Flunarizine

Flunarizine
Clinical data
Other names	1-[bis(4-fluorophenyl)methyl]-4-cinnamyl-piperazine
AHFS/Drugs.com	Micromedex Detailed Consumer Information
ATC code	N07CA03 (WHO) ;
Identifiers
	IUPAC name 1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine;
CAS Number	52468-60-7 ;
PubChem CID	941361;
DrugBank	DB04841 ;
ChemSpider	819216 ;
UNII	R7PLA2DM0J;
KEGG	D07971 ;
ChEMBL	ChEMBL30008 ;
CompTox Dashboard (EPA)	DTXSID6045616 ;
ECHA InfoCard	100.052.652
Chemical and physical data
Formula	C26H26F2N2
Molar mass	404.495 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Fc1ccc(cc1)C(c2ccc(F)cc2)N3CCN(CC3)C\C=C\c4ccccc4;
	InChI InChI=1S/C26H26F2N2/c27-24-12-8-22(9-13-24)26(23-10-14-25(28)15-11-23)30-19-17-29(18-20-30)16-4-7-21-5-2-1-3-6-21/h1-15,26H,16-20H2/b7-4+ ; Key:SMANXXCATUTDDT-QPJJXVBHSA-N ;
	(verify)

Flunarizine is a drug classified as a calcium channel blocker.^[1] Flunarizine is a non-selective calcium entry blocker with other actions including histamine H₁ receptor blocking activity. It is effective in the prophylaxis of migraine,^[2] occlusive peripheral vascular disease, vertigo of central and peripheral origin, and as an adjuvant in the therapy of epilepsy. It may help to reduce the severity and duration of attacks of paralysis associated with the more serious form of alternating hemiplegia, as well as being effective in rapid onset dystonia-parkinsonism (RDP). Both these conditions share a mutation in the ATP13A gene; flunarizine is not available by prescription in the U.S. or Japan.^[3] Flunarizine has been shown to significantly reduce headache frequency and severity in both adults and children. Flunarizine was discovered at Janssen Pharmaceutica in 1968.

Side effects and contraindications

Flunarizine has some side effects including weight gain, extrapyramidal effects, drowsiness and depression, it is contraindicated in hypotension, heart failure and arrhythmia. Flunarizine use is avoided in patients with depression, severe constipation or those with extrapyramidal disorders.

Brand Name

Sibelium 5 mg by Janssen Pharmaceutica. Rizelium 5 mg and 10 mg Capsule by UniMed & UniHealth Mfg. Ltd (Bangladesh)

Synthesis

Condensation of piperazine with 4,4'-difluorobenzhydryl chloride gives the monoalkylation product. Further reaction of with cinnamyl bromide affords flunarizine.^[4]

Medibazine

References

^ Calium channel blocker
^ Effective in migraine
^ ATP13A mutation,and response to flunarizine
^ P. A. J. Janssen, DE 1929330 (1972).

External References

Therapeutic Choices, sixth edition, Canadian Pharmacists Association, 2011.

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[1] Calium channel blocker

[2] Effective in migraine

[3] ATP13A mutation,and response to flunarizine

[4] P. A. J. Janssen, DE 1929330 (1972).

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