025` Edited by `admin` on `Mon Mar 31 20:24:05 GMT 2025`
Record UNII	7GBN705NH1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-60522

Preferred Name

English

Imidazole

Official Name

English

ENALAPRIL MALEATE IMPURITY I [EP IMPURITY]

Common Name

English

1H-IMIDAZOLE

Systematic Name

English

CLOTRIMAZOLE IMPURITY D [EP IMPURITY]

Common Name

English

ONDANSETRON HYDROCHLORIDE IMPURITY, IMIDAZOLE- [USP IMPURITY]

Common Name

English

SILDENAFIL CITRATE IMPURITY E [EP IMPURITY]

Common Name

English

FLUTRIMAZOLE IMPURITY A [EP IMPURITY]

Systematic Name

English

IMIDAZOLE [MI]

Common Name

English

ENALAPRIL IMPURITY I

Common Name

English

Imidazole [WHO-DD]

Common Name

English

IMIDAZOLE [USP-RS]

Common Name

English

ONDANSETRON HYDROCHLORIDE DIHYDRATE IMPURITY E [EP IMPURITY]

Common Name

English

Code System Code Type Description

DAILYMED

7GBN705NH1