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Details

Stereochemistry ACHIRAL
Molecular Formula C15H17FN4O2
Molecular Weight 304.3201
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUPIRTINE

SMILES

CCOC(=Nc1ccc(=NCc2ccc(cc2)F)[nH]c1N)O

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)

HIDE SMILES / InChI
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

PubMed

TitleDatePubMed
Quantitation of flupirtine and its active acetylated metabolite by reversed-phase high-performance liquid chromatography using fluorometric detection.
1984 Jan 13
[General pharmacologic studies on the analgesic flupirtine].
1985
Pharmacokinetics of flupirtine in elderly volunteers and in patients with moderate renal impairment.
1988 May
Pharmacological mechanisms of action of flupirtine: a novel, centrally acting, nonopioid analgesic evaluated by its discriminative effects in the rat.
1988 Sep
Antiparkinsonian and other motor effects of flupirtine alone and in combination with dopaminergic drugs.
1997 May 26
Melatonin counteracts ischemia-induced apoptosis in human retinal pigment epithelial cells.
1998 Nov
[Efficacy of katadolon and cranial-spine electromagnetic neuromodulation in patients with discogenic radiculopathy].
2008
Systematic review of therapeutic interventions in human prion disease.
2008 Apr 8
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
Combination therapy with flupirtine and opioid: studies in rat pain models.
2008 Oct
Bimodal effects of the Kv7 channel activator retigabine on vascular K+ currents.
2008 Sep
Enhancing m currents: a way out for neuropathic pain?
2009
Neural KCNQ (Kv7) channels.
2009 Apr
Safety and efficacy of quinacrine in human prion disease (PRION-1 study): a patient-preference trial.
2009 Apr
Clinical trials for prion disease: difficult challenges, but hope for the future.
2009 Apr
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
An in vitro screening cascade to identify neuroprotective antioxidants in ALS.
2009 Apr 15
[Systematic review of the therapeutics for prion diseases].
2009 Aug
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
Therapeutic trials in human transmissible spongiform encephalo-pathies: recent advances and problems to address.
2009 Feb
KCNQ currents and their contribution to resting membrane potential and the excitability of interstitial cells of Cajal from the guinea pig bladder.
2009 Jul
A girl with headache, confusion and green urine.
2009 Jul
Flupirtine: pharmacology and clinical applications of a nonopioid analgesic and potentially neuroprotective compound.
2009 Jun
A KCNQ channel opener for experimental neonatal seizures and status epilepticus.
2009 Mar
Investigation of the in vitro metabolism of the analgesic flupirtine.
2009 Mar
Neuronal potassium channel openers in the management of epilepsy: role and potential of retigabine.
2010
[New approaches to the treatment of chronic daily headache].
2010
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
Positive reinforcing effects of flupirtine--two case reports.
2010 Aug 16
Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.
2010 Dec
Flupirtine may stop the progressive course of subacute sclerosing panencephalitis.
2010 Dec
Enhancement of axonal potassium conductance reduces nerve hyperexcitability in an in vitro model of oxaliplatin-induced acute neuropathy.
2010 Dec
Evidence of key tinnitus-related brain regions documented by a unique combination of manganese-enhanced MRI and acoustic startle reflex testing.
2010 Dec 15
[2010 German Pain Congress. Backache - new data, specific muscle etiology and targeted therapy].
2010 Dec 16
[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
Discrepancy between prevalence and perceived effectiveness of treatment methods in myofascial pain syndrome: results of a cross-sectional, nationwide survey.
2010 Feb 11
The Kv7 potassium channel activator flupirtine affects clinical excitability parameters of myelinated axons in isolated rat sural nerve.
2010 Mar
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
Patents

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.
Name Type Language
FLUPIRTINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ETHYL 2-AMINO-6-((P-FLUOROBENZYL)AMINO)-3-PYRIDINECARBAMATE
Common Name English
FLUPIRTINTE [VANDF]
Common Name English
FLUPIRTINE [INN]
Common Name English
FLUPIRTINE [MI]
Common Name English
FLUPIRTINE [VANDF]
Common Name English
FLUPIRTINE [WHO-DD]
Common Name English
W-2964
Common Name English
CARBAMIC ACID, (2-AMINO-6-(((4-FLUOROPHENYL)METHYL)AMINO)-3-PYRIDINYL)-, ETHYL ESTER, (Z)-2-
Common Name English
Classification Tree Code System Code
WHO-ATC N02BG07
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
NCI_THESAURUS C241
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
WHO-VATC QN02BG07
Created by admin on Fri Jun 25 22:20:10 UTC 2021 , Edited by admin on Fri Jun 25 22:20:10 UTC 2021
Code System Code Type Description
CAS
56995-20-1
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
PRIMARY
FDA UNII
MOH3ET196H
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
PRIMARY
MERCK INDEX
M5491
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
PRIMARY Merck Index
RXCUI
25193
Created by admin on Fri Jun 25 22:20:10 UTC 2021 , Edited by admin on Fri Jun 25 22:20:10 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
260-503-8
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
PRIMARY
MESH
C034161
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
PRIMARY
WIKIPEDIA
FLUPIRTINE
Created by admin on Fri Jun 25 22:20:10 UTC 2021 , Edited by admin on Fri Jun 25 22:20:10 UTC 2021
PRIMARY
DRUG CENTRAL
1215
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
PRIMARY
ChEMBL
CHEMBL255044
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
PRIMARY
PUBCHEM
53276
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
PRIMARY
EPA CompTox
56995-20-1
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
PRIMARY
EVMPD
SUB07732MIG
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
PRIMARY
INN
3976
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
PRIMARY
DRUG BANK
DB06623
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
PRIMARY
NCI_THESAURUS
C72116
Created by admin on Fri Jun 25 22:20:09 UTC 2021 , Edited by admin on Fri Jun 25 22:20:09 UTC 2021
PRIMARY