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L7795

Sigma-Aldrich

Levocetirizine dihydrochloride

≥98% (HPLC)

Sinónimos:

Levocetirizine dihydrochloride, (-)-Cetirizine dihydrochloride; 2-[2-[4-[(R)-(4-chlorophenyl)-phenyl-methyl]piperazin-1-yl]ethoxy]acetic acid dihydrochloride

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About This Item

Fórmula empírica (notación de Hill):
C21H25ClN2O3·2HCl
Número de CAS:
130018-87-0
Peso molecular:
461.81
MDL number:
MFCD07366507
UNSPSC Code:
12352200
PubChem Substance ID:
329817657
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

solubility

H2O: ≥23 mg/mL

storage temp.

room temp

SMILES string

Cl.Cl.OC(=O)COCCN1CCN(CC1)[C@H](c2ccccc2)c3ccc(Cl)cc3

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/t21-;;/m1../s1

InChI key

PGLIUCLTXOYQMV-GHVWMZMZSA-N

Gene Information

human ... HRH1(3269)

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General description

Levocetirizine dihydrochloride is the R-enantiomer of cetirizine and is used for treating seasonal allergic rhinitis and chronic idiopathic urticaria. The liver metabolizes 14% of levocetirizine and rest is excreted in urine. The response of levocetirizine to histamine is comparatively higher to cetirizine.

Application

Levocetirizine dihydrochloride has been used as standard in the thin layer chromatography optimization and in preparation of racemic cetirizine standard for subcritical fluid chromatography-tandem mass spectrometry analysis.

Biochem/physiol Actions

Levocetirizine hydrochloride is a nonsedating antihistamine. It is a histamine H1-receptor antagonist, the active isomer of cetirizine. Levocetirizine has high bioavailability, high affinity for and occupancy of the H1 receptor.

Features and Benefits

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 markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H302,H400

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Nurul Atika Razali et al.
BMC complementary and alternative medicine, 18(1), 217-217 (2018-07-18)
Histamine is a well-known mediator involved in skin allergic responses through up-regulation of pro-inflammatory cytokines. Antihistamines remain the mainstay of allergy treatment, but they were found limited in efficacy and associated with several common side effects. Therefore, alternative therapeutic preferences
Levocetirizine does not prolong the QT/QTc interval in healthy subjects: results from a thorough QT study
Hulhoven R, et al.
European Journal of Pharmacology, 63(11), 1011-1017 (2007)
A double-blind, randomized, single-dose, crossover comparison of levocetirizine with ebastine, fexofenadine, loratadine, mizolastine, and placebo: suppression of histamine-induced wheal-and-flare response during 24 hours in healthy male subjects
Grant JA, et al.
Annals of Allergy, Asthma & Immunology, 88(2), 190-197 (2002)
Shigeru Hishinuma et al.
International journal of molecular sciences, 19(12) (2018-12-19)
Cetirizine is a zwitterionic second-generation antihistamine containing R- and S-enantiomers, levocetirizine, and (S)-cetirizine. Levocetirizine is known to have a higher affinity for the histamine H₁ receptors than (S)-cetirizine; ligand-receptor docking simulations have suggested the importance of the formation of a
Dhagla R Choudhary et al.
Scientia pharmaceutica, 80(3), 779-787 (2012-09-26)
A fast-dissolving film containing levocetirizine, a non-sedative antihistamine drug, was developed using pullulan, xanthan gum, propylene glycol, and tween 80 as the base materials. The drug content of the prepared films was within an acceptable limit as prescribed by the
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