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Identification
NameCetirizine
Accession NumberDB00341  (APRD00630)
TypeSmall Molecule
GroupsApproved
Description

A potent second-generation histamine H1 antagonist that is effective in the treatment of allergic rhinitis, chronic urticaria, and pollen-induced asthma. Unlike many traditional antihistamines, it does not cause drowsiness or anticholinergic side effects. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
CetirizinGermanNot Available
CetirizinaSpanishINN
CetirizinumLatinINN
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cetirizine Hydrochloridesolution5 mg/5mLoralAmneal Pharmaceuticals2009-10-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cetirizine Hydrochloridetablet10 mgoralRugby Laboratories Inc2012-03-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cetirizinetablet10 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-12-27Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cetirizine Hydrochloridetablet, film coated10 mgoralNorthstar Rx LLC2009-10-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cetirizineliquid5 mg/5mLoralRebel Distributors Corp2008-06-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cetirizine Hydrochloridetablet10 mgoralShopko Stores Operating Co., LLC2007-12-27Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Leader All Day Allergytablet10 mgoralCardinal Health2007-12-27Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyrtectablet, film coated10 mgoralMc Neil Consumer Healthcare Division Of Mc Neil Ppc, Inc.2008-10-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyrtectablet, orally disintegrating10 mgoralMc Neil Consumer Healthcare Div. Mc Neil Ppc, Inc2014-01-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Zyrteccapsule, liquid filled10 mgoralMc Neil Consumer Healthcare Div Mc Neil Ppc, Inc2010-02-08Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cetirizinetablet10 mgoralbryant ranch prepack2008-01-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Kirklands Childrens Aller Tecliquid5 mg/5mLoralCostco Wholesale Company2009-08-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cetirizine Hydrochloridesolution5 mg/5mLoralAmneal Pharmaceuticals2009-10-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cetirizine Hydrochloridesolution5 mg/5mLoralAmneal Pharmaceuticals2009-10-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cetirizine Hydrochloridetablet5 mgoralAmneal Pharmaceuticals2010-01-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cetirizine Hydrochloridetablet10 mgoralAmneal Pharmaceuticals2010-01-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cetirizine Hydrochloride Hives Relieftablet5 mgoralAmneal Pharmaceuticals2010-01-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cetirizine Hydrochloride Hives Relieftablet10 mgoralAmneal Pharmaceuticals2010-01-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Cetirizinetablet10 mgoralLife Line Home Care Services, Inc.2012-02-03Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
International Brands
NameCompany
AlerlisinNot Available
CetrynNot Available
FormistinNot Available
HitrizinNot Available
ReactineJohnson & Johnson Inc.
VirlixNot Available
ZirtekNot Available
ZyrlexNot Available
Brand mixtures
Brand NameIngredients
Zyrtec-DCetirizine + pseudoephedrine hydrochloride
SaltsNot Available
Categories
CAS number83881-51-0
WeightAverage: 388.888
Monoisotopic: 388.155370383
Chemical FormulaC21H25ClN2O3
InChI KeyZKLPARSLTMPFCP-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Aralkylamine
  • N-alkylpiperazine
  • Halobenzene
  • Chlorobenzene
  • Piperazine
  • 1,4-diazinane
  • Aryl halide
  • Aryl chloride
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the relief of symptoms associated with seasonal allergic rhinitis, perennial allergic rhinitis and the treatment of the uncomplicated skin manifestations of chronic idiopathic urticaria
PharmacodynamicsCetirizine, the active metabolite of the piperazine H1-receptor antagonist hydroxyzine, is used to treat chronic idiopathic urticaria, perennial allergic rhinitis, seasonal allergic rhinitis, allergic asthma, physical urticaria, and atopic dermatitis.
Mechanism of actionCetirizine competes with histamine for binding at H1-receptor sites on the effector cell surface, resulting in suppression of histaminic edema, flare, and pruritus. The low incidence of sedation can be attributed to reduced penetration of cetirizine into the CNS as a result of the less lipophilic carboxyl group on the ethylamine side chain.
Absorptionmean peak plasma concentration (Cmax) of 114 ng/mL at a time (Tmax) of 2.2 hours postdose was observed for cetirizine
Volume of distributionNot Available
Protein bindingVery high (93%) plasma protein binding
MetabolismNot Available
Route of eliminationNot Available
Half life8.3 hours
Clearance
  • 53 mL/min [healthy]
ToxicitySomnolence (sleepiness or unusual drowsiness), restlessness, irritability
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6863
Blood Brain Barrier+0.7576
Caco-2 permeable-0.5879
P-glycoprotein substrateSubstrate0.7862
P-glycoprotein inhibitor IInhibitor0.7364
P-glycoprotein inhibitor IINon-inhibitor0.7624
Renal organic cation transporterNon-inhibitor0.5232
