CETIRIZINE

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 Search

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf	Antagonist 2778		8.2 null [pKi]

Conditions

Condition	Modality	Highest Phase	Product
Perennial allergic rhinitis 47 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf	Palliative	Approved 8429	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 1995
Seasonal allergic rhinitis 64 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf	Palliative	Approved 8429	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 1995
Allergic rhinitis 100 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/076677lbl.pdf	Palliative	Approved 8429	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 1995

C_max

Value	Dose	Co-administered	Analyte	Population
311 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2571627/	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

Value	Dose	Co-administered	Analyte	Population
6375.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2571627/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.3 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2571627/	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
7% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf	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

Dose	Population	Adverse events
180 mg single, oral Overdose Dose: 180 mg Route: oral Route: single Dose: 180 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9215262	unhealthy, 18 months n = 1 Health Status: unhealthy Age Group: 18 months Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9215262	Sources: https://pubmed.ncbi.nlm.nih.gov/9215262
270 mg single, oral Overdose Dose: 270 mg Route: oral Route: single Dose: 270 mg Sources: https://pubmed.ncbi.nlm.nih.gov/15521622	unhealthy, 18 years n = 1 Health Status: unhealthy Age Group: 18 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15521622	Other AEs: Metabolic acidosis, Hypokalemia... Other AEs: Metabolic acidosis (grade 5, 1 patient) Hypokalemia (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/15521622
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: https://pubmed.ncbi.nlm.nih.gov/23673913	unhealthy, 18 years n = 1 Health Status: unhealthy Condition: allergic rhinitis Age Group: 18 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/23673913	Disc. AE: Delusions, Depression... AEs leading to discontinuation/dose reduction: Delusions (1 patient) Depression (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/23673913
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: https://pubmed.ncbi.nlm.nih.gov/20375960/	unhealthy, 23 months n = 1 Health Status: unhealthy Condition: chronic rhinitis Age Group: 23 months Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20375960/	Disc. AE: Insomnia... AEs leading to discontinuation/dose reduction: Insomnia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/20375960/
10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211415s000lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211415Orig1s000MultidisciplineR.pdf	unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211415s000lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211415Orig1s000MultidisciplineR.pdf	Other AEs: Dyspepsia, Feeling hot... Other AEs: Dyspepsia (1%) Feeling hot (1%) Dysgeusia (1%) Headache (1%) Paresthesia (1%) Presyncope (1%) Hyperhidrosis (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211415s000lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211415Orig1s000MultidisciplineR.pdf
60 mg single, oral Overdose Dose: 60 mg Route: oral Route: single Dose: 60 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9786037	healthy, 4 years n = 1 Health Status: healthy Age Group: 4 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9786037	Other AEs: Drowsiness, Sedation... Other AEs: Drowsiness (severe, 1 patient) Sedation (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/9786037
50 mg 1 times / day multiple, oral Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12769407	unhealthy, 46 years n = 1 Health Status: unhealthy Condition: chronic idiopathic urticaria Age Group: 46 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/12769407	Sources: https://pubmed.ncbi.nlm.nih.gov/12769407
5 mg 1 times / day multiple, oral Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/32946371	unhealthy, 6 years n = 1 Health Status: unhealthy Condition: allergic rhinitis Age Group: 6 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/32946371	Disc. AE: Dystonic reaction... AEs leading to discontinuation/dose reduction: Dystonic reaction (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/32946371
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022155s000_MedR_P1.pdf Page: p. 24	unhealthy, > 12 years n = 2034 Health Status: unhealthy Age Group: > 12 years Sex: M+F Population Size: 2034 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022155s000_MedR_P1.pdf Page: p. 24	Other AEs: Somnolence, Fatigue... Other AEs: Somnolence (13.7%) Fatigue (5.9%) Dry mouth (5%) Dizziness (2%) Pharyngitis (2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022155s000_MedR_P1.pdf Page: p. 24
0.24 % 2 times / day multiple, ophthalmic Recommended Dose: 0.24 %, 2 times / day Route: ophthalmic Route: multiple Dose: 0.24 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208694s000lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208694Orig1s000MedR.pdf	unhealthy, adult n = 511 Health Status: unhealthy Condition: ocular itching Age Group: adult Population Size: 511 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208694s000lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208694Orig1s000MedR.pdf	Other AEs: Ocular hyperemia, Visual acuity reduced... Other AEs: Ocular hyperemia (2%) Visual acuity reduced (0.6%) Conjunctival hyperemia (5.3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208694s000lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208694Orig1s000MedR.pdf

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3561	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3561
ChemicalBook	CB3440625	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3440625
MolPort	MolPort-002-506-309	https://www.molport.com/shop/molecule-link/MolPort-002-506-309
eMolecules	901608	https://www.emolecules.com/cgi-bin/more?vid=901608

