Hydroxyzine
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Identification
- Summary
Hydroxyzine is an antihistamine used to treat anxiety and tension associated with psychoneuroses, as well as allergic conditions such as pruritus and chronic urticaria.
- Brand Names
- Atarax, Vistaril
- Generic Name
- Hydroxyzine
- DrugBank Accession Number
- DB00557
- Background
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
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 374.904
Monoisotopic: 374.176105825 - Chemical Formula
- C21H27ClN2O2
- Synonyms
- Hidroxizina
- Hychotine
- Hydroksyzyny
- Hydroxine
- Hydroxizine
- Hydroxizinum
- Hydroxycine
- Hydroxyzin
- Hydroxyzine
- Hydroxyzinum
- Idrossizina
- External IDs
- U.C.B-4492
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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prevention of Anxiety •••••••••••• Adjunct therapy in treatment of Anxiety •••••••••••• Symptomatic treatment of Anxiety •••••••••••• Symptomatic treatment of Nausea and vomiting •••••••••••• Treatment of Pruritus •••••••••••• - Contraindications & Blackbox Warnings
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- 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
Target Actions Organism AHistamine H1 receptor inverse agonistHumans UVoltage-gated inwardly rectifying potassium channel KCNH2 inhibitorHumans - 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
Hover over products below to view reaction partners
- 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
- Adverse Effects
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- 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
- Pathways
Pathway Category Hydroxyzine H1-Antihistamine Action Drug 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine Hydroxyzine may increase the central nervous system depressant (CNS depressant) activities of 1,2-Benzodiazepine. Abametapir The serum concentration of Hydroxyzine can be increased when it is combined with Abametapir. Abatacept The metabolism of Hydroxyzine can be increased when combined with Abatacept. Acalabrutinib The metabolism of Hydroxyzine can be decreased when combined with Acalabrutinib. Acebutolol The risk or severity of QTc prolongation can be increased when Acebutolol is combined with Hydroxyzine. - Food Interactions
- Avoid alcohol. Co-administration with alcohol may potentiate the CNS adverse effects of hydroxyzine.
- Avoid grapefruit products. Co-administration with grapefruit inhibits hydroxyzine metabolism and can result in elevated serum concentrations.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Hydroxyzine hydrochloride 76755771U3 2192-20-3 ANOMHKZSQFYSBR-UHFFFAOYSA-N Hydroxyzine pamoate M20215MUFR 10246-75-0 ASDOKGIIKXGMNB-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Hyzine (Hyrex) / Masmoran (Pfizer) / Rezine / Vistaject-50 / Vistazine
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Atarax Syrup 10 mg / 5 mL Oral Searchlight Pharma Inc 1956-12-31 Not applicable Canada Atarax Syrup 10 mg/5mL Oral Roerig 2006-06-20 2016-06-16 US Atarax Tablet 25 mg/1 Oral Roerig 2006-06-20 2016-06-16 US Atarax Tablet 100 mg/1 Oral Roerig 2006-06-20 2016-06-16 US Atarax Tablet 10 mg/1 Oral Roerig 2006-06-20 2016-06-16 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Hydroxyzine Injection, solution 50 mg/1mL Intramuscular Henry Schein, Inc. 2022-01-17 Not applicable US Hydroxyzine Injection, solution 50 mg/1mL Intramuscular General Injectables & Vaccines, Inc 2010-03-01 2023-08-31 US Hydroxyzine Injection, solution 50 mg/1mL Intramuscular General Injectables & Vaccines, Inc 2010-03-01 Not applicable US Hydroxyzine