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

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 8297
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 1430
autophagy 17 Target ID: GO:0006914 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25422052	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9679284	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Synergy of lysozyme and lanoconazole on the morphology of Candida albicans.	2001	11291959
Biophysical analysis of natural, double-helical DNA modified by anticancer heterocyclic complexes of ruthenium(III) in cell-free media.	2001 Apr	11372202
Chemical and biological prerequisites for novel bisphosphonate molecules: results of comparative preclinical studies.	2001 Apr	11346859
The enhancement of riboflavin-mediated photo-oxidation of doxorubicin by histidine and urocanic acid.	2001 Apr	11345651
1:2 Complexes of chloranilic acid with pyrazole and imidazole, and the acetonitrile solvate of a 1:1 complex with imidazole.	2001 Apr	11313599
Azole. 45(1). Uber 2,4-Dinitrophenylhydrazone von Morpholinonitroimidazolderivaten.	2001 Apr	11313595
Inhibition of the acute effects of angiotensin II by the receptor antagonist irbesartan in normotensive men.	2001 Apr	11300658
Sequence recognition of DNA by lexitropsins.	2001 Apr	11281838
Structures of Escherichia coli histidinol-phosphate aminotransferase and its complexes with histidinol-phosphate and N-(5'-phosphopyridoxyl)-L-glutamate: double substrate recognition of the enzyme.	2001 Apr 17	11294630
Fmoc solid phase synthesis of polyamides containing pyrrole and imidazole amino acids.	2001 Apr 19	11348194
Quantitation of rate enhancements attained by the binding of cobalamin to methionine synthase.	2001 Apr 24	11305922
Affinity chromatography of polyhistidine tagged enzymes. New dextran-coated immobilized metal ion affinity chromatography matrices for prevention of undesired multipoint adsorptions.	2001 Apr 27	11358266
Evidence for an essential histidine residue in the ascorbate-binding site of cytochrome b561.	2001 Apr 3	11300772
Polymer versus monomer as displacer in immobilized metal affinity chromatography.	2001 Apr 5	11334341
Polynucleating open-chain systems with imidazole and proton-ionizable 1,2,4-triazole structural motifs.	2001 Apr 6	11281768
Syntheses of the first amine-dicarboxyboranes and their bis(methylester) and bis(N-ethylamide) derivatives.	2001 Apr 9	11312731
An essential role of active site arginine residue in iodide binding and histidine residue in electron transfer for iodide oxidation by horseradish peroxidase.	2001 Feb	11330823
Inhibitors of leukotriene A4 (LTA4) hydrolase as potential anti-inflammatory agents.	2001 Feb	11311111
Oxidations of N(omega)-hydroxyarginine analogues and various N-hydroxyguanidines by NO synthase II: key role of tetrahydrobiopterin in the reaction mechanism and substrate selectivity.	2001 Feb	11258969
New antimetastatic hypoxic cell radiosensitizers: design, synthesis, and biological activities of 2-nitroimidazole-acetamide, TX-1877, and its analogues.	2001 Feb	11249137
Mechanistic features and structure of the nitrogenase alpha-Gln195 MoFe protein.	2001 Feb 13	11327812
Short-strong hydrogen bonds and a low barrier transition state for the proton transfer reaction in RNase A catalysis: a quantum chemical study.	2001 Feb 15	11254205
An examination of the purported reverse anomeric effect beyond acetylated N-xylosyl- and N-glucosylimidazoles.	2001 Feb 23	11312934
Cs(2) fixation by carbonic anhydrase model systems-a new substrate in the catalytic cycle.	2001 Feb 26	11259012
In-situ FTIR study on adsorption and oxidation of native and thermally denatured calf thymus DNA at glassy carbon electrodes.	2001 Jan 31	11246748
Selective adenosine A2A receptor antagonists.	2001 Jan-Feb	11347973
Thermodynamic and multinuclear magnetic resonance study of dimethyltin (IV) complexes with some imidazoles in aqueous solutions.	2001 Jan-Feb	11329772
Functionalized biopolymers as soluble macromolecular chelating agents.	2001 Jan-Feb	11329763
[Drug-induced taste disorders: analysis of the French Pharmacovigilance Database and literature review].	2001 Jan-Feb	11322016
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 Jul 20	11346639
Kinetic and mechanistic studies of prolyl oligopeptidase from the hyperthermophile Pyrococcus furiosus.	2001 Jun 1	11278687
Synthesis of primary aromatic amides by aminocarbonylation of aryl halides using formamide as an ammonia synthon.	2001 Jun 15	11397169
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 Jun 20	11403599
Investigations of new lead structures for the design of selective estrogen receptor modulators.	2001 Jun 7	11384241
Sequence-specific recognition of DNA in the nucleosome by pyrrole-imidazole polyamides.	2001 Jun 8	11397084
Identification of catalytically active groups of Penicillium canescens F-436 beta-galactosidase.	2001 Mar	11333160
Detection of biomolecules in electrophoresis gels with salts of imidazole and zinc II: a decade of research.	2001 Mar	11332754
Formation of mu-oxo dimer by the reaction of (meso-tetraphenylporphyrinato)iron(III) with various imidazoles.	2001 Mar	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 Mar	11315565
Interaction of metal ions with lupin seed conglutin gamma.	2001 Mar	11281129
Characterization of carbonic anhydrase from Neisseria gonorrhoeae.	2001 Mar	11248679
Optimization of force constants with an Urey-Bradley force field avoiding normal mode crossings.	2001 Mar 1	11300565
Probing the influence of local coordination environment on the properties of Fe-type nitrile hydratase model complexes.	2001 Mar 26	11261975
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 May	11358494
Contact imidazole activity against resistant bacteria and fungi.	2001 May	11337226
Short, strong hydrogen bonds at the active site of human acetylcholinesterase: proton NMR studies.	2001 May 15	11341833
Protonation of histidine and histidine-tryptophan interaction in the activation of the M2 ion channel from influenza a virus.	2001 May 22	11352741
Coordination chemistry of the heme in cystathionine beta-synthase: formation of iron(II)-isonitrile complexes.	2001 May 4	11327727
Substrate binding is the rate-limiting step in thromboxane synthase catalysis.	2001 May 4	11297515
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 May 7	11354358

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.

Name

Type

Language

IMIDAZOLE

Official Name

English

NSC-60522

Code

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 [INCI]

Common 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