Identification

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Name
Hydroxyzine
Accession Number
DB00557  (APRD00688)
Type
Small Molecule
Groups
Approved
Description

Hydroxyzine is a first-generation histamine H1-receptor antagonist of the dephenylmethane and piperazine classes that exhibits sedative, anxiolytic, and antiemetic properties.2,12 It was first developed in 1955,10 and has since remained a relatively common treatment for allergic conditions such as pruritus, urticaria, dermatoses, and histamine-mediated pruritus.18 The active metabolite of hydroxyzine, cetirizine, is also available as an active ingredient in allergic medications, and is responsible for much of its hydroxyzine's antihistaminic effect.13 Hydroxyzine is also used for generalized anxiety disorder, tension caused by psychoneurosis, and other conditions with manifestations of anxiety.18

Structure
Thumb
Synonyms
  • Hidroxizina
  • Hychotine
  • Hydroksyzyny
  • Hydroxine
  • Hydroxizine
  • Hydroxizinum
  • Hydroxycine
  • Hydroxyzin
  • Hydroxyzine
  • Hydroxyzinum
  • Idrossizina
External IDs
U.C.B-4492
Product Ingredients
IngredientUNIICASInChI Key
Hydroxyzine hydrochloride76755771U32192-20-3ANOMHKZSQFYSBR-UHFFFAOYSA-N
Hydroxyzine pamoateM20215MUFR10246-75-0ASDOKGIIKXGMNB-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AtaraxTablet100 mg/1OralRoerig2006-06-20Not applicableUs
AtaraxTablet50 mg/1OralRoerig2006-06-20Not applicableUs
AtaraxTablet25 mg/1OralRoerig2006-06-20Not applicableUs
AtaraxTablet10 mg/1OralRoerig2006-06-20Not applicableUs
AtaraxSyrup10 mg/5mLOralRoerig2006-06-20Not applicableUs
Atarax Cap 10mgCapsuleOralErfa Canada 2012 Inc1956-12-312005-09-15Canada
Atarax Cap 25mgCapsuleOralErfa Canada 2012 Inc1956-12-312005-09-15Canada
Atarax Cap 50mgCapsuleOralErfa Canada 2012 Inc1959-12-312005-09-15Canada
Atarax Im Sol 50mg/mlSolutionIntramuscularErfa Canada 2012 Inc1957-12-312005-08-18Canada
Atarax Syrup 2mg/mlSyrupOralErfa Canada 2012 Inc1956-12-31Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
HydroxyzineInjection, solution50 mg/1mLIntramuscularGeneral Injectables & Vaccines, Inc2010-03-01Not applicableUs
HydroxyzineTablet, film coated50 mg/1OralMajor Pharmaceuticals2007-03-20Not applicableUs
HydroxyzineTablet, film coated10 mg/1OralBlenheim Pharmacal, Inc.2009-12-28Not applicableUs50111 0307 01 nlmimage10 8429422a
HydroxyzineTablet, film coated25 mg/1OralPliva, Inc.2010-08-022010-12-05Us
HydroxyzineTablet, film coated25 mg/1OralMajor Pharmaceuticals2007-03-20Not applicableUs
HydroxyzineTablet, film coated50 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-03-20Not applicableUs
HydroxyzineTablet, film coated25 mg/1OralBlenheim Pharmacal, Inc.2010-05-17Not applicableUs50111 0308 01 nlmimage10 94294a3a
HydroxyzineTablet, film coated10 mg/1OralPliva, Inc.2010-08-022010-12-05Us
HydroxyzineTablet, film coated25 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-03-20Not applicableUs
HydroxyzineTablet, film coated10 mg/1OralMajor Pharmaceuticals2007-03-202012-11-30Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
MKH Dose PackHydroxyzine hydrochloride (10 mg/1) + Ketamine hydrochloride (25 mg/1) + Midazolam (3 mg/1)TrocheSublingualImprimis Njof, Llc2019-03-04Not applicableUs
International/Other Brands
Hyzine (Hyrex) / Masmoran (Pfizer) / Rezine / Vistaject-50 / Vistazine
Categories
UNII
30S50YM8OG
CAS number
68-88-2
Weight
Average: 374.904
Monoisotopic: 374.176105825
Chemical Formula
C21H27ClN2O2
InChI Key
ZQDWXGKKHFNSQK-UHFFFAOYSA-N
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
IUPAC Name
2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)ethan-1-ol
SMILES
OCCOCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1

