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 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
Bactericidal and inhibitory effects of azole antifungal compounds on Mycobacterium smegmatis.	2000 Nov 15	11064188
Biosynthesis of riboflavin.	2001	11153262
Sequence recognition of DNA by lexitropsins.	2001 Apr	11281838
Novel non-peptide ligands for the somatostatin sst3 receptor.	2001 Apr 23	11327607
Antifungal and immunomodulating activities of 1,4-benzothiazine azole derivatives: review.	2001 Feb	11233807
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
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
Olive fruit cell wall: degradation of pectic polysaccharides during ripening.	2001 Jan	11170606
Studies of the chemical selectivity of hapten, reactivity, and skin sensitization potency. 1. Synthesis and studies on the reactivity toward model nucleophiles of the (13)C-labeled skin sensitizers hex-1-ene- and hexane-1,3-sultones.	2001 Jan	11170514
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
Structures of prolyl oligopeptidase substrate/inhibitor complexes. Use of inhibitor binding for titration of the catalytic histidine residue.	2001 Jan 12	11031266
Haem-linked interactions in horseradish peroxidase revealed by spectroscopic analysis of the Phe-221-->Met mutant.	2001 Jan 15	11139379
Ring opening is not rate-limiting in the GTP cyclohydrolase I reaction.	2001 Jan 26	11056154
Histidylated polylysine as DNA vector: elevation of the imidazole protonation and reduced cellular uptake without change in the polyfection efficiency of serum stabilized negative polyplexes.	2001 Jan-Feb	11170371
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
Effect of zinc ion on the inhibition of carboxypeptidase A by imidazole-bearing substrate analogues.	2001 Jun 4	11378369
Detection of biomolecules in electrophoresis gels with salts of imidazole and zinc II: a decade of research.	2001 Mar	11332754
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
Analysis of alcohols, as dimethylglycine esters, by electrospray ionization tandem mass spectrometry.	2001 Mar	11312519
Interaction of metal ions with lupin seed conglutin gamma.	2001 Mar	11281129
RNase activity of a DNA minor groove binder with a minimalist catalytic motif from RNase A.	2001 Mar	11243875
Optimization of force constants with an Urey-Bradley force field avoiding normal mode crossings.	2001 Mar 1	11300565
Inner-sphere reorganization energy of iron-sulfur clusters studied with theoretical methods.	2001 May 21	11350228
Substrate binding is the rate-limiting step in thromboxane synthase catalysis.	2001 May 4	11297515

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 `Fri Dec 15 22:07:15 GMT 2023` Edited by `admin` on `Fri Dec 15 22:07:15 GMT 2023`
Record UNII	7GBN705NH1
Record Status	`Validated (UNII)`
Record Version

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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