hydroxyzine   Click here for help

GtoPdb Ligand ID: 7199

Synonyms: Atarax® | hydroxyzine hydrochloride | hydroxyzine pamoate | Vistaril®
Approved drug Immunopharmacology Ligand
hydroxyzine is an approved drug (FDA (1956))
Compound class: Synthetic organic
Comment: Hydroxyzine is a first-generation diphenylmethane and piperazine class antihistamine. Second-generation antihistamine cetirizine is one of the metabolites of hydroxyzine, but cetirizine differs in that it appears not to cross the blood-brain barrier to any significant level.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 35.94
Molecular weight 374.18
XLogP 2.71
No. Lipinski's rules broken 0
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Canonical SMILES OCCOCCN1CCN(CC1)C(c1ccc(cc1)Cl)c1ccccc1
Isomeric SMILES OCCOCCN1CCN(CC1)C(c1ccc(cc1)Cl)c1ccccc1
InChI InChI=1S/C21H27ClN2O2/c22-20-8-6-19(7-9-20)21(18-4-2-1-3-5-18)24-12-10-23(11-13-24)14-16-26-17-15-25/h1-9,21,25H,10-17H2
1. Gillard M, Van Der Perren C, Moguilevsky N, Massingham R, Chatelain P. (2002)
Binding characteristics of cetirizine and levocetirizine to human H(1) histamine receptors: contribution of Lys(191) and Thr(194).
Mol Pharmacol, 61 (2): 391-9. [PMID:11809864]