Pharmacology

Indication

Hydroxyzine is indicated for the symptomatic relief of anxiety and tension associated with psychoneuroses, and as an adjunct in organic disease states in which anxiety is manifested.18 It is also indicated in the treatment of histamine-mediated pruritus and pruritus due to allergic conditions such as chronic urticaria.18

Canadian labeling states that hydroxyzine is also indicated in adults and children as a premedication prior to medical procedures, such as dental surgery.15 It is also used in the control of nausea and vomiting, excluding nausea and vomiting of pregnancy.15

Associated Conditions
Pharmacodynamics

Hydroxyzine blocks the activity of histamine to relieve allergic symptoms such as pruritus.18 Activity at off-targets also allows for its use as a sedative anxiolytic and an antiemetic in certain disease states.15

Hydroxyzine is relatively fast-acting, with an onset of effect that occurs between 15 and 60 minutes and a duration of action between 4-6 hours.2 Hydroxyzine may potentiate the effects of central nervous system (CNS) depressants following general anesthesia - patients maintained on hydroxyzine should receive reduced doses of any CNS depressants required.18 Hydroxyzine is reported to prolong the QT/QTc interval based on postmarketing reports of rare events of Torsade de Pointes, cardiac arrest, and sudden death, and should be used with caution in patients with an increased baseline risk for QTc prolongation.15,10

Mechanism of action

The H1 histamine receptor is responsible for mediating hypersensitivity and allergic reactions. Exposure to an allergen results in degranulation of mast cells and basophils, which then release histamine and other inflammatory mediators. Histamine binds to, and activates, H1 receptors, which results in the further release of pro-inflammatory cytokines, such as interleukins, from basophils and mast cells. These downstream effects of histamine binding are responsible for a wide variety of allergic symptoms, such as pruritus, rhinorrhea, and watery eyes.11

Hydroxyzine is a potent inverse agonist of histamine H1-receptors2 - inverse agonists are agents that are considered to have a "negative efficacy", so rather than simply blocking activity at a receptor they actively dampen its activity.14 Inverse agonism at these receptors is responsible for hydroxyzine's efficacy in the treatment of histaminic edema, flare, and pruritus.

Hydroxyzine is not a cortical depressant, so its sedative properties likely occur at the subcortical level of the CNS.18 These sedative properties allow activity as an anxiolytic. Antiemetic efficacy is likely secondary to activity at off-targets.13

TargetActionsOrganism
AHistamine H1 receptor
inverse agonist
Humans
UPotassium voltage-gated channel subfamily H member 2
inhibitor
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

The absolute bioavailability of hydroxyzine has not been ascertained, as intravenous formulations are unavailable due to a risk of hemolysis.2 Hydroxyzine is rapidly absorbed from the gastrointestinal tract upon oral administration,18 reaching its maximum plasma concentration (Tmax) approximately 2 hours following administration.9

Volume of distribution

The mean volume of distribution is 16.0 ± 3.0 L/kg. Higher concentrations are found in the skin than in the plasma.2

Protein binding

Hydroxyzine has been shown to bind to human albumin in vitro,8 but the extent of protein binding in plasma has not been evaluated.

