A selective histamine H1 receptor antagonist
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(R)-Cetirizine (hydrochloride)

Item No. 23992

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[2-[4-[(R)-(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid, dihydrochloride
CAS Number
130018-87-0
Synonyms
  • Levocetirizine
Molecular Formula
C21H25ClN2O3 • 2HCl
Formula Weight
461.8
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 3 mg/mlDMSO: 12 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
228 nm
SMILES
ClC1=CC=C([C@H](N2CCN(CCOCC(O)=O)CC2)C3=CC=CC=C3)C=C1.Cl.Cl
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    (R)-Cetirizine is the (R)-enantiomer of the histamine H1 receptor antagonist and second generation antihistamine cetirizine (Item No. 19686).1 (R)-Cetirizine binds to the H1 receptor with higher affinity than cetirizine (Kis = 3 and 6 nM, respectively) and is 25,000-100,000-fold selective for H1 receptors over muscarinic M1-M5 receptors.2 It decreases production of RANTES and eotaxin following antigen stimulation in mouse eosinophils in vitro in a concentration-dependent manner with a minimum effective concentration (MEC) of 0.05 µM.3 Intranasal administration of (R)-cetirizine (0.01-1%) dose-dependently decreases histamine-induced nasal rubbing and sneezing in mice.4 Formulations containing (R)-cetirizine have been used in the treatment of allergic rhinitis and chronic idiopathic urticaria.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhang, L., Cheng, L., and Hong, J. The clinical use of cetirizine in the treatment of allergic rhinitis. Pharmacology 92(1-2), 14-25 (2013).

    2. Gillard, M., Christophe, B., Wels, B., et al. H1 antagonists: Receptor affinity versus selectivity. Inflamm. Res. 52(Suppl 1), S49-S50 (2003).

    3. Kanei, A., Asano, K., Kanai, K., et al. Inhibitory action of levocetirizine on the production of eosinophil chemoattractants RANTES and eotaxin in vitro and in vivo. In Vivo 28(4), 657-666 (2014).

    4. Kitayama-Sugiyama, C., Mochizuki, N., Murata, H., et al. Attenuation of histamine-induced airway effects by intranasal application of levocetirizine in mice. Immunopharmacol. Immunotoxicol. 35(5), 545-548 (2013).