(RS)-hydroxyzine

Also known as Hydroxyzine

Hydroxyzine, sold under the brand names Atarax and Vistaril among others, is an antihistamine medication. It is used in the treatment of itchiness, anxiety, insomnia, and nausea (including that due to motion sickness). It is used either by mouth or injection into a muscle.

Chemical data

Formula: C21H27ClN2O2
Molecular weight: 374.9 g/mol
IUPAC name: 2-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]ethanol
SMILES: C1CN(CCN1CCOCCO)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl
InChIKey: ZQDWXGKKHFNSQK-UHFFFAOYSA-N
XLogP: 3.7
Polar surface area: 35.9 Å²
H-bond donors: 1
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

15 papers

Enantioselective UFLC Determination of Hydroxyzine Enantiomers and Application to a Pharmacokinetic Study in Rabbits.Journal of chromatographic science · 2016
Design of resonance Rayleigh scattering and spectrofluorimetric methods for the determination of the antihistaminic drug, hydroxyzine, based on its interaction with 2,4,5,7-tetraiodofluorescein: Evaluation of analytical eco-scale and greenness/whiteness algorithms.Luminescence : the journal of biological and chemical luminescence · 2024
Phosphated maltodextrin as an anionic chiral selector for capillary electrophoresis: Application to the enantiomeric separation of basic drugs.Journal of chromatography. A · 2026
In vitro and in vivo evaluation of hydroxyzine hydrochloride microsponges for topical delivery.AAPS PharmSciTech · 2011
Enantioseparation of Six Antihistamines with Immobilized Cellulose Chiral Stationary Phase by HPLC.Journal of chromatographic science · 2016

via PubMed

Wikidata facts

Mass: 374.176106

Show 6 more facts

chemical formula: C₂₁H₂₇ClN₂O₂
Commons category: Hydroxyzine
canonical SMILES: C1CN(CCN1CCOCCO)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl
World Health Organisation international non-proprietary name: hydroxyzine
stylized name: hydrOXYzine
defined daily dose: 75

Sources (6)

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Article

12 sections

Contents

Medical uses
Contraindications
Side effects
Pharmacology
Pharmacodynamics
Pharmacokinetics
Chemistry
Analogues
Society and culture
Brand names
See also
References

{{Drugbox | verifiedrevid = 461774177 | image = Hydroxyzine.svg | image_class = skin-invert-image | width = 250 | alt = | image2 = Hydroxyzine-3d-sticks.png | image_class2 = bg-transparent | width2 = 250 | alt2 = | pronounce = | tradename = Atarax, Vistaril, others | Drugs.com = | MedlinePlus = a682866 | DailyMedID = Hydroxyzine | pregnancy_AU = | pregnancy_AU_comment = | pregnancy_category = | dependency_liability = Very Low | addiction_liability = None-Very Low | routes_of_administration = By mouth, intramuscular | class = First-generation antihistamine | ATC_prefix = N05 | ATC_suffix = BB01 | ATC_supplemental = | legal_AU = S4 | legal_CA = Rx-only | legal_EU = Rx-only | legal_UK = POM | legal_US = Rx-only | legal_status = SE: Rx-only