General
Preferred name
CETIRIZINE
Synonyms
CETIRIZINE HYDROCHLORIDE ()
CETIRIZINE DIHYDROCHLORIDE ()
Cetirizine HCl ()
Cetirocol ()
Piriteze ()
Zyrtec ()
Allertek ()
Ziralton ()
Becoallergy ()
P-071 ()
Allacan ()
Cetec ()
Pollenshield ()
Zynor ()
Zirtek ()
LEVOCETIRIZINE ()
Cetirizine (D8 dihydrochloride) ()
Cetirizine (D4 dihydrochloride) ()
P071 ()
Cetirizine DiHCl ()
UCB P071 ()
OX-NLA ()
Cetirizine (dihydrochloride) ()
Cetirizine83881-51-0 ()
Zyrtec, Reactine,UCB P071 ()
Children's zyrtec hives relief ()
Cetirizine hydrochloride hives ()
Quzyttir ()
Children's cetirizine hydrochloride hives relief ()
Cetirizine dihydrochloride ()
Zerviate ()
Cetirizine ()
Cetirizine hydrochloride hives relief ()
Children's zyrtec allergy ()
Children's cetirizine hydrochloride allergy ()
Cetrine ()
NSC-759102 ()
Zyrtec allergy ()
P 071 ()
Zyrtec hives relief ()
Cetirizine hydrochloride allergy ()
Cetiderm ()
AC-170 ()
Cetirizine (hydrochloride) ()
Cetirizine-d8 (hydrochloride) ()
P&D ID
PD003052
CAS
83881-51-0
83881-52-1
2070015-04-0
Tags
natural product
drug
available
Approved by
FDA
First approval
1995
Drug Status
approved
Drug indication
Allergic rhinitis
Antihistaminic
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION The approved drug cetirizine is a racemic mixture of two enantiomers, and , each of which are listed on Guide to PHARMACOLOGY with activity data. The structure shown here does not specify stereochemistry and represents the mixture.
HALF-LIFE Plasma elimination half-life is 8.3 hours [FDA label].
ROE Mainly eliminated in the urine [FDA label], [A175051]. Between 70 – 85% of an orally administered dose can be found in the urine and 10 – 13% in the feces [A175051].
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 [FDA label]. **Effects on urticaria/anti-inflammatory effects** It has anti-inflammatory properties that may play a role in asthma management [A175051]. 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 [A175051]. Concomitant use of cetirizine reduces the duration and dose of topical anti-inflammatory formulas used for the treatment of atopic dermatitis [A175051].
MOA 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 [FDA label].
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 [FDA 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 [FDA 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 [FDA 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 [A175051]. 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 [FDA label].
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 [FDA 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 [FDA 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 [FDA label].
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 [FDA label]. ; ; **Effects on urticaria/anti-inflammatory effects**; ; It has anti-inflammatory properties that may play a role in asthma management [A175051]. 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 [A175051]. Concomitant use of cetirizine reduces the duration and dose of topical anti-inflammatory formulas used for the treatment of atopic dermatitis [A175051].
ROE Mainly eliminated in the urine [FDA label], [A175051]. ; ; Between 70 – 85% of an orally administered dose can be found in the urine and 10 – 13% in the feces [A175051].
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 [FDA 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 [FDA 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 [FDA label].
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 [FDA 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 [FDA 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 [FDA label].
DESCRIPTION Cetirizine( hydrochloride) is an orally active and selective histamine H1 receptor antagonist. The approved drug is a racemic mixture of two enantiomers, and , each of which are listed on Guide to PHARMACOLOGY with activity data. The structure shown here does not specify stereochemistry and represents the mixture. (GtoPdb)
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 [FDA 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 [FDA 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) [FDA 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 [FDA 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 [FDA 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 [FDA 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 [FDA 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) [FDA 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 [FDA 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 [FDA 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 [A175051]. ; ; 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 [FDA label].
DESCRIPTION Orally active, non-sedating, and selective H1 histamine receptor antagonist; antihistamine;. (LOPAC library)
DESCRIPTION Selective H1 antagonist (Tocriscreen Total)
DESCRIPTION High affinity and potent 5-HT2A agonist (Tocris Bioactive Compound Library)
Cell lines
0
Organisms
3
Compound Sets
34
AdooQ Bioactive Compound Library
A15041
Axon Medchem Screening Library
3373
Cayman Chemical Bioactives
19686
26445
ChEMBL Approved Drugs
CHEMBL1607273
CHEMBL1000
ChEMBL Drugs
CHEMBL1607273
CHEMBL1000
Concise Guide to Pharmacology 2017/18
1222
Concise Guide to Pharmacology 2019/20
1222
Concise Guide to Pharmacology 2021/22
1222
Concise Guide to Pharmacology 2023/24
1222
DrugBank
DB00341
DrugBank Approved Drugs
DB00341
DrugCentral
581
DrugCentral Approved Drugs
581
DrugMAP
DMPEHBJ
DMOMP9U
DrugMAP Approved Drugs
DMOMP9U
DrugMatrix
Enamine BioReference Compounds
Guide to Pharmacology
1222
Ki Database
Cetirizine
Levocetirizine
LOPAC library
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL1000
MedChem Express Bioactive Compound Library
HY-17042A
HY-17042
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
YO7261ME24
NIH Clinical Collections (NCC)
NPC Screening Collection
Other bioactive compounds
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Cetirizine-Dihydrochloride
TargetMol Bioactive Compound Library
T0089
The Spectrum Collection
Tocris Bioactive Compound Library
2577
Tocriscreen Total
External IDs
79
Properties
(calculated by RDKit )
Molecular Weight
388.16
Hydrogen Bond Acceptors
4
Hydrogen Bond Donors
1
Rotatable Bonds
8
Ring Count
3
Aromatic Ring Count
2
cLogP
3.15
TPSA
53.01
Fraction CSP3
0.38
Chiral centers
1.0
Largest ring
6.0
QED
0.7
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Selectivity
H1
Target
Histamine Receptor
H1 receptor
H1 antagonist
Pathway
Immunology/Inflammation
GPCR/G protein
Neuronal Signaling
Neuroscience
Primary Target
Histamine H1 Receptors
MOA
Histamine Receptor antagonist
Antagonist
Therapeutic Indication
Antihistamine
Therapeutic Class
Respiratory
Antiallergic Agents
Source data