Identification

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

A histamine H1 receptor antagonist that is effective in the treatment of chronic urticaria, dermatitis, and histamine-mediated pruritus. Unlike its major metabolite cetirizine, it does cause drowsiness. It is also effective as an antiemetic, for relief of anxiety and tension, and as a sedative. [PubChem]

Structure
Thumb
Synonyms
  • Hidroxizina
  • Hychotine
  • Hydroksyzyny
  • Hydroxine
  • Hydroxizine
  • Hydroxizinum
  • Hydroxycine
  • Hydroxyzin
  • Hydroxyzine
  • Hydroxyzinum
Product Ingredients
IngredientUNIICASInChI Key
Hydroxyzine hydrochloride76755771U32192-20-3ANOMHKZSQFYSBR-UHFFFAOYSA-N
Hydroxyzine pamoateM20215MUFR10246-75-0ASDOKGIIKXGMNB-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Hydroxyzine Cap 10mgCapsule10 mgOralApotex Corporation1986-12-31Not applicableCanada
Apo Hydroxyzine Cap 25mgCapsule25 mgOralApotex Corporation1986-12-31Not applicableCanada
Apo Hydroxyzine Cap 50mgCapsule50 mgOralApotex Corporation1986-12-31Not applicableCanada
Atarax Cap 10mgCapsule10 mgOralErfa Canada 2012 Inc1956-12-312005-09-15Canada
Atarax Cap 25mgCapsule25 mgOralErfa Canada 2012 Inc1956-12-312005-09-15Canada
Atarax Cap 50mgCapsule50 mgOralErfa Canada 2012 Inc1959-12-312005-09-15Canada
Atarax Im Sol 50mg/mlSolution50 mgIntramuscularErfa Canada 2012 Inc1957-12-312005-08-18Canada
Atarax Syrup 2mg/mlSyrup10 mgOralErfa Canada 2012 Inc1956-12-31Not applicableCanada
Hydroxyzine Hydrochloride InjectionLiquid50 mgIntramuscularFresenius Kabi2001-04-05Not applicableCanada
Hydroxyzine Hydrochloride Injection USPLiquid50 mgIntramuscularSandoz Canada Incorporated1987-12-31Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
HydroxyzineInjection, solution50 mg/1mLIntramuscularGeneral Injectables & Vaccines2010-03-01Not applicableUs
HydroxyzineTablet, film coated50 mg/1OralMajor Pharmaceuticals2007-03-20Not applicableUs
HydroxyzineTablet, film coated10 mg/1OralMajor Pharmaceuticals2007-03-202012-11-30Us
HydroxyzineTablet, film coated10 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-03-20Not applicableUs
HydroxyzineTablet, film coated25 mg/1OralPliva, Inc.2010-08-022010-12-05Us
HydroxyzineSolution10 mg/5mLOralPreferreed Pharmaceuticals Inc.2015-08-21Not applicableUs
HydroxyzineTablet, film coated10 mg/1OralBlenheim Pharmacal, Inc.2009-12-28Not applicableUs50111 0307 01 nlmimage10 8429422a
HydroxyzineTablet, film coated50 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-03-20Not applicableUs
HydroxyzineInjection, solution25 mg/1mLIntramuscularGeneral Injectables & Vaccines2010-03-012017-01-17Us
HydroxyzineTablet, film coated10 mg/1OralPliva, Inc.2010-08-022010-12-05Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AtaraxHydroxyzine hydrochloride (100 mg/1)TabletOralRoerig2006-06-20Not applicableUs
AtaraxHydroxyzine hydrochloride (10 mg/1)TabletOralRoerig2006-06-20Not applicableUs
AtaraxHydroxyzine hydrochloride (50 mg/1)TabletOralRoerig2006-06-20Not applicableUs
AtaraxHydroxyzine hydrochloride (10 mg/5mL)SyrupOralRoerig2006-06-20Not applicableUs
AtaraxHydroxyzine hydrochloride (25 mg/1)TabletOralRoerig2006-06-20Not applicableUs
Hydroxyzine HydrochlorideHydroxyzine hydrochloride (25 mg/1)Tablet, film coatedOralVintage Pharmaceuticals, LLC2007-03-152007-03-15Us
Hydroxyzine HydrochlorideHydroxyzine hydrochloride (50 mg/1)TabletOralWatson Laboratories, Inc2006-11-272006-11-27Us
Hydroxyzine hydrochlorideHydroxyzine hydrochloride (50 mg/1)Tablet, film coatedOralMutual Pharmaceutical2007-01-19Not applicableUs
Hydroxyzine HydrochlorideHydroxyzine hydrochloride (10 mg/5mL)SolutionOralVintage Pharmaceuticals, LLC2006-12-292006-12-29Us
Hydroxyzine hydrochlorideHydroxyzine hydrochloride (50 mg/1)Tablet, film coatedOralMutual Pharmaceutical2007-01-19Not applicableUs
International/Other Brands
Atarax (UCB) / 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

For symptomatic relief of anxiety and tension associated with psychoneurosis and as an adjunct in organic disease states in which anxiety is manifested. Useful in the management of pruritus due to allergic conditions such as chronic urticaria.