Metabolism

Hydroxyzine is metabolized in the liver2 by CYP3A4 and CYP3A5.18 While the precise metabolic fate of hydroxyzine is unclear, its main and active metabolite (~45 to 60% of an orally administered dose),13 generated by oxidation of its alcohol moiety to a carboxylic acid, is the second-generation antihistamine cetirizine.2 Hydroxyzine is likely broken down into several other metabolites, though specific structures and pathways have not been elucidated in humans.7

Route of elimination

Approximately 70% of hydroxyzine's active metabolite, cetirizine, is excreted unchanged in the urine.3 The precise extent of renal and fecal excretion in humans has not been determined.18

Half life

The half-life of hydroxyzine is reportedly 14-25 hours,2 and appears to be, on average, shorter in children (~7.1 hours) than in adults (~20 hours).6 Elimination half-life is prolonged in the elderly, averaging approximately 29 hours,3 and is likely to be similarly prolonged in patients with renal or hepatic impairment.15

Clearance

Clearance of hydroxyzine has been reported to be 31.1 ± 11.1 mL/min/kg in children and 9.8 ± 3.3 mL/min/kg in adults.6

Toxicity

The oral LD50 is 840 mg/kg in rats and 400 mg/kg in mice.16

Overdose from hydroxyzine is most commonly characterized by hypersedation, but may also manifest as convulsions, stupor, nausea, and vomiting.18 In cases of overdose, consider the induction of vomiting and the use of gastric lavage. Other treatment should involve general symptomatic and supportive care. Hypotension may be controlled by intravenous fluids and pressors, and caffeine and sodium benzoate injection may be used to counteract any observed CNS depressant effects. Hemodialysis is unlikely to provide any benefit in the treatment hydroxyzine overdose.18

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Hydroxyzine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Hydroxyzine.
2,5-Dimethoxy-4-ethylthioamphetamineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AbataceptThe metabolism of Hydroxyzine can be increased when combined with Abatacept.
AbemaciclibThe serum concentration of Hydroxyzine can be increased when it is combined with Abemaciclib.
AbexinostatThe risk or severity of QTc prolongation can be increased when Abexinostat is combined with Hydroxyzine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • Avoid alcohol.
  • Take with food.

References

Synthesis Reference

U.S. Patent 2,899,436.

General References
  1. Clark BG, Araki M, Brown HW: Hydroxyzine-associated tardive dyskinesia. Ann Neurol. 1982 Apr;11(4):435. [PubMed:7103423]
  2. Altamura AC, Moliterno D, Paletta S, Maffini M, Mauri MC, Bareggi S: Understanding the pharmacokinetics of anxiolytic drugs. Expert Opin Drug Metab Toxicol. 2013 Apr;9(4):423-40. doi: 10.1517/17425255.2013.759209. Epub 2013 Jan 21. [PubMed:23330992]
  3. Simons KJ, Watson WT, Chen XY, Simons FE: Pharmacokinetic and pharmacodynamic studies of the H1-receptor antagonist hydroxyzine in the elderly. Clin Pharmacol Ther. 1989 Jan;45(1):9-14. doi: 10.1038/clpt.1989.2. [PubMed:2562944]
  4. Lee BH, Lee SH, Chu D, Hyun JW, Choe H, Choi BH, Jo SH: Effects of the histamine H(1) receptor antagonist hydroxyzine on hERG K(+) channels and cardiac action potential duration. Acta Pharmacol Sin. 2011 Sep;32(9):1128-37. doi: 10.1038/aps.2011.66. [PubMed:21892192]
  5. Crowe A, Wright C: The impact of P-glycoprotein mediated efflux on absorption of 11 sedating and less-sedating antihistamines using Caco-2 monolayers. Xenobiotica. 2012 Jun;42(6):538-49. doi: 10.3109/00498254.2011.643256. Epub 2011 Dec 22. [PubMed:22188412]
  6. Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [PubMed:2866055]
  7. Fouda HG, Hobbs DC, Stambaugh JE: Sensitive assay for determination of hydroxyzine in plasma and its human pharmacokinetics. J Pharm Sci. 1979 Nov;68(11):1456-8. doi: 10.1002/jps.2600681134. [PubMed:512901]
  8. Martinez-Gomez MA, Villanueva-Camanas RM, Sagrado S, Medina-Hernandez MJ: Evaluation of enantioselective binding of antihistamines to human serum albumin by ACE. Electrophoresis. 2007 Aug;28(15):2635-43. doi: 10.1002/elps.200600742. [PubMed:17605150]
  9. Simons FE, Simons KJ, Frith EM: The pharmacokinetics and antihistaminic of the H1 receptor antagonist hydroxyzine. J Allergy Clin Immunol. 1984 Jan;73(1 Pt 1):69-75. doi: 10.1016/0091-6749(84)90486-x. [PubMed:6141198]
  10. Schlit AF, Delaunois A, Colomar A, Claudio B, Cariolato L, Boev R, Valentin JP, Peters C, Sloan VS, Bentz JWG: Risk of QT prolongation and torsade de pointes associated with exposure to hydroxyzine: re-evaluation of an established drug. Pharmacol Res Perspect. 2017 Apr 21;5(3):e00309. doi: 10.1002/prp2.309. eCollection 2017 Jun. [PubMed:28480041]
  11. Devillier P, Roche N, Faisy C: Clinical pharmacokinetics and pharmacodynamics of desloratadine, fexofenadine and levocetirizine : a comparative review. Clin Pharmacokinet. 2008;47(4):217-30. [PubMed:18336052]
  12. Sawantdesai NS, Kale PP, Savai J: Evaluation of anxiolytic effects of aripiprazole and hydroxyzine as a combination in mice. J Basic Clin Pharm. 2016 Sep;7(4):97-104. doi: 10.4103/0976-0105.189429. [PubMed:27999468]
  13. Gengo FM, Dabronzo J, Yurchak A, Love S, Miller JK: The relative antihistaminic and psychomotor effects of hydroxyzine and cetirizine. Clin Pharmacol Ther. 1987 Sep;42(3):265-72. doi: 10.1038/clpt.1987.145. [PubMed:2887328]
  14. How drugs act: General principles. (2020). In Rang and Dale's Pharmacology (9th ed.). Edinburgh: Elsevier. [ISBN:9780702080609]
  15. Health Canada Product Monograph: Hydroxyzine HCl oral capsules [Link]
  16. CaymanChem: Hydroxyzine MSDS [Link]
  17. FDA Approved Drug Products: Hydroxyzine HCl oral tablets [Link]
  18. FDA Approved Drug Products: Vistaril (hydroxyzine pamoate) [Link]
External Links
Human Metabolome Database
HMDB0014697
KEGG Drug
D08054
KEGG Compound
C07045
PubChem Compound
3658
PubChem Substance
46508556
ChemSpider
3531
BindingDB
22875
ChEBI
5818
ChEMBL
CHEMBL896
Therapeutic Targets Database
DAP000324
PharmGKB
PA449943
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Hydroxyzine
ATC Codes
N05BB01 — HydroxyzineN05BB51 — Hydroxyzine, combinations
AHFS Codes
  • 28:24.92 — Miscellaneous Anxiolytics Sedatives and Hypnotics

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedNot AvailableAnxiety1
3CompletedTreatmentBehavior, Child1
3RecruitingTreatmentAquagenic pruritus / Myeloproliferative Disorders1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenia1
4Active Not RecruitingTreatmentCessation, Smoking / Nausea / Sleep Disturbances / Stress1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedPreventionNausea / Pruritus / Vomiting1
4CompletedTreatmentChronic Urticaria1
4CompletedTreatmentPain1
4Not Yet RecruitingTreatmentAgitation on Recovery From Sedation1
4Not Yet RecruitingTreatmentAnxiety1
4RecruitingTreatmentDental Caries in Children / Hydroxyzine / Meperidine / Midazolam / Pediatric Dental Sedation1
4TerminatedPreventionHealthy Volunteers1
4WithdrawnTreatmentAnxiety in Those Patients With Anorexia Nervosa / Anxiety in Those Patients With Anorexia Nervosa or Eating Disorder Not Otherwise Specified, Specifically With Low BMI(≤ 18) / Eating Disorder Not Otherwise Specified, BMI (<=18)1
Not AvailableCompletedNot AvailableBradycardia Sinus / Hydroxyzine / Reflex, Oculocardiac / Strabismus1
Not AvailableCompletedBasic SciencePlacebo Drug Interaction / Placebo Effect1
Not AvailableCompletedTreatmentSubstance-Related Disorders1