CYP450 2C9 substrateNon-substrate0.8408
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.907
CYP450 2D6 substrateNon-inhibitor0.8885
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.9465
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6917
Ames testNon AMES toxic0.7815
CarcinogenicityNon-carcinogens0.9426
BiodegradationNot ready biodegradable0.9974
Rat acute toxicity2.6841 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.866
hERG inhibition (predictor II)Inhibitor0.6517
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
Dosage forms
FormRouteStrength
Capsule, liquid filledoral10 mg
Liquidoral5 mg/5mL
Solutionoral5 mg/5mL
Tabletoral10 mg
Tabletoral5 mg
Tablet, film coatedoral10 mg
Tablet, orally disintegratingoral10 mg
Prices
Unit descriptionCostUnit
Cetirizine HCl 100 10 mg tablet Bottle259.71USD bottle
Cetirizine HCl 100 5 mg tablet Bottle259.71USD bottle
Zyrtec 10 mg tablet2.66USD tablet
Zyrtec 5 mg tablet2.66USD tablet
Zyrtec itchy eye 0.025% drops2.62USD ml
Cetirizine hcl 5 mg chew tablet2.5USD tablet
Cetirizine hcl 10 mg tablet2.49USD tablet
Cetirizine hcl 5 mg tablet2.49USD tablet
Zyrtec-d tablet1.33USD tablet
Child's zyrtec chew tablet0.9USD tablet
CVS Pharmacy allergy relief 10 mg tablet0.74USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States64555331998-07-022018-07-02
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point112.5 °CPhysProp
water solubility101 mg/LNot Available
logP2.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0658 mg/mLALOGPS
logP2.98ALOGPS
logP0.86ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
pKa (Strongest Basic)7.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.01 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity106.87 m3·mol-1ChemAxon
Polarizability41.88 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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 ReferenceNot Available
External Links
ATC CodesR06AE07
AHFS Codes
  • 04:08.00
PDB EntriesNot Available
FDA labelDownload (54.2 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AclidiniumMay enhance the anticholinergic effect of Anticholinergic Agents.
AmphetamineMay diminish the sedative effect of Antihistamines.
Benzylpenicilloyl PolylysineAntihistamines may diminish the diagnostic effect of Benzylpenicilloyl Polylysine.
BetahistineAntihistamines may diminish the therapeutic effect of Betahistine.
BuprenorphineCNS Depressants may enhance the CNS depressant effect of Buprenorphine.
CathinoneMay diminish the sedative effect of Antihistamines.
DoxylamineMay enhance the CNS depressant effect of CNS Depressants.
DronabinolMay enhance the CNS depressant effect of CNS Depressants.
DroperidolMay enhance the CNS depressant effect of CNS Depressants.
HyaluronidaseAntihistamines may diminish the therapeutic effect of Hyaluronidase.
HydrocodoneCNS Depressants may enhance the CNS depressant effect of Hydrocodone.
HydroxyzineMay enhance the CNS depressant effect of CNS Depressants.
ItoprideAnticholinergic Agents may diminish the therapeutic effect of Itopride.
Magnesium SulfateMay enhance the CNS depressant effect of CNS Depressants.
MethotrimeprazineCNS Depressants may enhance the CNS depressant effect of Methotrimeprazine. Methotrimeprazine may enhance the CNS depressant effect of CNS Depressants.
MetoclopramideAnticholinergic Agents may diminish the therapeutic effect of Metoclopramide.
MetyrosineCNS Depressants may enhance the sedative effect of Metyrosine.
MianserinMay enhance the anticholinergic effect of Anticholinergic Agents.
MirabegronAnticholinergic Agents may enhance the adverse/toxic effect of Mirabegron.
MirtazapineCNS Depressants may enhance the CNS depressant effect of Mirtazapine.
NabiloneMay enhance the CNS depressant effect of CNS Depressants.
OrphenadrineCNS Depressants may enhance the CNS depressant effect of Orphenadrine.
PerampanelMay enhance the CNS depressant effect of CNS Depressants.
Potassium ChlorideAnticholinergic Agents may enhance the ulcerogenic effect of Potassium Chloride.
PramipexoleCNS Depressants may enhance the sedative effect of Pramipexole.
PramlintideMay enhance the anticholinergic effect of Anticholinergic Agents. These effects are specific to the GI tract.
RopiniroleCNS Depressants may enhance the sedative effect of ROPINIRole.
RotigotineCNS Depressants may enhance the sedative effect of Rotigotine.
RufinamideMay enhance the adverse/toxic effect of CNS Depressants. Specifically, sleepiness and dizziness may be enhanced.
SecretinAnticholinergic Agents may diminish the therapeutic effect of Secretin.
SuvorexantCNS Depressants may enhance the CNS depressant effect of Suvorexant.
TapentadolMay enhance the CNS depressant effect of CNS Depressants.
ThalidomideCNS Depressants may enhance the CNS depressant effect of Thalidomide.
TiotropiumAnticholinergic Agents may enhance the anticholinergic effect of Tiotropium.
TopiramateAnticholinergic Agents may enhance the adverse/toxic effect of Topiramate.
ZolpidemCNS Depressants may enhance the CNS depressant effect of Zolpidem.
Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.

Targets

1. Histamine H1 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H1 receptor P35367 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:09