ContaminantDB: Cetirizine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:38 UTC

Update Date

2026-03-26 18:30:00 UTC

Accession Number

CHEM002175

Identification

Common Name

Cetirizine

Class

Small Molecule

Description

Cetirizine is a medication used for the treatment of allergies, hay fever, angioedema, and hives. It is a second-generation H1-receptor antagonist antihistamine and works by blocking H1 histamine receptors. It is a major metabolite of hydroxyzine, and has the same basic side effects, including dry mouth. A potent second-generation histamine H1 antagonist that is effective in the treatment of allergic rhinitis, chronic urticaria, and pollen-induced asthma. Unlike many traditional antihistamines, it does not cause drowsiness or anticholinergic side effects. Cetirizine hydrochloride is a medication used for the treatment of allergies, hay fever, angioedema, and hives. It is a second-generation H1-receptor antagonist antihistamine and works by blocking H1 histamine receptors. It is a major metabolite of hydroxyzine, and has the same basic side effects, including dry mouth.

Contaminant Sources

FooDB Chemicals
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Anti-Allergic Agent
Drug
Ether
Food Toxin
Histamine Antagonist
Histamine H1 Antagonist, Non-Sedating
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Cetirizin	ChEBI
Cetirizina	ChEBI
Cetirizinum	ChEBI
Cetiderm	Kegg
Benaday	HMDB
Cetirizine hydrochloride	HMDB
Humex	HMDB
Reactine	HMDB, MeSH
Virlix	HMDB, MeSH
Zirtek	HMDB, MeSH
Zyrlex	HMDB
Zyrtec	HMDB, MeSH
Alpharma brand OF cetirizine dihydrochloride	MeSH, HMDB
Ceti-puren	MeSH, HMDB
CetiLich	MeSH, HMDB
Cetirigamma	MeSH, HMDB
Cetirizin al	MeSH, HMDB
Dihydrochloride, cetirizine	MeSH, HMDB
glaxo Wellcome brand OF cetirizine dihydrochloride	MeSH, HMDB
TAD brand OF cetirizine dihydrochloride	MeSH, HMDB
UCB brand OF cetirizine dihydrochloride	MeSH, HMDB
Voltric	MeSH, HMDB
CT-Arzneimittel brand OF cetirizine dihydrochloride	MeSH, HMDB
Azupharma brand OF cetirizine dihydrochloride	MeSH, HMDB
Basics brand OF cetirizine dihydrochloride	MeSH, HMDB
Cetalerg	MeSH, HMDB
Dermapharm brand OF cetirizine dihydrochloride	MeSH, HMDB
Krewel brand OF cetirizine dihydrochloride	MeSH, HMDB
Lacer brand OF cetirizine dihydrochloride	MeSH, HMDB
Menarini brand OF cetirizine dihydrochloride	MeSH, HMDB
Pfizer brand OF cetirizine dihydrochloride	MeSH, HMDB
Pfizer consumer healthcare brand OF cetirizine dihydrochloride	MeSH, HMDB
UCB pharma brand OF cetirizine dihydrochloride	MeSH, HMDB
AWD.pharma brand OF cetirizine dihydrochloride	MeSH, HMDB
Aliud brand OF cetirizine dihydrochloride	MeSH, HMDB
Ceti tad	MeSH, HMDB
Cetidura	MeSH, HMDB
Cetirizin azu	MeSH, HMDB
Cetirizine dihydrochloride	MeSH, HMDB
Cetirlan	MeSH, HMDB
Lichtenstein brand OF cetirizine dihydrochloride	MeSH, HMDB
Rodleben brand OF cetirizine	MeSH, HMDB
United drug brand OF cetirizine dihydrochloride	MeSH, HMDB
Wolff brand OF cetirizine dihydrochloride	MeSH, HMDB
(2-(4-((4-Chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)acetic acid	MeSH, HMDB
Alerlisin	MeSH, HMDB
Ceterifug	MeSH, HMDB
Cetil von CT	MeSH, HMDB
Cetirizin basics	MeSH, HMDB
Merck dura brand OF cetirizine dihydrochloride	MeSH, HMDB
Sanofi synthelabo brand OF cetirizine dihydrochloride	MeSH, HMDB
Wörwag brand OF cetirizine dihydrochloride	MeSH, HMDB
Zetir	MeSH, HMDB

