Cinnarizin

Bezeichnung:Cinnarizin

CAS-Nr298-57-7

Englisch Name:Stugeron

CBNumberCB6384748

SummenformelC26H28N2

Molgewicht368.51

MOL-Datei298-57-7.mol

Synonyma

Cinnarizin

Cinnarizin physikalisch-chemischer Eigenschaften

Schmelzpunkt	117-120°C
Siedepunkt	488.83°C (rough estimate)
Dichte	1.1818 (rough estimate)
Brechungsindex	1.7620 (estimate)
storage temp.	Sealed in dry,2-8°C
Löslichkeit	Soluble in chloroform at 50mg/ml
pka	pKa 7.47(H2O t=25.0 ) (Uncertain)
Aggregatzustand	powder
Farbe	white
Wasserlöslichkeit	0.75g/L(temperature not stated)
Merck	14,2305
InChIKey	DERZBLKQOCDDDZ-JLHYYAGUSA-N
CAS Datenbank	298-57-7(CAS DataBase Reference)
NIST chemische Informationen	Cinnarizine(298-57-7)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	20/22-36/37/38-42/43
S-Sätze:	22-24/25-36-26
WGK Germany	2
RTECS-Nr.	TL3430000
HS Code	2933.59.2100
Toxizität	LD50 oral in rat: > 6500mg/kg

Gefahreninformationscode (GHS)

Stugeron Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/22:Gesundheitsschädlich beim Einatmen und Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Chemische Eigenschaften
White or almost white powder.
Originator
Stugeron,Janssen,UK,1961
Verwenden
For the treatment of vertigo/meniere's disease, nausea and vomiting, motion sickness and also useful for vestibular symptoms of other origins.
Verwenden
Histamine H1 receptor antagonist; antihistamine.
Verwenden
glucocorticoid, antiinflammatory
Verwenden
Calcium channel blocker with antiallergic and anti-vasoconstricting activity. Antihistaminic
Definition
ChEBI: Cinnarizine is a N-alkylpiperazine, a diarylmethane and an olefinic compound. It has a role as an antiemetic, a histamine antagonist, a calcium channel blocker, a muscarinic antagonist, an anti-allergic agent, a H1-receptor antagonist and a geroprotector.
Manufacturing Process
This compound can be prepared by the reaction of cinnamoyl chloride with benzhydryl piperazine. The reaction is carried out in dry benzene under reflux. The benzene is then evaporated, the residue taken up in chloroform, washed with dilute HCl and then made alkaline.
The chloroform layer is washed with a dilute aqueous sodium hydroxide solution, thereafter with water, and is finally dried over potassium carbonate. The residue, which is obtained after evaporation of the chloroform, is dissolved by heating in a mixture of 25% of toluene and 75% of heptane. On cooling this solution to about 20°C the product precipitates. That compound is reduced with LiAlH4, to give cinnarizine.
Trademarks
Rinomar.
Therapeutic Function
Antihistaminic
Weltgesundheitsorganisation (WHO)
Cinnarizine, an antihistaminic and vasodilator agent, was introduced into medicine in 1962. It is indicated for the treatment of labyrinthine disturbances and vascular disorders, although its effectiveness in the latter indication has not been convincingly demonstrated.
Allgemeine Beschreibung
Cinnarizine is a piperazine derivative, which is extracted from wood reed roots. It exhibits antihistaminic and calcium antagonist property. Cinnarizine is used to treat vertigo, unsteadiness and cognitive disorders. Cinnarizine has anticholinergic, antiserotonergic and antidopaminergic effects. It enhances cerebral blood flow. Cinnarizine blocks the contraction of smooth muscles cells and also acts as a skin whitening agent.
Biologische Aktivität
cinnarizine is a calcium channel blocker.blockers of calcium channel are drugs disrupting the calcium movement via calcium channels, which are usually used as antihypertensive therapies to decrease blood pressure in hypertension patients.
Biochem/physiol Actions
Cinnarizine is a piperazine and a specific anti-vertigo agent. It is used to treat and prevent vertigo and motion sickness. In addition, cinnarizine is also used as an anti-histamine agent. Chronic use of this drug leads to side effects such as extrapyramidal reactions (Parkinson, tremor and akathisia) and depression.
Mechanism of action
In addition to its antihistaminic activity, cinnarizine possesses Ca2+ channel blocking activity. Its vasodilator effect probably results from blocking the Ca2+ channels in the vascular smooth muscle cells.
Clinical Use

Vestibular disorders

Motion sickness
Synthese
Cinnarinzine is prepared by alkylation of 1-diphenylmethyl piperazine with 3-phenyl-2-propenyl chloride .
in vitro
previous study found that cinnarizine could inhibit the phosphorylation of both arterial myosin p-light chain and arterial actomyosin superprecipitation. moreover, the concomitant inhibition of arterial superprecipitation and phosphorylation by perhexiline and cinnarizine was found to be similar to that of w-7. such inhibitary effect was then characterized by a rightward shift in the pca superprecipitation, depressed maximum activity as well as attenuation by exogenous calmodulin [1].
in vivo
previous animal study showed that augmented effects were obtained in mes seizure model when cinnarizine was combined with sodium valproate. whereas, in ptz-induced seizures, augmented effects were obtained when nifedipine was combined with sodium valproate [2].
Arzneimittelwechselwirkung
Potentially hazardous interactions with other drugs
Analgesics: possibly increased sedative effects with opioid analgesics.
Stoffwechsel
Cinnarizine is extensively metabolised mainly via CYP2D6, but there is considerable inter-individual variation in the extent of metabolism. The elimination of metabolites occurs as follows: one third in the urine (unchanged as metabolites and glucuronide conjugates) and two thirds in the faeces.
Einzelnachweise
[1] silver pj,dachiw j,ambrose jm,pinto pb. effects of the calcium antagonists perhexiline and cinnarizine on vascular and cardiac contractile protein function. j pharmacol exp ther.1985 sep;234(3):629-35.
[2] brahmane ri,wanmali vv,pathak ss,salwe kj. role of cinnarizine and nifedipine on anticonvulsant effect of sodium valproate and carbamazepine in maximal electroshock and pentylenetetrazole model of seizures in mice. j pharmacol pharmacother.2010 jul;1(2):78-81.
[3] hausler r,sabani e,rohr m. effect of cinnarizine on various types of vertigo. clinical and electronystagmographic results of a double-blind study. acta otorhinolaryngol belg.1989;43(2):177-85.

Stugeron Upstream-Materialien And Downstream Produkte

Cinnarizin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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