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| Targets |
Imidazenil targets the GABA-A (GABAA) receptor, a ligand-gated ion channel that mediates fast inhibitory neurotransmission in the central nervous system. Specifically, Imidazenil acts as a partial agonist at GABAA receptors containing the alpha5 subunit, which is highly expressed in the hippocampus and involved in learning, memory, and anxiety. Unlike classical benzodiazepines (full agonists), partial agonists produce less GABA-potentiating effect, resulting in reduced tolerance, dependence, sedation, and amnesia. Imidazenil also has lower efficacy at alpha1-containing receptors (associated with sedation), contributing to its improved side effect profile.
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| ln Vitro |
Imidazenil has been characterized as a partial agonist with high affinity for GABAA receptors. Specific IC50/EC50 values are not provided in the available literature. In functional assays, imidazenil potentiates GABA-induced chloride currents with a lower maximal effect compared to diazepam, indicating partial agonism. It has shown anticonvulsant activity (against pentylenetetrazole-induced seizures), anxiolytic effects (in elevated plus maze), and myorelaxant activity with a broader separation between effective doses and sedative/amnestic doses compared to full agonists. It lacks tolerance upon repeated administration and does not produce physical dependence in animal models.
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| ln Vivo |
Imidazenil has demonstrated efficacy in numerous in vivo models. It exhibits anticonvulsant activity against pentylenetetrazole (PTZ)-induced seizures. In models of ischemia, imidazenil has shown neuroprotective effects, reducing neurodegeneration and improving neurological outcomes. Its anxiolytic effects have been demonstrated in the elevated plus maze and other models. Importantly, imidazenil shows reduced sedation, motor impairment, and memory impairment compared to diazepam, even at doses that produce full anticonvulsant effects. No physical dependence or tolerance is observed with repeated administration, a key advantage over classical benzodiazepines.
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| Enzyme Assay |
Standard GABAA receptor binding assay (receptor binding): Rat brain cortical or hippocampal membranes (100-200 ug protein) are prepared. Membranes are incubated with 0.5-2 nM [3H]-flunitrazepam or [3H]-Ro15-1788 (flumazenil) and varying concentrations of Imidazenil (0.01-10,000 nM) in 50 mM Tris-citrate buffer (pH 7.1) at 4degC for 60-90 minutes. Nonspecific binding is determined using 10 uM diazepam or clonazepam. Bound radioactivity is separated by filtration through GF/B filters and counted. Ki values are calculated. For selectivity, binding to alpha1-, alpha2-, alpha3-, alpha5-containing GABAA receptor subtypes can be assessed using membranes from cells expressing specific subunit combinations.
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| Cell Assay |
Standard functional GABAA receptor assay (electrophysiology): Xenopus oocytes are injected with cRNAs for various GABAA receptor subunits (e.g., alpha1beta2gamma2, alpha2beta2gamma2, alpha3beta2gamma2, alpha5beta2gamma2) to express specific receptor subtypes. Two-electrode voltage-clamp recordings are performed at -70 mV. GABA (0.1-10 uM) and Imidazenil (0.01-1000 nM) are co-applied. Potentiation of GABA-evoked currents is measured. The EC50 for potentiation and maximal potentiation (% of full agonist diazepam's effect) are calculated. For cell-based assays, HEK293 cells stably expressing specific GABAA receptor subtypes are used with patch-clamp recordings or fluorescence-based membrane potential assays. No specific protocol is provided.
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| Animal Protocol |
Model for anticonvulsant activity: Male Swiss-Webster or CD-1 mice (20-30 g) are administered Imidazenil intraperitoneally (0.1-10 mg/kg) 30-60 minutes before testing. Pentylenetetrazole (PTZ, 60-100 mg/kg, IP) is administered to induce clonic and tonic seizures. The latency to and incidence of clonic seizures, tonic seizures, and death are recorded. The ED50 for protection against PTZ-induced seizures is calculated. Model for anxiolytic activity: Elevated plus maze. Mice are treated with Imidazenil (0.1-3 mg/kg, IP) and placed in the plus maze. The percentage of time spent in open arms and the number of open arm entries are measured. Model for sedative activity: Locomotor activity chambers; the distance traveled and time spent moving are measured. Model for ischemia: Middle cerebral artery occlusion (MCAO) model in rats; Imidazenil is administered post-ischemia, and infarct volume is measured by TTC staining. No specific data is provided for Imidazenil.
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| ADME/Pharmacokinetics |
No specific PK data for Imidazenil is provided. Like other benzodiazepines, imidazenil is expected to be well-absorbed after oral administration, with good CNS penetration due to its lipophilicity. It is metabolized in the liver, likely by CYP450 enzymes, and has a half-life that may be intermediate compared to other benzodiazepines. Detailed PK parameters (absorption, half-life, clearance, oral bioavailability) are not reported in the available literature.
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| Toxicity/Toxicokinetics |
Imidazenil has been shown to have a lower propensity for tolerance, dependence, sedation, and cognitive impairment compared to classical benzodiazepines. However, as a CNS-active GABAA receptor modulator, it can still cause ataxia, drowsiness, and muscle relaxation at higher doses. No specific toxicology data (LD50, reproductive toxicity, carcinogenicity) is provided. The compound is a research chemical and is not approved for clinical use. It should be handled with standard laboratory safety precautions. Not for human consumption.
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| References |
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| Additional Infomation |
γ-aminobutyric acid (GABA) is a partial positive allosteric modulator of GABA(A) receptors; structure is described in the first source.
Imidazenil (FID 03-479) is an imidazobenzodiazepine derivative and a selective partial agonist at alpha5-containing GABAA receptors. It exhibits anticonvulsant, anxiolytic, myorelaxant, and neuroprotective properties with reduced sedative and amnestic side effects and minimal tolerance/dependence. It has been investigated as a potential improved CNS therapeutic but is not clinically approved. For research use only, not for human therapeutic applications. |
| Molecular Formula |
C18H12BRFN4O
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|---|---|
| Molecular Weight |
399.22
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| Exact Mass |
398.018
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| CAS # |
151271-08-8
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| PubChem CID |
119194
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| Appearance |
White to off-white solid powder
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| Density |
1.67g/cm3
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| Boiling Point |
587ºC at 760mmHg
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| Flash Point |
308.8ºC
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| Vapour Pressure |
9.25E-14mmHg at 25°C
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| Index of Refraction |
1.735
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| LogP |
3.544
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
25
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| Complexity |
559
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| Defined Atom Stereocenter Count |
0
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| SMILES |
NC(C1N=CN2C3C=CC(F)=CC=3C(C3=CC=CC=C3Br)=NCC=12)=O
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| InChi Key |
OCJHYHKWUWSHEN-UHFFFAOYSA-N
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| InChi Code |
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)
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| Chemical Name |
6-(2-bromophenyl)-8-fluoro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide
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| Synonyms |
Medaxini
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~125.24 mM; with ultrasonication (<60°C))
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5049 mL | 12.5244 mL | 25.0488 mL | |
| 5 mM | 0.5010 mL | 2.5049 mL | 5.0098 mL | |
| 10 mM | 0.2505 mL | 1.2524 mL | 2.5049 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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