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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
Structure of CINNARIZINE

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
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
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Blocker
537
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8429
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
8429
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).
PubMed

PubMed

TitleDatePubMed
Protective effect of creatinol O-phosphate (COP) on ventricular fibrillation and death induced by intravenous CaCl2 in mice.
1979
Flunarizine- and cinnarizine-induced extrapyramidal reactions.
1987 May
Aggravation of Parkinson's disease by cinnarizine.
1988 Jan
Parkinsonism, tremor, and depression induced by cinnarizine and flunarizine.
1988 Sep 17
Movement disorders and depression due to flunarizine and cinnarizine.
1989
Extrapyramidal and depressive side reactions with flunarizine and cinarizine.
1989 Feb
Cholestasis associated with cinnarizine.
1990 Dec 1
Cinnarizine-induced parkinsonism in primates.
1992 Apr
Calcium-entry blockers-induced parkinsonism: possible role of inherited susceptibility.
1992 Spring
Effects of the combination of ketoconazole and calcium channel antagonists against Candida albicans in vitro.
1993 Jul
Possible pharmacokinetic and pharmacodynamic factors affecting parkinsonism inducement by cinnarizine and flunarizine.
1995 Nov 9
A long-term follow-up study of cinnarizine- and flunarizine-induced parkinsonism.
1997 Jan
Subacute cutaneous lupus erythematosus associated with cinnarizine and thiethylperazine therapy.
1998
[Drug-induced parkinsonism. Clinical aspects compared with Parkinson disease].
1998 Jul
Etiology of parkinsonism in a Brazilian movement disorders clinic.
1998 Jun
Cinnarizine-induced parkinsonism: ten years later.
1998 May
[Akathisia, parkinsonism and depression induced by cinnarizine: a case report].
1999 May 1-15
Quantitative prediction of catalepsy induced by amoxapine, cinnarizine and cyclophosphamide in mice.
2000 May
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
Parkinsonism and other movement disorders in outpatients in chronic use of cinnarizine and flunarizine.
2004 Sep
Effects of cinnarizine, a calcium antagonist that produces human parkinsonism, in parkin knock out mice.
2005 Aug
Tardive blepharospasm associated with cinnarizine use.
2006 Jul-Aug
[Parkinsonism due to the medication].
2009
Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.
2010 Dec
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle.
2010 Feb 23
The differential diagnoses of parkinsonism: findings from a cohort of 1528 patients and a 10 years comparison in tertiary movement disorders clinics.
2010 Jun
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
2013 Nov
Patents

Patents

JP2002511777A
414
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.
Name Type Language
CINNARIZINE
EP   INN   JAN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
GLANIL
Brand Name English
SPADERIZINE
Brand Name English
STUTGIN
Common Name English
GIGANTEN
Brand Name English
cinnarizine [INN]
Common Name English
KATOSERAN
Brand Name English
R 516
Code English
CINNARIZINE [MI]
Common Name English
CINARIZINE
Common Name English
PIPERAZINE, 1-(DIPHENYLMETHYL)-4-(3-PHENYL-2-PROPEN-1-YL)-
Systematic Name English
CORATHIEM
Brand Name English
PROCESSINE
Brand Name English
CEREPAR
Brand Name English
516-MD
Code English
R-516
Code English
LABYRIN
Brand Name English
ARTATE
Brand Name English
CINAPERAZINE
Brand Name English
CINNIPIRINE
Common Name English
APLACTAN
Brand Name English
DIMITRON
Brand Name English
EGLEN
Brand Name English
Cinnarizine [WHO-DD]
Common Name English
NSC-758400
Code English
CINNARIZINE [EP MONOGRAPH]
Common Name English
HILACTAN
Brand Name English
1-(DIPHENYLMETHYL)-4-(3-PHENYL-2-PROPEN-1-YL)PIPERAZINE
Systematic Name English
FOLCODAL
Brand Name English
STUTGERON
Brand Name English
R-1575
Code English
CARECIN
Brand Name English
CINNARIZINE [USAN]
Common Name English
CINNARIZINE [MART.]
Common Name English
CINNACET
Brand Name English
SEPAN
Brand Name English
CINAZYN
Brand Name English
STUNARONE
Brand Name English
516 MD
Code English
1-Cinnamyl-4-(diphenylmethyl)piperazine
Systematic Name English
APLEXAL
Brand Name English
R 1575
Code English
CINNARIZINE [JAN]
Common Name English
SEDATROMIN
Brand Name English
MIDRONAL
Brand Name English
CEREBOLAN
Brand Name English
IXERTOL
Brand Name English
DENAPOL
Brand Name English
OLAMIN
Brand Name English
MITRONAL
Brand Name English
STUGERON
Brand Name English
CINNAGERON
Brand Name English
CINNARIZINE [EP IMPURITY]
Common Name English
SIPTAZIN
Brand Name English
Classification Tree Code System Code
WHO-ATC N07CA02
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
WHO-ATC N07CA52
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
WHO-VATC QN07CA02
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
WHO-VATC QN07CA52
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
Code System Code Type Description
PUBCHEM
1547484
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID3022821
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
DRUG CENTRAL
654
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
NSC
758400
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
CHEBI
31403
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
WIKIPEDIA
CINNARIZINE
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
MERCK INDEX
m3576
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY Merck Index
MESH
D002936
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
EVMPD
SUB06302MIG
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
FDA UNII
3DI2E1X18L
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
LACTMED
Cinnarizine
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
INN
1021
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
RXCUI
2549
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB00568
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
CAS
298-57-7
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
SMS_ID
100000092166
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-064-8
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
NCI_THESAURUS
C76060
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
ChEMBL
CHEMBL43064
Created by admin on Fri Dec 15 15:02:25 GMT 2023 , Edited by admin on Fri Dec 15 15:02:25 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of CINNARIZINE
SALT/SOLVATE (PARENT)
Structure of CINNARIZINE HYDROCHLORIDE
SALT/SOLVATE (PARENT)
Structure of CINNARIZINE CLOFIBRATE
NIH
NCATS
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