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L7795

Sigma-Aldrich

Levocetirizine dihydrochloride

≥98% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C21H25ClN2O3·2HCl
CAS Number:
Molecular Weight:
461.81
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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COMPARISON OF DIFFERENT WAYS OF CHROMATOGRAPHIC SPOTS VISUALIZATION IN DETERMINATION OF ANTYHISTAMINE SUBSTANCES
Bober K
International Research Journal of Pharmacy, 5(7) (2014)
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
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)
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
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)

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