Pharmacoeconomics

Manufacturers
  • Baxter healthcare corp anesthesia and critical care
  • Altana inc
  • App pharmaceuticals llc
  • Hospira inc
  • Luitpold pharmaceuticals inc
  • Pharmafair inc
  • Smith and nephew solopak div smith and nephew
  • Solopak medical products inc
  • Solopak laboratories inc
  • Watson laboratories inc
  • Wyeth ayerst laboratories
  • Organon usa inc
  • Pfizer laboratories div pfizer inc
  • Roerig div pfizer inc
  • Actavis mid atlantic llc
  • Alpharma us pharmaceuticals division
  • Hi tech pharmacal co inc
  • Kv pharmaceutical co
  • Vintage pharmaceuticals inc
  • Wockhardt eu operations (swiss) ag
  • Pfizer inc
  • Able laboratories inc
  • Actavis totowa llc
  • Amneal pharmaceutical
  • Halsey drug co inc
  • Heritage pharmaceuticals inc
  • Hetero drugs ltd unit iii
  • Invagen pharmaceuticals inc
  • Ivax pharmaceuticals inc
  • Kvk tech inc
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Northstar healthcare holdings ltd
  • Pliva inc
  • Purepac pharmaceutical co
  • Quantum pharmics ltd
  • Sandoz inc
  • Sun pharmaceutical industries inc
  • Superpharm corp
  • Usl pharma inc
  • Vintage pharmaceuticals llc
  • Barr laboratories inc
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Par pharmaceutical inc
  • Vangard laboratories inc div midway medical co
  • Teva pharmaceuticals usa inc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • American Regent
  • Amerisource Health Services Corp.
  • Anda Inc.
  • Apotheca Inc.
  • APP Pharmaceuticals
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Barr Pharmaceuticals
  • Blenheim Pharmacal
  • Bryant Ranch Prepack
  • C.O. Truxton Inc.
  • Caraco Pharmaceutical Labs
  • Cardinal Health
  • Caremark LLC
  • Carlisle Laboratories Inc.
  • Central Texas Community Health Centers
  • Clint Pharmaceutical Inc.
  • Co Med Pharmaceuticals Inc.
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Darby Dental Supply Co. Inc.
  • Dept Health Central Pharmacy
  • Direct Dispensing Inc.
  • Direct Pharmaceuticals Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Eon Labs
  • Glenmark Generics Ltd.
  • Goldline Laboratories Inc.
  • H and H Laboratories
  • H.J. Harkins Co. Inc.
  • Harris Pharmaceutical Inc.
  • Heartland Repack Services LLC
  • Heritage Pharmaceuticals
  • Hi Tech Pharmacal Co. Inc.
  • Innoviant Pharmacy Inc.
  • InvaGen Pharmaceuticals Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Keltman Pharmaceuticals Inc.
  • KVK-Tech Inc.
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Luitpold Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Martica Enterprises Inc.
  • Martin Surgical Supply
  • Medisca Inc.
  • Medvantx Inc.
  • Merit Pharmaceuticals
  • Merrell Pharmaceuticals Inc.
  • Monument Pharmaceutical Co. Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mutual Pharmaceutical Co.
  • Mylan
  • National Pharmaceuticals
  • Nightingale Medical Of Indiana LLC
  • Northstar Rx LLC
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Patheon Inc.
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacy Service Center
  • Pharmedix
  • Physicians Total Care Inc.
  • Piramal Healthcare
  • Pliva Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Prescription Dispensing Service Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Sun Pharmaceutical Industries Ltd.
  • Talbert Medical Management Corp.
