Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H17FN4O2 |
| Molecular Weight | 304.3195 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)NC1=CC=C(NCC2=CC=C(F)C=C2)N=C1N
InChI
InChIKey=JUUFBMODXQKSTD-UHFFFAOYSA-N
InChI=1S/C15H17FN4O2/c1-2-22-15(21)19-12-7-8-13(20-14(12)17)18-9-10-3-5-11(16)6-4-10/h3-8H,2,9H2,1H3,(H,19,21)(H3,17,18,20)
| Molecular Formula | C15H17FN4O2 |
| Molecular Weight | 304.3195 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Flupirtine is a triaminopyridine derivative having a chemical structure - 2-amino-3-ethoxy-carbonylamino-6-4-fluoro-benzylamino-pyridine. The basic molecule used for synthesis of flupirtine was 2, 6-dichoro 3-nitropyridine. It was first synthesized in 1980s in Germany and was marketed by Degussa Pharma. Flupirtine is a centrally acting, non-opioid analgesic that is available in a number of European countries for the treatment of a variety of pain states. The therapeutic benefits seen with flupirtine relate to its unique pharmacological properties. Flupirtine displays indirect NDMA receptor antagonism via activation of potassium channels and is the first representative of a pharmacological class denoted the 'selective neuronal potassium channel openers'. The generation of the M-current is facilitated by flupirtine via the opening of neuronal Kv7 potassium channels. The opening of these channels inhibits exaggerated neuronal action potential generation and controls neuronal excitability. Neuronal hyperexcitability is a physiological component of many pain states such as chronic pain, migraine and neurogenic pain.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Quantitation of flupirtine and its active acetylated metabolite by reversed-phase high-performance liquid chromatography using fluorometric detection. | 1984 Jan 13 |
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| [General pharmacologic studies on the analgesic flupirtine]. | 1985 |
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| Pharmacokinetics of flupirtine in elderly volunteers and in patients with moderate renal impairment. | 1988 May |
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| Pharmacological mechanisms of action of flupirtine: a novel, centrally acting, nonopioid analgesic evaluated by its discriminative effects in the rat. | 1988 Sep |
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| Antiparkinsonian and other motor effects of flupirtine alone and in combination with dopaminergic drugs. | 1997 May 26 |
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| Melatonin counteracts ischemia-induced apoptosis in human retinal pigment epithelial cells. | 1998 Nov |
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| [Efficacy of katadolon and cranial-spine electromagnetic neuromodulation in patients with discogenic radiculopathy]. | 2008 |
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| K(+)-channel openers suppress epileptiform activities induced by 4-aminopyridine in cultured rat hippocampal neurons. | 2008 Dec |
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| Analgesic efficacy and tolerability of flupirtine vs. tramadol in patients with subacute low back pain: a double-blind multicentre trial*. | 2008 Dec |
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| [Analgesic and muscle tonus normalizing effect of flupirtine retard in chronic back pain. Results of a standardized therapeutic evaluation applying objective methods for measuring pain pressure threshold, pain pressure tolerance and muscle tension]. | 2008 Jan 17 |
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| G-protein inwardly rectifying potassium channels are involved in the hypotensive effect of I1-imidazoline receptor selective ligands. | 2008 May |
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| Flupirtine as neuroprotective add-on therapy in autoimmune optic neuritis. | 2008 Nov |
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| Combination therapy with flupirtine and opioid: open-label case series in the treatment of neuropathic pain associated with cancer. | 2008 Oct |
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| Combination therapy with flupirtine and opioid: studies in rat pain models. | 2008 Oct |
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| Bimodal effects of the Kv7 channel activator retigabine on vascular K+ currents. | 2008 Sep |
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| Enhancing m currents: a way out for neuropathic pain? | 2009 |
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| Neural KCNQ (Kv7) channels. | 2009 Apr |
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| Safety and efficacy of quinacrine in human prion disease (PRION-1 study): a patient-preference trial. | 2009 Apr |
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| Clinical trials for prion disease: difficult challenges, but hope for the future. | 2009 Apr |
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| Activation of pre-synaptic M-type K+ channels inhibits [3H]D-aspartate release by reducing Ca2+ entry through P/Q-type voltage-gated Ca2+ channels. | 2009 Apr |
|
| KCNQ modulators reveal a key role for KCNQ potassium channels in regulating the tone of rat pulmonary artery smooth muscle. | 2009 Apr |
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| An in vitro screening cascade to identify neuroprotective antioxidants in ALS. | 2009 Apr 15 |
|
| [Systematic review of the therapeutics for prion diseases]. | 2009 Aug |
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| Treatment with the Kv7 potassium channel activator flupirtine is beneficial in two independent mouse models of pulmonary hypertension. | 2009 Aug |
|
