Flupirtine
Basic information
- CAS
56995-20-1- Standard SMILES
CCOC(=O)Nc1ccc(NCc2ccc(F)cc2)nc1N- InChIKey
JUUFBMODXQKSTD-UHFFFAOYSA-N- Molecular formula
- C15H17FN4O2
- Average molar mass
- 304.32 g/mol
- Monoisotopic mass
- 304.13355396
Overview
N-[2-amino-6-[(4-fluorophenyl)methylamino]-3-pyridinyl]carbamic acid ethyl ester is an aminopyridine.
Names & identifiers
- Preferred name
- Flupirtine
- IUPAC
- ethyl N-[2-amino-6-[(4-fluorophenyl)methylamino]-3-pyridinyl]carbamate
- English name
- Flupirtine
- Molecular formula
- C15H17FN4O2
- Molecular weight
- 304.32
Names & synonyms
Flupirtine56995-20-1Flupirtinumethyl N-[2-amino-6-[(4-fluorophenyl)methylamino]pyridin-3-yl]carbamateflupirtinaFlupirtinteMOH3ET196HDTXSID4048436W-2964ethyl 2-amino-6-((p-fluorobenzyl)amino)-3-pyridinecarbamateflupirtin maleateethyl N-(2-amino-6-((4-fluorophenyl)methylamino)pyridin-3-yl)carbamate
Show more names
W2964D-9998W 2964KatadolonFlupirtinTrancopal DoloFLUPIRITNE MALEATE
RefChem:141020DTXCID4028410N02BG07ethyl N-(2-amino-6-(((4-fluorophenyl)methyl)amino)pyridin-3-yl)carbamate260-503-8Flupirtine (INN)D 9998FLUPIRTINE [INN]
Database identifiers
- CAS
56995-20-1- PubChem CID
- 53276
- DTXSID
DTXSID4048436- ChEMBL
CHEMBL255044- ChEBI
CHEBI:94646- UNII
- MOH3ET196H
- EC Number
- 260-503-8
- Nikkaji
- J11.728E
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 89.3 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 350
Experimental & physicochemical properties
Drugs
Pharmaceuticals
Pharmaceuticals -> Nervous system -> Analgesics
Pharmaceuticals -> Listed in ZINC15
LogP2.57
Human DrugsPharmaceuticals
Physicochemical properties
- Melting point
- 115 · 115-116°
- Boiling point
- 445.15 °C · 445.15°C (rough estimate)
- Density
- 1.35 · 1.350±0.06 g/cm3(Predicted)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- solubility
- Soluble in DMSO
- form
- Powder
- pka
- 12.19 · 12.19±0.70(Predicted)
- Water Solubility
- 1 g/L · 1g/L(temperature not stated)
- Major Application
- forensics and toxicologyveterinary
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P301+P317, P304+P340, P317, P330, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Flupirtine
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Safety data
- wgk
- WGK 3
- Toxicity
- LD50 orally in mice, rats: 617, 1660 mg/kg (Jakovlev)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 13 - Non Combustible Solids
- Hazard statements
- H302-H312-H332
- Precautionary statements
- P280
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Mechanism of Action
Flupirtine upregulates Bcl-2, increases glutathione levels, activates an inwardly rectifying potassium channel, and delays loss of intermitochondrial membrane calcium retention capacity. Flupirtine acts like a NMDA receptor antagonists, but does not bind to the receptor. One study concluded that the discriminative effects of flupirtine are neither of opioid nor of alpha-1 adrenergic type, but are primarily mediated through alpha-2 adrenergic mechanisms [PMID: 2901483].
Biological Half-Life6.5 hrs (average), 11.2-16.8 hrs (average 14 hrs) (elderly), 8.7-10.9 hrs (average 9.8 hrs) (in those with moderate-level renal impairment).
Metabolism/MetabolitesHepatic to 2-amino-3-acetylamino-6-(para-fluorobenzylamino) pyridine (which has 20-30% the analgesic potential of its parent compound) and Para-fluorohippuric acid.
MeSH Pharmacological ClassificationCompounds capable of relieving pain without the loss of CONSCIOUSNESS.
Absorption, Distribution and Excretion
Bioavailability: 90% (oral), 70% (rectal)
72% of flupirtine and its metabolites appear in urine and 18% appear in faeces.
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >10000
Use ClassificationPharmaceuticals
Applications
UsesAnalgesic.
Therapeutic use of Flupirtine was discontinued due to drug induced liver injury (DILI). Since the mechanism of action is not related to its adverse effects, it is important to focus on chemical modifications.
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Related reactions
5 records
Compound notes
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