Flupirtine Maleate
Based on 1 publication(s) in Google Scholar
Flupirtine (D 9998) Maleate is an orally active, blood-brain barrier-crossing non-opioid analgesic and neuroprotective agent. Flupirtine Maleate is a neuronal potassium channel opener (Kv7 activator), a NMDA receptor antagonist and a GABA receptor activator. Flupirtine Maleate stabilizes blood-brain-barrier integrity, reduces oxidative stress and brain leukocyte infiltration, enhances angioneurogenesis, suppresses calcium influx, stabilizes neuronal resting membrane potential, and counteracts focal cerebral ischemia. Flupirtine Maleate exhibits analgesic, muscle relaxant properties, protects neurons from excitotoxic, ischemic, or cytokine-mediated death. Flupirtine Maleate functions as a non-opioid analgesic without antipyretic or antiphlogistic properties, shows no relevant affinity to opiate receptor. Flupirtine Maleate can be used for the research of focal cerebral ischemia, pain, Alzheimer’s disease, or multiple sclerosis.
For research use only. We do not sell to patients.
- Purity: 99.97%
- CAS No.: 75507-68-5
- Formula: C19H21FN4O6
- Molecular Weight:420.39
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Storage:
4°C, sealed storage, away from moisture
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
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Biological Activity
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Chemical Information
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Solvent & Solubility
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- References
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Publications Citing Use of MedChemExpress (MCE) Flupirtine Maleate
MoreAll iGluR Isoforms
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Biological Activity
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NMDA Receptor |
Flupirtine (0.1-100 μM for tsA cells; 3-30 μM for SCG neurons; 3-30 μM for hippocampal, DRG, DH neurons) Maleate enhances currents through KV7 channels in tsA 201 cells expressing KV7.2/7.3 subunits, rat SCG neurons, hippocampal neurons, DRG neurons, and DH neurons with EC50 values ranging from 4.4 to 6.1 μM[2].
Flupirtine (10, 30 μM) Maleate modulates GABAA receptors (enhancing low-concentration GABA currents) and NMDA receptors (inhibiting at 30 μM) but not TRPV1, non-NMDA glutamate, or glycine receptors in rat hippocampal neurons[2].
Flupirtine (30 μM) Maleate potentiates GABAA receptors in rat DRG, DH, and SCG neurons, with greater leftward shifts of GABA concentration-response curves in DRG and DH neurons than SCG neurons[2].
Flupirtine (0.1-100 μM) Maleate is more potent at enhancing GABAA receptor currents in rat DRG neurons (EC50 22 μM) than DH (EC50 53 μM) or hippocampal (EC50 65 μM) neurons, and therapeutic concentrations (3 μM) facilitate KV7 channels and GABAA receptors similarly in DRG/DH neurons[2].
Flupirtine (10-300 μM; 1.5 minutes) Maleate antagonizes NMDA-induced currents in cultured rat superior colliculus neurones with an IC50 of 182.1 μM for steady-state responses and 228.6 μM for peak responses[3].
Flupirtine (0.001-10 mM; 24 h) Maleate inhibits the growth of U373 MG cells with a GI50 of 0.47 mM, showing significant growth reduction at 1 and 10 mM after 24 h[4].
Flupirtine (1 mM; 24, 48 h) Maleate alters the cell cycle distribution of U373 MG cells, decreasing the percentage of cells in the G0-G1 phase compared to control after 24 and 48 h, with significant variations in cell cycle phases observed after 48 h[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:U373 malignant glioma cell lines
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Concentration:0.001, 0.01, 0.1, 1, and 10 mM
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Incubation Time:24 hours
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Result:Inhibited U373 MG cell growth with a GI50 of 0.47. Significantly reduced cell growth at high doses (1 and 10 mM) compared to low doses (0.001 to 0.1 mM) and control.
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Cell Line:U373 malignant glioma cell lines
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Concentration:1 mM
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Incubation Time:24 h; 48 h
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Result:Detected G0-G0 phase percentage of 45.48, Sub G0-G0 phase percentage of 2.49, S phase percentage of 24.47, and G₂-M phase percentage of 27.56 after 24 h treatment. Detected G0-G1 phase percentage of 56.39, Sub G0-G1 phase percentage of 1.82, S phase percentage of 18.99, and G2-M phase percentage of 22.80 after 48 h treatment. Observed significant variations in cell cycle phases after 48 h but not 24 h of treatment.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:C57BL6 (male, 22-25 g, transient focal cerebral ischemia via left middle cerebral artery thread occlusion for 30 min)[1]
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Dosage:1, 5, 10 mg/kg; 10 mg/kg (majority of experiments)
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Administration:i.p.; single dose; during reperfusion or at 3, 6, 9, 12 h post-stroke (9 h post-stroke for majority of experiments)
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Result:Reduced infarct volumes on day 2 post-stroke at 5 and 10 mg/kg (1 mg/kg had no effect); reduced infarct volumes, TUNEL+ cell counts, rt-PA-induced acute brain toxicity, Evans blue extravasation, oxidative stress (TBARS formation), intracerebral leukocyte infiltration, calpain activity, JNK and NF-κB activation, and proteasomal activity at 10 mg/kg (given up to 9 h post-stroke); increased STAT6 abundance, neuronal density (NeuN+ cells), CD31+ endothelial cells, Dcx+ immature neurons, and BrdU+/NeuN+ mature neurons on day 84; improved performance in rota rod, tight rope, corner turn, and foot fault tests up to day 84 at 10 mg/kg (given up to 9 h post-stroke).