Tablet, film coated 25 mg/1 Oral Ncs Health Care Of Ky, Inc Dba Vangard Labs 2007-03-20 Not applicable US Hydroxyzine Solution 10 mg/5mL Oral Preferred Pharmaceuticals Inc. 2015-08-21 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ซีนิซ Tablet 10 mg Oral บริษัท ไทยนครพัฒนา จำกัด 2007-03-26 Not applicable Thailand ดร็อกซิม Tablet 25 mg Oral บริษัท บุคคโล เทรดดิ้ง จำกัด จำกัด 2008-06-25 Not applicable Thailand - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ATARAX FILM TABLET, 30 ADET Hydroxyzine (10 mg) + Hydroxyzine (25 mg) Tablet Oral Ucb Pharma S.A. 1997-03-05 Not applicable Turkey ATARAX FILM TABLET, 30 ADET Hydroxyzine (10 mg) + Hydroxyzine (25 mg) Tablet Oral Ucb Pharma S.A. 1997-03-05 Not applicable Turkey - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image MKH Dose Pack Hydroxyzine hydrochloride (10 mg/1) + Ketamine hydrochloride (25 mg/1) + Midazolam (3 mg/1) Troche Sublingual Imprimis Njof, Llc 2019-03-04 Not applicable US
Categories
- ATC Codes
- N05BB01 — HydroxyzineN05BB51 — Hydroxyzine, combinations
- Drug Categories
- Anti-Anxiety Agents
- Antipruritics
- Central Nervous System Depressants
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dermatologicals
- Diphenylmethane Derivatives
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Histamine Receptor Antagonists
- Miscellaneous Anxiolytics Sedatives and Hypnotics
- Nervous System
- Neurotransmitter Agents
- P-glycoprotein substrates
- Piperazines
- Potential QTc-Prolonging Agents
- Psycholeptics
- QTc Prolonging Agents
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,4-diazinane / Alcohol / Amine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Chlorobenzene / Dialkyl ether show 17 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- monochlorobenzenes, N-alkylpiperazine, hydroxyether (CHEBI:5818)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 30S50YM8OG
- CAS number
- 68-88-2
- 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
References
- Synthesis Reference
U.S. Patent 2,899,436.
- General References
- Clark BG, Araki M, Brown HW: Hydroxyzine-associated tardive dyskinesia. Ann Neurol. 1982 Apr;11(4):435. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- How drugs act: General principles. (2020). In Rang and Dale's Pharmacology (9th ed.). Edinburgh: Elsevier. [ISBN:9780702080609]
- Health Canada Product Monograph: Hydroxyzine HCl oral capsules [Link]
- CaymanChem: Hydroxyzine MSDS [Link]
- FDA Approved Drug Products: Hydroxyzine HCl oral tablets [Link]
- FDA Approved Drug Products: Vistaril (hydroxyzine pamoate) [Link]
- FDA Approved Drug Products: VISTARIL (hydroxyzine pamoate) capsules and suspension [Link]
- DailyMed: hydroxyzine hydrochloride injection [Link]
- External Links
- Human Metabolome Database
- HMDB0014697
- KEGG Drug
- D08054
- KEGG Compound
- C07045
- PubChem Compound
- 3658
- PubChem Substance
- 46508556
- ChemSpider
- 3531
- BindingDB
- 22875
- 5553
- 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
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Hydroxyzine / Reflex, Oculocardiac / Sinus Bradycardia / Strabismus 1 somestatus stop reason just information to hide Not Available Completed Basic Science Placebo Drug Interaction / Placebo Effect 1 somestatus stop reason just information to hide Not Available Completed Supportive Care Chloral Hydrate / Electroencephalography / Hydroxyzine / Melatonin / Sleep Deprivation 1 somestatus stop reason just information to hide Not Available Completed Treatment Substance Related Disorders 1 somestatus stop reason just information to hide Not Available Unknown Status Prevention Preoperative Anxiety 1 somestatus stop reason just information to hide
