Hydroxyzine

Hydroxyzine

Clinical data
Trade names	Vistaril , Atarax
AHFS/Drugs.com	Monograph
MedlinePlus	a682866
Pregnancy category	AU: A US: C (Risk not ruled out)
Routes of administration	Oral, IM
ATC code	N05BB01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	High in-vivo
Protein binding	93%
Metabolism	Hepatic
Biological half-life	20–24 hours
Excretion	Urine, Feces
Identifiers
IUPAC name (±)-2-(2-{4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl}ethoxy)ethanol
CAS Number	68-88-2 Y
PubChem CID	3658
IUPHAR/BPS	7199
DrugBank	DB00557 Y
ChemSpider	3531 Y
UNII	30S50YM8OG
KEGG	D08054 Y
ChEBI	CHEBI:5818 Y
ChEMBL	CHEMBL896 Y
ECHA InfoCard	100.000.630
Chemical and physical data
Formula	C21H27ClN2O2
Molar mass	374.904 g/mol
3D model (Jmol)	Interactive image
SMILES Clc1ccc(cc1)C(c2ccccc2)N3CCN(CC3)CCOCCO
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 Y Key:ZQDWXGKKHFNSQK-UHFFFAOYSA-N Y

Hydroxyzine (/haɪˈdrɒksᵻziːn/) is a first-generation antihistamine of the diphenylmethane and piperazine class. It was first synthesized by Union Chimique Belge in 1956 and was marketed by Pfizer in the United States later the same year, and is still in widespread use today.

Due to its antagonistic effects on several receptor systems in the brain, hydroxyzine has strong anxiolytic and mild antiobsessive as well as antipsychotic properties. Today it is used primarily for the symptomatic relief of anxiety and tension associated with psychoneurosis and as an adjunct in organic disease states in which anxiety is manifested. Because of its antihistamine effects it can also be used for the treatment of severe cases of itching, hyperalgesia and motion sickness-induced nausea; it has also been used in some cases to relieve the effects of opioid withdrawal. Even though it is an effective sedative, hypnotic, and anxiolytic, it shares virtually none of the abuse, dependence, addiction, and toxicity potential of other drugs used for the same range of therapeutic reasons. Hydroxyzine has also been used to potentiate the analgesia of opioids and to alleviate some of their side effects, such as itching, nausea, and vomiting.