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Details

Stereochemistry RACEMIC
Molecular Formula C21H27ClN2O2
Molecular Weight 374.904
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROXYZINE

SMILES

OCCOCCN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=C(Cl)C=C3

InChI

InChIKey=ZQDWXGKKHFNSQK-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C21H27ClN2O2
Molecular Weight 374.904
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Hydroxyzine, a piperazine antihistamine structurally related to buclizine, cyclizine, and meclizine, is used to treat histamine-mediated pruritus or pruritus due to allergy, nausea and vomiting, and, in combination with an opiate agonist, anxiolytic pain. Hydroxyzine is also used as a perioperative sedative and anxiolytic and to manage acute alcohol withdrawal. Hydroxyzine competes with histamine for binding at H1-receptor sites on the effector cell surface, resulting in suppression of histaminic edema, flare, and pruritus. The sedative properties of hydroxyzine occur at the subcortical level of the CNS. Secondary to its central anticholinergic actions, hydroxyzine may be effective as an antiemetic. It is used for symptomatic relief of anxiety and tension associated with psychoneurosis and as an adjunct in organic disease states in which anxiety is manifested.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
59.57 µM [IC50]
38.0 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
VISTARIL
Palliative
VISTARIL

Cmax

ValueDoseCo-administeredAnalytePopulation
31.371 ng/mL
25 mg single, oral
HYDROXYZINE plasma
Homo sapiens
72.5 ng/mL
0.7 mg/kg bw single, oral
HYDROXYZINE serum
Homo sapiens
72.5 ng/mL
0.7 mg/kg bw single, oral
HYDROXYZINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
479.174 ng × h/mL
25 mg single, oral
HYDROXYZINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
18.4 h
25 mg single, oral
HYDROXYZINE plasma
Homo sapiens
20 h
0.7 mg/kg bw single, oral
HYDROXYZINE serum
Homo sapiens
20 h
0.7 mg/kg bw single, oral
HYDROXYZINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
For symptomatic relief of anxiety and tension associated with psychoneurosis and as an adjunct in organic disease states in which anxiety is manifested: in adults, 50-100 mg q.i.d.; children under 6 years, 50 mg daily in divided doses; and over 6 years, 50-100 mg daily in divided doses. For use in the management of pruritus due to allergic conditions such as chronic urticaria and atopic and contact dermatoses, and in histamine-mediated pruritus: in adults, 25 mg t.i.d. or q.i.d.; children under 6 years, 50 mg daily in divided doses; and over 6 years, 50-100 mg daily in divided doses. As a sedative when used as a premedication and following general anesthesia: 50-100 mg in adults, and 0.6 mg/kg in children.
Route of Administration: Oral
In Vitro Use Guide
Hydroxyzine reduced carbachol-induced serotonin release by 25% at 10(-6) M and 34% at 10(-5) M in rat bladder mast cells
Substance Class Chemical
Record UNII
30S50YM8OG
Record Status Validated (UNII)
Record Version