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Cetirizine - DrugBank

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Cetirizine

Targets (1)Transporters (1)Biointeractions (3)

Identification

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Name
Cetirizine
Accession Number
DB00341  (APRD00630)
Type
Small Molecule
Groups
Approved
Description

Cetirizine, also commonly known as Zyrtec, is an orally active second-generation histamine H1 antagonist proven effective in the treatment of various allergic symptoms, such as sneezing, coughing, nasal congestion, hives, and other symptoms 1, 2.

One of the most common uses for this drug is for a condition called allergic rhinitis. The prevalence of allergic rhinitis in the United States is about 15% according to physician diagnoses, and up to 30%, according to self-reported nasal symptoms. Allergic rhinitis is associated with multiple missed or unproductive days at work and school, problems with sleep, and other difficulties with day to day activities for many individuals 3. Furthermore, some antihistamine agents that are used to treat this condition cause undesirable, sedating effects 4.

Cetirizine is one of the first second-generation H1 antihistamines (SGAHs)formulated to selectively inhibit the H1 receptor without sedating effects 2.

Structure
3DMOLSDF3D-SDFPDBSMILESInChI Similar Structures

Structure for Cetirizine (DB00341)

Synonyms
  • Cetirizin
  • Cetirizina
  • Cetirizine
  • Cetirizinum
Product Ingredients
IngredientUNIICASInChI KeyCetirizine hydrochloride 64O047KTOA 83881-52-1 PGLIUCLTXOYQMV-UHFFFAOYSA-N
Product Images
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Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End Unlock Additional DataCetirizine Tablet 20 mg Oral Pro Doc Limitee 2016-06-13 Not applicable Canada Reactine 20mg Tablet Tablet Oral Mcneil Consumer Healthcare Division Of Johnson & Johnson Inc 2002-01-14 Not applicable Canada Rhinaris Relief Tablet Oral Pendopharm Division Of Pharmascience Inc Not applicable Not applicable Canada Zerviate Solution / drops 2.4 mg/1mL Ophthalmic Eyevance Pharmaceuticals 2019-02-19 Not applicable US Zyrtec Tablet, chewable 5 mg/1 Oral Pfizer Laboratories Div Pfizer Inc. 2004-03-16 2010-12-08 US Zyrtec Tablet, chewable 5 mg/1 Oral Physicians Total Care, Inc. 2007-03-30 2007-12-30 US Zyrtec Tablet, film coated 10 mg/1 Oral Pfizer Laboratories Div Pfizer Inc. 1995-12-08 2010-12-08 US Zyrtec Tablet 10 mg/1 Oral Physicians Total Care, Inc. 1996-12-18 2009-01-18 US Zyrtec Tablet, film coated 5 mg/1 Oral Pfizer Laboratories Div Pfizer Inc. 1995-12-08 2010-12-08 US Zyrtec Tablet 5 mg/1 Oral Physicians Total Care, Inc. 2002-12-16 2009-01-18 US Additional Data Available
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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End Unlock Additional DataApo-cetirizine Tablet Oral Apotex Corporation 2016-04-22 Not applicable Canada Cetirizine Hydrochloride Solution 1 mg/1mL Oral Carilion Materials Management 2008-07-24 Not applicable US Cetirizine Hydrochloride Solution 1 mg/1mL Oral Aidarex Pharmaceuticals LLC 2013-12-03 Not applicable US Cetirizine hydrochloride Solution 1 mg/1mL Oral A-S Medication Solutions 2016-09-02 Not applicable US Cetirizine Hydrochloride Solution 1 mg/1mL Oral Aidarex Pharmaceuticals LLC 2018-08-17 Not applicable US Cetirizine Hydrochloride Syrup 5 mg/5mL Oral Apotex Corporation 2008-06-18 2009-04-01 US Cetirizine Hydrochloride Syrup 5 mg/5mL Oral Lannett Company, Inc. 2012-05-11 Not applicable US Cetirizine Hydrochloride Tablet 5 mg/1 Oral bryant ranch prepack 2009-10-01 Not applicable US Cetirizine Hydrochloride Solution 1 mg/1mL Oral Carilion Materials Management 2013-12-03 Not applicable US Cetirizine Hydrochloride Tablet 10 mg/1 Oral Directrx 2016-12-22 Not applicable US Additional Data Available
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  • Product Code Product Code

