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
Heterocyclic HIV-1 protease inhibitors.	1999 Jul 29	10822561
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
New antimetastatic hypoxic cell radiosensitizers: design, synthesis, and biological activities of 2-nitroimidazole-acetamide, TX-1877, and its analogues.	2001 Feb	11249137
Amaryllidaceae, Sceletium, imidazole, oxazole, thiazole, peptide and miscellaneous alkaloids.	2001 Feb	11245403
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
Inhibition of neuronal nitric oxide synthase by N-phenacyl imidazoles.	2001 Feb	11178934
Structure of copper(II)-histidine based complexes in frozen aqueous solutions as determined from high-field pulsed electron nuclear double resonance.	2001 Feb 12	11225123
Cs(2) fixation by carbonic anhydrase model systems-a new substrate in the catalytic cycle.	2001 Feb 26	11259012
Replacement of the axial histidine ligand with imidazole in cytochrome c peroxidase. 2. Effects on heme coordination and function.	2001 Feb 6	11170453
Replacement of the axial histidine ligand with imidazole in cytochrome c peroxidase. 1. Effects on structure.	2001 Feb 6	11170452
Olive fruit cell wall: degradation of pectic polysaccharides during ripening.	2001 Jan	11170606
Solution structure and dynamic character of the histidine-containing phosphotransfer domain of anaerobic sensor kinase ArcB from Escherichia coli.	2001 Jan 16	11148031
Ring opening is not rate-limiting in the GTP cyclohydrolase I reaction.	2001 Jan 26	11056154
[Drug-induced taste disorders: analysis of the French Pharmacovigilance Database and literature review].	2001 Jan-Feb	11322016
Reaction of nitric oxide with synthetic hemoprotein, human serum albumin incorporating tetraphenylporphinatoiron(II) derivatives.	2001 Jan-Feb	11170368
Influence of imidazole replacement in different structural classes of histamine H(3)-receptor antagonists.	2001 Jun	11384847
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
Detection of biomolecules in electrophoresis gels with salts of imidazole and zinc II: a decade of research.	2001 Mar	11332754
Analysis of alcohols, as dimethylglycine esters, by electrospray ionization tandem mass spectrometry.	2001 Mar	11312519
Expanding the recognition of the minor groove of DNA by incorporation of beta-alanine in hairpin polyamides.	2001 Mar	11310600
A new class of nonsteroidal aromatase inhibitors: design and synthesis of chromone and xanthone derivatives and inhibition of the P450 enzymes aromatase and 17 alpha-hydroxylase/C17,20-lyase.	2001 Mar 1	11262078
Catalytic efficiency and sequence selectivity of a restriction endonuclease modulated by a distal manganese ion binding site.	2001 Mar 2	11243793
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
Inner-sphere reorganization energy of iron-sulfur clusters studied with theoretical methods.	2001 May 21	11350228
Flash vacuum pyrolysis over solid catalysts. 1. Pyrazoles over zeolites.	2001 May 4	11325258

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