Art. -Nr.: HY-17001A

Flupirtine

(Synonyms: D 9998)

1 Cited Publications

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Flupirtine (D 9998) is an orally active, blood-brain barrier-crossing non-opioid analgesic and neuroprotective agent. Flupirtine is a neuronal potassium channel opener (Kv7 activator), a NMDA receptor antagonist and a GABA receptor activator. Flupirtine 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 exhibits analgesic, muscle relaxant properties, protects neurons from excitotoxic, ischemic, or cytokine-mediated death. Flupirtine functions as a non-opioid analgesic without antipyretic or antiphlogistic properties, shows no relevant affinity to opiate receptor. Flupirtine can be used for the research of focal cerebral ischemia, pain, Alzheimer’s disease, or multiple sclerosis.

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Reinheit: 99.98%
CAS. Nr.: 56995-20-1
Formel: C₁₅H₁₇FN₄O₂
Molecular Weight:304.32

Speicherung:

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Flupirtine Chemical Structure

CAS. Nr.: 56995-20-1

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Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Publications (1)
Lösungsmittel & Löslichkeit
- In Vitro
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target

NMDA Receptor

Kv7

Alle iGluR Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
HEK293	EC₅₀	0.56 μM Compound: Retigabine	Agonist activity at human KCNQ2/3 expressed in HEK293 cells by FLIPR based thallium influx assay Agonist activity at human KCNQ2/3 expressed in HEK293 cells by FLIPR based thallium influx assay	[PMID: 31416667]

In Vitro

Flupirtine (0.1-100 μM for tsA cells; 3-30 μM for SCG neurons; 3-30 μM for hippocampal, DRG, DH neurons) enhances currents through K_V7 channels in tsA 201 cells expressing K_V7.2/7.3 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) modulates GABA_A 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) potentiates GABA_A 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) is more potent at enhancing GABA_A 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 K_V7 channels and GABA_A receptors similarly in DRG/DH neurons^[2].
Flupirtine (10-300 μM; 1.5 minutes) 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) 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) 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.

Cell Viability Assay^[4]

Cell Line:

U373 malignant glioma (MG) cells
Concentration:

0.001, 0.01, 0.1, 1, and 10 mM
Incubation Time:

24 h (0.001-10 mM); 24, 48 h (1 mM)
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.

Cell Cycle Analysis^[4]

Cell Line:

U373 malignant glioma (MG) cells
Concentration:

1 mM
Incubation Time:

24 h; 48 h
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.

In Vivo

Flupirtine (1-10 mg/kg; i.p.; single dose; up to 9 h post-stroke) induces sustained neuroprotection, enhanced neurological recovery, and angioneurogenesis in mice with transient focal cerebral ischemia, with 10 mg/kg being the most effective dose^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

C57BL6 (male, 22-25 g, transient focal cerebral ischemia via left middle cerebral artery thread occlusion for 30 min)^[1]
Dosage:

1, 5, 10 mg/kg; 10 mg/kg (majority of experiments)
Administration:

i.p.; single dose; during reperfusion or at 3, 6, 9, 12 h post-stroke (9 h post-stroke for majority of experiments)
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).

Chemical Information

CAS. Nr. 56995-20-1
Appearance Solid
Molecular Weight 304.32
Formel C₁₅H₁₇FN₄O₂
Color White to light yellow
SMILES

O=C(NC1=CC=C(N=C1N)NCC2=CC=C(C=C2)F)OCC
Synonyms

D 9998
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Publications (1)

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Journal Impact Factor

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

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 83.33 mg/mL (273.82 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

3.2860 mL

16.4301 mL

32.8601 mL

5 mM

0.6572 mL

3.2860 mL

6.5720 mL

10 mM

0.3286 mL

1.6430 mL

3.2860 mL

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 (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (279 KB)
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)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[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]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	3.2860 mL	16.4301 mL	32.8601 mL	82.1504 mL
	5 mM	0.6572 mL	3.2860 mL	6.5720 mL	16.4301 mL
	10 mM	0.3286 mL	1.6430 mL	3.2860 mL	8.2150 mL
	15 mM	0.2191 mL	1.0953 mL	2.1907 mL	5.4767 mL
	20 mM	0.1643 mL	0.8215 mL	1.6430 mL	4.1075 mL
	25 mM	0.1314 mL	0.6572 mL	1.3144 mL	3.2860 mL
	30 mM	0.1095 mL	0.5477 mL	1.0953 mL	2.7383 mL
	40 mM	0.0822 mL	0.4108 mL	0.8215 mL	2.0538 mL
	50 mM	0.0657 mL	0.3286 mL	0.6572 mL	1.6430 mL
	60 mM	0.0548 mL	0.2738 mL	0.5477 mL	1.3692 mL
	80 mM	0.0411 mL	0.2054 mL	0.4108 mL	1.0269 mL
	100 mM	0.0329 mL	0.1643 mL	0.3286 mL	0.8215 mL

Flupirtine

1 Cited Publications

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Flupirtine

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Publications Citing Use of MedChemExpress (MCE) Flupirtine

Alle iGluR Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Publications (1)

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Flupirtine Related Classifications

HY-17001A Related Classifications