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Vangard Labs Inc.
  • Veratex Corp.
  • Vintage Pharmaceuticals Inc.
  • Watson Pharmaceuticals
  • Wockhardt Ltd.
Dosage forms
FormRouteStrength
SyrupOral10 mg/5mL
TabletOral10 mg/1
TabletOral100 mg/1
TabletOral25 mg/1
TabletOral50 mg/1
SolutionIntramuscular
CapsuleOral10 mg
CapsuleOral25 mg
CapsuleOral50 mg
Injection, solutionIntramuscular50 mg/1mL
SolutionOral10 mg/5mL
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral25 mg/1
Tablet, film coatedOral50 mg/1
LiquidIntramuscular
CapsuleOral100 mg/1
CapsuleOral25 mg/1
CapsuleOral50 mg/1
TrocheSublingual
CapsuleOral
Injection, solutionIntramuscular25 mg/1mL
SyrupOral
SolutionIntramuscular50 mg/1mL
SuspensionOral25 mg/5mL
Prices
Unit descriptionCostUnit
Hydroxyzine Hcl 50 mg/ml4.42USD ml
Hydroxyzine 50 mg/ml vial3.96USD ml
Hydroxyzine 25 mg/ml vial3.6USD ml
Hydroxyzine hcl powder2.75USD g
Hydroxyzine pamoate powder2.14USD g
Vistaril 50 mg capsule2.03USD capsule
HydrOXYzine HCl 50 mg/ml vial1.78USD vial
Vistaril 25 mg capsule1.71USD capsule
Vistaril 100 mg capsule1.7USD capsule
Hydroxyzine hcl 50 mg tablet1.19USD tablet
Hydroxyzine hcl 10 mg tablet0.72USD tablet
Hydroxyzine hcl 25 mg tablet0.7USD tablet
HydrOXYzine Pamoate 100 mg capsule0.67USD capsule
Hydroxyzine pam 50 mg capsule0.64USD capsule
Hydroxyzine pam 100 mg capsule0.63USD capsule
Hydroxyzine pam 25 mg capsule0.46USD capsule
Vistaril 25 mg/5ml Suspension0.45USD ml
HydrOXYzine Pamoate 25 mg capsule0.3USD capsule
HydrOXYzine Pamoate 50 mg capsule0.23USD capsule
Apo-Hydroxyzine 50 mg Capsule0.22USD capsule
Novo-Hydroxyzin 50 mg Capsule0.22USD capsule
Apo-Hydroxyzine 25 mg Capsule0.15USD capsule
Novo-Hydroxyzin 25 mg Capsule0.15USD capsule
HydrOXYzine HCl 10 mg/5ml Syrup0.13USD ml
Apo-Hydroxyzine 10 mg Capsule0.12USD capsule
Novo-Hydroxyzin 10 mg Capsule0.12USD capsule
Atarax 2 mg/ml Syrup0.06USD ml
Pms-Hydroxyzine 2 mg/ml Syrup0.04USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)200CCanadian Label
Predicted Properties
PropertyValueSource
Water Solubility0.0914 mg/mLALOGPS
logP3.43ALOGPS
logP3.41ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)15.12ChemAxon
pKa (Strongest Basic)7.82ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area35.94 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity107.07 m3·mol-1ChemAxon
Polarizability41.99 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8623
Blood Brain Barrier+0.9516
Caco-2 permeable-0.5565
P-glycoprotein substrateSubstrate0.7447
P-glycoprotein inhibitor IInhibitor0.8563
P-glycoprotein inhibitor IIInhibitor0.6394
Renal organic cation transporterInhibitor0.592
CYP450 2C9 substrateNon-substrate0.8352
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7193
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9111
CYP450 2D6 inhibitorInhibitor0.8535
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9623
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7615
Ames testNon AMES toxic0.7558
CarcinogenicityNon-carcinogens0.9102
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6612 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5929
hERG inhibition (predictor II)Inhibitor0.7898
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0udi-6491000000-95c46c16c2b29900f4d9
Mass Spectrum (Electron Ionization)MSsplash10-0uxr-4591000000-d2e3424c44feae8a5d9c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0593000000-f20d2328497a3a80239b

