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Details

Stereochemistry RACEMIC
Molecular Formula C21H25ClN2O3
Molecular Weight 388.888
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CETIRIZINE

SMILES

OC(=O)COCCN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=C(Cl)C=C3

InChI

InChIKey=ZKLPARSLTMPFCP-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C21H25ClN2O3
Molecular Weight 388.888
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/pro/cetirizine.html

Cetirizine, a human metabolite of hydroxyzine, is an antihistamine; its principal effects are mediated via selective inhibition of peripheral H1 receptors. It is indicated for the relief of nasal and non-nasal symptoms associated with seasonal or perennial allergic rhinitis, hay fever and chronic idiopathic urticaria. Commonly reported adverse reactions of cetirizine include headache, dry mouth and drowsiness or fatigue. Pharmacokinetic interaction studies with Cetirizine in adults were conducted with pseudoephedrine, antipyrine, ketoconazole, erythromycin and azithromycin. No interactions were observed.

CNS Activity

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ZYRTEC HIVES RELIEF

Approved Use

Tablets should be administered when both the antihistaminic properties of cetirizine hydrochloride and the nasal decongestant properties of pseudoephedrine hydrochloride are desired.

Launch Date

8.183808E11
Palliative
ZYRTEC HIVES RELIEF

Approved Use

Tablets should be administered when both the antihistaminic properties of cetirizine hydrochloride and the nasal decongestant properties of pseudoephedrine hydrochloride are desired.

Launch Date

8.183808E11
Palliative
ZYRTEC HIVES RELIEF

Approved Use

Uses temporarily relieves these symptoms due to hay fever or other upper respiratory allergies: •runny nose •sneezing •itchy, watery eyes •itching of the nose or throat

Launch Date

8.183808E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
311 ng/mL
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CETIRIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
978.4 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CETIRIZINE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
6375.6 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CETIRIZINE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.3 h
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CETIRIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
6.9 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CETIRIZINE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
7%
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CETIRIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
180 mg single, oral
Overdose
Dose: 180 mg
Route: oral
Route: single
Dose: 180 mg
Sources:
unhealthy, 18 months
n = 1
Health Status: unhealthy
Age Group: 18 months
Sex: M
Population Size: 1
Sources:
270 mg single, oral
Overdose
Dose: 270 mg
Route: oral
Route: single
Dose: 270 mg
Sources:
unhealthy, 18 years
n = 1
Health Status: unhealthy
Age Group: 18 years
Sex: F
Population Size: 1
Sources:
Other AEs: Metabolic acidosis, Hypokalemia...
Other AEs:
Metabolic acidosis (grade 5, 1 patient)
Hypokalemia (grade 5, 1 patient)
Sources:
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 18 years
n = 1
Health Status: unhealthy
Condition: allergic rhinitis
Age Group: 18 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Delusions, Depression...
AEs leading to
discontinuation/dose reduction:
Delusions (1 patient)
Depression (1 patient)
Sources:
2.5 mg 1 times / day multiple, oral
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources:
unhealthy, 23 months
n = 1
Health Status: unhealthy
Condition: chronic rhinitis
Age Group: 23 months
Sex: M
Population Size: 1
Sources:
Disc. AE: Insomnia...
AEs leading to
discontinuation/dose reduction:
Insomnia (1 patient)
Sources:
10 mg single, intravenous
Recommended
unhealthy, 39 years
n = 127
Other AEs: Dyspepsia, Feeling hot...
Other AEs:
Dyspepsia (1%)
Feeling hot (1%)
Dysgeusia (1%)
Headache (1%)
Paresthesia (1%)
Presyncope (1%)
Hyperhidrosis (1%)
Sources:
60 mg single, oral
Overdose
Dose: 60 mg
Route: oral
Route: single
Dose: 60 mg
Sources:
healthy, 4 years
n = 1
Health Status: healthy
Age Group: 4 years
Sex: M
Population Size: 1
Sources:
Other AEs: Drowsiness, Sedation...
Other AEs:
Drowsiness (severe, 1 patient)
Sedation (1 patient)
Sources:
50 mg 1 times / day multiple, oral
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources:
unhealthy, 46 years
n = 1
Health Status: unhealthy
Condition: chronic idiopathic urticaria
Age Group: 46 years
Sex: M
Population Size: 1
Sources:
5 mg 1 times / day multiple, oral
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 6 years
n = 1
Health Status: unhealthy
Condition: allergic rhinitis
Age Group: 6 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Dystonic reaction...
AEs leading to
discontinuation/dose reduction:
Dystonic reaction (1 patient)
Sources:
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources: Page: p. 24
unhealthy, > 12 years
n = 2034
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Population Size: 2034
Sources: Page: p. 24
Other AEs: Somnolence, Fatigue...
Other AEs:
Somnolence (13.7%)
Fatigue (5.9%)
Dry mouth (5%)
Dizziness (2%)
Pharyngitis (2%)
Sources: Page: p. 24
0.24 % 2 times / day multiple, ophthalmic
Recommended
unhealthy, adult
n = 511
Other AEs: Ocular hyperemia, Visual acuity reduced...
AEs

