cinnarizine   Click here for help

GtoPdb Ligand ID: 9072

Synonyms: R-1575 | Stugeron®
Approved drug PDB Ligand
cinnarizine is an approved drug (UK (1989))
Compound class: Synthetic organic
Comment: Cinnarizine is used primarily for its anti-histaminic activity, but it also has anti-cholinergic and calcium channel blocking effects, which may account for some of its side-effects.The INN record for this drug specifies cinnarizine clofibrate (PubChem CID 6436096). Cinnarizine is the parent molecule of the fluorine derivative flunarizine. Both of these compounds induce parkinsonism as an adverse effect [2,4], likely due to antagonism of D2 receptors by the parent molecules and/or some of their bioactive metabolites [3].
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: cinnarizine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 6.48
Molecular weight 368.23
XLogP 5.3
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES c1ccc(cc1)C=CCN1CCN(CC1)C(c1ccccc1)c1ccccc1
Isomeric SMILES c1ccc(cc1)/C=C/CN1CCN(CC1)C(c1ccccc1)c1ccccc1
InChI 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+
No information available.
Summary of Clinical Use Click here for help
Used to treat motion sickness and for the control of vestibular disorders such as vertigo, tinnitus, nausea and vomiting such as is seen in Meniere's Disease.
This drug does not appear to have US FDA or EMA marketing authorisation, but it has been approved for use by many national authorisation agencies.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Cinnarizine interferes with the signal transmission between the vestibular apparatus of the inner ear and the vomiting centre of the hypothalamus, to abolish the disparity of signal processing between inner ear motion receptors and the visual senses which is believed to drive feelings of nausea and promote vomiting in indicated conditions.
Cinnarizine's calcium channel blocking activity causes cerebral vasorelaxation, with potential cognitive function enhancing (nootropic) ability.
External links Click here for help