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].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: cinnarizine

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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+
InChI Key DERZBLKQOCDDDZ-JLHYYAGUSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (UK (1989))
IUPAC Name Click here for help
1-[di(phenyl)methyl]-4-(3-phenylprop-2-enyl)piperazine
International Nonproprietary Names Click here for help
INN number INN
4272 cinnarizine clofibrate
Synonyms Click here for help
R-1575 | Stugeron®
Database Links Click here for help
Specialist databases
GPCRdb Ligand cinnarizine
Other databases
BindingDB Ligand 50017657
CAS Registry No. 298-57-7
ChEMBL Ligand CHEMBL43064
DrugBank Ligand DB00568
DrugCentral Ligand 654
GtoPdb PubChem SID 315661157
PubChem CID 1547484
RCSB PDB Ligand N90
Search Google for chemical match using the InChIKey DERZBLKQOCDDDZ-JLHYYAGUSA-N
Search Google for chemicals with the same backbone DERZBLKQOCDDDZ
Search PubMed clinical trials cinnarizine clofibrate
Search PubMed titles cinnarizine clofibrate
Search PubMed titles/abstracts cinnarizine clofibrate
UniChem Compound Search for chemical match using the InChIKey DERZBLKQOCDDDZ-JLHYYAGUSA-N
UniChem Connectivity Search for chemical match using the InChIKey DERZBLKQOCDDDZ-JLHYYAGUSA-N