AEs

AESignificanceDosePopulation
Hypokalemia grade 5, 1 patient
270 mg single, oral
Overdose
Dose: 270 mg
Route: oral
Route: single
Dose: 270 mg
Sources:
unhealthy, 18 years
n = 1
Health Status: unhealthy
Age Group: 18 years
Sex: F
Population Size: 1
Sources:
Metabolic acidosis grade 5, 1 patient
270 mg single, oral
Overdose
Dose: 270 mg
Route: oral
Route: single
Dose: 270 mg
Sources:
unhealthy, 18 years
n = 1
Health Status: unhealthy
Age Group: 18 years
Sex: F
Population Size: 1
Sources:
Delusions 1 patient
Disc. AE
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 18 years
n = 1
Health Status: unhealthy
Condition: allergic rhinitis
Age Group: 18 years
Sex: F
Population Size: 1
Sources:
Depression 1 patient
Disc. AE
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 18 years
n = 1
Health Status: unhealthy
Condition: allergic rhinitis
Age Group: 18 years
Sex: F
Population Size: 1
Sources:
Insomnia 1 patient
Disc. AE
2.5 mg 1 times / day multiple, oral
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources:
unhealthy, 23 months
n = 1
Health Status: unhealthy
Condition: chronic rhinitis
Age Group: 23 months
Sex: M
Population Size: 1
Sources:
Dysgeusia 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
n = 127
Dyspepsia 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
n = 127
Feeling hot 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
n = 127
Headache 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
n = 127
Hyperhidrosis 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
n = 127
Paresthesia 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
n = 127
Presyncope 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
n = 127
Sedation 1 patient
60 mg single, oral
Overdose
Dose: 60 mg
Route: oral
Route: single
Dose: 60 mg
Sources:
healthy, 4 years
n = 1
Health Status: healthy
Age Group: 4 years
Sex: M
Population Size: 1
Sources:
Drowsiness severe, 1 patient
60 mg single, oral
Overdose
Dose: 60 mg
Route: oral
Route: single
Dose: 60 mg
Sources:
healthy, 4 years
n = 1
Health Status: healthy
Age Group: 4 years
Sex: M
Population Size: 1
Sources:
Dystonic reaction 1 patient
Disc. AE
5 mg 1 times / day multiple, oral
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 6 years
n = 1
Health Status: unhealthy
Condition: allergic rhinitis
Age Group: 6 years
Sex: M
Population Size: 1
Sources:
Somnolence 13.7%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources: Page: p. 24
unhealthy, > 12 years
n = 2034
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Population Size: 2034
Sources: Page: p. 24
Dizziness 2%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources: Page: p. 24
unhealthy, > 12 years
n = 2034
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Population Size: 2034
Sources: Page: p. 24
Pharyngitis 2%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources: Page: p. 24
unhealthy, > 12 years
n = 2034
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Population Size: 2034
Sources: Page: p. 24
Dry mouth 5%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources: Page: p. 24
unhealthy, > 12 years
n = 2034
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Population Size: 2034
Sources: Page: p. 24
Fatigue 5.9%
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources: Page: p. 24
unhealthy, > 12 years
n = 2034
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Population Size: 2034
Sources: Page: p. 24
Visual acuity reduced 0.6%
0.24 % 2 times / day multiple, ophthalmic
Recommended
unhealthy, adult
n = 511
Ocular hyperemia 2%
0.24 % 2 times / day multiple, ophthalmic
Recommended
unhealthy, adult
n = 511
Conjunctival hyperemia 5.3%
0.24 % 2 times / day multiple, ophthalmic
Recommended
unhealthy, adult
n = 511
PubMed

