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
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
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
The theory and application of transition state pK(a) values: the reaction of papain with a series of trimethylene disulphide reactivity probes.	2001 Apr 21	11319891
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
Histamine H1 and H2 receptor antagonists accelerate skin barrier repair and prevent epidermal hyperplasia induced by barrier disruption in a dry environment.	2001 Feb	11180002
Hydrogen peroxide acts as a second messenger for the induction of defense genes in tomato plants in response to wounding, systemin, and methyl jasmonate.	2001 Jan	11158538
Haem-linked interactions in horseradish peroxidase revealed by spectroscopic analysis of the Phe-221-->Met mutant.	2001 Jan 15	11139379
Solution structure and dynamic character of the histidine-containing phosphotransfer domain of anaerobic sensor kinase ArcB from Escherichia coli.	2001 Jan 16	11148031
A new C-nucleoside analogue of tiazofurin: synthesis and biological evaluation of 2-beta-D-ribofuranosylimidazole-4-carboxamide (imidazofurin).	2001 Jan 8	11140736
Selective adenosine A2A receptor antagonists.	2001 Jan-Feb	11347973
Synthesis and characterization of polyamine-based biomimetic catalysts as artificial ribonuclease.	2001 Jan-Feb	11303558
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
Molecular modeling study of beta- and gamma-cyclodextrin complexes with miconazole.	2001 Jun	11384849
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
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
Characterization of carbonic anhydrase from Neisseria gonorrhoeae.	2001 Mar	11248679
A novel series of thromboxane A2 synthetase inhibitors with free radical scavenging and anti-peroxidative activities.	2001 May	11383607
Contact imidazole activity against resistant bacteria and fungi.	2001 May	11337226
Inner-sphere reorganization energy of iron-sulfur clusters studied with theoretical methods.	2001 May 21	11350228
A theoretical prediction of potentially observable lithium compounds with planar tetracoordinate carbons.	2001 May 3	11348206

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