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L7795

Sigma-Aldrich

Levocetirizine dihydrochloride

≥98% (HPLC)

Synonyme(s) :

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

Formule empirique (notation de Hill):
C21H25ClN2O3·2HCl
Numéro CAS:
130018-87-0
Poids moléculaire :
461.81
Numéro MDL:
MFCD07366507
Code UNSPSC :
12352200
ID de substance PubChem :
329817657
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Solubilité

H2O: ≥23 mg/mL

Température de stockage

room temp

Chaîne SMILES 

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

Clé InChI

PGLIUCLTXOYQMV-GHVWMZMZSA-N

Informations sur le gène

human ... HRH1(3269)

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Description générale

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Exclamation markEnvironment
GHS07,GHS09

Mention d'avertissement

Warning

Mentions de danger

H302,H400

Conseils de prudence

P273 - P301 + P312 + P330

Classification des risques

Acute Tox. 4 Oral - Aquatic Acute 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Rapid chiral separation of racemic cetirizine in human plasma using subcritical fluid chromatography-tandem mass spectrometry
Eom HY, et al.
Journal of Pharmaceutical and Biomedical Analysis, 117, 380-389 (2016)
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
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