56995-20-1,MFCD00864265
Catalog No.:AA019FSF

56995-20-1 | Flupirtine

This product is typically in stock,please click "Inquire" below or
contact us at [email protected] for pricing and availability information.
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA019FSF
Chemical Name:
Flupirtine
CAS Number:
56995-20-1
Molecular Formula:
C15H17FN4O2
Molecular Weight:
304.3195
MDL Number:
MFCD00864265
SMILES:
CCOC(=O)Nc1ccc(nc1N)NCc1ccc(cc1)F
Properties
Computed Properties
 
Complexity:
350  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0  
Rotatable Bond Count:
6  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
2.4  

Downstream Synthesis Route

[1]Kinarivala,Nihar;Patel,Ronak;Boustany,Rose-Mary;Al-Ahmad,Abraham;Trippier,PaulC.[JournalofMedicinalChemistry,2017,vol.60,#23,p.9739-9756]

[2]CurrentPatentAssignee:XIANDUCHUANGPHARMACEUTICALTECH-CN110317167,2019,ALocationinpatent:Paragraph0052-0054;0059-0060;0065;0070-0071;0076

[3]Schwoch;Kramer;Neidlein;Suschitzky[HelveticaChimicaActa,1994,vol.77,#8,p.2175-2190]

[1]Schwoch;Kramer;Neidlein;Suschitzky[HelveticaChimicaActa,1994,vol.77,#8,p.2175-2190]

[1]Schwoch;Kramer;Neidlein;Suschitzky[HelveticaChimicaActa,1994,vol.77,#8,p.2175-2190]

[1]Schwoch;Kramer;Neidlein;Suschitzky[HelveticaChimicaActa,1994,vol.77,#8,p.2175-2190]

Literature

Title: Efficacy and safety of flupirtine modified release for the management of moderate to severe chronic low back pain: results of SUPREME, a prospective randomized, double-blind, placebo- and active-controlled parallel-group phase IV study.

Journal: Current medical research and opinion 20121001

Title: Transcompartmental reversal of single fibre hyperexcitability in juxtaparanodal Kv1.1-deficient vagus nerve axons by activation of nodal KCNQ channels.

Journal: The Journal of physiology 20120815

Title: M-type potassium channels modulate Schaffer collateral-CA1 glutamatergic synaptic transmission.

Journal: The Journal of physiology 20120815

Title: Concomitant facilitation of GABAA receptors and KV7 channels by the non-opioid analgesic flupirtine.

Journal: British journal of pharmacology 20120701

Title: Unexpected frequent hepatotoxicity of a prescription drug, flupirtine, marketed for about 30 years.

Journal: British journal of clinical pharmacology 20120501

Title: Efficacy and safety of flupirtine maleate and tramadol hydrochloride in postoperative pain management--a prospective randomised double blinded study.

Journal: Journal of the Indian Medical Association 20120301

Title: [Chronic backache. Rational therapy of muscle-induced pain].

Journal: MMW Fortschritte der Medizin 20120223

Title: M channel enhancers and physiological M channel block.

Journal: The Journal of physiology 20120215

Title: The evolving understanding of the analgesic mechanism of action of flupirtine.

Journal: Journal of clinical pharmacy and therapeutics 20120201

Title: Retigabine, a K(V)7 (KCNQ) potassium channel opener, attenuates L-DOPA-induced dyskinesias in 6-OHDA-lesioned rats.

Journal: Neuropharmacology 20120201

Title: Flupirtine inhibits calcitonin-gene related peptide release from rat brainstem in vitro.

Journal: Neuroscience letters 20120111

Title: Kv7 potassium channels in airway smooth muscle cells: signal transduction intermediates and pharmacological targets for bronchodilator therapy.

Journal: American journal of physiology. Lung cellular and molecular physiology 20120101

Title: Neuroprotective function for ramified microglia in hippocampal excitotoxicity.

Journal: Journal of neuroinflammation 20120101

Title: Clinical utility of adjunctive retigabine in partial onset seizures in adults.

Journal: Therapeutics and clinical risk management 20120101

Title: CSF concentrations of cAMP and cGMP are lower in patients with Creutzfeldt-Jakob disease but not Parkinson's disease and amyotrophic lateral sclerosis.

Journal: PloS one 20120101

Title: The Effects of the KCNQ Openers Retigabine and Flupirtine on Myotonia in Mammalian Skeletal Muscle Induced by a Chloride Channel Blocker.

Journal: Evidence-based complementary and alternative medicine : eCAM 20120101

Title: Flupirtine: Clinical pharmacology.

Journal: Journal of anaesthesiology, clinical pharmacology 20120101

Title: Functional significance of M-type potassium channels in nociceptive cutaneous sensory endings.

Journal: Frontiers in molecular neuroscience 20120101

Title: Evidence for inhibitory effects of flupirtine, a centrally acting analgesic, on delayed rectifier k(+) currents in motor neuron-like cells.

Journal: Evidence-based complementary and alternative medicine : eCAM 20120101

Title: Protective effect of the KCNQ activator flupirtine on a model of repetitive febrile seizures.

Journal: Epilepsy research 20111101

Title: Efficacy and tolerability of flupirtine in subacute/ chronic musculoskeletal pain - results of a patient level, pooled re-analysis of randomized, double-blind, controlled trials.

Journal: International journal of clinical pharmacology and therapeutics 20111101

Title: Fatal prion disease in a mouse model of genetic E200K Creutzfeldt-Jakob disease.

Journal: PLoS pathogens 20111101

Title: Parent-reported benefits of flupirtine in juvenile neuronal ceroid lipofuscinosis (Batten disease; CLN3) are not supported by quantitative data.