Chemical Formula

C₂₁H₂₅ClN₂O₃

Average Molecular Mass

388.888 g/mol

Monoisotopic Mass

388.155 g/mol

CAS Registry Number

83881-51-0

IUPAC Name

2-(2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid

Traditional Name

cetirizine

SMILES

OC(=O)COCCN1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(Cl)C=C1

InChI Identifier

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)

InChI Key

ZKLPARSLTMPFCP-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Chlorobenzene
Halobenzene
N-alkylpiperazine
Aralkylamine
Aryl halide
1,4-diazinane
Aryl chloride
Piperazine
Amino acid
Amino acid or derivatives
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Monocarboxylic acid or derivatives
Azacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organohalogen compound
Amine
Organochloride
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:3561 )
ether (CHEBI:3561 )
monochlorobenzenes (CHEBI:3561 )
piperazines (CHEBI:3561 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Brain
Skin

Pathways

Not Available

Applications

Biological Roles

H1-receptor antagonist

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	112.5°C
Boiling Point	Not Available
Solubility	101 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.066 g/L	ALOGPS
logP	2.98	ALOGPS
logP	0.86	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.6	ChemAxon
pKa (Strongest Basic)	7.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	53.01 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	106.87 m³·mol⁻¹	ChemAxon
Polarizability	41.88 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-3292000000-e20abaab20740ce81a18	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0uds-7498000000-d6daecf118171395d6b7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000j-0900000000-9801bb859e79fa9922aa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0009000000-014b559d56b0f32984ff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0009000000-213bd47e17d5ab69ad4b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004r-9006000000-f496e22c8e0e293fe98c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0009000000-d8a55ab1a7aff0580a91	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0009000000-d8a55ab1a7aff0580a91	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0009000000-dc957bb6f947575ae4fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000b-0900000000-48fc0581ff9fff15e16d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0009000000-04ca95fadd952d0aaeb8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-000i-0009000000-014b559d56b0f32984ff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0006-0009000000-26a7769df28c2325ec53	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0006-0009000000-284c2e7b25733d7c9875	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-0009000000-04befed283d691217ba2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0190000000-14715ff4d57580fbb166	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0f79-0069000000-431df9c3533b77cf08bc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0090000000-e042b67e2048318e7dbd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0190000000-b0dfb67717c01fd0c0b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0gb9-0970000000-e2810b242fefb4a419e7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0900000000-72f7cddc4ff6d45f98c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0019000000-e2cc239f762011eb0c4d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w2i-1169000000-185e6899ae017256a767	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-3391000000-bfd70499959ae71093eb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-caf1604c9603d45a6712	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1119000000-61c40cd9a0e9b76b5e91	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9162000000-08731719ee47b215e4c7	Spectrum

Toxicity Profile

Route of Exposure

Oral; mean peak plasma concentration (Cmax) of 114 ng/mL at a time (Tmax) of 2.2 hours postdose was observed for cetirizine.

Mechanism of Toxicity

Cetirizine competes with histamine for binding at H₁-receptor sites on the effector cell surface, resulting in suppression of histaminic edema, flare, and pruritus. The low incidence of sedation can be attributed to reduced penetration of cetirizine into the CNS as a result of the less lipophilic carboxyl group on the ethylamine side chain.

Metabolism

Half Life: 8.3 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the relief of symptoms associated with seasonal allergic rhinitis, perennial allergic rhinitis and the treatment of the uncomplicated skin manifestations of chronic idiopathic urticaria

Minimum Risk Level

Not Available

Health Effects

Overdosage has been reported with ZYRTEC (cetirizine) . In one adult patient who took 150 mg of ZYRTEC (cetirizine) , the patient was somnolent but did not display any other clinical signs or abnormal blood chemistry or hematology results. In an 18 month old pediatric patient who took an overdose of ZYRTEC (cetirizine) (approximately 180 mg), restlessness and irritability were observed initially; this was followed by drowsiness. (13)

Symptoms

Somnolence (sleepiness or unusual drowsiness), restlessness, irritability.

Treatment

Should overdose occur, treatment should be symptomatic or supportive, taking into account any concomitantly ingested medications. There is no known specific antidote to Cetirizine. (13)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Cetirizine

Chemspider ID

2577

ChEBI ID

3561

PubChem Compound ID

Not Available

Kegg Compound ID

C07778

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Manne Reddy, “Polymorphic forms of dihydrochloride salts of cetirizine and processes for preparation thereof.” U.S. Patent US20040186112, issued September 23, 2004.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15850951

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20455340

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=8103703

Cetirizine (CHEM002175)

Structure for CHEM002175: Cetirizine