CINNARIZINE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H28N2
Molecular Weight	368.5139
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

C(\C=C\C1=CC=CC=C1)N2CCN(CC2)C(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=DERZBLKQOCDDDZ-JLHYYAGUSA-N

InChI=1S/C26H28N2/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25/h1-17,26H,18-22H2/b13-10+

HIDE SMILES / InChI

Description

Cinnarizine is a piperazine derivative with antihistaminic, antiserotonergic, antidopaminergic, and calcium channel-blocking activities. It inhibits calcium translocation across the vestibular sensory cells in the ampullae and maintains endolymph flow by preventing constriction of the stria vascularis. It is currently used for the treatment of nausea, vomiting, and vertigo caused by Meniere’s disease and other vestibular disorders. Cinnarizine is also used for prevention and treatment of motion sickness. Chronic use of cinnarizine may induce extrapyramidal symptoms.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D2 receptor 311	Antagonist 2,849
Voltage-gated calcium channel 37	Blocker 555
Histamine H1 receptor 316	Antagonist 2,849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Motion sickness 43	Preventing		Approved 8,583	STUGERON
Vestibular diseases 3	Preventing		Approved 8,583	STUGERON

C_max

Value	Dose	Analyte	Population
275 ng/mL	75 mg single, oral	CINNARIZINE plasma	Homo sapiens
41.4 ng/mL	25 mg single, oral	CINNARIZINE plasma	Homo sapiens
53.1 ng/mL	25 mg single, oral	CINNARIZINE plasma	Homo sapiens
122 ng/mL	75 mg single, oral	CINNARIZINE plasma	Homo sapiens
73.7 ng/mL	50 mg single, oral	CINNARIZINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
4437 ng × h/mL	75 mg single, oral	CINNARIZINE plasma	Homo sapiens
5074 ng × h/mL	75 mg 2 times / day steady-state, oral	CINNARIZINE plasma	Homo sapiens
301 ng × h/mL	25 mg single, oral	CINNARIZINE plasma	Homo sapiens
473 ng × h/mL	25 mg single, oral	CINNARIZINE plasma	Homo sapiens
855 ng × h/mL	75 mg single, oral	CINNARIZINE plasma	Homo sapiens
583 ng × h/mL	50 mg single, oral	CINNARIZINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
23.6 h	75 mg single, oral	CINNARIZINE plasma	Homo sapiens
8.5 h	25 mg single, oral	CINNARIZINE plasma	Homo sapiens
6.3 h	25 mg single, oral	CINNARIZINE plasma	Homo sapiens
2.7 h	75 mg single, oral	CINNARIZINE plasma	Homo sapiens
4.4 h	50 mg single, oral	CINNARIZINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
9%			CINNARIZINE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
225 mg single, oral Overdose	healthy, CHILD	Other AEs: Convulsion...
150 mg 1 times / day multiple, oral Studied dose	unhealthy	Other AEs: Weight gain...
75 mg 3 times / day multiple, oral Studied dose	unhealthy	Disc. AE: Cholestasis...
75 mg 3 times / day multiple, oral Studied dose	unhealthy	Disc. AE: Weight gain...

Showing 1 to 4 of 4 entries

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AEs

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AE	Significance	Dose	Population
Convulsion	1 pt	225 mg single, oral Overdose	healthy, CHILD
Weight gain		150 mg 1 times / day multiple, oral Studied dose	unhealthy
Cholestasis	1 pt Disc. AE	75 mg 3 times / day multiple, oral Studied dose	unhealthy
Weight gain	severe, 2 patients Disc. AE	75 mg 3 times / day multiple, oral Studied dose	unhealthy

Showing 1 to 4 of 4 entries

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PubMed

Show entries

Title	Date	PubMed
Anticonvulsive properties of cinnarizine and flunarizine in rats and mice.	1975 Sep	1242663
Protective effect of creatinol O-phosphate (COP) on ventricular fibrillation and death induced by intravenous CaCl2 in mice.	1979	575496
Cinnarizine-induced parkinsonism in primates.	1992 Apr	1375537
Possible pharmacokinetic and pharmacodynamic factors affecting parkinsonism inducement by cinnarizine and flunarizine.	1995 Nov 9	7503767
Treatment of vertigo due to acute unilateral vestibular loss with a fixed combination of cinnarizine and dimenhydrinate: a double-blind, randomized, parallel-group clinical study.	2004 Jun	15262457

Showing 1 to 5 of 12 entries

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Sample Use Guides

In Vivo Use Guide

Stugeron® 15 mg tablets Cinnarizine For travel sickness Adults and children over 12 years old: • 2 tablets 2 hours before travelling then • 1 tablet every 8 hours during the journey Children aged 5 – 12 years old: • 1 tablet 2 hours before travelling then • ½ a tablet every 8 hours during the journey For problems with balance Adults and children over 12 years old: • 2 tablets 3 times a day Children aged 5-12 years old: • 1 tablet 3 times a day

Route of Administration: Oral

In Vitro Use Guide

10 uM cinnarizine prevented histamine-induced rat mesangial cell and glomerular contraction.

Show entries

Name

Type

Language

APLACTAN

Preferred Name

English

CINNARIZINE

Official Name