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End Unlock Additional Data24 Hour Allergy Tablet, film coated 10 mg/1 Oral Meijer Distribution Inc 1997-07-07 Not applicable US 24 Hour Allergy Liquid 5 mg/5mL Oral Meijer Distribution 2008-04-16 2017-07-13 US 24 Hour Allergy Capsule 10 mg/1 Oral Walgreens 2018-09-14 Not applicable US 24 Hour Allergy Lil Drug Store Products Tablet 10 mg/1 Oral Lil' Drug Store Products, Inc. 2018-06-01 Not applicable US 24 Hour Allergy Lil Drug Store Products Tablet 10 mg/1 Oral Lil' Drug Store Products, Inc. 2014-11-01 Not applicable US 24-Hour All Day Allergy Tablet 10 mg/1 Oral Strategic Sourcing Services LLC 2012-04-27 2019-10-01 US 7 Select All Day Allergy Tablet 10 mg/1 Oral 7-Eleven 2014-04-29 2021-01-31 US 7 Select Childrens Allergy Relief Solution 5 mg/5mL Oral 7 Eleven 2014-08-05 Not applicable US All Day Allergy Capsule 10 mg/1 Oral TOP CARE (Topco Associates LLC) 2013-04-30 2021-12-31 US All Day Allergy Tablet 10 mg/1 Oral McKesson (Health Mart) 2019-07-01 Not applicable US Additional Data Available
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  • Product Code Product Code

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End12 Hour Allergy D Cetirizine hydrochloride (5 mg/1) + Pseudoephedrine hydrochloride (120 mg/1) Tablet, extended release Oral Meijer Distribution Inc 1988-07-15 Not applicable US All Day Allergy D Cetirizine hydrochloride (5 mg/1) + Pseudoephedrine hydrochloride (120 mg/1) Tablet, extended release Oral HYVEE INC 2008-05-05 2019-11-01 US All day Allergy d Cetirizine hydrochloride (5 mg/1) + Pseudoephedrine hydrochloride (120 mg/1) Tablet, extended release Oral Major Pharmaceuticals 2008-05-06 Not applicable US All Day Allergy D Cetirizine hydrochloride (5 mg/1) + Pseudoephedrine hydrochloride (120 mg/1) Tablet, extended release Oral Kroger Company 2014-02-19 Not applicable US all day Allergy Relief D Cetirizine hydrochloride (5 mg/1) + Pseudoephedrine hydrochloride (120 mg/1) Tablet, extended release Oral H E B 2008-05-02 Not applicable US All Day Allergy-D Cetirizine hydrochloride (5 mg/1) + Pseudoephedrine hydrochloride (120 mg/1) Tablet, extended release Oral L. Perrigo Company 2011-09-06 Not applicable US Allergy and Congestion Relief D Original Prescription Strength Cetirizine hydrochloride (5 mg/1) + Pseudoephedrine hydrochloride (120 mg/1) Tablet, extended release Oral Rite Aid Corporation 2008-04-10 Not applicable US Allergy Relief D Cetirizine hydrochloride (5 mg/1) + Pseudoephedrine hydrochloride (120 mg/1) Tablet, extended release Oral Shopko Stores Operating 2013-09-07 Not applicable US Allergy Relief D Cetirizine hydrochloride (5 mg/1) + Pseudoephedrine hydrochloride (120 mg/1) Tablet, extended release Oral H.E.B. 2018-01-19 Not applicable US Allergy Relief D Cetirizine hydrochloride (5 mg/1) + Pseudoephedrine hydrochloride (120 mg/1) Tablet, extended release Oral Publix Super Markets Inc 2010-03-11 Not applicable US
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndZyrtec Cetirizine hydrochloride (10 mg/1) Tablet Oral Physicians Total Care, Inc. 1996-12-18 2009-01-18 US Zyrtec Cetirizine hydrochloride (5 mg/1) Tablet Oral Physicians Total Care, Inc. 2002-12-16 2009-01-18 US
International/Other Brands
Alerlisin / Cetryn / Formistin / Hitrizin / Virlix / Zirtek / Zyrlex
Categories
UNII
YO7261ME24
CAS number
83881-51-0
Weight
Average: 388.888
Monoisotopic: 388.155370383
Chemical Formula
C21H25ClN2O3
InChI Key
ZKLPARSLTMPFCP-UHFFFAOYSA-N
InChI
InChI=1S/C21H25ClN2O3/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26/h1-9,21H,10-16H2,(H,25,26)
IUPAC Name
2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
SMILES
OC(=O)COCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1

Pharmacology

Indication

Seasonal Allergic Rhinitis: Indicated for the relief of symptoms associated with seasonal allergic rhinitis caused by allergens such as ragweed, grass and tree pollens in adults and children 2 years of age and above. Symptoms treated effectively include sneezing, rhinorrhea, nasal pruritus, ocular pruritus, tearing, and redness of the eyes Label.

Perennial allergic rhinitis: This drug is indicated for the relief of symptoms associated with perennial allergic rhinitis due to allergens including dust mites, animal dander, and molds in adults and children 6 months of age and older. Symptoms treated effectively include sneezing, rhinorrhea, postnasal discharge, nasal pruritus, ocular pruritus, and tearing Label.