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
Form Route Strength Capsule, liquid filled Oral 25 mg Tablet, film coated Oral 50 mg Tablet Oral 10.00 mg Injection, solution Intramuscular Syrup Oral Syrup Oral 10 mg/5mL Tablet Oral 10 mg/1 Tablet Oral 10.000 mg Tablet Oral 100 mg/1 Tablet Oral 25 mg/1 Tablet Oral 50 mg/1 Tablet, film coated Oral Syrup Oral 200 ml Solution Intramuscular 50 mg / mL Tablet, film coated Oral 30 mg Syrup Oral 300 mg Tablet Oral 500 mg Tablet Oral Tablet, chewable Buccal 25 mg Tablet, coated Oral 50 mg Solution Intramuscular 100 mg Solution Oral 10 mg Solution Oral 250 mg Syrup Oral 250 mg Solution Oral 0.25 g Tablet Oral 2500000 mg Syrup Oral 0.25 g Capsule Oral 10 mg Capsule Oral 25 mg Capsule Oral 50 mg Injection, solution Intramuscular 50 mg/1mL Solution Oral 10 mg/5mL Syrup Oral 50 mg/25mL Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 25 mg/1 Tablet, film coated Oral 50 mg/1 Liquid Intramuscular 50 mg / mL Tablet, film coated Oral 10.000 mg Tablet, film coated Oral 25.000 mg Capsule Oral 100 mg/1 Capsule Oral 25 mg/1 Capsule Oral 50 mg/1 Tablet, film coated Oral 10 mg Troche Sublingual Capsule Oral 10 mg / cap Capsule Oral 25 mg / cap Injection, solution Intramuscular 25 mg/1mL Syrup Oral 10 mg / 5 mL Solution / drops Oral 10 ml Solution / drops Oral 20 ml Solution Intramuscular 50 mg/1mL Suspension Oral 25 mg/5mL Tablet Oral 25.000 mg Tablet, coated Oral 25 mg Tablet Oral 25 mg Tablet Oral 10 mg Tablet, film coated Oral 25 mg Solution 10 mg/5ml Tablet, coated Oral 10 mg - Prices
Unit description Cost Unit Hydroxyzine Hcl 50 mg/ml 4.42USD ml Hydroxyzine 50 mg/ml vial 3.96USD ml Hydroxyzine 25 mg/ml vial 3.6USD ml Hydroxyzine hcl powder 2.75USD g Hydroxyzine pamoate powder 2.14USD g Vistaril 50 mg capsule 2.03USD capsule HydrOXYzine HCl 50 mg/ml vial 1.78USD vial Vistaril 25 mg capsule 1.71USD capsule Vistaril 100 mg capsule 1.7USD capsule Hydroxyzine hcl 50 mg tablet 1.19USD tablet Hydroxyzine hcl 10 mg tablet 0.72USD tablet Hydroxyzine hcl 25 mg tablet 0.7USD tablet HydrOXYzine Pamoate 100 mg capsule 0.67USD capsule Hydroxyzine pam 50 mg capsule 0.64USD capsule Hydroxyzine pam 100 mg capsule 0.63USD capsule Hydroxyzine pam 25 mg capsule 0.46USD capsule Vistaril 25 mg/5ml Suspension 0.45USD ml HydrOXYzine Pamoate 25 mg capsule 0.3USD capsule HydrOXYzine Pamoate 50 mg capsule 0.23USD capsule Apo-Hydroxyzine 50 mg Capsule 0.22USD capsule Novo-Hydroxyzin 50 mg Capsule 0.22USD capsule Apo-Hydroxyzine 25 mg Capsule 0.15USD capsule Novo-Hydroxyzin 25 mg Capsule 0.15USD capsule HydrOXYzine HCl 10 mg/5ml Syrup 0.13USD ml Apo-Hydroxyzine 10 mg Capsule 0.12USD capsule Novo-Hydroxyzin 10 mg Capsule 0.12USD capsule Atarax 2 mg/ml Syrup 0.06USD ml Pms-Hydroxyzine 2 mg/ml Syrup 0.04USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 200C Canadian Label - Predicted Properties
Property Value Source Water Solubility 0.0914 mg/mL ALOGPS logP 3.43 ALOGPS logP 3.41 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 15.12 Chemaxon pKa (Strongest Basic) 7.45 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 35.94 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 107.07 m3·mol-1 Chemaxon Polarizability 41.99 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8623 Blood Brain Barrier + 0.9516 Caco-2 permeable - 0.5565 P-glycoprotein substrate Substrate 0.7447 P-glycoprotein inhibitor I Inhibitor 0.8563 P-glycoprotein inhibitor II Inhibitor 0.6394 Renal organic cation transporter Inhibitor 0.592 CYP450 2C9 substrate Non-substrate 0.8352 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.7193 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9111 CYP450 2D6 inhibitor Inhibitor 0.8535 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.9623 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7615 Ames test Non AMES toxic 0.7558 Carcinogenicity Non-carcinogens 0.9102 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6612 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5929 hERG inhibition (predictor II) Inhibitor 0.7898
