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Merck

C3618

Sigma-Aldrich

Cetirizine dihydrochloride

≥98% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C21H25ClN2O3 · 2HCl
Número de CAS:
Peso molecular:
461.81
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

signalword

Warning

hcodes

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


Certificados de análisis (COA)

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Visite la Librería de documentos

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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