CETIRIZINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C21H25ClN2O3
Molecular Weight	388.8885
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1ccc(cc1)C(c2ccc(cc2)Cl)N3CCN(CC3)CCOCC(=O)O

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	388.8885
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 304 Target ID: CHEMBL231 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf	Antagonist 2575		8.2 null [pKi]

Conditions

Condition	Modality	Highest Phase	Product
Perennial allergic rhinitis 45 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf	Palliative	Approved 8043	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
Seasonal allergic rhinitis 61 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf	Palliative	Approved 8043	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
Allergic rhinitis 96 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/076677lbl.pdf	Palliative	Approved 8043	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

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
Cetirizine/pseudoephedrine.	2001	11772135
Impact of rhinitis on airway inflammation: biological and therapeutic implications.	2001	11737929
Treatment of urticaria. An evidence-based evaluation of antihistamines.	2001	11702618
[The effect of second generation histamine antagonists on the heart].	2001	11575008
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
Treatment of severe seasonal rhinoconjunctivitis by a combination of azelastine nasal spray and eye drops: a double-blind, double-placebo study.	2001	11436969
Design, synthesis and antihistaminic (H1)activity of some condensed 2-(substituted)arylaminoethylpyrimidin-4(3H)-ones.	2001	11304938
Effect of cetirizine, levocetirizine, and dextrocetirizine on histamine-induced nasal response in healthy adult volunteers.	2001 Apr	11284803
Newer antihistamines.	2001 Apr 30	11331439
[The allergic pregnant woman].	2001 Dec	11802481
Comparative onset of action and symptom relief with cetirizine, loratadine, or placebo in an environmental exposure unit in subjects with seasonal allergic rhinitis: confirmation of a test system.	2001 Dec	11770694
Sure outcomes of random events: a model for clinical trials.	2001 Feb 28	11223899
Effects of monotherapy with intra-nasal corticosteroid or combined oral histamine and leukotriene receptor antagonists in seasonal allergic rhinitis.	2001 Jan	11167952
Urticaria induced by cetirizine.	2001 Jan	11167712
Effect of cetirizine on bronchial hyperresponsiveness in patients with seasonal allergic rhinitis and asthma.	2001 Jan	11167350
Effects of cetirizine and epinastine on the skin response to histamine iontophoresis.	2001 Jan	11154865
Stability of cetirizine dihydrochloride in solid state.	2001 Jan-Feb	11370282
Double-blind multicenter study on the efficacy and tolerability of cetirizine compared with oxatomide in chronic idiopathic urticaria in preschool children.	2001 Jul	11476462
Stability indicating HPTLC method for the simultaneous determination of pseudoephedrine and cetirizine in pharmaceutical formulations.	2001 Jun	11377047
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
An investigation into the effects of cetirizine on cognitive function and psychomotor performance in healthy volunteers.	2001 Mar	11317473
[The course of allergy: principles for early diagnosis, prevention and early therapy of allergic diseases].	2001 May	11407225
Controlled comparison of the efficacy and safety of cetirizine 10 mg o.d. and fexofenadine 120 mg o.d. in reducing symptoms of seasonal allergic rhinitis.	2001 May	11385291
Efficacy of nimesulide alone and in combination with cetirizine in acute allergic rhinitis.	2001 May	11361264
[Efficacy and safety of fexofenadine and cetirizine in the treatment of allergic rhinitis].	2001 Nov-Dec	11802289
Multiwavelength spectrophotometric resolution of the micro-equilibria of cetirizine.	2001 Oct	11990597
Preclinical comparison of ebastine and other second generation H1-antihistamines.	2001 Oct	11881966
Effects of topical corticosteroid and combined mediator blockade on domiciliary and laboratory measurements of nasal function in seasonal allergic rhinitis.	2001 Oct	11686428
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
Serum tryptase in allergic rhinitis: effect of cetirizine and fluticasone propionate treatment.	2001 Sep-Oct	11794849
Photosensitivity disorders: cause, effect and management.	2002	12010069
Displacement of histamine from liver cells and cell components by ligands for cytochromes P450.	2002	11968021
Effects of antihistamines on leukotriene and cytokine release from dispersed nasal polyp cells.	2002	11878205
Comparison of five new antihistamines (H1-receptor antagonists) in patients with allergic rhinitis using nasal provocation studies and skin tests.	2002 Apr	11906367
Are antihistamines useful in managing asthma?	2002 Feb	11964751
Binding characteristics of cetirizine and levocetirizine to human H(1) histamine receptors: contribution of Lys(191) and Thr(194).	2002 Feb	11809864
Cardiotoxicity of new antihistamines and cisapride.	2002 Feb 28	12052668
Cetirizine decreases interleukin-4, interleukin-5, and interferon-gamma gene expressions in nasal-associated lymphoid tissue of sensitized mice.	2002 Jan-Feb	11895193
Comparison of cetirizine, ebastine and loratadine in the treatment of immediate mosquito-bite allergy.	2002 Jun	12028119
Extractionless and sensitive method for high-throughput quantitation of cetirizine in human plasma samples by liquid chromatography-tandem mass spectrometry.	2002 Jun 25	12031836
[Skin prick test results in snoring and sleep apnea patients].	2002 Mar	11967776
Gateways to clinical trials.	2002 May	12092009
Development and validation of a HPLC method for the determination of cetirizine in pharmaceutical dosage forms.	2002 May	12061254
Treating seasonal allergic rhinitis. Trial does not show that there is no difference between butterbur and cetirizine.	2002 May 25	12033216

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.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 22:45:46 UTC 2021` Edited by `admin` on `Fri Jun 25 22:45:46 UTC 2021`
Record UNII	YO7261ME24
Record Status	`Validated (UNII)`
Record Version

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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

ACETIC ACID, (2-(4-((4-CHLOROPHENYL)PHENYLMETHYL)-1-PIPERAZINYL)ETHOXY)-, (+/-)-

Common Name

English

CETIRIZINE [WHO-DD]

Common Name

English

CETIRIZINE [VANDF]

Common Name

English

CETIDERM

Brand Name

English

Classification Tree Code System Code

LIVERTOX

180