Levocetrizine is the (R)-enantiomer of cetirizine, featuring a substituted piperidine ring fused to a chlorophenyl group via an ether linkage, with an esterified carboxylic acid moiety at the terminal carbon. Its structure includes a tertiary amine and a methoxy substituent on the aromatic ring, conferring enhanced selectivity for peripheral H1-receptors compared to its racemic counterpart. The compound exists as a single enantiomer, synthesized via chiral resolution or asymmetric synthesis, and is utilized as an HPLC reference standard for quantifying levocetrizine in pharmaceutical formulations.
On RequestC1CN(CCN1CCOCC(=O)O)[C@H](C2=CC=CC=C2)C3=CC=C(C=C3)Cl
InChI=1S/C21H25ClN2O3/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)/t21-/m1/s1
ZKLPARSLTMPFCP-OAQYLSRUSA-N