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

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
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
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
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
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
A double-blinded, randomized, placebo-controlled trial of cetirizine in preventing the onset of asthma in children with atopic dermatitis: 18 months' treatment and 18 months' posttreatment follow-up.	2001 Dec	11742270
Antihistamines and the torsade de point in children with allergic rhinitis.	2001 Jul-Aug	12067082
Efficacy and safety of an oral formulation of cetirizine and prolonged-release pseudoephedrine versus xylometazoline nasal spray in nasal congestion.	2001 Nov	11765592
Inhibition of depolarization-induced [3H]noradrenaline release from SH-SY5Y human neuroblastoma cells by some second-generation H(1) receptor antagonists through blockade of store-operated Ca(2+) channels (SOCs).	2001 Nov 1	11705456
[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
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
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
Dissociable effects of histamine H1 antagonists on reaction-time performance in rats.	2001 Oct-Nov	11701216
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
Serum tryptase in allergic rhinitis: effect of cetirizine and fluticasone propionate treatment.	2001 Sep-Oct	11794849
Potential cardiac toxicity of H1-antihistamines.	2002	12113224
Photosensitivity disorders: cause, effect and management.	2002	12010069
[Comparative antihistamine and anti-allergic effects of various antihistamine preparations].	2002	11980129
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
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
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
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
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
Applications of derivative UV spectrophotometry for the determinations of cetirizine dihydrochloride in pharmaceutical preparations.	2002 Jan-Feb	12026109
Gateways to clinical trials.	2002 Jan-Feb	11980386
Cetirizine decreases interleukin-4, interleukin-5, and interferon-gamma gene expressions in nasal-associated lymphoid tissue of sensitized mice.	2002 Jan-Feb	11895193
Immune changes in patients with advanced breast cancer undergoing chemotherapy with taxanes.	2002 Jul 1	12085250
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
Effects of emedastine and cetirizine, alone and with alcohol, on actual driving of males and females.	2002 Mar	11949773
Early treatment of perennial rhinitis with budesonide or cetirizine and its effect on long-term outcome.	2002 Mar	11897986
[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
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
Treating seasonal allergic rhinitis. Well designed experiments should have been used.	2002 May 25	12028990

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 Dec 15 16:26:53 GMT 2023` Edited by `admin` on `Fri Dec 15 16:26:53 GMT 2023`
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

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