IMIDAZOLE OXOGLURATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H6O5.C3H4N2
Molecular Weight	214.1754
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N1C=CN=C1.OC(=O)CCC(=O)C(O)=O

InChI

InChIKey=BGCSODZZSVSCEN-UHFFFAOYSA-N

InChI=1S/C5H6O5.C3H4N2/c6-3(5(9)10)1-2-4(7)8;1-2-5-3-4-1/h1-2H2,(H,7,8)(H,9,10);1-3H,(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

Molecular Formula	C5H6O5
Molecular Weight	146.0981
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
Enzymatic active site of caspase-activated DNase (CAD) and its inhibition by inhibitor of CAD.	2001 Apr 1	11361146
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
Quantitation of rate enhancements attained by the binding of cobalamin to methionine synthase.	2001 Apr 24	11305922
Syntheses of the first amine-dicarboxyboranes and their bis(methylester) and bis(N-ethylamide) derivatives.	2001 Apr 9	11312731
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
Replacement of the axial histidine ligand with imidazole in cytochrome c peroxidase. 1. Effects on structure.	2001 Feb 6	11170452
Two 1-substituted 4-nitroimidazoles.	2001 Jan	11173416
Thermosensitive copolymers of N-vinylimidazole as displacers of proteins in immobilised metal affinity chromatography.	2001 Jan 12	11217018
Molecular modeling of the mechanochemical triggering mechanism for catalysis of carbon-cobalt bond homolysis in coenzyme B12.	2001 Jan 15	11237251
Single-run capillary electrophoretic determination of inorganic nitrogen species in rainwater.	2001 Jan 15	11199976
A new C-nucleoside analogue of tiazofurin: synthesis and biological evaluation of 2-beta-D-ribofuranosylimidazole-4-carboxamide (imidazofurin).	2001 Jan 8	11140736
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
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
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
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
Expanding the recognition of the minor groove of DNA by incorporation of beta-alanine in hairpin polyamides.	2001 Mar	11310600
Development and application of a sensitive and rapid immunoassay for the quantitation of N7-methyldeoxyguanosine in DNA samples.	2001 Mar	11258978
Optimization of force constants with an Urey-Bradley force field avoiding normal mode crossings.	2001 Mar 1	11300565
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
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
A theoretical prediction of potentially observable lithium compounds with planar tetracoordinate carbons.	2001 May 3	11348206
Coordination chemistry of the heme in cystathionine beta-synthase: formation of iron(II)-isonitrile complexes.	2001 May 4	11327727

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 `Sat Dec 16 09:57:36 GMT 2023` Edited by `admin` on `Sat Dec 16 09:57:36 GMT 2023`
Record UNII	79OF266LXF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IMIDAZOLE OXOGLURATE

Common Name

English

PENTANEDIOIC ACID, 2-OXO-, COMPD. WITH 1H-IMIDAZOLE

Common Name

English

1H-IMIDAZOLE, 2-OXOPENTANEDIOATE (1:1)

Systematic Name

English

IMIDAZOLE .ALPHA.-KETOGLUTARATE

Common Name

English

1H-IMIDAZOLE, 2-OXOPENTANEDIOATE

Systematic Name

English

IMIDAZOLE 2-OXOGLUTARATE

Systematic Name

English

PENTANEDIOIC ACID, 2-OXO-, COMPD. WITH 1H-IMIDAZOLE (1:1)

Systematic Name

English

IMIDAZOLE OXOGLURATE [MART.]

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

279-783-8