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
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Summary of Clinical Use Click here for help
The sedative action of hydroxyzine is used to treat anxiety and tension and is combined with other medications in anesthesia. Hydroxyzine may also be used to control nausea and vomiting and be used as an antihistamine to control pruritic symptoms.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Hydroxyzine's predominant mechanism of action is as a potent H1 receptor inverse agonist. Hydroxyzine acts to block the action of endogenous histamine at the histamine H1 receptor. The sedative action of the drug may be due to central anticholinergic activity, but this is less clearly understood.
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