Chronic urticaria: Cetirizine is indicated for the treatment of the uncomplicated skin manifestations of chronic idiopathic urticaria in adults and children 6 months of age and older. It markedly reduces the occurrence, severity, and duration of hives and significantly reduces pruritus Label.

Associated Conditions
Pharmacodynamics

General effects and respiratory effects

Cetirizine, the active metabolite of the piperazine H1-receptor antagonist hydroxyzine, minimizes or eliminates the symptoms of chronic idiopathic urticaria, perennial allergic rhinitis, seasonal allergic rhinitis, allergic asthma, physical urticaria, and atopic dermatitis. The clinical efficacy of cetirizine for allergic respiratory diseases has been well established in numerous trials Label.

Effects on urticaria/anti-inflammatory effects

It has anti-inflammatory properties that may play a role in asthma management 1. There is evidence that cetirizine improves symptoms of urticaria. Marked clinical inhibition of a wheal and flare response occurs in infants, children as well as adults within 20 minutes of one oral dose and lasts for 24 h 1. Concomitant use of cetirizine reduces the duration and dose of topical anti-inflammatory formulas used for the treatment of atopic dermatitis 1.

Mechanism of action

Cetirizine, a metabolite of hydroxyzine, is an antihistamine drug. Its main effects are achieved through selective inhibition of peripheral H1 receptors. The antihistamine activity of cetirizine has been shown in a variety of animal and human models. In vivo and ex vivo animal models have shown insignificant anticholinergic and antiserotonergic effects. In clinical studies, however, dry mouth was found to be more frequent with cetirizine than with a placebo. In vitro receptor binding studies have demonstrated no detectable affinity of cetirizine for histamine receptors other than the H1 receptors. Studies with radiolabeled cetirizine administration in the rat have demonstrated insignificant penetration into the brain. Ex vivo studies in the mouse have shown that systemically administered cetirizine does not occupy cerebral H1 receptors significantly Label.

TargetActionsOrganismAHistamine H1 receptor antagonist Humans
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Absorption

Cetirizine was rapidly absorbed with a time to maximum concentration (Tmax) of about 1 hour after oral administration of tablets or syrup formulation in adult volunteers Label. Bioavailability was found to be similar between the tablet and syrup dosage forms. When healthy study volunteers were given several doses of cetirizine (10 mg tablets once daily for 10 days), a mean peak plasma concentration (Cmax) of 311 ng/mL was measured Label.

Effect of food on absorption

Food had no effect on cetirizine exposure (AUC), however, Tmax was delayed by 1.7 hours and Cmax was decreased by 23% in the fed state Label.

Volume of distribution

Apparent volume of distribution: 0.44 +/- 0.19 L/kg 5.

Protein binding

The mean plasma protein binding of cetirizine is 93% Label.

Metabolism

A mass balance clinical trial comprised of 6 healthy male study volunteers showed that 70% of the administered radioactivity was measured in the urine and 10% in the feces after cetirizine administration. About 50% of the radioactivity was measured in the urine as unchanged cetirizine. Most of the rapid increase in peak plasma radioactivity was related to the parent drug, implying a low level of first pass metabolism. This prevents potential interactions of cetirizine with drugs interacting with hepatic cytochrome enzymes 1.

Cetirizine is metabolized partially by oxidative O-dealkylation to a metabolite with insignificant antihistaminic activity. The enzyme or enzymes responsible for this step in cetirizine metabolism have not yet been identified Label.

Route of elimination

Mainly eliminated in the urine Label, 1.

Between 70 – 85% of an orally administered dose can be found in the urine and 10 – 13% in the feces 1.

Half life

Plasma elimination half-life is 8.3 hours Label.

Clearance

Apparent total body clearance: approximately 53 mL/min Label.

Cetirizine is mainly eliminated by the kidneys 1, Label. Dose adjustment is required for patients with moderate to severe renal impairment and in patients on hemodialysis Label.

Toxicity

Oral LD50 (rat): 365 mg/kg; Intraperitoneal LDLO (mouse): 138 mg/kg; Oral TDLO (rat): 50 mg/kg; Oral TDLO (mouse): 0.1 mg/kg MSDS.

Carcinogenesis and mutagenesis: In a 2-year carcinogenicity study in rats, cetirizine was not shown to be carcinogenic at dietary doses up to 20 mg/kg (approximately 15 times the maximum recommended daily oral dose in adults). In a 2-year carcinogenicity study in mice, cetirizine administration lead to an incidence of benign liver tumors in males at a dietary dose of 16 mg/kg (approximately 6 times the maximum recommended daily oral dose in adults). The clinical significance of these findings during long-term use of cetirizine is unknown at this time Label.