Journal: Journal of inherited metabolic disease 20111001

Title: KV7 channels regulate muscle tone and nonadrenergic noncholinergic relaxation of the rat gastric fundus.

Journal: Pharmacological research 20111001

Title: Activation of vascular KCNQ (Kv7) potassium channels reverses spasmogen-induced constrictor responses in rat basilar artery.

Journal: British journal of pharmacology 20110901

Title: Flupirtine is a safe alternative drug in patients with hypersensitivity to NSAIDs.

Journal: European journal of clinical pharmacology 20110901

Title: Nucleotides control the excitability of sensory neurons via two P2Y receptors and a bifurcated signaling cascade.

Journal: Pain 20110801

Title: Flupirtine-induced hepatic failure requiring orthotopic liver transplant.

Journal: Experimental and clinical transplantation : official journal of the Middle East Society for Organ Transplantation 20110801

Title: KCNQ5 channels control resting properties and release probability of a synapse.

Journal: Nature neuroscience 20110701

Title: Pathology of flupirtine-induced liver injury: a histological and clinical study of six cases.

Journal: Virchows Archiv : an international journal of pathology 20110601

Title: N-(4-Fluoro-benz-yl)-3-nitro-pyridine-2,6-diamine.

Journal: Acta crystallographica. Section E, Structure reports online 20110601

Title: Transcriptional repression of the M channel subunit Kv7.2 in chronic nerve injury.

Journal: Pain 20110401

Title: The contribution of Kv7 channels to pregnant mouse and human myometrial contractility.

Journal: Journal of cellular and molecular medicine 20110301

Title: Novel role of KCNQ2/3 channels in regulating neuronal cell viability.

Journal: Cell death and differentiation 20110301

Title: Involvement of inward rectifier and M-type currents in carbachol-induced epileptiform synchronization.

Journal: Neuropharmacology 20110301

Title: Mumijo traditional medicine: fossil deposits from antarctica (chemical composition and beneficial bioactivity).

Journal: Evidence-based complementary and alternative medicine : eCAM 20110101

Title: Flupirtine antinociception in the rat orofacial formalin test: an analysis of combination therapies with morphine and tramadol.

Journal: Pharmacology, biochemistry, and behavior 20110101

Title: Rapidly progressive dementias and the treatment of human prion diseases.

Journal: Expert opinion on pharmacotherapy 20110101

Title: [Effect of maladaptive sets on the clinical picture and prediction of chronic headache of tension].

Journal: Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova 20110101

Title: The Voltage-Sensing Domain of K(v)7.2 Channels as a Molecular Target for Epilepsy-Causing Mutations and Anticonvulsants.

Journal: Frontiers in pharmacology 20110101

Title: Neuroprotective and anti-oxidant effects of caffeic acid isolated from Erigeron annuus leaf.

Journal: Chinese medicine 20110101

Title: [Flupirtin (katadolon): a nonstandard action on pain transmission].

Journal: Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova 20110101

Title: Drosophila KCNQ channel displays evolutionarily conserved electrophysiology and pharmacology with mammalian KCNQ channels.

Journal: PloS one 20110101

Title: Neuropathic pain: a personal case reflection on a critical incident.

Journal: Indian journal of palliative care 20110101

Title: Correlation versus causation? Pharmacovigilance of the analgesic flupirtine exemplifies the need for refined spontaneous ADR reporting.

Journal: PloS one 20110101

Title: Phantom limb pain: mechanisms and treatment approaches.

Journal: Pain research and treatment 20110101

Title: Bioanalytical method development, validation and quantification of flupirtine maleate in rat plasma by liquid chromatography-tandem mass spectrometry.

Journal: Arzneimittel-Forschung 20110101

Title: [2010 German Pain Congress. Backache - new data, specific muscle etiology and targeted therapy].

Journal: MMW Fortschritte der Medizin 20101216

Title: [Musculoskeletal pain. Pain relief with muscle relaxant].

Journal: MMW Fortschritte der Medizin 20101202

Title: Enhancement of axonal potassium conductance reduces nerve hyperexcitability in an in vitro model of oxaliplatin-induced acute neuropathy.

Journal: Neurotoxicology 20101201

Title: Flupirtine may stop the progressive course of subacute sclerosing panencephalitis.

Journal: Medical hypotheses 20101201

Title: Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20101201

Title: Green urine following exposure to flupirtine.

Journal: American journal of kidney diseases : the official journal of the National Kidney Foundation 20101101

Title: Flupirtine in pain management: pharmacological properties and clinical use.

Journal: CNS drugs 20101001

Title: M-type potassium channels modulate the intrinsic excitability of infralimbic neurons and regulate fear expression and extinction.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20100915

Title: Positive reinforcing effects of flupirtine--two case reports.

Journal: Progress in neuro-psychopharmacology & biological psychiatry 20100816

Title: [IGOST guideline for pharmacotherapy of low back pain].

Journal: MMW Fortschritte der Medizin 20100812

Title: The Kv7 potassium channel activator flupirtine affects clinical excitability parameters of myelinated axons in isolated rat sural nerve.

Journal: Journal of the peripheral nervous system : JPNS 20100301

Title: CNSB004 (Leconotide) causes antihyperalgesia without side effects when given intravenously: a comparison with ziconotide in a rat model of diabetic neuropathic pain.

Journal: Pain medicine (Malden, Mass.) 20100201

Title: Discrepancy between prevalence and perceived effectiveness of treatment methods in myofascial pain syndrome: results of a cross-sectional, nationwide survey.

Journal: BMC musculoskeletal disorders 20100101

Title: The M-channel blocker linopirdine is an agonist of the capsaicin receptor TRPV1.

