C3618

Sigma-Aldrich

Cetirizine dihydrochloride

≥98% (HPLC)

Synonym(s):
[2-[4-[(4-Chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic acid dihydrochloride
Empirical Formula (Hill Notation):
C21H25ClN2O3 · 2HCl
CAS Number:
Molecular Weight:
461.81
MDL number:
PubChem Substance ID:

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 5 mg/mL, clear

originator

Pfizer

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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Related Categories

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.

Packaging

50, 250 mg in glass bottle

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 also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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)
A designer cell-based histamine-specific human allergy profiler
Auslander D, et al.
Nature Communications, 5, 4408-4408 (2014)
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)
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...
Ko-Haung Lue et al.
International journal of pediatric otorhinolaryngology, 76(7), 994-1001 (2012-04-20)
Supplementary consumption of probiotics may temporarily alter the intestinal microflora of infants and children, thereby preventing and treating allergic disorders. To compare the clinical efficacy of levocetirizine with that of levocetirizine plus Lactobacillus johnsonii EM1 (Lj EM1) for treating perennial...
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