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Identification
Name Cetirizine
Accession Number DB00341 (APRD00630)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Cetirizina [Spanish]
  • Cetirizinum [Latin]
  • Cetrizine Hcl
Brand names
  • Alerlisin
  • Cetryn
  • Formistin
  • Hitrizin Film Tablet
  • Reactine
  • Setir
  • Virlix
  • Ziptek
  • Zirtek
  • Zyrlex
  • Zyrtec
  • Zyrtec Syrup
  • Zyrtec-D
Brand name mixtures Not Available
Categories
  • Anti-Allergic Agents
  • Antihistamines
  • Histamine H1 Antagonists, Non-Sedating
CAS number 83881-51-0
Weight Average: 388.888
Monoisotopic: 388.155370383
Chemical Formula C21H25ClN2O3
InChI Key InChIKey=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)
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Diphenylmethanes
Substructures
  • Hydroxy Compounds
  • Acetates
  • Short-chain Hydroxy Acids
  • Piperazines
  • Ethers
  • Benzene and Derivatives
  • Aryl Halides
  • Halobenzenes
  • Carboxylic Acids and Derivatives
  • Aliphatic and Aryl Amines
  • Diphenylmethanes
  • Heterocyclic compounds
  • Aromatic compounds
Pharmacology
Indication For the relief of symptoms associated with seasonal allergic rhinitis, perennial allergic rhinitis and the treatment of the uncomplicated skin manifestations of chronic idiopathic urticaria
Pharmacodynamics Cetirizine, 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 action Cetirizine 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.
Absorption mean peak plasma concentration (Cmax) of 114 ng/mL at a time (Tmax) of 2.2 hours postdose was observed for cetirizine
Volume of distribution Not Available
Protein binding Very high (93%) plasma protein binding
Metabolism
Route of elimination Not Available
Half life 8.3 hours
Clearance
  • 53 mL/min [healthy]
Toxicity Somnolence (sleepiness or unusual drowsiness), restlessness, irritability
Affected organisms
  • Humans and other mammals
Pathways Not Available
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
Form Route Strength
Syrup Oral
Tablet Oral
Prices
Unit description Cost Unit
Cetirizine HCl 100 10 mg tablet Bottle 259.71 USD bottle
Cetirizine HCl 100 5 mg tablet Bottle 259.71 USD bottle
Zyrtec 10 mg tablet 2.66 USD tablet
Zyrtec 5 mg tablet 2.66 USD tablet
Zyrtec itchy eye 0.025% drops 2.62 USD ml
Cetirizine hcl 5 mg chew tablet 2.5 USD tablet
Cetirizine hcl 10 mg tablet 2.49 USD tablet
Cetirizine hcl 5 mg tablet 2.49 USD tablet
Zyrtec-d tablet 1.33 USD tablet
Child's zyrtec chew tablet 0.9 USD tablet
CVS Pharmacy allergy relief 10 mg tablet 0.74 USD each
Patents
Country Patent Number Approved Expires
United States 6455533 1998-07-02 2018-07-02
Properties
State solid
Melting point 110-115oC
Experimental Properties
Property Value Source
water solubility 101 mg/L PhysProp
logP 2.8 PhysProp
Predicted Properties
Property Value Source
water solubility 6.58e-02 g/l ALOGPS
logP 2.98 ALOGPS
logP 0.34 ChemAxon Molconvert
logS -3.77 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 5 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 53.01 ChemAxon Molconvert
rotatable bond count 8 ChemAxon Molconvert
refractivity 106.87 ChemAxon Molconvert
polarizability 41.88 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07778 Link_out
PubChem Compound 2678 Link_out
PubChem Substance 46508368 Link_out
ChemSpider 2577 Link_out
BindingDB 22890 Link_out
ChEBI 3561 Link_out
ChEMBL 3561 Link_out
Therapeutic Targets Database DAP000323 Link_out
Drug Product Database 2240910 Link_out
RxList http://www.rxlist.com/cgi/generic/cetiriz.htm Link_out
Drugs.com http://www.drugs.com/cetirizine-hcl.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Cetirizine Link_out
ATC Codes
  • R06AE07
  • R06AE09
AHFS Codes
  • 04:08.00
PDB Entries Not Available
FDA label show (54.2 KB)
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.
Targets

1. Histamine H1 receptor

Pharmacological action: yes
Actions: antagonist

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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system

Organism class: human
UniProt ID: P35367 Link_out
Gene: HRH1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 July 29, 2011 09:35

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.