Journal: Journal of pharmacological sciences 20100101

Title: Evidence of key tinnitus-related brain regions documented by a unique combination of manganese-enhanced MRI and acoustic startle reflex testing.

Journal: PloS one 20100101

Title: [New approaches to the treatment of chronic daily headache].

Journal: Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova 20100101

Title: Neuronal potassium channel openers in the management of epilepsy: role and potential of retigabine.

Journal: Clinical pharmacology : advances and applications 20100101

Title: [Efficient treatment of chronic backache].

Journal: MMW Fortschritte der Medizin 20091210

Title: Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20091201

Title: Treatment with the Kv7 potassium channel activator flupirtine is beneficial in two independent mouse models of pulmonary hypertension.

Journal: British journal of pharmacology 20090801

Title: [Systematic review of the therapeutics for prion diseases].

Journal: Brain and nerve = Shinkei kenkyu no shinpo 20090801

Title: A girl with headache, confusion and green urine.

Journal: Journal of neurology 20090701

Title: KCNQ currents and their contribution to resting membrane potential and the excitability of interstitial cells of Cajal from the guinea pig bladder.

Journal: The Journal of urology 20090701

Title: Flupirtine: pharmacology and clinical applications of a nonopioid analgesic and potentially neuroprotective compound.

Journal: Expert opinion on pharmacotherapy 20090601

Title: An in vitro screening cascade to identify neuroprotective antioxidants in ALS.

Journal: Free radical biology & medicine 20090415

Title: KCNQ modulators reveal a key role for KCNQ potassium channels in regulating the tone of rat pulmonary artery smooth muscle.

Journal: The Journal of pharmacology and experimental therapeutics 20090401

Title: 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.

Journal: Journal of neurochemistry 20090401

Title: Clinical trials for prion disease: difficult challenges, but hope for the future.

Journal: The Lancet. Neurology 20090401

Title: Safety and efficacy of quinacrine in human prion disease (PRION-1 study): a patient-preference trial.

Journal: The Lancet. Neurology 20090401

Title: Neural KCNQ (Kv7) channels.

Journal: British journal of pharmacology 20090401

Title: Investigation of the in vitro metabolism of the analgesic flupirtine.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20090301

Title: A KCNQ channel opener for experimental neonatal seizures and status epilepticus.

Journal: Annals of neurology 20090301

Title: Therapeutic trials in human transmissible spongiform encephalo-pathies: recent advances and problems to address.

Journal: Infectious disorders drug targets 20090201

Title: GDNF selectively induces microglial activation and neuronal survival in CA1/CA3 hippocampal regions exposed to NMDA insult through Ret/ERK signalling.

Journal: PloS one 20090101

Title: Enhancing m currents: a way out for neuropathic pain?

Journal: Frontiers in molecular neuroscience 20090101

Title: Efficacy and safety of bilateral continuous theta burst stimulation (cTBS) for the treatment of chronic tinnitus: design of a three-armed randomized controlled trial.

Journal: Trials 20090101

Title: Analgesic efficacy and tolerability of flupirtine vs. tramadol in patients with subacute low back pain: a double-blind multicentre trial*.

Journal: Current medical research and opinion 20081201

Title: K(+)-channel openers suppress epileptiform activities induced by 4-aminopyridine in cultured rat hippocampal neurons.

Journal: Journal of pharmacological sciences 20081201

Title: Flupirtine as neuroprotective add-on therapy in autoimmune optic neuritis.

Journal: The American journal of pathology 20081101

Title: Combination therapy with flupirtine and opioid: studies in rat pain models.

Journal: Pain medicine (Malden, Mass.) 20081001

Title: Combination therapy with flupirtine and opioid: open-label case series in the treatment of neuropathic pain associated with cancer.

Journal: Pain medicine (Malden, Mass.) 20081001

Title: Bimodal effects of the Kv7 channel activator retigabine on vascular K+ currents.

Journal: British journal of pharmacology 20080901

Title: Vascular KCNQ potassium channels as novel targets for the control of mesenteric artery constriction by vasopressin, based on studies in single cells, pressurized arteries, and in vivo measurements of mesenteric vascular resistance.

Journal: The Journal of pharmacology and experimental therapeutics 20080501

Title: G-protein inwardly rectifying potassium channels are involved in the hypotensive effect of I1-imidazoline receptor selective ligands.

Journal: Journal of hypertension 20080501

Title: Systematic review of therapeutic interventions in human prion disease.

Journal: Neurology 20080408

Title: Molecular pharmacology and therapeutic potential of neuronal Kv7-modulating drugs.

Journal: Current opinion in pharmacology 20080201

Title: Identification of new functional inhibitors of acid sphingomyelinase using a structure-property-activity relation model.

Journal: Journal of medicinal chemistry 20080124

Title: [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].

Journal: MMW Fortschritte der Medizin 20080117

Title: Antihyperalgesic and analgesic properties of the N-methyl-D-aspartate (NMDA) receptor antagonist neramexane in a human surrogate model of neurogenic hyperalgesia.

Journal: European journal of pain (London, England) 20080101

Title: The efficacy of tetracyclines in peripheral and intracerebral prion infection.

Journal: PloS one 20080101

Title: [Efficacy of katadolon and cranial-spine electromagnetic neuromodulation in patients with discogenic radiculopathy].

Journal: Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova 20080101

Title: [Analgesic and muscle tonus normalizing effect of flupirtine retard in chronic back pain].

Journal: MMW Fortschritte der Medizin 20071025

Title: Flupirtine attenuates sodium nitroprusside-induced damage to retinal photoreceptors, in situ.

