2305. Cinnarizine

Nomenclature

CAS number: 298-57-7
1-(Diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine; 1-cinnamyl-4-diphenylmethylpiperazine; N-benzhydryl-N′-trans-cinnamylpiperazine; 1-trans-cinnamyl-4-diphenylmethylpiperazine; 1-cinnamyl-4-benzhydrylpiperazine; 1-diphenylmethyl-4-trans-cinnamylpiperazine; cinnipirine; 516-MD; Aplactan (Eisai); Aplexal (Taiyo); Apotomin (Kowa); Artate (Nippon Chemiphar); Carecin (Zensei Yakuhin); Cerebolan (Tobishi); Cerepar (Mepha); Cinaperazine (Yakult); Cinazyn (Italchimici); Cinnacet (Schwarzhaupt); Cinnageron (Streuli); Corathiem (Ohta); Denapol (Nagase); Dimitron; Eglen (Tatsumi); Folcodal (Syncro); Giganten (Troponwerke); Glanil (Janssen); Hilactan (Kyoritsu); Ixertol (Rottendorf); Katoseran (Hishiyama); Labyrin; Midronal (Delalande); Mitronal (Searle); Olamin (Sigamed); Processine (Sanko); Sedatromin (Takata); Sepan (Janssen); Siptazin (Isei); Spaderizine (Kotobuki); Stugeron (Janssen); Stutgeron (Janssen); Stutgin; Toliman (Corvi).
C26H28N2; mol wt 368.51.
C 84.74%, H 7.66%, N 7.60%.

Description and references

Calcium channel blocker with anti-allergic and anti-vasoconstricting activity. Prepn: Janssen, US 2882271 (1959, Janssen). Pharmacology: Van Nueten, Janssen, Arch. Int. Pharmacodyn. Ther. 204, 37 (1973). Metabolism: Soudijn, van Wijngaarden, Life Sci. 7, 231 (1968). Clinical study in treatment of intermittent claudication: J. H. Barber et al., Pharmatherapeutica 2, 401 (1980). Assessment of calcium antagonist effects: M. Spedding, Arch. Pharmacol. 318, 234 (1982). HPLC determn in blood and plasma: M. Puttemans et al., J. Liq. Chromatogr. 7, 2237 (1984). Comparison of clinical pharmacokinetics with other antihistamines: D. M. Paton, D. R. Webster, Clin. Pharmacokinet. 10, 477-497 (1985).

Chemical structure

Derivative

Hydrochloride.
C26H28N2.HCl; mol wt 404.97.
C 77.11%, H 7.22%, N 6.92%, Cl 8.75%.

Properties

mp 192° (dec). Soly in water: 2 mg/100 ml.

Derivative

Mixture with vitamin B6.

Nomenclature

Emesazine.

Therapeutic Category

Antihistaminic. Vasodilator (peripheral, cerebral).

Keywords

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