Associated Conditions
Associated Therapies
Pharmacodynamics

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's active metabolite, cetirizine, is also used as an H1-antagonist.

Mechanism of action

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.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
Absorption

Rapidly absorbed from the gastrointestinal tract

Volume of distribution
Not Available
Protein binding

93%

Metabolism

Hepatic

Route of elimination
Not Available
Half life

20 to 25 hours

Clearance
Not Available
Toxicity

Oral, rat LD50: 950 mg/kg. Symptoms of overexposure include hypersedation.

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

Interactions

Drug Interactions
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.
3,4-MethylenedioxyamphetamineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of 3,4-Methylenedioxyamphetamine.
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.
AbexinostatThe risk or severity of QTc prolongation can be increased when Hydroxyzine is combined with Abexinostat.
AcepromazineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Acepromazine.
Food Interactions
  • Avoid alcohol.
  • Take with food.

References

Synthesis Reference

U.S. Patent 2,899,436.

General References
  1. HUTCHEON DE, MORRIS DL, SCRIABINE A: Cardiovascular action of hydroxyzine (atarax). J Pharmacol Exp Ther. 1956 Dec;118(4):451-60. [PubMed:13385806]
  2. DOLAN CM: Management of emotional disturbances; use of hydroxyzine (atarax) in general practice. Calif Med. 1958 Jun;88(6):443-4. [PubMed:13536863]
  3. Clark BG, Araki M, Brown HW: Hydroxyzine-associated tardive dyskinesia. Ann Neurol. 1982 Apr;11(4):435. [PubMed:7103423]
External Links
Human Metabolome Database
HMDB0014697
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
N05BB51 — Hydroxyzine, combinationsN05BB01 — Hydroxyzine
AHFS Codes
  • 28:24.92 — Miscellaneous Anxiolytics Sedatives and Hypnotics
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Not Yet RecruitingTreatmentBladder Small Cell Neuroendocrine Carcinoma / Castration-Resistant Prostate Carcinoma / Metastatic Bladder Urothelial Carcinoma / Metastatic Urethral Urothelial Carcinoma / Prostate Carcinoma Metastatic in the Bone / Prostate Neuroendocrine Neoplasm / Prostate Small Cell Carcinoma / Stage III Bladder Cancer AJCC v8 / Stage III Prostate Cancer AJCC v8 / Stage III Urethral Cancer AJCC v8 / Stage IV Bladder Cancer AJCC v8 / Stage IV Prostate Cancer AJCC v8 / Stage IV Urethral Cancer AJCC v8 / Stage IVA Bladder Cancer AJCC v8 / Stage IVB Bladder Cancer AJCC v8 / Transitional Cell Carcinoma / Ureter Small Cell Carcinoma1
2Active Not RecruitingTreatmentSickle Cell Disorders1
2CompletedNot AvailableFeeling Anxious1
2RecruitingTreatmentDouble-hit Lymphoma / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Mantle Cell Lymphoma (MCL) / Peripheral T Cell Lymphoma (PTCL)1
2RecruitingTreatmentNasal Cavity Adenocarcinoma / Nasal Cavity Tumor / Paranasal Sinus Cancer1
3RecruitingTreatmentAcute Lymphoblastic Leukemia, Pediatric1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedPreventionNausea / Pruritus / Vomiting1
4CompletedTreatmentPain1
4Not Yet RecruitingTreatmentFeeling Anxious1
4Not Yet RecruitingTreatmentMyocardial Inflammation / Myocarditis in RA / Rheumatoid Arthritis1
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 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
CapsuleOral10 mg
CapsuleOral25 mg
CapsuleOral50 mg
SyrupOral10 mg/5mL
TabletOral10 mg/1
TabletOral100 mg/1
TabletOral25 mg/1
TabletOral50 mg/1
SolutionIntramuscular50 mg
Injection, solutionIntramuscular50 mg/1mL
SolutionOral10 mg/5mL
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral25 mg/1
Tablet, film coatedOral50 mg/1
LiquidIntramuscular50 mg
CapsuleOral100 mg/1
CapsuleOral25 mg/1
CapsuleOral50 mg/1
Injection, solutionIntramuscular25 mg/1mL
SyrupOral10 mg
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)193 °CU.S. Patent 2,899,436.
water solubility< 700 mg/mLNot Available
logP2.7Not Available
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
Human
Pharmacological action
Yes
Actions
Antagonist
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. 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]
  3. 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]
  4. Chen C: Physicochemical, pharmacological and pharmacokinetic properties of the zwitterionic antihistamines cetirizine and levocetirizine. Curr Med Chem. 2008;15(21):2173-91. [PubMed:18781943]
  5. Snowman AM, Snyder SH: Cetirizine: actions on neurotransmitter receptors. J Allergy Clin Immunol. 1990 Dec;86(6 Pt 2):1025-8. [PubMed:1979798]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Drug created on June 13, 2005 07:24 / Updated on September 23, 2018 19:37