Journal: Brain research bulletin 20070712

Title: Molecular expression and pharmacological identification of a role for K(v)7 channels in murine vascular reactivity.

Journal: British journal of pharmacology 20070701

Title: [Many faces--one disease: fibromyalgia].

Journal: Kinderkrankenschwester : Organ der Sektion Kinderkrankenpflege 20070701

Title: Vasopressin stimulates action potential firing by protein kinase C-dependent inhibition of KCNQ5 in A7r5 rat aortic smooth muscle cells.

Journal: American journal of physiology. Heart and circulatory physiology 20070301

Title: Activators of potassium M currents have anticonvulsant actions in two rat models of encephalitis.

Journal: European journal of pharmacology 20070119

Title: The use of flupirtine in treatment of tinnitus.

Journal: Acta oto-laryngologica. Supplementum 20061201

Title: Antidystonic effects of Kv7 (KCNQ) channel openers in the dt sz mutant, an animal model of primary paroxysmal dystonia.

Journal: British journal of pharmacology 20061101

Title: KCNQ/M-currents contribute to the resting membrane potential in rat visceral sensory neurons.

Journal: The Journal of physiology 20060815

Title: Retigabine and flupirtine exert neuroprotective actions in organotypic hippocampal cultures.

Journal: Neuropharmacology 20060801

Title: [Backache is often caused by strained muscles].

Journal: MMW Fortschritte der Medizin 20060525

Title: [The use of katadolon (flupirtine) in the treatment of lower back pain].

Journal: Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova 20060101

Title: HIV neurotoxicity: potential therapeutic interventions.

Journal: Journal of biomedicine & biotechnology 20060101

Title: [Use of katadolon in the treatment of abuse headache].

Journal: Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova 20060101

Title: [The use of katadolon in patients with spondylogenic dorsalgia].

Journal: Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova 20060101

Title: Tumor-necrosis-factor-related apoptosis-inducing-ligand (TRAIL)-mediated death of neurons in living human brain tissue is inhibited by flupirtine-maleate.

Journal: Journal of neuroimmunology 20051001

Title: Recent developments on KCNQ potassium channel openers.

Journal: Current medicinal chemistry 20050101

Title: The potassium channel modulator flupirtine shifts the frequency-response function of hippocampal synapses to favour LTD in mice.

Journal: Neuroscience letters 20041111

Title: [Parental administration of flupirtine in musculoskeletal pain. Results of a postmarket surveillance study].

Journal: MMW Fortschritte der Medizin 20040524

Title: Efficacy of flupirtine on cognitive function in patients with CJD: A double-blind study.

Journal: Neurology 20040309

Title: Pharmacological characterisation of acid-induced muscle allodynia in rats.

Journal: European journal of pharmacology 20040308

Title: M channels containing KCNQ2 subunits modulate norepinephrine, aspartate, and GABA release from hippocampal nerve terminals.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20040121

Title: Dissociation of morphine analgesia and sedation evaluated by EEG measures in healthy volunteers.

Journal: Arzneimittel-Forschung 20040101

Title: Paradoxical cerebral cortical hyperexcitability following flupirtine overdose.

Journal: Journal of toxicology. Clinical toxicology 20040101

Title: The therapeutic potential of neuronal KCNQ channel modulators.

Journal: Expert opinion on therapeutic targets 20031201

Title: [Flupirtine in acute and chronic pain associated with muscle tenseness. Results of a postmarket surveillance study].

Journal: MMW Fortschritte der Medizin 20030310

Title: Attenuation of methamphetamine induced dopaminergic neurotoxicity by flupirtine: microdialysis study on dopamine release and free radical generation.

Journal: Journal of neural transmission (Vienna, Austria : 1996) 20030201

Title: Analgesic efficacy of flupirtine in primary care of patients with osteoporosis related pain. A multivariate analysis.

Journal: Arzneimittel-Forschung 20030101

Title: [Flupirtine in acute and chronic pain associated with muscle tenseness. Results of a postmarket surveillance study].

Journal: Fortschritte der Medizin. Originalien 20030101

Title: Effect of functional NMDA-antagonist flupirtine on automatic postural responses in Parkinson's disease.

Journal: Journal of neurology 20020701

Title: Treatment of spasticity.

Journal: Spinal cord 20020601

Title: Advanced fibre optical scanning in thin-layer chromatography for drug identification.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020525

Title: [Centrally acting analgesic against fibromyalgia. The body's own pain control is activated].

Journal: MMW Fortschritte der Medizin 20020506

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Flupirtine blocks apoptosis in batten patient lymphoblasts and in human postmitotic CLN3- and CLN2-deficient neurons.

Journal: Annals of neurology 20020401

Title: Neuroprotective effect of flupirtine in prion disease.

Journal: Drugs of today (Barcelona, Spain : 1998) 20020101

Title: Applications of liquid chromatography-tandem mass spectrometry in drug and biomedical analyses.

Journal: Clinica chimica acta; international journal of clinical chemistry 20011101

Title: Synthesis and pharmacological evaluation of (indol-3-yl)alkylamides as potent analgesic agents.

Journal: Arzneimittel-Forschung 20011001

Title: Simultaneous determination of flupirtine and its major active metabolite in human plasma by liquid chromatography-tandem mass spectrometry.

Journal: Journal of chromatography. B, Biomedical sciences and applications 20010505

Title: Novel approaches in diagnosis and therapy of Creutzfeldt-Jakob disease.

Journal: Mechanisms of ageing and development 20000731

Title: [Asymptomatic diclofenac-induced acute hepatitis].