PubMed

TitleDatePubMed
Cetirizine and loratadine: a comparison using the ED50 in skin reactions.
2000 Mar-Apr
Efficacy and safety of levocetirizine in seasonal allergic rhinitis.
2001
[The effect of second generation histamine antagonists on the heart].
2001
Is it Crohn's disease? A severe systemic granulomatous reaction to sulfasalazine in patient with rheumatoid arthritis.
2001
Treatment of severe seasonal rhinoconjunctivitis by a combination of azelastine nasal spray and eye drops: a double-blind, double-placebo study.
2001
Newer antihistamines.
2001 Apr 30
Severe hepatitis in a patient taking cetirizine.
2001 Jul 17
Acute urticaria with elevated circulating interleukin-6 is resistant to anti-histamine treatment.
2001 May
Preclinical comparison of ebastine and other second generation H1-antihistamines.
2001 Oct
Pharmacokinetics of cetirizine in tear fluid after a single oral dose.
2002
Effects of antihistamines on leukotriene and cytokine release from dispersed nasal polyp cells.
2002
Comparison of five new antihistamines (H1-receptor antagonists) in patients with allergic rhinitis using nasal provocation studies and skin tests.
2002 Apr
Are antihistamines useful in managing asthma?
2002 Feb
A double-blind, randomized, single-dose, crossover comparison of levocetirizine with ebastine, fexofenadine, loratadine, mizolastine, and placebo: suppression of histamine-induced wheal-and-flare response during 24 hours in healthy male subjects.
2002 Feb
Randomised controlled trial of butterbur and cetirizine for treating seasonal allergic rhinitis.
2002 Jan 19
Applications of derivative UV spectrophotometry for the determinations of cetirizine dihydrochloride in pharmaceutical preparations.
2002 Jan-Feb
Comparison of cetirizine, ebastine and loratadine in the treatment of immediate mosquito-bite allergy.
2002 Jun
[Skin prick test results in snoring and sleep apnea patients].
2002 Mar
Comparative activity of cetirizine and mizolastine on histamine-induced skin wheal and flare responses at 24 h.
2002 Mar
Patents

Sample Use Guides

1 to 2 tablets once daily depending upon severity of symptoms; do not take more than 2 tablets in 24 hours
Route of Administration: Oral
In Vitro Use Guide
Cetirizine (10 micrograms/ml) significantly enhanced IL-1 release by human monocytes stimulated by a weak LPS concentration (1 microgram/ml) but could not modify the maximal increase of IL-1 release induced by 10 micrograms/ml of LPS. It did not exert any effect on resting cells. Cetirizine (0.1-10 micrograms/ml) enhanced PGE2 release by resting human monocytes. Concentrations of 1 and 10 micrograms/ml enhanced PGE2 release by LPS-stimulated monocytes, and by healthy and inflamed rat macrophages.
Substance Class Chemical
Created
by admin
on Fri Dec 16 20:11:57 UTC 2022
Edited
by admin
on Fri Dec 16 20:11:57 UTC 2022
Record UNII
YO7261ME24
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CETIRIZINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
CETIRIZINE [MI]
Common Name English
(±)-(2-(4-(P-CHLORO-A-PHENYLBENZYL)-1-PIPERAZINYL)ETHOXY)ACETIC ACID
Common Name English
CETIRIZINE [HSDB]
Common Name English
AC-170
Code English
cetirizine [INN]
Common Name English
Cetirizine [WHO-DD]
Common Name English
ACETIC ACID, (2-(4-((4-CHLOROPHENYL)PHENYLMETHYL)-1-PIPERAZINYL)ETHOXY)-, (±)-
Common Name English
CETIRIZINE [VANDF]
Common Name English
CETIDERM
Brand Name English
Classification Tree Code System Code
LIVERTOX 180
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
NCI_THESAURUS C29578
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
NDF-RT N0000175587
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
WHO-VATC QR06AE07
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
NDF-RT N0000000190
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
WHO-ATC R06AE07
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
Code System Code Type Description
ChEMBL
CHEMBL1000
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
WIKIPEDIA
CETIRIZINE
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
LACTMED
Cetirizine
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
EPA CompTox
DTXSID4022787
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
DRUG BANK
DB00341
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
INN
5520
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
MERCK INDEX
M3291
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY Merck Index
RXCUI
20610
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY RxNorm
PUBCHEM
2678
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
DAILYMED
YO7261ME24
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
EVMPD
SUB07451MIG
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
DRUG CENTRAL
581
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
CHEBI
3561
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
CAS
83881-51-0
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
NCI_THESAURUS
C1042
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
MESH
D017332
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
IUPHAR
1222
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
HSDB
7739
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
FDA UNII
YO7261ME24
Created by admin on Fri Dec 16 20:11:57 UTC 2022 , Edited by admin on Fri Dec 16 20:11:57 UTC 2022
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
TRANSPORTER -> INHIBITOR
ENANTIOMER -> RACEMATE
TRANSPORTER -> SUBSTRATE
ENANTIOMER -> RACEMATE
Related Record Type Details
PARENT -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC