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C3618

Sigma-Aldrich

Cetirizine dihydrochloride

≥98% (HPLC)

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Synonym(s):
[2-[4-[(4-Chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic acid dihydrochloride
Empirical Formula (Hill Notation):
C21H25ClN2O3 · 2HCl
CAS Number:
83881-52-1
Molecular Weight:
461.81
MDL number:
MFCD00941428
UNSPSC Code:
12352200
PubChem Substance ID:
329775040
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 5 mg/mL, clear

relevant disease(s)

allergies

SMILES string

OC(COCCN1CCN(C(C2=CC=C(Cl)C=C2)C3=CC=CC=C3)CC1)=O.[H]Cl.[H]Cl

InChI

1S/C21H25ClN2O3.2ClH/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);2*1H

InChI key

PGLIUCLTXOYQMV-UHFFFAOYSA-N

Gene Information

human ... HRH1(3269)

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Application

Cetirizine dihydrochloride has been used as an antagonist for histamine receptors H1 in HSDSEAP (poly) clonal cells derived from human embryonic kidney HEK-293 cells. It has also been used as a ligand in the crystallization of equine serum albumin cetirizine complex.

Biochem/physiol Actions

Cetirizine hydrochloride is an orally active and selective H1-receptor antagonist. Antihistaminic; Piperazines. Non-sedating type histamine H1-receptor antagonist; major metabolite of hydroxyzine. Pharmacological activity resides primarily in the (R)-isomer.
Cetirizine is a racemic mixture of (R)-levocetirizine and (S)-dextrocetirizine. It exists as a zwitterion at acidic pH and gets absorbed by passive diffusion. Cetirizine is a prescribed drug for allergic rhinitis and chronic idiopathic urticaria.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Histamine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Compared pharmacological characteristics in humans of racemic cetirizine and levocetirizine, two histamine H1-receptor antagonists
Tillement JP, et al.
Biochemical Pharmacology, 66(7), 1123-1126 (2003)
A designer cell-based histamine-specific human allergy profiler
Auslander D, et al.
Nature Communications, 5, 4408-4408 (2014)
Crystal structure of equine serum albumin in complex with cetirizine reveals a novel drug binding site
Handing K, et al.
Molecular Immunology, 71, 143-151 (2016)
Françoise Bree et al.
Fundamental & clinical pharmacology, 16(6), 471-478 (2003-04-11)
The aim of the present study was to determine (1) the extent of levocetirizine binding to human blood cells, plasma and individual plasma proteins; (2) the parameters for levocetirizine binding to individual plasma proteins both at their physiological concentrations and
Arnold Bahlmann et al.
Chemosphere, 89(11), 1278-1286 (2012-06-12)
Carbamazepine (CBZ), caffeine and cetirizine were monitored by enzyme-linked immunosorbent assays (ELISAs) in surface and wastewaters from Berlin, Germany. This fast and cost-efficient method enabled to assess the spatial and temporal variation of these anthropogenic markers in a high-throughput screening.
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