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Flupirtine

Flupirtine structure

CAS No:
56995-20-1
Formula:
C15H17FN4O2
Chemical Name:
Flupirtine
Synonyms:
Carbamic acid,N-[2-amino-6-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]-,ethyl ester;Carbamic acid,[2-amino-6-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]-,ethyl ester;Flupirtine;Katadolon;D 9998;Trancopal Dolo;Ethyl [2-Amino-6-[(4-fluorobenzyl)amino]pyridin-3-yl]carbamate;[2-Amino-6-(4-fluoro-benzylamino)-pyridin-3-yl]-carbamic acid ethyl ester
Categories:
Organic Chemistry > Amides

Description

N-[2-amino-6-[(4-fluorophenyl)methylamino]-3-pyridinyl]carbamic acid ethyl ester is an aminopyridine.|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.

Flupirtine Basic Attributes

Molecular Weight：

304.32

Exact Mass：

304.13355396

EC Number：

260-503-8

UNII：

MOH3ET196H

DSSTox ID：

DTXSID4048436

ATC Code：

N - Nervous system

Characteristics

Melting Point：

115.5 °C

Safety Information

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P301+P312, P304+P312, P304+P340, P312, P330, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Toxicity

Toxicity Summary：

Oral, mouse: LD50 = 300 mg/kg; Oral, rabbit: LD50 = 3200 mg/kg; Oral, rat: LD50 = 980 mg/kg.

Drug Information

Drug Indication：

Investigated for use/treatment in fibromyalgia.

MeSH：

Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)

Absorption：

Bioavailability: 90% (oral), 70% (rectal)|72% of flupirtine and its metabolites appear in urine and 18% appear in faeces.

Metabolism/Metabolites：

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.

Biological Half-Life：

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).

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].

MeSH Entry Terms：

D 9998

Flupirtine Use and Manufacturing

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:304.32
XLogP3:2.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:6
Exact Mass:304.13355396
Monoisotopic Mass:304.13355396
Topological Polar Surface Area:89.3
Heavy Atom Count:22
Complexity:350
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes