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C5270

Sigma-Aldrich

Cinnarizine

powder

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Synonym(s):
1-trans-Cinnamyl-4-diphenylmethylpiperazine
Empirical Formula (Hill Notation):
C26H28N2
CAS Number:
298-57-7
Molecular Weight:
368.51
EC Number:
206-064-8
MDL number:
MFCD00056037
PubChem Substance ID:
24278320

form

powder

Quality Level

100

color

white

originator

Johnson & Johnson

SMILES string

C1CN(CCN1C\C=C\c2ccccc2)C(c3ccccc3)c4ccccc4

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+

InChI key

DERZBLKQOCDDDZ-JLHYYAGUSA-N

Gene Information

human ... CACNA1A(773) , CACNA1C(775) , CACNA1D(776) , CACNA1F(778) , CACNA1S(779) , DRD2(1813) , HRH1(3269)

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General description

Cinnarizine is a piperazine derivative, which is extracted from wood reed roots. It exhibits antihistaminic and calcium antagonist property. Cinnarizine is used to treat vertigo, unsteadiness and cognitive disorders. Cinnarizine has anticholinergic, antiserotonergic and antidopaminergic effects. It enhances cerebral blood flow. Cinnarizine blocks the contraction of smooth muscles cells and also acts as a skin whitening agent.

Application

Cinnarizine has been used to block pressure-dependent changes in potassium currents in acutely isolated inner hair cells of the guinea-pig cochlea using whole-cell voltage-clamp techniques. It has also been used in the in vivo and in vitro studies, to analyze the impact of drug load and physical form of cinnarizine in self-nanoemulsifying drug delivery systems (SNEDDS) on absorption in rats.
Cinnarizine has been used:
  • to study its role in self-nano emulsifying drug delivery systems (SNEDDS)(8)(10)
  • to test Ca2+ signaling is pivotal for cancer-associated fibroblasts (CAFs) retraction(9)
  • as a model drug to develop a high-throughput in vitro intestinal lipolysis (HTP) model(11)

Biochem/physiol Actions

Ca2+ channel blocker; central and peripheral vasodilator.
Cinnarizine is a piperazine and a specific anti-vertigo agent. It is used to treat and prevent vertigo and motion sickness. In addition, cinnarizine is also used as an anti-histamine agent. Chronic use of this drug leads to side effects such as extrapyramidal reactions (Parkinson, tremor and akathisia) and depression.

Features and Benefits

This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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The effect of pressure on potassium currents in the inner hair cells isolated from guinea-pig cochlea
Kimitsuki T
Acta Neurobiologiae Experimentalis, 73, 521-528 (2013)
Aggravation of Parkinson's disease by cinnarizine.
Masso JFM, et al.
Journal of Neurology, Neurosurgery, and Psychiatry, 50(6), 804-805 (1987)
Flunarizine-and cinnarizine-induced extrapyramidal reactions
Micheli F, et al.
Neurology, 37(5), 881-881 (1987)
Influence of drug load and physical form of cinnarizine in new SNEDDS dosing regimens: in vivo and in vitro evaluations
Siqueira SDVS, et al.
The AAPS Journal, 19(2), 587-594 (2017)
Cinnarizine in the treatment of peripheral vascular disease: mechanisms related to its clinical action
Emanuel MB and Will JA
Proceedings of the Royal Society of Medicine, 70(8), 7-12 (1977)
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