Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H17FN4O2.C4H4O4 |
| Molecular Weight | 420.3916 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C/C(O)=O.CCOC(=O)NC1=C(N)N=C(NCC2=CC=C(F)C=C2)C=C1
InChI
InChIKey=DPYIXBFZUMCMJM-BTJKTKAUSA-N
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-
| Molecular Formula | C4H4O4 |
| Molecular Weight | 116.0722 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
| 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 |
|---|---|---|
| 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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| Novel approaches in diagnosis and therapy of Creutzfeldt-Jakob disease. | 2000 Jul 31 |
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| [Asymptomatic diclofenac-induced acute hepatitis]. | 2000 Jun 23 |
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| Applications of liquid chromatography-tandem mass spectrometry in drug and biomedical analyses. | 2001 Nov |
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| Neuroprotective effect of flupirtine in prion disease. | 2002 Jan |
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| Treatment of spasticity. | 2002 Jun |
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| Analgesic efficacy of flupirtine in primary care of patients with osteoporosis related pain. A multivariate analysis. | 2003 |
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| Paradoxical cerebral cortical hyperexcitability following flupirtine overdose. | 2004 |
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| Dissociation of morphine analgesia and sedation evaluated by EEG measures in healthy volunteers. | 2004 |
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| Pharmacological characterisation of acid-induced muscle allodynia in rats. | 2004 Mar 8 |
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| Efficacy of flupirtine on cognitive function in patients with CJD: A double-blind study. | 2004 Mar 9 |
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| The potassium channel modulator flupirtine shifts the frequency-response function of hippocampal synapses to favour LTD in mice. | 2004 Nov 11 |
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| Tumor-necrosis-factor-related apoptosis-inducing-ligand (TRAIL)-mediated death of neurons in living human brain tissue is inhibited by flupirtine-maleate. | 2005 Oct |
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| [The use of katadolon in patients with spondylogenic dorsalgia]. | 2006 |
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| [Use of katadolon in the treatment of abuse headache]. | 2006 |
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| HIV neurotoxicity: potential therapeutic interventions. | 2006 |
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| [The use of katadolon (flupirtine) in the treatment of lower back pain]. | 2006 |
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| Retigabine and flupirtine exert neuroprotective actions in organotypic hippocampal cultures. | 2006 Aug |
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| KCNQ/M-currents contribute to the resting membrane potential in rat visceral sensory neurons. | 2006 Aug 15 |
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| The use of flupirtine in treatment of tinnitus. | 2006 Dec |
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| [Backache is often caused by strained muscles]. | 2006 May 25 |
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| Antidystonic effects of Kv7 (KCNQ) channel openers in the dt sz mutant, an animal model of primary paroxysmal dystonia. | 2006 Nov |
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| Activators of potassium M currents have anticonvulsant actions in two rat models of encephalitis. | 2007 Jan 19 |
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| Flupirtine attenuates sodium nitroprusside-induced damage to retinal photoreceptors, in situ. | 2007 Jul 12 |
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| Vasopressin stimulates action potential firing by protein kinase C-dependent inhibition of KCNQ5 in A7r5 rat aortic smooth muscle cells. | 2007 Mar |
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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 |
|
| Analgesic efficacy and tolerability of flupirtine vs. tramadol in patients with subacute low back pain: a double-blind multicentre trial*. | 2008 Dec |
|
| The efficacy of tetracyclines in peripheral and intracerebral prion infection. | 2008 Mar 26 |
|
| Flupirtine as neuroprotective add-on therapy in autoimmune optic neuritis. | 2008 Nov |
|
| 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 |
|
| KCNQ modulators reveal a key role for KCNQ potassium channels in regulating the tone of rat pulmonary artery smooth muscle. | 2009 Apr |
|
| An in vitro screening cascade to identify neuroprotective antioxidants in ALS. | 2009 Apr 15 |
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| [Systematic review of the therapeutics for prion diseases]. | 2009 Aug |
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| 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 |
|
| 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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| Positive reinforcing effects of flupirtine--two case reports. | 2010 Aug 16 |
|
| CNSB004 (Leconotide) causes antihyperalgesia without side effects when given intravenously: a comparison with ziconotide in a rat model of diabetic neuropathic pain. | 2010 Feb |
|
| Discrepancy between prevalence and perceived effectiveness of treatment methods in myofascial pain syndrome: results of a cross-sectional, nationwide survey. | 2010 Feb 11 |
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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admin
on
Edited
Fri Dec 15 16:21:10 GMT 2023
by
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on
Fri Dec 15 16:21:10 GMT 2023
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| Record UNII |
0VCI53PK4A
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Validated (UNII)
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C241
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ACTIVE MOIETY |