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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
SaltsNot Available
Brand names
NameCompany
AlerlisinNot Available
CetrynNot Available
FormistinNot Available
HitrizinNot Available
ReactineJohnson & Johnson Inc.
VirlixNot Available
ZirtekNot Available
ZyrlexNot Available
ZyrtecMcNEIL-PPC, Inc.
Brand mixtures
Brand NameIngredients
Zyrtec-DCetirizine + pseudoephedrine hydrochloride
Categories
CAS number83881-51-0
WeightAverage: 388.888
Monoisotopic: 388.155370383
Chemical FormulaC21H25ClN2O3
InChI KeyInChIKey=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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassDiphenylmethanes
Direct parentDiphenylmethanes
Alternative parentsChlorobenzenes; Aryl Chlorides; Piperazines; Diazinanes; Tertiary Amines; Enolates; Ethers; Carboxylic Acids; Polyamines; Organochlorides
Substituentschlorobenzene; aryl halide; 1,4-diazinane; piperazine; aryl chloride; tertiary amine; polyamine; carboxylic acid derivative; carboxylic acid; enolate; ether; organohalogen; amine; organonitrogen compound; organochloride
Classification descriptionThis compound belongs to the diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
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
Metabolism
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
Property Value Probability
Human 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 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Non-inhibitor 0.8885
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate 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
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
SyrupOral
TabletOral
Prices
Unit descriptionCostUnit
Cetirizine HCl 100 10 mg tablet Bottle259.71USDbottle
Cetirizine HCl 100 5 mg tablet Bottle259.71USDbottle
Zyrtec 10 mg tablet2.66USDtablet
Zyrtec 5 mg tablet2.66USDtablet
Zyrtec itchy eye 0.025% drops2.62USDml
Cetirizine hcl 5 mg chew tablet2.5USDtablet
Cetirizine hcl 10 mg tablet2.49USDtablet
Cetirizine hcl 5 mg tablet2.49USDtablet
Zyrtec-d tablet1.33USDtablet
Child's zyrtec chew tablet0.9USDtablet
CVS Pharmacy allergy relief 10 mg tablet0.74USDeach
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 solubility6.58e-02 g/lALOGPS
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 area53.01ChemAxon
rotatable bond count8ChemAxon
refractivity106.87ChemAxon
polarizability41.88ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
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
ResourceLink
KEGG CompoundC07778
PubChem Compound2678
PubChem Substance46508368
ChemSpider2577
BindingDB22890
ChEBI3561
ChEMBLCHEMBL1000
Therapeutic Targets DatabaseDAP000323
PharmGKBPA448905
IUPHAR1222
Guide to Pharmacology1222
Drug Product Database2240910
RxListhttp://www.rxlist.com/cgi/generic/cetiriz.htm
Drugs.comhttp://www.drugs.com/cetirizine-hcl.html
WikipediaCetirizine
ATC CodesR06AE07R06AE09
AHFS Codes
  • 04:08.00
PDB EntriesNot Available
FDA labelshow(54.2 KB)
MSDSNot Available
Interactions
Drug InteractionsSearched, but no interactions found.
Food InteractionsNot Available

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

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