CINNARIZINE

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 Search

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

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26051684
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7714010	Antagonist 2778
Voltage-gated calcium channel 37 Target ID: CHEMBL2363032 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6299605 \| https://www.ncbi.nlm.nih.gov/pubmed/6572372 \| https://www.ncbi.nlm.nih.gov/pubmed/7000939 \| https://www.ncbi.nlm.nih.gov/pubmed/464337 \| https://books.google.ru/books?id=XZLnCAAAQBAJ&printsec=frontcover&hl=ru#v=onepage&q&f=false	Blocker 537
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: http://npra.moh.gov.my/images/reg-and-noti/PI/scheduled-poison/Cinnarizine_Tablet.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/23409520 \| https://books.google.ru/books?id=XZLnCAAAQBAJ&printsec=frontcover&hl=ru#v=onepage&q&f=false	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Motion sickness 43 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7000939 https://www.ncbi.nlm.nih.gov/pubmed/26051684	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).
Vestibular diseases 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7000939 https://www.ncbi.nlm.nih.gov/pubmed/26051684	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

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
Flunarizine- and cinnarizine-induced extrapyramidal reactions.	1987 May	3574697
Cholestasis associated with cinnarizine.	1990 Dec 1	2271847
Cinnarizine-induced parkinsonism in primates.	1992 Apr	1375537
Calcium-entry blockers-induced parkinsonism: possible role of inherited susceptibility.	1992 Spring	1508427
Effects of the combination of ketoconazole and calcium channel antagonists against Candida albicans in vitro.	1993 Jul	8369013
Possible pharmacokinetic and pharmacodynamic factors affecting parkinsonism inducement by cinnarizine and flunarizine.	1995 Nov 9	7503767
A long-term follow-up study of cinnarizine- and flunarizine-induced parkinsonism.	1997 Jan	8990063
Subacute cutaneous lupus erythematosus associated with cinnarizine and thiethylperazine therapy.	1998	9696142
[Drug-induced parkinsonism. Clinical aspects compared with Parkinson disease].	1998 Jul	9674021
Cinnarizine-induced parkinsonism: ten years later.	1998 May	9613736
Cinnarizine-induced cholestasis.	1999 Mar	10190745
[Akathisia, parkinsonism and depression induced by cinnarizine: a case report].	1999 May 1-15	10390751
Quantitative prediction of catalepsy induced by amoxapine, cinnarizine and cyclophosphamide in mice.	2000 May	11180191
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
Parkinsonism and other movement disorders in outpatients in chronic use of cinnarizine and flunarizine.	2004 Sep	15476069
Effects of cinnarizine, a calcium antagonist that produces human parkinsonism, in parkin knock out mice.	2005 Aug	15993444
Tardive blepharospasm associated with cinnarizine use.	2006 Jul-Aug	16855418
[Parkinsonism due to the medication].	2009	19900308
Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.	2010 Dec	20829430
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle.	2010 Feb 23	20142494
The differential diagnoses of parkinsonism: findings from a cohort of 1528 patients and a 10 years comparison in tertiary movement disorders clinics.	2010 Jun	20347518
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.	2013 Nov	23956101

Patents

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 by `admin` on `Fri Dec 15 15:02:25 GMT 2023` Edited by `admin` on `Fri Dec 15 15:02:25 GMT 2023`
Record UNII	3DI2E1X18L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CINNARIZINE

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