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Chemical Structure| 75507-68-5 Chemical Structure| 75507-68-5

Structure of Flupirtine Maleate
CAS No.: 75507-68-5

Chemical Structure| 75507-68-5

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Flupirtine maleate is a non-opioid analgesic of KV7 potassium channels. Flupirtine also inderectly antagonizes NMDA receptor and GABAa receptors. It exhibits the relaxantion of muscles and neuroprotective.

Synonyms: Flupirtine (maleate)

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Product Details of Flupirtine Maleate

CAS No. :75507-68-5
Formula : C19H21FN4O6
M.W : 420.39
SMILES Code : O=C(NC1=CC=C(N=C1N)NCC2=CC=C(C=C2)F)OCC.O=C(/C=C\C(O)=O)O
Synonyms :
Flupirtine (maleate)
MDL No. :MFCD00941415
InChI Key :DPYIXBFZUMCMJM-BTJKTKAUSA-N
Pubchem ID :6435335

Safety of Flupirtine Maleate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Isoform Comparison

Biological Activity

Description
Flupirtine maleate is a non-opioid central analgesic with strong permeability and high oral bioavailability. Flupirtine maleate is an indirect antagonist of N-methyl-D-aspartate receptor (NMDAR) with neuroprotective properties [1],[2].

In Vitro:

Cell Line
Concentration Treated Time Description References
Hcrt neurons 50 μM 5-10 min Flupirtine increased the M-current in Hcrt neurons, hyperpolarized the RMP, and reduced the firing frequency. Science. 2022 Feb 25;375(6583):eabh3021.
WT mouse mesenteric artery smooth muscle cells 1 nM–0.1 mM Flupirtine induced relaxation in WT mouse mesenteric arteries, with the maximal relaxation response reaching 94±8% at 30 μM. Br J Pharmacol. 2009 Aug;157(7):1241-9.
SERT+ mouse pulmonary artery smooth muscle cells 1 nM–0.1 mM Flupirtine induced relaxation in SERT+ mouse pulmonary arteries, but the effect was less potent than in WT vessels. Br J Pharmacol. 2009 Aug;157(7):1241-9.
WT mouse pulmonary artery smooth muscle cells 1 nM–0.1 mM Flupirtine induced ~40% and ~60% relaxation in WT mouse pulmonary arteries at 10 and 30 μM respectively. Br J Pharmacol. 2009 Aug;157(7):1241-9.
hippocampal neurons 100 μM 48 h Flupirtine, as a KCNQ channel opener, caused significant cell death in hippocampal neurons, which was largely prevented by the KCNQ channel inhibitor XE991. Cell Death Differ. 2011 Mar;18(3):493-505.
murine aortic smooth muscle cells 20 μM Flupirtine relaxed phenylephrine-precontracted aortic segments by activating Kv7 channels Br J Pharmacol. 2007 Jul;151(6):758-70.
U373 malignant glioma cells 1 mM 24 and 48 h To investigate the neuroprotective effects of flupirtine on U373 malignant glioma cells. Results showed that flupirtine significantly reduced the growth of U373 MG cells at high doses (1 and 10 mM) compared with low doses (0.001 to 0.1 mM) and control (P<0.001). Cancer Biol Med. 2013 Sep;10(3):142-7.
A7r5 rat aortic smooth muscle cells 10 μM Flupirtine significantly and reversibly enhanced KCNQ channel currents and transiently inhibited AVP-stimulated Ca2+ spiking Am J Physiol Heart Circ Physiol. 2007 Mar;292(3):H1352-63.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Mice Aged mice Intraperitoneal injection 20 mg/kg Single dose Flupirtine significantly increased the amount and stability of NREM sleep and elevated theta band power in aged mice. Science. 2022 Feb 25;375(6583):eabh3021.
Mice Chronic hypoxia-induced PAH model and SERT+ mouse model Oral 30 mg/kg Once daily for 14 days Flupirtine significantly attenuated development of chronic hypoxia-induced PAH in mice and reversed established PAH in SERT+ mice. Br J Pharmacol. 2009 Aug;157(7):1241-9.
Rats Anesthetized adult rats Microdialysis perfusion into the preBötC 300 μM Single administration, lasting 30 minutes To investigate the effect of Flupirtine on respiratory rate, results showed that Flupirtine significantly reduced respiratory rate and diaphragm amplitude. Anesthesiology. 2016 Mar;124(3):641-50
Syrian golden hamsters Dtsz mutant hamster model Intraperitoneal injection 10 and 20 mg/kg Single administration, observed for 3 hours Evaluate the antidystonic effects of Flupirtine in dtsz mutant hamsters. Results showed that 20 mg/kg dose significantly improved dystonia, delayed onset time, and reduced maximum severity. Br J Pharmacol. 2006 Nov;149(6):747-53

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.38mL

0.48mL

0.24mL

11.89mL

2.38mL

1.19mL

23.79mL

4.76mL

2.38mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

 

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