CINNARIZINE HYDROCHLORIDE

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 Search

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

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
Extrapyramidal and depressive side reactions with flunarizine and cinarizine.	1989 Feb	2703850
Cholestasis associated with cinnarizine.	1990 Dec 1	2271847
Calcium-entry blockers-induced parkinsonism: possible role of inherited susceptibility.	1992 Spring	1508427
[Drug-induced parkinsonism. Clinical aspects compared with Parkinson disease].	1998 Jul	9674021
Etiology of parkinsonism in a Brazilian movement disorders clinic.	1998 Jun	9698723
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
Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.	2010 Dec	20829430

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.

Name

Type

Language

CINNARIZINE HYDROCHLORIDE

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

CINNARIZINE HYDROCHLORIDE [MI]

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