Flupirtine, also known as W-2964, is an aminopyridine that functions as a centrally acting non-opioid analgesic. It first became available in Europe in 1984, and is sold mainly under the names Katadolon, Trancolong, Awegal, Efiret, Trancopal Dolo, and Metanor. Like nefopam, it is unique among analgesics in that it is a non-opioid, non-NSAID, non-steroidal centrally acting analgesic. Flupirtine is a selective neuronal potassium channel opener that also has NMDA receptor antagonist and GABAA receptor modulatory properties.

Product information

CAS Number: 75507-68-5

Molecular Weight: 420.39

Formula: C19H21FN4O6

Synonym:

W-2964M

W2964M

W 2964M

W-2964

W2964

W 2964

D-9998

Katadolon

Flupirtine maleate

Related CAS Number:

56995-20-1 (Flupirtine free base)

33400-45-2 (Flupirtine HCl)

815586-85-7 (Flupirtine gluconate)

Chemical Name: ethyl (2-amino-6-((4-fluorobenzyl)amino)pyridin-3-yl)carbamate maleate

Smiles: CCOC(=O)NC1=CC=C(NCC2C=CC(F)=CC=2)N=C1N.OC(=O)/C=C\C(O)=O

InChiKey: DPYIXBFZUMCMJM-BTJKTKAUSA-N

InChi: InChI=1S/C15H17FN4O2.C4H4O4/c1-2-22-15(21)19-12-7-8-13(20-14(12)17)18-9-10-3-5-11(16)6-4-10;5-3(6)1-2-4(7)8/h3-8H,2,9H2,1H3,(H,19,21)(H3,17,18,20);1-2H,(H,5,6)(H,7,8)/b;2-1-

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO: 84 mg/mL(199.81 mM). Water: Insoluble.

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Flupirtine pre-incubated for 2 hours prevents cell death in rat cortical neurons induced by NMDA and gp120 of HIV-1. Flupirtine is capable of protecting primary neurons against glutamate-induced cytotoxicity by reducing calcium ion concentrations at 1-10 mM. Flupirtine pretreated for 2 hours preventsβ-amyloid-induced apoptosis in primary neuronal cells at concentrations of 1 or 5μg/mL. Flupirtine at concentration of 10 μM markedly decreases nonreceptor-mediated necrotic cell death in PC 12 cultures treated with 10 mM L-glutamate, meanwhile, Flupirtine exerts anti-oxidative effects in PC 12 cultures. Flupirtine-maleate at concentrations of 1 μM and 10 μM decreases TRAIL-mediated death of human living brain tissue culture. Flupirtine activates inwardly rectifying potassium ion channels and thus stabilizes the resting membrane potential at a therapeutically relevant concentration.

In Vivo:

Pre-treatment with Flupirtine exerts a protective effect on hippocampal and striatal neuronal damage and on deficits in spatial learning in rats with cerebral ischemia. Flupirtine administered centrally inhibits the nociceptive responses induced by chemical, thermal, mechanical and electrical stimuli in animal studies. Flupirtine exerts muscle relaxant effects in rat.

References:

1. Müller WE, et al. J Neurochem, 1997, 68(6), 2371-237
2. Rupalla K, et al. Eur J Pharmacol, 1995, 294(2-3), 469-473
3. Perovic S, et al. Eur J Pharmacol, 1994, 288(1), 27-33.

Products are for research use only. Not for human use.