cetirizine   Click here for help

GtoPdb Ligand ID: 1222

Synonyms: Reactine® | Zyrtec®
Approved drug Immunopharmacology Ligand
cetirizine is an approved drug (FDA (1995))
Compound class: Synthetic organic
Comment: Cetirizine( hydrochloride) is an orally active and selective histamine H1 receptor antagonist. The approved drug is a racemic mixture of two enantiomers, (S)-cetirizine and (R)-cetirizine, each of which are listed on Guide to PHARMACOLOGY with activity data. The structure shown here does not specify stereochemistry and represents the mixture.
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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

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View more information in the IUPHAR Pharmacology Education Project: cetirizine

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 CDK toolkit. 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 5
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 53.01
Molecular weight 388.16
XLogP 2.81
No. Lipinski's rules broken 0
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.

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Canonical SMILES OC(=O)COCCN1CCN(CC1)C(c1ccc(cc1)Cl)c1ccccc1
Isomeric SMILES OC(=O)COCCN1CCN(CC1)C(c1ccc(cc1)Cl)c1ccccc1
InChI InChI=1S/C21H25ClN2O3/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26/h1-9,21H,10-16H2,(H,25,26)
InChI Key ZKLPARSLTMPFCP-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1995))
IUPAC Name Click here for help
2-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetic acid
International Nonproprietary Names Click here for help
INN number INN
5520 cetirizine
Synonyms Click here for help
Reactine® | Zyrtec®
Database Links Click here for help
Specialist databases
GPCRdb Ligand cetirizine
Other databases
BindingDB Ligand 22890
CAS Registry No. 83881-51-0
ChEBI CHEBI:3561
ChEMBL Ligand CHEMBL1000
DrugBank Ligand DB00341
DrugCentral Ligand 581
GtoPdb PubChem SID 135650064
PubChem CID 2678
Search Google for chemical match using the InChIKey ZKLPARSLTMPFCP-UHFFFAOYSA-N
Search Google for chemicals with the same backbone ZKLPARSLTMPFCP
Search PubMed clinical trials cetirizine
Search PubMed titles cetirizine
Search PubMed titles/abstracts cetirizine
UniChem Compound Search for chemical match using the InChIKey ZKLPARSLTMPFCP-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZKLPARSLTMPFCP-UHFFFAOYSA-N
Wikipedia Cetirizine