IMIDAZENIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H12BrFN4O
Molecular Weight	399.216
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)C1=C2CN=C(C3=CC=CC=C3Br)C4=CC(F)=CC=C4N2C=N1

InChI

InChIKey=OCJHYHKWUWSHEN-UHFFFAOYSA-N

InChI=1S/C18H12BrFN4O/c19-13-4-2-1-3-11(13)16-12-7-10(20)5-6-14(12)24-9-23-17(18(21)25)15(24)8-22-16/h1-7,9H,8H2,(H2,21,25)

HIDE SMILES / InChI

Molecular Formula	C18H12BrFN4O
Molecular Weight	399.216
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8669126
Curator's Comment: description was created based on several sources, including: http://www.wikidoc.org/index.php/Imidazenil | http://adisinsight.springer.com/drugs/800005625

Imidazenil is an imidazo-benzodiazepine derivative with high intrinsic efficacy and selectivity for α2-, α3-, and α5- but low intrinsic efficacy for α1-containing GABA(A) receptors. It has an unusual profile of effects, producing some of the effects associated with normal benzodiazepines such as anticonvulsant and anxiolytic effects, yet without any notable sedative or amnestic effects. It has been suggested as a safe and effective treatment for anxiety, a potent yet non-sedating anticonvulsant and as a novel treatment for schizophrenia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8394902 \| https://www.ncbi.nlm.nih.gov/pubmed/21097996	Positive Allosteric Modulator 179		50.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Cocaine addiction 28 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9765322	Primary	Preclinical	Unknown Approved Use Unknown
Epilepsy 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8646409 https://www.ncbi.nlm.nih.gov/pubmed/21903116	Primary	Preclinical	Unknown Approved Use Unknown
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7714771	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Imidazenil, a new partial agonist of benzodiazepine receptors, reverses the inhibitory action of isoniazid and stress on gamma-aminobutyric acidA receptor function.	1994 Apr	8169838
Antagonism of isoniazid-induced convulsions by abecarnil in mice tolerant to diazepam.	1995 Oct	8577786
GABAA receptors and benzodiazepines: a role for dendritic resident subunit mRNAs.	2002 Nov	12423662
Relation between discriminative and reinforcing effects of midazolam, pentobarbital, chlordiazepoxide, zolpidem, and imidazenil in baboons.	2002 Oct	12373448
A GABAergic cortical deficit dominates schizophrenia pathophysiology.	2004	15581395
Imidazenil: a potent and safe protective agent against diisopropyl fluorophosphate toxicity.	2004 Mar	14975695
GABAergic dysfunction in schizophrenia: new treatment strategies on the horizon.	2005 Jul	15864560
Valproate corrects the schizophrenia-like epigenetic behavioral modifications induced by methionine in mice.	2005 Mar 1	15737665
Imidazenil: an antagonist of the sedative but not the anticonvulsant action of diazepam.	2005 Sep	15964602
Imidazenil: a low efficacy agonist at alpha1- but high efficacy at alpha5-GABAA receptors fail to show anticonvulsant cross tolerance to diazepam or zolpidem.	2008 Aug	18555494
The combination of huperzine A and imidazenil is an effective strategy to prevent diisopropyl fluorophosphate toxicity in mice.	2008 Sep 16	18784370
Imidazenil, a non-sedating anticonvulsant benzodiazepine, is more potent than diazepam in protecting against DFP-induced seizures and neuronal damage.	2009 Feb 27	19111886
Pharmacological agents in the prophylaxis/treatment of organophosphorous pesticide intoxication.	2010 Jul	20929049
Anticonvulsant, anxiolytic, and non-sedating actions of imidazenil and other imidazo-benzodiazepine carboxamide derivatives.	2010 Jun	20227434
Acute imidazenil treatment after the onset of DFP-induced seizure is more effective and longer lasting than midazolam at preventing seizure activity and brain neuropathology.	2011 Mar	21097996
Neuroprotective effects of imidazenil against chemical warfare nerve agent soman toxicity in guinea pigs.	2012 Mar	22245390

Patents

Sample Use Guides

In Vivo Use Guide

0.25, 0.5, and 1.25 uMl/kg were given orally once daily 60 min presession.

Route of Administration: Other

In Vitro Use Guide

In the cerebellum and the cortex the slope (nH) of the [3H]flumazenil displacement curve by imidazenil is close to 1, but in the spinal cord this value is 0.57. GABA (50 uM) added to cerebellar membranes increases by 1.7-fold the potency of imidazenil (IC50 in the presence of GABA = 0.58 ± 0.050 nM, n = 6) and by 4.6-fold that of diazepam (IC50 in the presence of GABA = 8.3 ± 1.4 nM, n = 6).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:22:03 UTC 2023` Edited by `admin` on `Fri Dec 15 19:22:03 UTC 2023`
Record UNII	7N95V6864R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IMIDAZENIL

Common Name

English

4H-IMIDAZO(1,5-A)(1,4)BENZODIAZEPINE-3-CARBOXAMIDE, 6-(2-BROMOPHENYL)-8-FLUORO-

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

IMIDAZENIL