| Efficacy and safety of bilateral continuous theta burst stimulation (cTBS) for the treatment of chronic tinnitus: design of a three-armed randomized controlled trial. | 2009 Aug 21 |
|
| GDNF selectively induces microglial activation and neuronal survival in CA1/CA3 hippocampal regions exposed to NMDA insult through Ret/ERK signalling. | 2009 Aug 3 |
|
| [Efficient treatment of chronic backache]. | 2009 Dec 10 |
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| Therapeutic trials in human transmissible spongiform encephalo-pathies: recent advances and problems to address. | 2009 Feb |
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| KCNQ currents and their contribution to resting membrane potential and the excitability of interstitial cells of Cajal from the guinea pig bladder. | 2009 Jul |
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| A girl with headache, confusion and green urine. | 2009 Jul |
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| Flupirtine: pharmacology and clinical applications of a nonopioid analgesic and potentially neuroprotective compound. | 2009 Jun |
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| A KCNQ channel opener for experimental neonatal seizures and status epilepticus. | 2009 Mar |
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| Investigation of the in vitro metabolism of the analgesic flupirtine. | 2009 Mar |
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| Neuronal potassium channel openers in the management of epilepsy: role and potential of retigabine. | 2010 |
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| [New approaches to the treatment of chronic daily headache]. | 2010 |
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| The M-channel blocker linopirdine is an agonist of the capsaicin receptor TRPV1. | 2010 |
|
| [IGOST guideline for pharmacotherapy of low back pain]. | 2010 Aug 12 |
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| Positive reinforcing effects of flupirtine--two case reports. | 2010 Aug 16 |
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| Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. | 2010 Dec |
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| Flupirtine may stop the progressive course of subacute sclerosing panencephalitis. | 2010 Dec |
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| Enhancement of axonal potassium conductance reduces nerve hyperexcitability in an in vitro model of oxaliplatin-induced acute neuropathy. | 2010 Dec |
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| Evidence of key tinnitus-related brain regions documented by a unique combination of manganese-enhanced MRI and acoustic startle reflex testing. | 2010 Dec 15 |
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| [2010 German Pain Congress. Backache - new data, specific muscle etiology and targeted therapy]. | 2010 Dec 16 |
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| [Musculoskeletal pain. Pain relief with muscle relaxant]. | 2010 Dec 2 |
|
| CNSB004 (Leconotide) causes antihyperalgesia without side effects when given intravenously: a comparison with ziconotide in a rat model of diabetic neuropathic pain. | 2010 Feb |
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| Discrepancy between prevalence and perceived effectiveness of treatment methods in myofascial pain syndrome: results of a cross-sectional, nationwide survey. | 2010 Feb 11 |
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| The Kv7 potassium channel activator flupirtine affects clinical excitability parameters of myelinated axons in isolated rat sural nerve. | 2010 Mar |
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| Green urine following exposure to flupirtine. | 2010 Nov |
|
| Flupirtine in pain management: pharmacological properties and clinical use. | 2010 Oct |
|
| M-type potassium channels modulate the intrinsic excitability of infralimbic neurons and regulate fear expression and extinction. | 2010 Sep 15 |
Sample Use Guides
Flupirtine can be administered by oral and rectal routes. It is available as 50 and 100 mg for oral administration. Adult dose is 300–400 mg per day and can be increased to 600 mg per day. Dose in children is 150–200 mg per day in 3–4 divided doses. Rectal suppositories are administered in the dose range of 450–600 mg per day in adults and 150–250 mg per day in children.
Route of Administration:
Other
Variations in the growth of U373 MG cells in 5 mM N-methyl-D-aspartate (NMDA), 1 mM flupirtine, and combined treatment indicated the antagonistic effects of NMDA and flupirtine on MG cell lines. The variation in the percentage of gated cell population in different cell cycle phases showed significant variations after 48 h of treatment.
| Substance Class |
Chemical
Created
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| Record UNII |
MOH3ET196H
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Validated (UNII)
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N02BG07
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C241
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QN02BG07
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56995-20-1
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MOH3ET196H
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25193
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260-503-8
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C034161
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FLUPIRTINE
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DB06623
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C72116
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METABOLITE TOXIC -> PARENT |
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Unit: percent of total dose (radio activity)
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ACTIVE MOIETY |