| NCT Number | Sponsor | Condition | Start Date |
Phase
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|---|---|---|---|---|
| NCT01329991 | Plexxikon| | 2011-05 | PHASE1 |
Chemical Information
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CAS No. 75507-68-5
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Appearance Solid
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Molecular Weight 420.39
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Formula C19H21FN4O6
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Color White to off-white
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SMILES
O=C(NC1=CC=C(N=C1N)NCC2=CC=C(C=C2)F)OCC.O=C(/C=C\C(O)=O)O
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Synonyms
D 9998 Maleate
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
4°C, sealed storage, away from moisture
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
Publications (1)
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Journal Impact Factor
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Most Recent
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Biochem Pharmacol
In vitro approach to elucidate the relevance of carboxylesterase 2 and N-acetyltransferase 2 to flupirtine-induced liver injury. [Abstract]2018 Sep:155:242-251. PMID: 30028988
Solvent & Solubility
DMSO : 100 mg/mL (237.87 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
H2O : 1.43 mg/mL (3.40 mM; ultrasonic and warming and heat to 60°C)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (5.95 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.5 mg/mL (5.95 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL. * In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation
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Data Sheet (278 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Handling Instructions (2659 KB)
References
[1]. Jaeger HM, et al. The indirect NMDAR inhibitor flupirtine induces sustained post-ischemic recovery, neuroprotection and angioneurogenesis. Oncotarget. 2015;6(16):14033-14044. [Content Brief]
[2]. Klinger F, et al. Concomitant facilitation of GABAA receptors and KV7 channels by the non-opioid analgesic flupirtine. Br J Pharmacol. 2012;166(5):1631-1642. [Content Brief]
[3]. Kornhuber J, et al. Flupirtine shows functional NMDA receptor antagonism by enhancing Mg2+ block via activation of voltage independent potassium channels. Rapid communication. J Neural Transm (Vienna). 1999;106(9-10):857-67. [Content Brief]
[4]. Panchanathan E, et al. Effect of flupirtine on the growth and viability of U373 malignant glioma cells. Cancer Biol Med. 2013;10(3):142-147. [Content Brief]
[5]. Dörr J, et al. Disease Modification in Multiple Sclerosis by Flupirtine-Results of a Randomized Placebo Controlled Phase II Trial. Front Neurol. 2018;9:842. Published 2018 Oct 9. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| H2O / DMSO | 1 mM | 2.3787 mL | 11.8937 mL | 23.7874 mL | 59.4686 mL |
| DMSO | 5 mM | 0.4757 mL | 2.3787 mL | 4.7575 mL | 11.8937 mL |
| 10 mM | 0.2379 mL | 1.1894 mL | 2.3787 mL | 5.9469 mL | |
| 15 mM | 0.1586 mL | 0.7929 mL | 1.5858 mL | 3.9646 mL | |
| 20 mM | 0.1189 mL | 0.5947 mL | 1.1894 mL | 2.9734 mL | |
| 25 mM | 0.0951 mL | 0.4757 mL | 0.9515 mL | 2.3787 mL | |
| 30 mM | 0.0793 mL | 0.3965 mL | 0.7929 mL | 1.9823 mL | |
| 40 mM | 0.0595 mL | 0.2973 mL | 0.5947 mL | 1.4867 mL | |
| 50 mM | 0.0476 mL | 0.2379 mL | 0.4757 mL | 1.1894 mL | |
| 60 mM | 0.0396 mL | 0.1982 mL | 0.3965 mL | 0.9911 mL | |
| 80 mM | 0.0297 mL | 0.1487 mL | 0.2973 mL | 0.7434 mL | |
| 100 mM | 0.0238 mL | 0.1189 mL | 0.2379 mL | 0.5947 mL |
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Flupirtine Maleate Related Classifications
HY-17001 Related Classifications
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