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 201.4104609 predictedDarkChem Lite v0.1.0 [M-H]- 185.55614 predictedDeepCCS 1.0 (2019) [M+H]+ 201.0609609 predictedDarkChem Lite v0.1.0 [M+H]+ 187.91415 predictedDeepCCS 1.0 (2019) [M+Na]+ 201.2974609 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.821 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inverse agonist
- General Function
- G-protein-coupled receptor for histamine, a biogenic amine that functions as an immune modulator and a neurotransmitter (PubMed:33828102, PubMed:8280179). Through the H1 receptor, histamine mediates the contraction of smooth muscles and increases capillary permeability due to contraction of terminal venules. Also mediates neurotransmission in the central nervous system and thereby regulates circadian rhythms, emotional and locomotor activities as well as cognitive functions (By similarity)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel (PubMed:10219239, PubMed:10753933, PubMed:10790218, PubMed:10837251, PubMed:11997281, PubMed:12063277, PubMed:18559421, PubMed:22314138, PubMed:22359612, PubMed:26363003, PubMed:27916661, PubMed:9230439, PubMed:9351446, PubMed:9765245). Channel properties are modulated by cAMP and subunit assembly (PubMed:10837251). Characterized by unusual gating kinetics by producing relatively small outward currents during membrane depolarization and large inward currents during subsequent repolarization which reflect a rapid inactivation during depolarization and quick recovery from inactivation but slow deactivation (closing) during repolarization (PubMed:10219239, PubMed:10753933, PubMed:10790218, PubMed:10837251, PubMed:11997281, PubMed:12063277, PubMed:18559421, PubMed:22314138, PubMed:22359612, PubMed:26363003, PubMed:27916661, PubMed:9230439, PubMed:9351446, PubMed:9765245). Channel properties are modulated by cAMP and subunit assembly (PubMed:10837251). Forms a stable complex with KCNE1 or KCNE2, and that this heteromultimerization regulates inward rectifier potassium channel activity (PubMed:10219239, PubMed:9230439)
- Specific Function
- delayed rectifier potassium channel activity
- Gene Name
- KCNH2
- Uniprot ID
- Q12809
- Uniprot Name
- Voltage-gated inwardly rectifying potassium channel KCNH2
- Molecular Weight
- 126653.52 Da
References
- 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. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Health Canada Product Monograph: Hydroxyzine HCl oral capsules [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
- Specific Function
- aromatase activity
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Health Canada Product Monograph: Hydroxyzine HCl oral capsules [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateRegulator
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- 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. [Article]
- Martinez-Gomez MA, Carril-Aviles MM, Sagrado S, Villanueva-Camanas RM, Medina-Hernandez MJ: Characterization of antihistamine-human serum protein interactions by capillary electrophoresis. J Chromatogr A. 2007 Apr 20;1147(2):261-9. doi: 10.1016/j.chroma.2007.02.054. Epub 2007 Feb 22. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 30, 2024 23:02