Flunarizine

Title: Flunarizine
CAS Registry Number: 52468-60-7
CAS Name: (E)-1-[Bis(4-fluorophenyl)methyl]-4-(3-phenyl-2-propenyl)piperazine
Additional Names: (E)-1-[bis(p-fluorophenyl)-methyl]-4-cinnamylpiperazine; 1-cinnamyl-4-(di-p-fluorobenzhydryl)piperazine
Molecular Formula: C26H26F2N2
Molecular Weight: 404.49
Percent Composition: C 77.20%, H 6.48%, F 9.39%, N 6.93%
Literature References: Calcium channel blocker; fluorinated deriv of cinnarizine, q.v. Prepn: P. A. J. Janssen, DE 1929330 and FR 2014487; idem, US 3773939 (1970, 1970, 1973, all to Janssen). Pharmacology: L. K. Desmedt et al., Arzneim.-Forsch. 25, 1408 (1975); T. Godfraind, Eur. J. Pharmacol. 53, 273 (1979). Clinical studies: J. Schetz et al., Curr. Ther. Res. 23, 131 (1978); G. Rudofsky et al., Angiology 30, 479 (1979). Rheological effects in humans: J. D. Cree et al., ibid. 505. Mechanism of calcium blocking activity: T. Godfraind, Fed. Proc. 40, 2866 (1981). Clinical study in retinal vasculopathy: P. Nihard, Angiology 33, 37 (1982). Clinical trial in chronic cerebrovascular disorders: A. Agnoli et al., Int. J. Clin. Pharmacol. Res. 8, 189 (1988). Series of articles on absorption, distribution, excretion and metabolism: Arzneim.-Forsch. 33, 1135-1151 (1983). Review of pharmacology, toxicology and clinical studies: B. Holmes et al., Drugs 27, 6 (1984).
Derivative Type: Dihydrochloride
CAS Registry Number: 30484-77-6
Trademarks: Dinaplex (Sidus); Flugeral (Italfarmaco); Flunagen (Gentili); Flunarl (Kyowa Hakko); Fluxarten (SKB); Gradient (Polifarma); Issium (Lifepharma); Mondus (Labinca); Sibelium (Janssen)
Molecular Formula: C26H26F2N2.2HCl
Molecular Weight: 477.42
Percent Composition: C 65.41%, H 5.91%, F 7.96%, N 5.87%, Cl 14.85%
Properties: Crystals from a mixture of 2-propanol/ethanol, mp 251.5°.
Melting point: mp 251.5°
Therap-Cat: Vasodilator (cerebral and peripheral).
Keywords: Calcium Channel Blocker; Piperazine Derivatives; Vasodilator (Cerebral); Vasodilator (Peripheral).
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Flunarizine
Flunarizine.png
Systematic (IUPAC) name
1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine
Clinical data
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Identifiers
CAS number 52468-60-7 YesY
ATC code N07CA03
PubChem CID 941361
DrugBank DB04841
ChemSpider 819216 YesY
UNII R7PLA2DM0J YesY
KEGG D07971 YesY
ChEMBL CHEMBL30008 YesY
Synonyms 1-[bis(4-fluorophenyl)methyl]-4-cinnamyl-piperazine
Chemical data
Formula C26H26F2N2 
Mol. mass 404.495
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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 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. Flunarizine was discovered at Janssen Pharmaceutica in 1968.