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(F)=CC=C3N2C=N1)C4=C(Br)C=CC=C4

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 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8394902 \| https://www.ncbi.nlm.nih.gov/pubmed/21097996	Positive Allosteric Modulator 186		50.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Cocaine addiction 29 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 275 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7714771	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Neuroprotective effects of imidazenil against chemical warfare nerve agent soman toxicity in guinea pigs.	2012-03	22245390
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.	2011-03	21097996
Pharmacological agents in the prophylaxis/treatment of organophosphorous pesticide intoxication.	2010-07	20929049
Anticonvulsant, anxiolytic, and non-sedating actions of imidazenil and other imidazo-benzodiazepine carboxamide derivatives.	2010-06	20227434
Imidazenil, a non-sedating anticonvulsant benzodiazepine, is more potent than diazepam in protecting against DFP-induced seizures and neuronal damage.	2009-02-27	19111886
The combination of huperzine A and imidazenil is an effective strategy to prevent diisopropyl fluorophosphate toxicity in mice.	2008-09-16	18784370
Imidazenil: a low efficacy agonist at alpha1- but high efficacy at alpha5-GABAA receptors fail to show anticonvulsant cross tolerance to diazepam or zolpidem.	2008-08	18555494
Imidazenil: an antagonist of the sedative but not the anticonvulsant action of diazepam.	2005-09	15964602
GABAergic dysfunction in schizophrenia: new treatment strategies on the horizon.	2005-07	15864560
Valproate corrects the schizophrenia-like epigenetic behavioral modifications induced by methionine in mice.	2005-03-01	15737665
Imidazenil: a potent and safe protective agent against diisopropyl fluorophosphate toxicity.	2004-03	14975695
A GABAergic cortical deficit dominates schizophrenia pathophysiology.	2004	15581395
Anxioselective compounds acting at the GABA(A) receptor benzodiazepine binding site.	2003-08	12871032
Selectivity in generalization to GABAergic drugs in midazolam-trained baboons.	2003-05	12873636
GABAA receptors and benzodiazepines: a role for dendritic resident subunit mRNAs.	2002-11	12423662
5-ethoxymethyl-7-fluoro-3-oxo-1,2,3,5-tetrahydrobenzo[4,5]imidazo[1,2a]pyridine-4-N-(2-fluorophenyl)carboxamide (RWJ-51204), a new nonbenzodiazepine anxiolytic.	2002-11	12388665
Relation between discriminative and reinforcing effects of midazolam, pentobarbital, chlordiazepoxide, zolpidem, and imidazenil in baboons.	2002-10	12373448
Increase in expression of the GABA(A) receptor alpha(4) subunit gene induced by withdrawal of, but not by long-term treatment with, benzodiazepine full or partial agonists.	2001-08-15	11483250
Antagonism of isoniazid-induced convulsions by abecarnil in mice tolerant to diazepam.	1995-10	8577786
Imidazenil, a new partial agonist of benzodiazepine receptors, reverses the inhibitory action of isoniazid and stress on gamma-aminobutyric acidA receptor function.	1994-04	8169838

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 `Mon Mar 31 19:43:58 GMT 2025` Edited by `admin` on `Mon Mar 31 19:43:58 GMT 2025`
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-

Preferred Name

English

Code System Code Type Description

WIKIPEDIA

IMIDAZENIL