Flupirtine is a pyridine derivative that is in clinical use as a nonopioid analgesic. It was approved for the treatment of pain in 1984 in Europe. It is not approved for use in the U.S. or Canada, but is currently in phase II trials for the treatment of fibromyalgia.
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|Weight||Average: 304.3195 |
Investigated for use/treatment in fibromyalgia.
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|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].
Bioavailability: 90% (oral), 70% (rectal)
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|Protein binding||Not Available|
Hepatic to 2-amino-3-acetylamino-6-(para-fluorobenzylamino) pyridine (which has 20-30% the analgesic potential of its parent compound) and Para-fluorohippuric acid.
|Route of elimination|
72% of flupirtine and its metabolites appear in urine and 18% appear in faeces.
6.5 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).
Oral, mouse: LD50 = 300 mg/kg; Oral, rabbit: LD50 = 3200 mg/kg; Oral, rat: LD50 = 980 mg/kg.
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|ATC Codes||N02BG07 — Flupirtine|
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|MSDS||Download (568 KB)|
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|Predicted ADMET features|
|Mass Spec (NIST)||Not Available|
|Description||This compound belongs to the class of organic compounds known as 2-benzylaminopyridines. These are aromatic compounds containing pyridine ring substituted at the 2-position by a benzylamine group.|
|Class||Benzene and substituted derivatives|
|Alternative Parents||Secondary alkylarylamines / Fluorobenzenes / Aminopyridines and derivatives / Imidolactams / Aryl fluorides / Heteroaromatic compounds / Carbamate esters / Organic carbonic acids and derivatives / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organofluorides / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds|
|Substituents||2-benzylaminopyridine / Aminopyridine / Fluorobenzene / Halobenzene / Secondary aliphatic/aromatic amine / Aryl fluoride / Aryl halide / Pyridine / Imidolactam / Heteroaromatic compound/ Carbamic acid ester / Carbonic acid derivative / Secondary amine / Azacycle / Organoheterocyclic compound / Hydrocarbon derivative / Organooxygen compound / Organonitrogen compound / Organofluoride / Organohalogen compound / Primary amine / Organopnictogen compound / Organic oxygen compound / Carbonyl group / Organic nitrogen compound / Organic oxide / Amine / Aromatic heteromonocyclic compound|
|Molecular Framework||Aromatic heteromonocyclic compounds|
|External Descriptors||Not Available|
- Pharmacological action
- General Function:
- Thioesterase binding
- Specific Function:
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianser...
- Gene Name:
- Uniprot ID:
- Uniprot Name:
- Alpha-2A adrenergic receptor
- Molecular Weight:
- 48956.275 Da
- Swedberg MD, Shannon HE, Nickel B, Goldberg SR: 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. [PubMed:2901483 ]