Journal: Deutsche medizinische Wochenschrift (1946) 20000623

Title: Melatonin counteracts ischemia-induced apoptosis in human retinal pigment epithelial cells.

Journal: Investigative ophthalmology & visual science 19981101

Title: Antiparkinsonian and other motor effects of flupirtine alone and in combination with dopaminergic drugs.

Journal: European journal of pharmacology 19970526

Title: Pharmacological mechanisms of action of flupirtine: a novel, centrally acting, nonopioid analgesic evaluated by its discriminative effects in the rat.

Journal: The Journal of pharmacology and experimental therapeutics 19880901

Title: Pharmacokinetics of flupirtine in elderly volunteers and in patients with moderate renal impairment.

Journal: Postgraduate medical journal 19880501

Title: [General pharmacologic studies on the analgesic flupirtine].

Journal: Arzneimittel-Forschung 19850101

Title: Quantitation of flupirtine and its active acetylated metabolite by reversed-phase high-performance liquid chromatography using fluorometric detection.

Journal: Journal of chromatography 19840113

Title: Kornhuber J, et al. Flupirtine shows functional NMDA receptor antagonism by enhancing Mg2+ block via activation of voltageindependent potassium channels. Rapid communication. J Neural Transm. 1999;106(9-10):857-67.

Title: Klinger F, et al. Concomitant facilitation of GABAA receptors and KV7 channels by the non-opioid analgesic flupirtine. Br J Pharmacol. 2012 Jul;166(5):1631-42.

Title: Swedberg MD, et al. Pharmacological mechanisms of action of flupirtine: a novel, centrally acting, nonopioid analgesic evaluated by its discriminative effects in the rat. J Pharmacol Exp Ther. 1988 Sep;246(3):1067-74.

Title: Wu SN, et al. Evidence for inhibitory effects of flupirtine, a centrally acting analgesic, on delayed rectifier k(+) currents in motor neuron-like cells. Evid Based Complement Alternat Med. 2012;2012:148403.

Title: Kolosov A, et al. Flupirtine enhances the anti-hyperalgesic effects of morphine in a rat model of prostate bone metastasis. Pain Med. 2012 Nov;13(11):1444-56.

Title: Michel MC, et al. Unexpected frequent hepatotoxicity of a prescription drug, flupirtine, marketed for about 30 years. Br J Clin Pharmacol. 2012 May;73(5):821-5.

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Tags:56995-20-1 Molecular Formula|56995-20-1 MDL|56995-20-1 SMILES|56995-20-1 Flupirtine
Catalog No.: AA019FSF
56995-20-1,MFCD00864265
56995-20-1 | Flupirtine
This product is typically in stock,please click "Inquire" below or contact us at [email protected]for pricing and availability information.
Inquire
Technical Information
Catalog Number: AA019FSF
Chemical Name: Flupirtine
CAS Number: 56995-20-1
Molecular Formula: C15H17FN4O2
Molecular Weight: 304.3195
MDL Number: MFCD00864265
SMILES: CCOC(=O)Nc1ccc(nc1N)NCc1ccc(cc1)F
Properties
Complexity: 350  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 22  
Hydrogen Bond Acceptor Count: 6  
Hydrogen Bond Donor Count: 3  
Isotope Atom Count: 0  
Rotatable Bond Count: 6  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 2.4  
Downstream Synthesis Route
541-41-3    112523-78-1    56995-20-1 

[1]Kinarivala,Nihar;Patel,Ronak;Boustany,Rose-Mary;Al-Ahmad,Abraham;Trippier,PaulC.[JournalofMedicinalChemistry,2017,vol.60,#23,p.9739-9756]

[2]CurrentPatentAssignee:XIANDUCHUANGPHARMACEUTICALTECH-CN110317167,2019,ALocationinpatent:Paragraph0052-0054;0059-0060;0065;0070-0071;0076

[3]Schwoch;Kramer;Neidlein;Suschitzky[HelveticaChimicaActa,1994,vol.77,#8,p.2175-2190]

452-58-4    56995-20-1 

[1]Schwoch;Kramer;Neidlein;Suschitzky[HelveticaChimicaActa,1994,vol.77,#8,p.2175-2190]

76902-24-4    56995-20-1 

[1]Schwoch;Kramer;Neidlein;Suschitzky[HelveticaChimicaActa,1994,vol.77,#8,p.2175-2190]

161263-86-1    56995-20-1 

[1]Schwoch;Kramer;Neidlein;Suschitzky[HelveticaChimicaActa,1994,vol.77,#8,p.2175-2190]

Literature fold

Title: Efficacy and safety of flupirtine modified release for the management of moderate to severe chronic low back pain: results of SUPREME, a prospective randomized, double-blind, placebo- and active-controlled parallel-group phase IV study.

Journal: Current medical research and opinion20121001

Title: Transcompartmental reversal of single fibre hyperexcitability in juxtaparanodal Kv1.1-deficient vagus nerve axons by activation of nodal KCNQ channels.

Journal: The Journal of physiology20120815

Title: M-type potassium channels modulate Schaffer collateral-CA1 glutamatergic synaptic transmission.

Journal: The Journal of physiology20120815

Title: Concomitant facilitation of GABAA receptors and KV7 channels by the non-opioid analgesic flupirtine.

Journal: British journal of pharmacology20120701

Title: Unexpected frequent hepatotoxicity of a prescription drug, flupirtine, marketed for about 30 years.

Journal: British journal of clinical pharmacology20120501

Title: Efficacy and safety of flupirtine maleate and tramadol hydrochloride in postoperative pain management--a prospective randomised double blinded study.

