U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C26H28N2.ClH
Molecular Weight 404.975
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CINNARIZINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=LYXJDKBTSDYXQV-RSGUCCNWSA-N
InChI=1S/C26H28N2.ClH/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;1H/b13-10+;

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C26H28N2
Molecular Weight 368.5139
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2015612

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

Janssen Pharmaceutica
51
Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/26051684 # Janssen Pharmaceutical

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
Blocker
555
Antagonist
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8583
STUGERON

Approved Use

Cinnarizine helps symptoms caused by balance or movement problems. Cinnarizine tablets are used to control travel sickness, and for problems with balance (such as Ménières disease) to treat symptoms of feeling dizzy or lightheaded, ringing in the ears, feeling sick (nausea) and being sick (vomiting).
Preventing
Approved
8583
STUGERON

Approved Use

Cinnarizine helps symptoms caused by balance or movement problems. Cinnarizine tablets are used to control travel sickness, and for problems with balance (such as Ménières disease) to treat symptoms of feeling dizzy or lightheaded, ringing in the ears, feeling sick (nausea) and being sick (vomiting).
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
275 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8328998/
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
41.4 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26775868/
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
53.1 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26775868/
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
122 ng/mL
EXPERIMENT
https://www.tandfonline.com/doi/abs/10.1080/01483918408068873
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
73.7 ng/mL
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S0378434700817211
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4437 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8328998/
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
5074 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8328998/
75 mg 2 times / day steady-state, oral
dose: 75 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
301 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26775868/
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
473 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26775868/
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
855 ng × h/mL
EXPERIMENT
https://www.tandfonline.com/doi/abs/10.1080/01483918408068873
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
583 ng × h/mL
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S0378434700817211
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
23.6 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8328998/
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
8.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26775868/
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.3 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26775868/
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
2.7 h
EXPERIMENT
https://www.tandfonline.com/doi/abs/10.1080/01483918408068873
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.4 h
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S0378434700817211
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CINNARIZINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
9%
OTHER GOV'T
https://www.medicines.org.uk/emc/search?q=CINNARIZINE | https://mhraproducts4853.blob.core.windows.net/docs/c2da91b40d9fa5e87f4e8c0fa45abf0c622ee820#page=5
CINNARIZINE plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/16636115/
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: unknown
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/16636115/
Other AEs: Convulsion...
Other AEs:
Convulsion (1 pt)
Sources:
https://pubmed.ncbi.nlm.nih.gov/16636115/
150 mg 1 times / day multiple, oral
Studied dose
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1504403/
unhealthy
Health Status: unhealthy
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/1504403/
Other AEs: Weight gain...
Other AEs:
Weight gain
Sources:
https://pubmed.ncbi.nlm.nih.gov/1504403/
75 mg 3 times / day multiple, oral
Studied dose
Dose: 75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 75 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10190745/
unhealthy
Health Status: unhealthy
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/10190745/
Disc. AE: Cholestasis...
AEs leading to
discontinuation/dose reduction:
Cholestasis (1 pt)
Sources:
https://pubmed.ncbi.nlm.nih.gov/10190745/
75 mg 3 times / day multiple, oral
Studied dose
Dose: 75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 75 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18286231/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/18286231/
Disc. AE: Weight gain...
AEs leading to
discontinuation/dose reduction:
Weight gain (severe, 2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/18286231/
AEs

AEs

AESignificanceDosePopulation
Convulsion 1 pt
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/16636115/
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: unknown
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/16636115/
Weight gain
150 mg 1 times / day multiple, oral
Studied dose
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1504403/
unhealthy
Health Status: unhealthy
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/1504403/
Cholestasis 1 pt
Disc. AE
75 mg 3 times / day multiple, oral
Studied dose
Dose: 75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 75 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10190745/
unhealthy
Health Status: unhealthy
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/10190745/
Weight gain severe, 2 patients
Disc. AE
75 mg 3 times / day multiple, oral
Studied dose
Dose: 75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 75 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18286231/
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/18286231/
PubMed

