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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2D Structure
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Physico-chemical Properties
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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
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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)
Bioactivity Comments
In rodent studies, systemically administered cetirizine shows negligible brain penetration or binding to cerebral H1 receptors.
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
H1 receptor Primary target of this compound Hs Antagonist Inverse agonist 8.2 pKi - 1
pKi 8.2 [1]
Ligand mentioned in the following text fields