Journal: Journal of the Indian Medical Association20120301

Title: [Chronic backache. Rational therapy of muscle-induced pain].

Journal: MMW Fortschritte der Medizin20120223

Title: M channel enhancers and physiological M channel block.

Journal: The Journal of physiology20120215

Title: The evolving understanding of the analgesic mechanism of action of flupirtine.

Journal: Journal of clinical pharmacy and therapeutics20120201

Title: Retigabine, a K(V)7 (KCNQ) potassium channel opener, attenuates L-DOPA-induced dyskinesias in 6-OHDA-lesioned rats.

Journal: Neuropharmacology20120201

Title: Flupirtine inhibits calcitonin-gene related peptide release from rat brainstem in vitro.

Journal: Neuroscience letters20120111

Title: Kv7 potassium channels in airway smooth muscle cells: signal transduction intermediates and pharmacological targets for bronchodilator therapy.

Journal: American journal of physiology. Lung cellular and molecular physiology20120101

Title: Neuroprotective function for ramified microglia in hippocampal excitotoxicity.

Journal: Journal of neuroinflammation20120101

Title: Clinical utility of adjunctive retigabine in partial onset seizures in adults.

Journal: Therapeutics and clinical risk management20120101

Title: CSF concentrations of cAMP and cGMP are lower in patients with Creutzfeldt-Jakob disease but not Parkinson's disease and amyotrophic lateral sclerosis.

Journal: PloS one20120101

Title: The Effects of the KCNQ Openers Retigabine and Flupirtine on Myotonia in Mammalian Skeletal Muscle Induced by a Chloride Channel Blocker.

Journal: Evidence-based complementary and alternative medicine : eCAM20120101

Title: Flupirtine: Clinical pharmacology.

Journal: Journal of anaesthesiology, clinical pharmacology20120101

Title: Functional significance of M-type potassium channels in nociceptive cutaneous sensory endings.

Journal: Frontiers in molecular neuroscience20120101

Title: Evidence for inhibitory effects of flupirtine, a centrally acting analgesic, on delayed rectifier k(+) currents in motor neuron-like cells.

Journal: Evidence-based complementary and alternative medicine : eCAM20120101

Title: Protective effect of the KCNQ activator flupirtine on a model of repetitive febrile seizures.

Journal: Epilepsy research20111101

Title: Efficacy and tolerability of flupirtine in subacute/ chronic musculoskeletal pain - results of a patient level, pooled re-analysis of randomized, double-blind, controlled trials.

Journal: International journal of clinical pharmacology and therapeutics20111101

Title: Fatal prion disease in a mouse model of genetic E200K Creutzfeldt-Jakob disease.

Journal: PLoS pathogens20111101

Title: Parent-reported benefits of flupirtine in juvenile neuronal ceroid lipofuscinosis (Batten disease; CLN3) are not supported by quantitative data.

Journal: Journal of inherited metabolic disease20111001

Title: KV7 channels regulate muscle tone and nonadrenergic noncholinergic relaxation of the rat gastric fundus.

Journal: Pharmacological research20111001

Title: Activation of vascular KCNQ (Kv7) potassium channels reverses spasmogen-induced constrictor responses in rat basilar artery.

Journal: British journal of pharmacology20110901

Title: Flupirtine is a safe alternative drug in patients with hypersensitivity to NSAIDs.

Journal: European journal of clinical pharmacology20110901

Title: Nucleotides control the excitability of sensory neurons via two P2Y receptors and a bifurcated signaling cascade.

Journal: Pain20110801

Title: Flupirtine-induced hepatic failure requiring orthotopic liver transplant.

Journal: Experimental and clinical transplantation : official journal of the Middle East Society for Organ Transplantation20110801

Title: KCNQ5 channels control resting properties and release probability of a synapse.

Journal: Nature neuroscience20110701

Title: Pathology of flupirtine-induced liver injury: a histological and clinical study of six cases.

Journal: Virchows Archiv : an international journal of pathology20110601

Title: N-(4-Fluoro-benz-yl)-3-nitro-pyridine-2,6-diamine.

Journal: Acta crystallographica. Section E, Structure reports online20110601

Title: Transcriptional repression of the M channel subunit Kv7.2 in chronic nerve injury.

Journal: Pain20110401

Title: The contribution of Kv7 channels to pregnant mouse and human myometrial contractility.

Journal: Journal of cellular and molecular medicine20110301

Title: Novel role of KCNQ2/3 channels in regulating neuronal cell viability.

Journal: Cell death and differentiation20110301

Title: Involvement of inward rectifier and M-type currents in carbachol-induced epileptiform synchronization.

Journal: Neuropharmacology20110301

Title: Mumijo traditional medicine: fossil deposits from antarctica (chemical composition and beneficial bioactivity).

Journal: Evidence-based complementary and alternative medicine : eCAM20110101

Title: Flupirtine antinociception in the rat orofacial formalin test: an analysis of combination therapies with morphine and tramadol.

Journal: Pharmacology, biochemistry, and behavior20110101

Title: Rapidly progressive dementias and the treatment of human prion diseases.

Journal: Expert opinion on pharmacotherapy20110101

Title: [Effect of maladaptive sets on the clinical picture and prediction of chronic headache of tension].

Journal: Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova20110101

Title: The Voltage-Sensing Domain of K(v)7.2 Channels as a Molecular Target for Epilepsy-Causing Mutations and Anticonvulsants.

Journal: Frontiers in pharmacology20110101

Title: Neuroprotective and anti-oxidant effects of caffeic acid isolated from Erigeron annuus leaf.

Journal: Chinese medicine20110101

Title: [Flupirtin (katadolon): a nonstandard action on pain transmission].

Journal: Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova20110101

Title: Drosophila KCNQ channel displays evolutionarily conserved electrophysiology and pharmacology with mammalian KCNQ channels.

Journal: PloS one20110101

Title: Neuropathic pain: a personal case reflection on a critical incident.

Journal: Indian journal of palliative care20110101

Title: Correlation versus causation? Pharmacovigilance of the analgesic flupirtine exemplifies the need for refined spontaneous ADR reporting.

Journal: PloS one20110101

Title: Phantom limb pain: mechanisms and treatment approaches.

Journal: Pain research and treatment20110101

Title: Bioanalytical method development, validation and quantification of flupirtine maleate in rat plasma by liquid chromatography-tandem mass spectrometry.

Journal: Arzneimittel-Forschung20110101

Title: [2010 German Pain Congress. Backache - new data, specific muscle etiology and targeted therapy].

Journal: MMW Fortschritte der Medizin20101216

Title: [Musculoskeletal pain. Pain relief with muscle relaxant].

Journal: MMW Fortschritte der Medizin20101202

Title: Enhancement of axonal potassium conductance reduces nerve hyperexcitability in an in vitro model of oxaliplatin-induced acute neuropathy.

Journal: Neurotoxicology20101201

Title: Flupirtine may stop the progressive course of subacute sclerosing panencephalitis.

Journal: Medical hypotheses20101201

Title: Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.

Journal: Toxicological sciences : an official journal of the Society of Toxicology20101201

Title: Green urine following exposure to flupirtine.

Journal: American journal of kidney diseases : the official journal of the National Kidney Foundation20101101

Title: Flupirtine in pain management: pharmacological properties and clinical use.

Journal: CNS drugs20101001

Title: M-type potassium channels modulate the intrinsic excitability of infralimbic neurons and regulate fear expression and extinction.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience20100915

Title: Positive reinforcing effects of flupirtine--two case reports.

Journal: Progress in neuro-psychopharmacology & biological psychiatry20100816

Title: [IGOST guideline for pharmacotherapy of low back pain].

Journal: MMW Fortschritte der Medizin20100812

Title: The Kv7 potassium channel activator flupirtine affects clinical excitability parameters of myelinated axons in isolated rat sural nerve.

Journal: Journal of the peripheral nervous system : JPNS20100301

Title: CNSB004 (Leconotide) causes antihyperalgesia without side effects when given intravenously: a comparison with ziconotide in a rat model of diabetic neuropathic pain.

Journal: Pain medicine (Malden, Mass.)20100201

Title: Discrepancy between prevalence and perceived effectiveness of treatment methods in myofascial pain syndrome: results of a cross-sectional, nationwide survey.

Journal: BMC musculoskeletal disorders20100101

Title: The M-channel blocker linopirdine is an agonist of the capsaicin receptor TRPV1.

Journal: Journal of pharmacological sciences20100101

Title: Evidence of key tinnitus-related brain regions documented by a unique combination of manganese-enhanced MRI and acoustic startle reflex testing.

Journal: PloS one20100101

Title: [New approaches to the treatment of chronic daily headache].

Journal: Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova20100101

Title: Neuronal potassium channel openers in the management of epilepsy: role and potential of retigabine.

Journal: Clinical pharmacology : advances and applications20100101

Title: [Efficient treatment of chronic backache].

Journal: MMW Fortschritte der Medizin20091210

Title: Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.

Journal: Bioorganic & medicinal chemistry letters20091201

Title: Treatment with the Kv7 potassium channel activator flupirtine is beneficial in two independent mouse models of pulmonary hypertension.

Journal: British journal of pharmacology20090801

Title: [Systematic review of the therapeutics for prion diseases].

Journal: Brain and nerve = Shinkei kenkyu no shinpo20090801

Title: A girl with headache, confusion and green urine.

Journal: Journal of neurology20090701

Title: KCNQ currents and their contribution to resting membrane potential and the excitability of interstitial cells of Cajal from the guinea pig bladder.

Journal: The Journal of urology20090701

Title: Flupirtine: pharmacology and clinical applications of a nonopioid analgesic and potentially neuroprotective compound.

Journal: Expert opinion on pharmacotherapy20090601

Title: An in vitro screening cascade to identify neuroprotective antioxidants in ALS.

Journal: Free radical biology & medicine20090415

Title: KCNQ modulators reveal a key role for KCNQ potassium channels in regulating the tone of rat pulmonary artery smooth muscle.

Journal: The Journal of pharmacology and experimental therapeutics20090401

Title: 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.

Journal: Journal of neurochemistry20090401

Title: Clinical trials for prion disease: difficult challenges, but hope for the future.

Journal: The Lancet. Neurology20090401

Title: Safety and efficacy of quinacrine in human prion disease (PRION-1 study): a patient-preference trial.

Journal: The Lancet. Neurology20090401

Title: Neural KCNQ (Kv7) channels.

Journal: British journal of pharmacology20090401

Title: Investigation of the in vitro metabolism of the analgesic flupirtine.

Journal: Drug metabolism and disposition: the biological fate of chemicals20090301

Title: A KCNQ channel opener for experimental neonatal seizures and status epilepticus.

Journal: Annals of neurology20090301

Title: Therapeutic trials in human transmissible spongiform encephalo-pathies: recent advances and problems to address.

Journal: Infectious disorders drug targets20090201

Title: GDNF selectively induces microglial activation and neuronal survival in CA1/CA3 hippocampal regions exposed to NMDA insult through Ret/ERK signalling.

Journal: PloS one20090101

Title: Enhancing m currents: a way out for neuropathic pain?

