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:: 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 300 Target ID: CHEMBL231 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf	Antagonist 2575	Perennial allergic rhinitis Seasonal allergic rhinitis Allergic rhinitis	8.19999999999999929 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Perennial allergic rhinitis 45 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf	Palliative	Histamine H1 receptor	Approved 7968	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 818380800000
Seasonal allergic rhinitis 61 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf	Palliative	Histamine H1 receptor	Approved 7968	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 818380800000
Allergic rhinitis 100 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/076677lbl.pdf	Palliative	Histamine H1 receptor	Approved 7968	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 818380800000

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 Health Status: unhealthy Age Group: 18 months Sex: M 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 Health Status: unhealthy Age Group: 18 years Sex: F 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 Health Status: unhealthy Age Group: 18 years Sex: F 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 Health Status: unhealthy Age Group: 23 months Sex: M 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 Health Status: unhealthy Age Group: 39 years Sex: M+F 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 Health Status: healthy Age Group: 4 years Sex: M 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 Health Status: unhealthy Age Group: 46 years Sex: M 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 Health Status: unhealthy Age Group: 6 years Sex: M 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	unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022155s000_MedR_P1.pdf	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
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 Health Status: unhealthy Age Group: adult 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
MolPort	MolPort-002-506-309	https://www.molport.com/shop/molecule-link/MolPort-002-506-309

PubMed

Title	Date	PubMed
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
[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
Cetirizine reduces the number of tryptase-positive mast cells in psoriatic patients: a double-blind controlled study.	2001	11517856
Treatment of severe seasonal rhinoconjunctivitis by a combination of azelastine nasal spray and eye drops: a double-blind, double-placebo study.	2001	11436969
[Eosinophilic pustular folliculitis in childhood].	2001 Aug	11472668
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
Severe hepatitis in a patient taking cetirizine.	2001 Jul 17	11453719
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
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
The comparison of the efficacy of fluticasone propionate with cetirizine in perennial allergic rhinitis.	2001 Mar-Apr	11420028
Lipophilicity behaviour of the Zwitterionic antihistamine cetirizine in phosphatidylcholine liposomes/water systems.	2001 May	11465428
Acute urticaria with elevated circulating interleukin-6 is resistant to anti-histamine treatment.	2001 May	11436361
[The course of allergy: principles for early diagnosis, prevention and early therapy of allergic diseases].	2001 May	11407225
A descriptive analysis of the use and cost of new-generation antihistamines in the treatment of allergic rhinitis: a retrospective database analysis.	2001 May	11392821
A randomized trial of leukotriene receptor antagonist montelukast in moderate-to-severe atopic dermatitis of adults.	2001 May-Jun	11358726
Efficacy and safety of an oral formulation of cetirizine and prolonged-release pseudoephedrine versus xylometazoline nasal spray in nasal congestion.	2001 Nov	11765592
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
Absorption, distribution, metabolism and excretion of [14C]levocetirizine, the R enantiomer of cetirizine, in healthy volunteers.	2001 Oct	11758635
Effects of topical corticosteroid and combined mediator blockade on domiciliary and laboratory measurements of nasal function in seasonal allergic rhinitis.	2001 Oct	11686428
The costs of nonsedating antihistamine therapy for allergic rhinitis in managed care: an updated analysis.	2001 Oct	11680261
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
Comparison of the effects of levocetirizine and loratadine on histamine-induced wheal, flare, and itch in human skin.	2001 Oct	11576078
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
Potential cardiac toxicity of H1-antihistamines.	2002	12113224
Pharmacokinetics of cetirizine in tear fluid after a single oral dose.	2002	12083980
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
[The first case of lasting pigmented toxidermia induced by cetirizine (Zyrtec, Virlix) and ticlopidine].	2002 Apr	12055559
Acute hepatitis associated with cetirizine intake.	2002 Apr	11907376
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
Cardiotoxicity of new antihistamines and cisapride.	2002 Feb 28	12052668
Titrimetric and spectrophotometric assay of some antihistamines through the determination of the chloride of their hydrochlorides.	2002 Jan	11902650
Randomised controlled trial of butterbur and cetirizine for treating seasonal allergic rhinitis.	2002 Jan 19	11799030
Cetirizine decreases interleukin-4, interleukin-5, and interferon-gamma gene expressions in nasal-associated lymphoid tissue of sensitized mice.	2002 Jan-Feb	11895193
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
Comparative activity of cetirizine and mizolastine on histamine-induced skin wheal and flare responses at 24 h.	2002 Mar	11874388
Gateways to clinical trials.	2002 May	12092009
Urticarial intolerance reaction to cetirizine.	2002 May	12072003
Development and validation of a HPLC method for the determination of cetirizine in pharmaceutical dosage forms.	2002 May	12061254

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