Cetirizine was not mutagenic in the Ames test, and not clastogenic in the human lymphocyte assay, the mouse lymphoma assay, and in vivo micronucleus test in rats Label.

Impairment of fertility

In a fertility and reproduction study in mice, cetirizine did not negatively impact fertility at an oral dose of 64 mg/kg (approximately 25 times the maximum recommended daily oral dose in adults) Label.

Pregnancy Category B:

In mice, rats, and rabbits, cetirizine was not teratogenic at oral doses up to 96, 225, and 135 mg/kg, respectively (approximately 40, 180 and 220 times the maximum recommended daily oral dose in adults). There are no adequate and well-controlled studies in pregnant women. Because animal studies are not always predictive of human response, cetirizine should be used in pregnancy only if clearly needed Label.

Use in breastfeeding/nursing

Cetirizine has been reported to be excreted in human breast milk. The use of cetirizine in nursing mothers is not recommended Label.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategoryCetirizine 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. DrugInteraction Unlock Additional Data2,5-Dimethoxy-4-ethylamphetamine 2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Cetirizine. 2,5-Dimethoxy-4-ethylthioamphetamine 2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Cetirizine. 4-Bromo-2,5-dimethoxyamphetamine 4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Cetirizine. 4-Methoxyamphetamine The risk or severity of adverse effects can be increased when Cetirizine is combined with 4-Methoxyamphetamine. 5-methoxy-N,N-dimethyltryptamine The risk or severity of adverse effects can be increased when Cetirizine is combined with 5-methoxy-N,N-dimethyltryptamine. 7-Nitroindazole The risk or severity of adverse effects can be increased when Cetirizine is combined with 7-Nitroindazole. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline The risk or severity of adverse effects can be increased when Cetirizine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline. Abacavir Cetirizine may decrease the excretion rate of Abacavir which could result in a higher serum level. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Cetirizine. Abexinostat The risk or severity of QTc prolongation can be increased when Cetirizine is combined with Abexinostat. Additional Data Available
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Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.

References

Synthesis Reference

Manne Reddy, "Polymorphic forms of dihydrochloride salts of cetirizine and processes for preparation thereof." U.S. Patent US20040186112, issued September 23, 2004.