Journal: Frontiers in molecular neuroscience20090101

Title: Efficacy and safety of bilateral continuous theta burst stimulation (cTBS) for the treatment of chronic tinnitus: design of a three-armed randomized controlled trial.

Journal: Trials20090101

Title: Analgesic efficacy and tolerability of flupirtine vs. tramadol in patients with subacute low back pain: a double-blind multicentre trial*.

Journal: Current medical research and opinion20081201

Title: K(+)-channel openers suppress epileptiform activities induced by 4-aminopyridine in cultured rat hippocampal neurons.

Journal: Journal of pharmacological sciences20081201

Title: Flupirtine as neuroprotective add-on therapy in autoimmune optic neuritis.

Journal: The American journal of pathology20081101

Title: Combination therapy with flupirtine and opioid: studies in rat pain models.

Journal: Pain medicine (Malden, Mass.)20081001

Title: Combination therapy with flupirtine and opioid: open-label case series in the treatment of neuropathic pain associated with cancer.

Journal: Pain medicine (Malden, Mass.)20081001

Title: Bimodal effects of the Kv7 channel activator retigabine on vascular K+ currents.

Journal: British journal of pharmacology20080901

Title: Vascular KCNQ potassium channels as novel targets for the control of mesenteric artery constriction by vasopressin, based on studies in single cells, pressurized arteries, and in vivo measurements of mesenteric vascular resistance.

Journal: The Journal of pharmacology and experimental therapeutics20080501

Title: G-protein inwardly rectifying potassium channels are involved in the hypotensive effect of I1-imidazoline receptor selective ligands.

Journal: Journal of hypertension20080501

Title: Systematic review of therapeutic interventions in human prion disease.

Journal: Neurology20080408

Title: Molecular pharmacology and therapeutic potential of neuronal Kv7-modulating drugs.

Journal: Current opinion in pharmacology20080201

Title: Identification of new functional inhibitors of acid sphingomyelinase using a structure-property-activity relation model.

Journal: Journal of medicinal chemistry20080124

Title: [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].

Journal: MMW Fortschritte der Medizin20080117

Title: Antihyperalgesic and analgesic properties of the N-methyl-D-aspartate (NMDA) receptor antagonist neramexane in a human surrogate model of neurogenic hyperalgesia.

Journal: European journal of pain (London, England)20080101

Title: The efficacy of tetracyclines in peripheral and intracerebral prion infection.

Journal: PloS one20080101

Title: [Efficacy of katadolon and cranial-spine electromagnetic neuromodulation in patients with discogenic radiculopathy].

Journal: Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova20080101

Title: [Analgesic and muscle tonus normalizing effect of flupirtine retard in chronic back pain].

Journal: MMW Fortschritte der Medizin20071025

Title: Flupirtine attenuates sodium nitroprusside-induced damage to retinal photoreceptors, in situ.

Journal: Brain research bulletin20070712

Title: Molecular expression and pharmacological identification of a role for K(v)7 channels in murine vascular reactivity.

Journal: British journal of pharmacology20070701

Title: [Many faces--one disease: fibromyalgia].

Journal: Kinderkrankenschwester : Organ der Sektion Kinderkrankenpflege20070701

Title: Vasopressin stimulates action potential firing by protein kinase C-dependent inhibition of KCNQ5 in A7r5 rat aortic smooth muscle cells.

Journal: American journal of physiology. Heart and circulatory physiology20070301

Title: Activators of potassium M currents have anticonvulsant actions in two rat models of encephalitis.

Journal: European journal of pharmacology20070119

Title: The use of flupirtine in treatment of tinnitus.

Journal: Acta oto-laryngologica. Supplementum20061201

Title: Antidystonic effects of Kv7 (KCNQ) channel openers in the dt sz mutant, an animal model of primary paroxysmal dystonia.

Journal: British journal of pharmacology20061101

Title: KCNQ/M-currents contribute to the resting membrane potential in rat visceral sensory neurons.

Journal: The Journal of physiology20060815

Title: Retigabine and flupirtine exert neuroprotective actions in organotypic hippocampal cultures.

Journal: Neuropharmacology20060801

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Journal: MMW Fortschritte der Medizin20060525

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Title: HIV neurotoxicity: potential therapeutic interventions.

Journal: Journal of biomedicine & biotechnology20060101

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Title: [The use of katadolon in patients with spondylogenic dorsalgia].

Journal: Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova20060101

Title: Tumor-necrosis-factor-related apoptosis-inducing-ligand (TRAIL)-mediated death of neurons in living human brain tissue is inhibited by flupirtine-maleate.

Journal: Journal of neuroimmunology20051001

Title: Recent developments on KCNQ potassium channel openers.

Journal: Current medicinal chemistry20050101

Title: The potassium channel modulator flupirtine shifts the frequency-response function of hippocampal synapses to favour LTD in mice.

Journal: Neuroscience letters20041111

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Journal: MMW Fortschritte der Medizin20040524

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Journal: Neurology20040309

Title: Pharmacological characterisation of acid-induced muscle allodynia in rats.

Journal: European journal of pharmacology20040308

Title: M channels containing KCNQ2 subunits modulate norepinephrine, aspartate, and GABA release from hippocampal nerve terminals.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience20040121

Title: Dissociation of morphine analgesia and sedation evaluated by EEG measures in healthy volunteers.

Journal: Arzneimittel-Forschung20040101

Title: Paradoxical cerebral cortical hyperexcitability following flupirtine overdose.

Journal: Journal of toxicology. Clinical toxicology20040101

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Journal: MMW Fortschritte der Medizin20030310

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Journal: Journal of neurology20020701

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Journal: Spinal cord20020601

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