PubMed

TitleDatePubMed
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
2013-11
Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.
2010-12
The differential diagnoses of parkinsonism: findings from a cohort of 1528 patients and a 10 years comparison in tertiary movement disorders clinics.
2010-06
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle.
2010-02-23
[Parkinsonism due to the medication].
2009
Tardive blepharospasm associated with cinnarizine use.
2006-07-21
Effects of cinnarizine, a calcium antagonist that produces human parkinsonism, in parkin knock out mice.
2005-08
Parkinsonism and other movement disorders in outpatients in chronic use of cinnarizine and flunarizine.
2004-09
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.
2004-06
Quantitative prediction of catalepsy induced by amoxapine, cinnarizine and cyclophosphamide in mice.
2000-05
[Akathisia, parkinsonism and depression induced by cinnarizine: a case report].
1999-07-03
Cinnarizine-induced cholestasis.
1999-03
[Drug-induced parkinsonism. Clinical aspects compared with Parkinson disease].
1998-07
Etiology of parkinsonism in a Brazilian movement disorders clinic.
1998-06
Cinnarizine-induced parkinsonism: ten years later.
1998-05
Subacute cutaneous lupus erythematosus associated with cinnarizine and thiethylperazine therapy.
1998
A long-term follow-up study of cinnarizine- and flunarizine-induced parkinsonism.
1997-01
Possible pharmacokinetic and pharmacodynamic factors affecting parkinsonism inducement by cinnarizine and flunarizine.
1995-11-09
Effects of the combination of ketoconazole and calcium channel antagonists against Candida albicans in vitro.
1993-07
Cinnarizine-induced parkinsonism in primates.
1992-04
Calcium-entry blockers-induced parkinsonism: possible role of inherited susceptibility.
1992
Cholestasis associated with cinnarizine.
1990-12-01
Extrapyramidal and depressive side reactions with flunarizine and cinarizine.
1989-02
Movement disorders and depression due to flunarizine and cinnarizine.
1989
Parkinsonism, tremor, and depression induced by cinnarizine and flunarizine.
1988-09-17
Aggravation of Parkinson's disease by cinnarizine.
1988-01
Flunarizine- and cinnarizine-induced extrapyramidal reactions.
1987-05
Protective effect of creatinol O-phosphate (COP) on ventricular fibrillation and death induced by intravenous CaCl2 in mice.
1979
Anticonvulsive properties of cinnarizine and flunarizine in rats and mice.
1975-09
Patents

Patents

JP2002511777A
420
JP2002537317A
97
JP2011140502A
3
JPH01238509A
3
JPH01238543A
5
JPH02167213A
3
JPH04209650A
5
JPH0753358A
3
JPH0761937A
11
JPS06259212A
3
JPS57136518A
3
JPS58134033A
3
JPS58164582A
3
JPS58210077A
3
JPS61161272A
3
JPS61223647A
3
JPS61249922A
3
JPS62298579A
3
JPS6253921A
3
JPS6259212A
3

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.
Substance Class Chemical
Created
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on Mon Mar 31 21:07:55 GMT 2025
Edited
by admin
on Mon Mar 31 21:07:55 GMT 2025
Record UNII
5AKM4OA6VO
Record Status Validated (UNII)
Record Version
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Name Type Language
CINNARIZINE HYDROCHLORIDE [MI]
Preferred Name English
CINNARIZINE HYDROCHLORIDE
MI   WHO-DD  
Common Name English
CINNARIZINE MONOHYDROCHLORIDE
Common Name English
PIPERAZINE, 1-CINNAMYL-4-(DIPHENYLMETHYL)-, MONOHYDROCHLORIDE
Common Name English
PIPERAZINE, 1-(DIPHENYLMETHYL)-4-(3-PHENYL-2-PROPENYL)-, MONOHYDROCHLORIDE
Common Name English
PIPERAZINE, 1-(DIPHENYLMETHYL)-4-(3-PHENYL-2-PROPEN-1-YL)-, HYDROCHLORIDE (1:1)
Systematic Name English
PIPERAZINE, 1-CINNAMYL-4-DIPHENYLMETHYL-, HYDROCHLORIDE
Systematic Name English
Cinnarizine hydrochloride [WHO-DD]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID30179975
Created by admin on Mon Mar 31 21:07:55 GMT 2025 , Edited by admin on Mon Mar 31 21:07:55 GMT 2025
PRIMARY
DRUG BANK
DBSALT002261
Created by admin on Mon Mar 31 21:07:55 GMT 2025 , Edited by admin on Mon Mar 31 21:07:55 GMT 2025
PRIMARY
CAS
25332-14-3
Created by admin on Mon Mar 31 21:07:55 GMT 2025 , Edited by admin on Mon Mar 31 21:07:55 GMT 2025
PRIMARY
SMS_ID
100000138675
Created by admin on Mon Mar 31 21:07:55 GMT 2025 , Edited by admin on Mon Mar 31 21:07:55 GMT 2025
PRIMARY
FDA UNII
5AKM4OA6VO
Created by admin on Mon Mar 31 21:07:55 GMT 2025 , Edited by admin on Mon Mar 31 21:07:55 GMT 2025
PRIMARY
PUBCHEM
21454432
Created by admin on Mon Mar 31 21:07:55 GMT 2025 , Edited by admin on Mon Mar 31 21:07:55 GMT 2025
PRIMARY
MERCK INDEX
m3576
Created by admin on Mon Mar 31 21:07:55 GMT 2025 , Edited by admin on Mon Mar 31 21:07:55 GMT 2025
PRIMARY Merck Index
EVMPD
SUB78343
Created by admin on Mon Mar 31 21:07:55 GMT 2025 , Edited by admin on Mon Mar 31 21:07:55 GMT 2025
PRIMARY
Related Record Type Details
Structure of CINNARIZINE
PARENT -> SALT/SOLVATE
NIH
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