US20040186112
General References
  1. Portnoy JM, Dinakar C: Review of cetirizine hydrochloride for the treatment of allergic disorders. Expert Opin Pharmacother. 2004 Jan;5(1):125-35. doi: 10.1517/14656566.5.1.125 . [PubMed:14680442]
  2. Zhang L, Cheng L, Hong J: The clinical use of cetirizine in the treatment of allergic rhinitis. Pharmacology. 2013;92(1-2):14-25. doi: 10.1159/000351843. Epub 2013 Jul 18. [PubMed:23867423]
  3. Wheatley LM, Togias A: Clinical practice. Allergic rhinitis. N Engl J Med. 2015 Jan 29;372(5):456-63. doi: 10.1056/NEJMcp1412282. [PubMed:25629743]
  4. Church MK, Church DS: Pharmacology of antihistamines. Indian J Dermatol. 2013 May;58(3):219-24. doi: 10.4103/0019-5154.110832. [PubMed:23723474]
  5. Spicak V, Dab I, Hulhoven R, Desager JP, Klanova M, de Longueville M, Harvengt C: Pharmacokinetics and pharmacodynamics of cetirizine in infants and toddlers. Clin Pharmacol Ther. 1997 Mar;61(3):325-30. doi: 10.1016/S0009-9236(97)90165-X. [PubMed:9084458]
External Links
Human Metabolome Database
HMDB0005032
KEGG Compound
C07778
PubChem Compound
2678
PubChem Substance
46508368
ChemSpider
2577
BindingDB
22890
ChEBI
3561
ChEMBL
CHEMBL1000
Therapeutic Targets Database
DAP000323
PharmGKB
PA448905
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Cetirizine
ATC Codes
R06AE07 — Cetirizine
AHFS Codes
  • 04:08.00 — Second Generation Antihistamines
FDA label
Download (54.2 KB)
MSDS
Download (26.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount0 Recruiting Basic Science Chronic Prostatitis With Chronic Pelvic Pain Syndrome 1 1 Completed Not Available Healthy Volunteers 4 1 Completed Not Available Rhinitis, Allergic, Perennial and Seasonal 1 1 Completed Basic Science Allergies 1 1 Completed Other Allergies 1 1 Completed Prevention Skin Inflammation 1 1 Completed Treatment Acute Urticaria 1 1 Completed Treatment Allergies 2 1 Completed Treatment Healthy Volunteers 3 1 Not Yet Recruiting Other Allergies 1 1 Terminated Basic Science Migraine 1 1, 2 Completed Treatment Neuromyelitis Optica 1 2 Completed Treatment Allergic Rhinitis (AR) 2 2 Completed Treatment Allergic Rhinitis (AR) / Rhinitis, Allergic, Seasonal 1 2 Completed Treatment Allergic / Rhinitis / Rhinitis, Allergic, Seasonal / Seasonal 1 2 Completed Treatment Rhinitis, Allergic, Seasonal 1 2 Completed Treatment Seasonal Allergic Rhinitis (SAR) 4 3 Completed Not Available Allergic Rhinitis (AR) 2 3 Completed Treatment Atopic Dermatitis (AD) 1 3 Completed Treatment Dermatitis, Eczematous / Skin Inflammation 1 3 Completed Treatment Perennial Allergic Rhinitis (PAR) 2 3 Completed Treatment Perennial Allergic Rhinitis (PAR) / Rhinitis, Allergic, Perennial 1 3 Completed Treatment Pruritus 1 3 Completed Treatment Rhinitis, Allergic, Perennial 3 3 Completed Treatment Seasonal Allergic Rhinitis (SAR) 2 3 Terminated Treatment Pemphigus 1 4 Completed Not Available Allergies 2 4 Completed Not Available Perennial Allergic Rhinitis (PAR) / Seasonal Allergic Rhinitis (SAR) 3 4 Completed Diagnostic Asthma Bronchial 1 4 Completed Other Allergic Rhinitis (AR) 1 4 Completed Treatment Allergic Rhinitis (AR) 1 4 Completed Treatment Allergic Rhinitis (AR) / Asthma Bronchial 1 4 Completed Treatment Allergic Rhinitis (AR) / Pollen Allergy / Rhinitis, Allergic, Seasonal / Severe Acute Respiratory Syndrome 1 4 Completed Treatment Diabetic Neuropathy, Painful / Pain, Neuropathic / Type 2 Diabetes Mellitus 1 4 Completed Treatment Disseminated Sclerosis 1 4 Completed Treatment Relapsing Remitting Multiple Sclerosis (RRMS) 1 4 Completed Treatment Rhinitis, Allergic, Perennial and Seasonal 1 4 Completed Treatment Urticarias 2 4 Recruiting Basic Science Exercise Intolerance at Altitude 1 4 Recruiting Treatment Allergic Rhinitis (AR) / Asthma Bronchial 1 4 Terminated Treatment Pruritus 1 4 Terminated Treatment Urticarias 1 4 Unknown Status Treatment Seasonal Allergic Rhinitis (SAR) 1 Not Available Completed Not Available Cognition / Driving Ability / Seasonal Allergic Rhinitis (SAR) 1 Not Available Completed Not Available Healthy Volunteers 2 Not Available Completed Not Available Seasonal Allergic Rhinitis (SAR) / Sinusitis 1 Not Available Completed Treatment Actinic Keratosis (AK) 1 Not Available Completed Treatment Seasonal Allergic Rhinitis (SAR) 2

