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C3618

Sigma-Aldrich

Cetirizine dihydrochloride

≥98% (HPLC), histamine H1-receptor antagonist, powder

Synonym(s):

[2-[4-[(4-Chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]acetic acid dihydrochloride

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About This Item

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

Key Documents

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Product Name

Cetirizine dihydrochloride, ≥98% (HPLC)

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 a non-sedating type histamine H1-receptor antagonist.
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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
126M4751V
122M4712V
042M4707V
022M4748V
100M4726

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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
Agnieszka Biedroł et al.
Pediatrics, 133(4), e1068-e1071 (2014-03-26)
The occurrence of stabbing headaches in children requires a thorough diagnostic approach that excludes secondary headaches. The organic background should be taken into consideration when alarming symptoms occur, such as a purely 1-sided location, a change in the character of
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