4144. Flunarizine

Nomenclature

CAS number: 52468-60-7
(E)-1-[Bis(4-fluorophenyl)methyl]-4-(3-phenyl-2-propenyl)piperazine; (E)-1-[bis(p-fluorophenyl)-methyl]-4-cinnamylpiperazine; 1-cinnamyl-4-(di-p-fluorobenzhydryl)piperazine.
C26H26F2N2; mol wt 404.49.
C 77.20%, H 6.48%, F 9.39%, N 6.93%.

Description and 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).

Chemical structure

Derivative

Dihydrochloride.

Nomenclature

CAS number: 30484-77-6
Dinaplex (Sidus); Flugeral (Italfarmaco); Flunagen (Gentili); Flunarl (Kyowa Hakko); Fluxarten (SKB); Gradient (Polifarma); Issium (Lifepharma); Mondus (Labinca); Sibelium (Janssen).
C26H26F2N2.2HCl; mol wt 477.42.
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°.

Therapeutic Category

Vasodilator (cerebral and peripheral).

Keywords

Calcium Channel Blocker; Piperazine Derivatives; Vasodilator (Cerebral); Vasodilator (Peripheral)