PubMed

Title	Date	PubMed
Measurement of interstitial cetirizine concentrations in human skin: correlation of drug levels with inhibition of histamine-induced skin responses.	1999 Jun	10435475
Cetirizine and loratadine: a comparison using the ED50 in skin reactions.	2000 Mar-Apr	10898119
The acute and sub-chronic effects of levocetirizine, cetirizine, loratadine, promethazine and placebo on cognitive function, psychomotor performance, and weal and flare.	2001	11922397
Efficacy and safety of levocetirizine in seasonal allergic rhinitis.	2001	11859651
Cetirizine/pseudoephedrine.	2001	11772135
Is it Crohn's disease? A severe systemic granulomatous reaction to sulfasalazine in patient with rheumatoid arthritis.	2001	11570976
Clinical prescribing of allergic rhinitis medication in the preschool and young school-age child: what are the options?	2001	11520256
Cetirizine reduces the number of tryptase-positive mast cells in psoriatic patients: a double-blind controlled study.	2001	11517856
Safety of antihistamines in children.	2001	11235817
Effect of cetirizine, levocetirizine, and dextrocetirizine on histamine-induced nasal response in healthy adult volunteers.	2001 Apr	11284803
[The allergic pregnant woman].	2001 Dec	11802481
[Prednicarbate and cetirizin dihydrochloride in the treatment of atopic eczema in the acute phase in children].	2001 Jan	11242833
Double-blind multicenter study on the efficacy and tolerability of cetirizine compared with oxatomide in chronic idiopathic urticaria in preschool children.	2001 Jul	11476462
Antihistamines and the torsade de point in children with allergic rhinitis.	2001 Jul-Aug	12067082
Burn wound itch control using H1 and H2 antagonists.	2001 Jul-Aug	11482684
Stanozolol in chronic urticaria: a double blind, placebo controlled trial.	2001 Jun	11476107
Distributions of results of cetirizine dihydrochloride assay in bulk material.	2001 Jun 19	11397577
[Co-administration of histamine H1 antagonist and oral anticoagulants].	2001 Jun-Jul	11526654
Local safety of intranasal triamcinolone acetonide: clinical and histological aspects of nasal mucosa in the long-term treatment of perennial allergic rhinitis.	2001 Mar	11340690
Do antihistamines have a role in asthma therapy?	2001 Mar	11253865
The comparison of the efficacy of fluticasone propionate with cetirizine in perennial allergic rhinitis.	2001 Mar-Apr	11420028
[Efficacy and safety of fexofenadine and cetirizine in the treatment of allergic rhinitis].	2001 Nov-Dec	11802289
Efficacy of leukotriene receptor antagonist in chronic urticaria. A double-blind, placebo-controlled comparison of treatment with montelukast and cetirizine in patients with chronic urticaria with intolerance to food additive and/or acetylsalicylic acid.	2001 Oct	11678862
Antiallergic/antiasthmatic effect of novel antiallergic hexapeptide-95/220 in various experimental models.	2001 Sep	11831367
Cetirizine inhibits skin reactions but not mediator release in immediate and developing late-phase allergic cutaneous reactions. A double-blind, placebo-controlled study.	2001 Sep	11591187
Long-term cetirizine treatment reduces allergic symptoms and drug prescriptions in children with mite allergy.	2001 Sep	11570619
Pharmacokinetics of cetirizine in chronic hemodialysis patients: multiple-dose study.	2001 Sep	11528239
Potential cardiac toxicity of H1-antihistamines.	2002	12113224
Pharmacokinetics of cetirizine in tear fluid after a single oral dose.	2002	12083980
Major role for the carboxylic function of cetirizine and levocetirizine in their binding characteristics to human H1-histamine-receptors.	2002 Apr	12013421
Binding characteristics of [3H]levocetirizine to cloned human H1-histamine-receptors expressed in CHO cells.	2002 Apr	12013420
Are antihistamines useful in managing asthma?	2002 Feb	11964751
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	11868924
Binding characteristics of cetirizine and levocetirizine to human H(1) histamine receptors: contribution of Lys(191) and Thr(194).	2002 Feb	11809864
Lack of effect of single and repeated doses of levocetirizine, a new antihistamine drug, on cognitive and psychomotor functions in healthy volunteers.	2002 Jul	12100225
Immune changes in patients with advanced breast cancer undergoing chemotherapy with taxanes.	2002 Jul 1	12085250
[Skin prick test results in snoring and sleep apnea patients].	2002 Mar	11967776
Effects of emedastine and cetirizine, alone and with alcohol, on actual driving of males and females.	2002 Mar	11949773
[Already allergic to pollen in early childhood. Can future asthma still be prevented?].	2002 Mar 7	11928274
Gateways to clinical trials.	2002 May	12092009
Urticarial intolerance reaction to cetirizine.	2002 May	12072003

Patents

Sample Use Guides

In Vivo Use Guide

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.

Name

Type

Language

CETIRIZINE

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