Pharmacoeconomics

Manufacturers
  • Banner pharmacaps inc
  • Actavis mid atlantic llc
  • Amneal pharmaceuticals
  • Apotex inc
  • Aurobindo pharma ltd
  • Cypress pharmaceutical inc
  • Dr reddys laboratories ltd
  • Perrigo israel pharmaceuticals ltd
  • Ranbaxy laboratories ltd
  • Sun pharmaceutical industries inc
  • Taro pharmaceutical industries ltd
  • Teva pharmaceuticals usa
  • Vintage pharmaceuticals llc
  • Wockhardt ltd
  • Perrigo r and d co
  • Mcneil consumer healthcare div mcneil ppc inc
  • Caraco pharmaceutical laboratories ltd
  • Sandoz inc
  • Pfizer inc
  • Actavis elizabeth llc
  • Amneal pharmaceuticals ny llc
  • Cadista pharmaceuticals inc
  • Contract pharmacal corp
  • Mylan pharmaceuticals inc
  • Orchid healthcare
  • Torrent pharmaceuticals llc
  • Unichem laboratories ltd
  • Unique pharmaceutical laboratories
Packagers
  • Actavis Group
  • Advanced Pharmaceutical Services Inc.
  • Apotex Inc.
  • Apotheca Inc.
  • AQ Pharmaceuticals Inc.
  • Atlantic Biologicals Corporation
  • Aurobindo Pharma Ltd.
  • Bryant Ranch Prepack
  • Caraco Pharmaceutical Labs
  • Cardinal Health
  • CVS Pharmacy
  • Cypress Pharmaceutical Inc.
  • Direct Dispensing Inc.
  • Direct Pharmaceuticals Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • EZ-EM Inc.
  • H.J. Harkins Co. Inc.
  • J.B. Chemicals & Pharmaceuticals
  • Kaiser Foundation Hospital
  • L Perrigo Co.
  • Lake Erie Medical and Surgical Supply
  • McNeil Laboratories
  • Medvantx Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Ohm Laboratories Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Perrigo Co.
  • Pfizer Inc.
  • Pharmacy Service Center
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Qualitest
  • Ranbaxy Laboratories
  • Redpharm Drug
  • Resource Optimization and Innovation LLC
  • Sandoz
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • US Pharmaceutical Group
  • Vangard Labs Inc.
  • Warner Chilcott Co. Inc.
  • Wockhardt Ltd.
Dosage forms
FormRouteStrengthCapsule Oral 10 mg/1 Tablet Oral 10 mg Tablet Oral 5 mg Syrup Oral 1 mg/1 Tablet Oral 10.0 mg/1 Tablet Oral 20 mg Tablet, film coated, extended release Oral Capsule, liquid filled Oral 10 mg/1 Solution Oral 1 mg/1mL Solution Oral 5 mg/5mL Syrup Oral 1 mg/1mL Syrup Oral 5 mg/5mL Tablet Oral 10 mg/1 Tablet Oral 5 mg/1 Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 5 mg/1 Liquid Oral 5 mg/5mL Suspension Oral 1 mg/1mL Tablet, orally disintegrating Oral 10 mg/1 Tablet, coated Oral 10 mg/1 Tablet, extended release Oral Syrup Oral Tablet Oral Capsule Oral Tablet, chewable Oral Tablet, orally disintegrating Oral Solution / drops Ophthalmic 2.4 mg/1mL Tablet, chewable Oral 10 mg/1 Tablet, chewable Oral 5 mg/1 Tablet, multilayer, extended release Oral
Prices
Unit descriptionCostUnitCetirizine HCl 100 10 mg tablet Bottle 259.71USD bottle Cetirizine HCl 100 5 mg tablet Bottle 259.71USD bottle Zyrtec 10 mg tablet 2.66USD tablet Zyrtec 5 mg tablet 2.66USD tablet Zyrtec itchy eye 0.025% drops 2.62USD ml Cetirizine hcl 5 mg chew tablet 2.5USD tablet Cetirizine hcl 10 mg tablet 2.49USD tablet Cetirizine hcl 5 mg tablet 2.49USD tablet Zyrtec-d tablet 1.33USD tablet Child's zyrtec chew tablet 0.9USD tablet CVS Pharmacy allergy relief 10 mg tablet 0.74USD each DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated) Unlock Additional DataUS6469009 No 2002-10-22 2019-07-13 US US7226614 No 2007-06-05 2022-06-10 US US6489329 No 2002-12-03 2016-04-08 US US7014867 No 2006-03-21 2022-06-10 US US6455533 No 2002-09-24 2018-07-02 US US9254286 Yes 2016-02-09 2033-01-09 US US8829005 Yes 2014-09-09 2030-09-15 US US9750684 No 2017-09-05 2030-03-15 US US9993471 No 2018-06-12 2030-03-15 US Additional Data Available
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Properties

State
Solid
Experimental Properties
PropertyValueSourcemelting point (°C) 110-115°C https://www.chemicalbook.com/ChemicalProductProperty_US_CB3440625.aspx boiling point (°C) 542.1 °C at 760 mmHg https://www.lookchem.com/Cetirizine-hydrochloride/ water solubility 101 mg/L https://www.chemicalbook.com/ChemicalProductProperty_US_CB3440625.aspx logP 2.8 http://www.t3db.ca/toxins/T3D2756 Caco2 permeability 1.14 https://core.ac.uk/download/pdf/76975249.pdf pKa 1.52, 2.92 and 8.27 https://www.researchgate.net/publication/42768947_Isolation_and_Characterization_of_Cetirizine_Degradation_Product_Mechanism_of_Cetirizine_Oxidation
Predicted Properties
PropertyValueSourceWater Solubility 0.0658 mg/mL ALOGPS logP 2.98 ALOGPS logP 0.86 ChemAxon logS -3.8 ALOGPS pKa (Strongest Acidic) 3.6 ChemAxon pKa (Strongest Basic) 7.79 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 53.01 Å2 ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 106.87 m3·mol-1 ChemAxon Polarizability 41.88 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon
Predicted ADMET features
PropertyValueProbabilityHuman Intestinal Absorption + 0.6863 Blood Brain Barrier + 0.7576 Caco-2 permeable - 0.5879 P-glycoprotein substrate Substrate 0.7862 P-glycoprotein inhibitor I Inhibitor 0.7364 P-glycoprotein inhibitor II Non-inhibitor 0.7624 Renal organic cation transporter Non-inhibitor 0.5232 CYP450 2C9 substrate Non-substrate 0.8408 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.7 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.8885 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9465 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6917 Ames test Non AMES toxic 0.7815 Carcinogenicity Non-carcinogens 0.9426 Biodegradation Not ready biodegradable 0.9974 Rat acute toxicity 2.6841 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.866 hERG inhibition (predictor II) Inhibitor 0.6517 ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash KeyPredicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-ITFT , negative LC-MS/MS splash10-000j-0900000000-9801bb859e79fa9922aa LC-MS/MS Spectrum - LC-ESI-ITFT , negative LC-MS/MS splash10-000i-0009000000-014b559d56b0f32984ff LC-MS/MS Spectrum - LC-ESI-ITFT , negative LC-MS/MS splash10-000i-0009000000-213bd47e17d5ab69ad4b LC-MS/MS Spectrum - LC-ESI-ITFT , negative LC-MS/MS splash10-004r-9006000000-f496e22c8e0e293fe98c LC-MS/MS Spectrum - LC-ESI-ITFT , negative LC-MS/MS splash10-000i-0009000000-d8a55ab1a7aff0580a91 LC-MS/MS Spectrum - LC-ESI-ITFT , negative LC-MS/MS splash10-000i-0009000000-d8a55ab1a7aff0580a91 LC-MS/MS Spectrum - LC-ESI-ITFT , negative LC-MS/MS splash10-000i-0009000000-dc957bb6f947575ae4fa LC-MS/MS Spectrum - LC-ESI-ITFT , negative LC-MS/MS splash10-000b-0900000000-48fc0581ff9fff15e16d LC-MS/MS Spectrum - LC-ESI-ITFT , negative LC-MS/MS splash10-000i-0009000000-04ca95fadd952d0aaeb8 LC-MS/MS Spectrum - LC-ESI-ITFT , negative LC-MS/MS splash10-000i-0009000000-014b559d56b0f32984ff LC-MS/MS Spectrum - LC-ESI-ITFT , negative LC-MS/MS splash10-0006-0009000000-26a7769df28c2325ec53 LC-MS/MS Spectrum - LC-ESI-ITFT , negative LC-MS/MS splash10-0006-0009000000-284c2e7b25733d7c9875 LC-MS/MS Spectrum - LC-ESI-QFT , negative LC-MS/MS splash10-000i-0009000000-04befed283d691217ba2 LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0udi-0190000000-14715ff4d57580fbb166 LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0f79-0069000000-431df9c3533b77cf08bc LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0udi-0090000000-e042b67e2048318e7dbd LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0udi-0190000000-b0dfb67717c01fd0c0b9 LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0gb9-0970000000-e2810b242fefb4a419e7 LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-014i-0900000000-72f7cddc4ff6d45f98c0 LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-014i-0900000000-d6044767562f707c8061 LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0f79-0059000000-15be2621a731a6c2b0ea LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0udi-0090000000-01f33b4e54bcb6c8720c LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0udi-0190000000-f28111ea9c76c1bd27dd LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0gb9-0970000000-673301f54b883df73a2a LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-014i-0900000000-81ab05c275bd28fa3dfb LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-014i-0900000000-82d8eb507c79b7342917 LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0udi-0190000000-0f667566feb3af808386 LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0uxr-0690000000-0d4336539c5ebe9050c8 LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-014i-0900000000-1638816057d01db5eaa1 LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0udi-0190000000-de2feb9a65604f442606 LC-MS/MS Spectrum - LC-ESI-ITFT , positive LC-MS/MS splash10-0udi-0190000000-58d302681ca058e5706c MS/MS Spectrum - , positive LC-MS/MS splash10-0udi-0391000000-7af5014f07bed862bba6 LC-MS/MS Spectrum - LC-ESI-QFT , positive LC-MS/MS splash10-0udi-0491000000-ac48bba9129fe5016c4b

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 / Amino acids / Monocarboxylic acids and derivatives / Dialkyl ethers / Carboxylic acids / Azacyclic compoundsOrganopnictogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Diphenylmethane / Chlorobenzene / Halobenzene / N-alkylpiperazine / Aralkylamine / Aryl halide / 1,4-diazinane / Aryl chloride / Piperazine / Amino acidAmino acid or derivatives / Tertiary amine / Tertiary aliphatic amine / Organoheterocyclic compound / Carboxylic acid derivative / Carboxylic acid / Dialkyl ether / Monocarboxylic acid or derivatives / Azacycle / Ether / Organic oxygen compound / Organic nitrogen compound / Organopnictogen compound / Organohalogen compound / Amine / Organochloride / Organonitrogen compound / Carbonyl group / Hydrocarbon derivative / Organooxygen compound / Organic oxide / Aromatic heteromonocyclic compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
monocarboxylic acid, ether, monochlorobenzenes, piperazines (CHEBI:3561)

Targets

Binding Properties
PropertyMeasurementpHTemperature (°C)ReferencesKi (nM) 100 N/A N/A 8903934 Ki (nM) 14 N/A N/A 15081022 / 15482930 / 16220969 Ki (nM) 3.16 N/A N/A 8903934 / 11809864 Ki (nM) 5.89 N/A N/A 15686917 Ki (nM) 50 N/A N/A 15771458 Ki (nM) 50.12 N/A N/A 16408006 Ki (nM) 79.43 N/A N/A 11809864 Details1. Histamine H1 receptor
Kind
Protein
Organism
Humans
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. Christophe B, Carlier B, Gillard M, Chatelain P, Peck M, Massingham R: Histamine H1 receptor antagonism by cetirizine in isolated guinea pig tissues: influence of receptor reserve and dissociation kinetics. Eur J Pharmacol. 2003 May 30;470(1-2):87-94. [PubMed:12787835]
  2. Tashiro M, Sakurada Y, Iwabuchi K, Mochizuki H, Kato M, Aoki M, Funaki Y, Itoh M, Iwata R, Wong DF, Yanai K: Central effects of fexofenadine and cetirizine: measurement of psychomotor performance, subjective sleepiness, and brain histamine H1-receptor occupancy using 11C-doxepin positron emission tomography. J Clin Pharmacol. 2004 Aug;44(8):890-900. [PubMed:15286093]
  3. Tillement JP, Testa B, Bree F: Compared pharmacological characteristics in humans of racemic cetirizine and levocetirizine, two histamine H1-receptor antagonists. Biochem Pharmacol. 2003 Oct 1;66(7):1123-6. [PubMed:14505791]
  4. Cavero I, Mestre M, Guillon JM, Heuillet E, Roach AG: Preclinical in vitro cardiac electrophysiology: a method of predicting arrhythmogenic potential of antihistamines in humans? Drug Saf. 1999;21 Suppl 1:19-31; discussion 81-7. [PubMed:10597865]
  5. Tamura T, Masaki S, Ohmori K, Karasawa A: Effect of olopatadine and other histamine H1 receptor antagonists on the skin inflammation induced by repeated topical application of oxazolone in mice. Pharmacology. 2005 Dec;75(1):45-52. Epub 2005 Jun 7. [PubMed:15942272]
  6. Portnoy JM, Dinakar C: Review of cetirizine hydrochloride for the treatment of allergic disorders. Expert Opin Pharmacother. 2004 Jan;5(1):125-35. doi: 10.1517/14656566.5.1.125 . [PubMed:14680442]
  7. Zhang L, Cheng L, Hong J: The clinical use of cetirizine in the treatment of allergic rhinitis. Pharmacology. 2013;92(1-2):14-25. doi: 10.1159/000351843. Epub 2013 Jul 18. [PubMed:23867423]
  8. Cetirizine FDA label [File]

Transporters

Details1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate Inhibitor
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. Mesgari Abbasi M, Valizadeh H, Hamishekar H, Mohammadnejad L, Zakeri-Milani P: The Effects of Cetirizine on P-glycoprotein Expression and Function In vitro and In situ. Adv Pharm Bull. 2016 Mar;6(1):111-8. doi: 10.15171/apb.2016.017. Epub 2016 Mar 17. [PubMed:27123426]
  2. Polli JW, Baughman TM, Humphreys JE, Jordan KH, Mote AL, Salisbury JA, Tippin TK, Serabjit-Singh CJ: P-glycoprotein influences the brain concentrations of cetirizine (Zyrtec), a second-generation non-sedating antihistamine. J Pharm Sci. 2003 Oct;92(10):2082-9. doi: 10.1002/jps.10453. [PubMed:14502547]
  3. Conen S, Theunissen EL, Vermeeren A, van Ruitenbeek P, Stiers P, Mehta MA, Toennes SW, Ramaekers JG: The role of P-glycoprotein in CNS antihistamine effects. Psychopharmacology (Berl). 2013 Sep;229(1):9-19. doi: 10.1007/s00213-013-3075-z. Epub 2013 Apr 7. [PubMed:23564211]
  4. Obradovic T, Dobson GG, Shingaki T, Kungu T, Hidalgo IJ: Assessment of the first and second generation antihistamines brain penetration and role of P-glycoprotein. Pharm Res. 2007 Feb;24(2):318-27. doi: 10.1007/s11095-006-9149-4. Epub 2006 Dec 19. [PubMed:17180728]
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Drug created on June 13, 2005 07:24 / Updated on October 17, 2019 21:19

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