Flunarizine

Names

[ Name ]:
Flunarizine

[Synonym ]:
flunarazine
(E)-1-[bis(4-fluorophenyl)methyl]-4-(cinnamyl)piperazine
Sibelium
1-[bis(4-fluorophenyl)methyl]-4-cinnamylpiperazine
1-[Bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenyl-2-propenyl]piperazine
EINECS 257-937-5
(E)-1-[Bis-(p-fluorophenyl)methyl]-4-cinnamylpiperazine
Fluarizine
(e)-piperazin
1-[Bis(4-fluorophenyl)methyl]-4-[(E)-3-phenyl-2-propenyl]piperazine
1-[bis(4-fluorophenyl)methyl]-4-(3-phenyl-2-propenyl)piperazine
(e)-1-[bis(4-fluorophenyl)methyl]-4-(3-phenyl-2-propenyl)piperazine
MFCD00242731
Piperazine,1-[bis(4-fluorophenyl)methyl]-4-(3-phenyl-2-propenyl)-,(E)

Biological Activity

[Description]:

Flunarizine is a potent dual Na+/Ca2+ channel (T-type) blocker. Flunarizine is a D2 dopamine receptor antagonist. Flunarizine shows anticonvulsive and antimigraine activity, and peripheral vasodilator effects[1][2][3][4][5].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor

Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor

Research Areas >> Neurological Disease

[Target]

D2 Receptor

[In Vitro]

Flunarizine blocks sodium currents (INa) and calcium currents (ICa) with IC50 values of 0.94 μM and 1.77 μM in cultured rat cortical neurons, respectively[2]. Flunarizine (10 and 30 μM; 24 h) shows cytotoxic effects to chromaffin cells[4]. Flunarizine (1-30 μM) causes clear cytoprotection of chromaffin cell at concentrations of 3-10 μM[4]. Cell Cytotoxicity Assay[4] Cell Line: Chromaffin cells[4] Concentration: 10 and 30 μM Incubation Time: 24 hours Result: Showed a tendency to increase cell death at the concentration of 10 μM, and showed near 100% cell loss at the concentration of 30 μM.

[In Vivo]

Flunarizine (intraperitoneal injection; 30 mg/kg; once) protects mice from lipopolysaccharide- (LPS-) induced acute lung injury (ALI)[5]. Animal Model: Male BALB/c mice (6-8 weeks old) with acute lung injury induced by lipopolysaccharide[5] Dosage: 30 mg/kg Administration: Intraperitoneal injection; 30 mg/kg; once Result: Suppressed the LPS-induced cell influx, protein leakage, and inflammatory cytokines release. Inhibited the pulmonary inflammation.

Chemical & Physical Properties

[ Density]:
1.17 g/cm3

[ Boiling Point ]:
511.3ºC at 760 mmHg

[ Molecular Formula ]:
C₂₆H₂₆F₂N₂

[ Molecular Weight ]:
404.49500

[ Exact Mass ]:
404.20600

[ PSA ]:
6.48000

[ LogP ]:
5.26100

[ Index of Refraction ]:
1.606

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TK9188600

CHEMICAL NAME :: Piperazine, 1-(bis(4-fluorophenyl)methyl)-4-(3-phenyl-2-propenyl) -, (E)-

CAS REGISTRY NUMBER :: 52468-60-7

LAST UPDATED :: 199206

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C26-H26-F2-N2

MOLECULAR WEIGHT :: 404.54

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 4286 ug/kg/30D-I

TOXIC EFFECTS :: Behavioral - tremor

REFERENCE :: NEURAI Neurology. (Modern Medicine Pub., Inc., 1 E. First St., Duluth, MN 55802) V.1- 1951- Volume(issue)/page/year: 37,881,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 18 mg/kg/90D-I

TOXIC EFFECTS :: Behavioral - tremor

REFERENCE :: NEURAI Neurology. (Modern Medicine Pub., Inc., 1 E. First St., Duluth, MN 55802) V.1- 1951- Volume(issue)/page/year: 37,881,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 960 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 37,1103,1987

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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