| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
Cav1.2 55 μM (IC50) CaV1.3 37 μM (IC50)
N-Desalkylflurazepam is a positive allosteric modulator (PAM) at the GABAA receptor, binding to the benzodiazepine site to enhance the effect of GABA. Additionally, it inhibits L-type voltage-gated calcium channels with IC50 values of 55 uM for Cav1.2 and 37 uM for Cav1.3, though this is not its primary mechanism of action. |
|---|---|
| ln Vitro |
N-Desalkylflurazepam, a long-acting metabolite of flurazepam, lowers the amplitudes of each component of an evoked potential (EP)[1].
In vitro, N-Desalkylflurazepam acts as a long-acting benzodiazepine site agonist on GABAA receptors. It also inhibits L-type voltage-gated calcium channels with moderate potency, showing IC50 values of 55 uM for Cav1.2 and 37 uM for Cav1.3. This dual activity distinguishes it from some other benzodiazepine metabolites. |
| ln Vivo |
In vivo, N-Desalkylflurazepam has a long elimination half-life and accumulates during repeated dosage of its parent drugs, contributing to extended sedative, anxiolytic, and muscle relaxant effects. Studies show that after administration of flurazepam, the serum concentration of N-desalkylflurazepam is much greater than that of the parent compound at all sampling times, indicating significant accumulation.
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| Enzyme Assay |
The binding affinity of N-Desalkylflurazepam is determined via radioligand competition assays. Rat brain cortical membranes (expressing GABAA receptors) are incubated with [3H]flumazenil (a benzodiazepine antagonist) and varying concentrations of the compound in Tris-HCl buffer for 60 min at 0-4degC. Nonspecific binding is defined with 10 uM diazepam, and bound radioligand is separated by filtration.
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| Cell Assay |
Cell-based assays are not standard for this metabolite, as its primary mechanism is on GABAA receptors. Functional activity can be measured in HEK-293 cells transfected with human GABAA receptor subunits (alpha1beta3gamma2). Using patch-clamp electrophysiology, cells are voltage-clamped at -60 mV, and the potentiation of GABA-evoked chloride currents by N-Desalkylflurazepam is measured.
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| Animal Protocol |
In vivo pharmacokinetic studies are performed by administering flurazepam or flutoprazepam to rats or human subjects. Blood or plasma samples are collected at multiple time points post-dose. N-Desalkylflurazepam concentrations are quantified by LC-MS/MS or GC-MS following protein precipitation or solid-phase extraction to determine its formation rate, half-life, and accumulation profile.
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| ADME/Pharmacokinetics |
Metabolism/Metabolites
N-Dealkyl-2-oxoquinazopane is a known human metabolite of 2-oxoquinazopane. In humans, N-Desalkylflurazepam exhibits a long elimination half-life (reported up to 47-100 hours for its parent flutoprazepam). It is the major circulating metabolite following flurazepam or flutoprazepam administration, with serum concentrations exceeding those of the parent drug. Its long half-life leads to significant accumulation upon repeated dosing. |
| Toxicity/Toxicokinetics |
N-Desalkylflurazepam is a Schedule IV controlled substance in many jurisdictions due to its pharmacological activity. Like other benzodiazepines, it can cause sedation, dependence, and withdrawal symptoms upon discontinuation. It is not approved as a standalone drug but is a well-characterized active metabolite of several approved benzodiazepines.
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| References |
[1]. J J Kulikowski, et al. Are the amplitudes of visual evoked potentials sensitive indices of hangover effects after repeated doses of benzodiazepines? Psychopharmacology Suppl. 1984;1:154-64.
[2]. Damien E Earl, et al. Inhibition of recombinant L-type voltage-gated calcium channels by positive allosteric modulators of GABAA receptors. J Pharmacol Exp Ther. 2011 Apr;337(1):301-11. |
| Additional Infomation |
Desalkylflurazepam is a benzodiazepine.
See also: Desethylflurazepam (note moved to). N-Desalkylflurazepam is unique among benzodiazepine metabolites due to its exceptionally long half-life and role in the accumulation and prolonged action of drugs like flurazepam. It is a critical biomarker in forensic toxicology for detecting past use of flurazepam, flutoprazepam, and ethyl loflazepate, as it remains detectable in urine and plasma long after the parent drugs have been eliminated. |
| Molecular Formula |
C15H10CLFN2O
|
|---|---|
| Molecular Weight |
288.70
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| Exact Mass |
288.046
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| CAS # |
2886-65-9
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| PubChem CID |
4540
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
463.5±55.0 °C at 760 mmHg
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| Melting Point |
204-206°C
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| Flash Point |
234.1±31.5 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.648
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| LogP |
2.4
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
20
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| Complexity |
415
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClC1C([H])=C([H])C2=C(C=1[H])C(C1=C([H])C([H])=C([H])C([H])=C1F)=NC([H])([H])C(N2[H])=O
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| InChi Key |
UVCOILFBWYKHHB-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H10ClFN2O/c16-9-5-6-13-11(7-9)15(18-8-14(20)19-13)10-3-1-2-4-12(10)17/h1-7H,8H2,(H,19,20)
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| Chemical Name |
7-chloro-5-(2-fluorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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: 100 mg/mL (346.38 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.66 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.66 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (8.66 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4638 mL | 17.3190 mL | 34.6380 mL | |
| 5 mM | 0.6928 mL | 3.4638 mL | 6.9276 mL | |
| 10 mM | 0.3464 mL | 1.7319 mL | 3.4638 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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