CINNARIZINE CLOFIBRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H28N2.C10H11ClO3
Molecular Weight	583.159
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(OC1=CC=C(Cl)C=C1)C(O)=O.C(\C=C\C2=CC=CC=C2)N3CCN(CC3)C(C4=CC=CC=C4)C5=CC=CC=C5

InChI

InChIKey=GNQQJMWZCJAUJT-RSGUCCNWSA-N

InChI=1S/C26H28N2.C10H11ClO3/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;1-10(2,9(12)13)14-8-5-3-7(11)4-6-8/h1-17,26H,18-22H2;3-6H,1-2H3,(H,12,13)/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

Molecular Formula	C10H11ClO3
Molecular Weight	214.646
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
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
Movement disorders and depression due to flunarizine and cinnarizine.	1989	2733706
Extrapyramidal and depressive side reactions with flunarizine and cinarizine.	1989 Feb	2703850
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
Subacute cutaneous lupus erythematosus associated with cinnarizine and thiethylperazine therapy.	1998	9696142
[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
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
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

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 16:13:39 GMT 2023` Edited by `admin` on `Fri Dec 15 16:13:39 GMT 2023`
Record UNII	8RJ419895I
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CINNARIZINE CLOFIBRATE

Official Name

English

cinnarizine clofibrate [INN]

Common Name

English

2-(P-CHLOROPHENOXY)-2-METHYLPROPIONIC ACID COMPOUND WITH (E)-1-CINNAMYL-4-(DIPHENYLMETHYL)PIPERAZINE (1:1)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C270