Structure via PubChem · Public domain (PubChem)
flupirtine
Sign in to saveFlupirtine is an aminopyridine that functions as a centrally acting non-opioid analgesic that was originally used as an analgesic for acute and chronic pain but in 2013 due to issues with liver toxicity, the European Medicines Agency restricted its use to acute pain, for no more than two weeks, and only for people who cannot use other painkillers. In March 2018, marketing authorisations for flupirtine were withdrawn following a European Medicines Agency recommendation based on the finding that the restrictions introduced in 2013 had not been sufficiently followed in clinical practice, and case
Chemical data
- Formula
- C15H17FN4O2
- Molecular weight
- 304.32 g/mol
- IUPAC name
- ethyl N-[2-amino-6-[(4-fluorophenyl)methylamino]-3-pyridinyl]carbamate
- SMILES
- CCOC(=O)NC1=C(N=C(C=C1)NCC2=CC=C(C=C2)F)N
- InChIKey
- JUUFBMODXQKSTD-UHFFFAOYSA-N
- XLogP
- 2.4
- Polar surface area
- 89.3 Ų
- H-bond donors
- 3
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- Indications
- pain, relapsing-remitting multiple sclerosis, Fever
via ChEMBL · EBI
Research
409 papers- Flupirtine in pain management: pharmacological properties and clinical use.CNS drugs · 2010
- Flupirtine, a re-discovered drug, revisited.Inflammation research : official journal of the European Histamine Research Society ... [et al.] · 2013
- Hyperexcitable arousal circuits drive sleep instability during aging.Science (New York, N.Y.) · 2022
- Flupirtine. A review of its pharmacological properties, and therapeutic efficacy in pain states.Drugs · 1993
- Flupirtine and antihistamines exert synergistic anti-nociceptive effects in mice.Psychopharmacology · 2023
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 304.134
- Has use
- medication
Show 6 more facts
- chemical formula
- C₁₅H₁₇FN₄O₂
- World Health Organisation international non-proprietary name
- flupirtine
- canonical SMILES
- CCOC(=O)NC1=C(N=C(C=C1)NCC2=CC=C(C=C2)F)N
- defined daily dose
- 0.4
- subject has role
- analgesic
- Commons category
- Flupirtine
via Wikidata · CC0
~6 min read
Encyclopedic overview
7 sectionsContents
- Uses
- Side effects
- Recreational use
- Mechanism of action
- History
- Research
- References
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| tradename = | Drugs.com = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =
Excerpted from Wikipedia’s “flupirtine” article, available under the CC BY-SA 4.0 licence.