Taxonomy

Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
N-alkylpiperazines / Chlorobenzenes / Aralkylamines / Aryl chlorides / Trialkylamines / Dialkyl ethers / Azacyclic compounds / Primary alcohols / Organopnictogen compounds / Organochlorides
show 1 more
Substituents
Diphenylmethane / Chlorobenzene / Aralkylamine / Halobenzene / N-alkylpiperazine / Aryl chloride / Aryl halide / 1,4-diazinane / Piperazine / Tertiary aliphatic amine
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
monochlorobenzenes, N-alkylpiperazine, hydroxyether (CHEBI:5818)

Targets

Details
1. Histamine H1 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inverse agonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Spahr L, Coeytaux A, Giostra E, Hadengue A, Annoni JM: Histamine H1 blocker hydroxyzine improves sleep in patients with cirrhosis and minimal hepatic encephalopathy: a randomized controlled pilot trial. Am J Gastroenterol. 2007 Apr;102(4):744-53. Epub 2007 Jan 11. [PubMed:17222324]
  2. Altamura AC, Moliterno D, Paletta S, Maffini M, Mauri MC, Bareggi S: Understanding the pharmacokinetics of anxiolytic drugs. Expert Opin Drug Metab Toxicol. 2013 Apr;9(4):423-40. doi: 10.1517/17425255.2013.759209. Epub 2013 Jan 21. [PubMed:23330992]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Potassium voltage-gated channel subfamily H member 2
Molecular Weight
126653.52 Da
References
  1. Lee BH, Lee SH, Chu D, Hyun JW, Choe H, Choi BH, Jo SH: Effects of the histamine H(1) receptor antagonist hydroxyzine on hERG K(+) channels and cardiac action potential duration. Acta Pharmacol Sin. 2011 Sep;32(9):1128-37. doi: 10.1038/aps.2011.66. [PubMed:21892192]
  2. Sakaguchi T, Itoh H, Ding WG, Tsuji K, Nagaoka I, Oka Y, Ashihara T, Ito M, Yumoto Y, Zenda N, Higashi Y, Takeyama Y, Matsuura H, Horie M: Hydroxyzine, a first generation H(1)-receptor antagonist, inhibits human ether-a-go-go-related gene (HERG) current and causes syncope in a patient with the HERG mutation. J Pharmacol Sci. 2008 Dec;108(4):462-71. Epub 2008 Dec 5. [PubMed:19057127]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Hamelin BA, Bouayad A, Drolet B, Gravel A, Turgeon J: In vitro characterization of cytochrome P450 2D6 inhibition by classic histamine H1 receptor antagonists. Drug Metab Dispos. 1998 Jun;26(6):536-9. [PubMed:9616188]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Health Canada Product Monograph: Hydroxyzine HCl oral capsules [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Health Canada Product Monograph: Hydroxyzine HCl oral capsules [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Martinez-Gomez MA, Villanueva-Camanas RM, Sagrado S, Medina-Hernandez MJ: Evaluation of enantioselective binding of antihistamines to human serum albumin by ACE. Electrophoresis. 2007 Aug;28(15):2635-43. doi: 10.1002/elps.200600742. [PubMed:17605150]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Crowe A, Wright C: The impact of P-glycoprotein mediated efflux on absorption of 11 sedating and less-sedating antihistamines using Caco-2 monolayers. Xenobiotica. 2012 Jun;42(6):538-49. doi: 10.3109/00498254.2011.643256. Epub 2011 Dec 22. [PubMed:22188412]

Drug created on June 13, 2005 07:24 / Updated on January 20, 2020 02:44