Levocetirizine

Levocetirizine

Systematic (IUPAC) name
2-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
Clinical data
Trade names	Xyzal
AHFS/Drugs.com	monograph
MedlinePlus	a607056
Pregnancy category	US: B (No risk in non-human studies)
Legal status	UK: POM (Prescription only) US: ℞-only
Routes of administration	Oral
Pharmacokinetic data
Bioavailability	High
Protein binding	90%
Metabolism	Hepatic 14% CYP3A4
Biological half-life	6 to 10 hours
Excretion	Renal and fecal
Identifiers
CAS Number	130018-77-8 N
ATC code	R06AE09 (WHO)
PubChem	CID: 1549000
IUPHAR/BPS	1214
ChemSpider	1266001 Y
UNII	6U5EA9RT2O Y
KEGG	D07402 Y
ChEMBL	CHEMBL1201191 N
Chemical data
Formula	C21H25ClN2O3
Molecular mass	388.888 g/mol
SMILES Clc1ccc(cc1)[C@H](N2CCN(CCOCC(=O)O)CC2)c3ccccc3
InChI 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 Y Key:ZKLPARSLTMPFCP-OAQYLSRUSA-N Y
NY (what is this?)  (verify)

Levocetirizine (as levocetirizine dihydrochloride) is a third-generation non-sedative antihistamine, developed from the second-generation antihistamine cetirizine. Chemically, levocetirizine is the active enantiomer of cetirizine. It is the R-enantiomer of the cetirizine racemate. Levocetirizine is an inverse agonist that decreases activity at histamine H1 receptors. This in turn prevents the release of other allergy chemicals and increased blood supply to the area, and provides relief from the typical symptoms of hay fever. It does not prevent the actual release of histamine from mast cells.

The manufacturers claim it to be more effective with fewer side effects than the second-generation drugs; however, there have been no published studies supporting this assertion. A study part-funded by the manufacturer UCB concluded it may be more effective than some other second- and third-generation anti-histamines, but didn't compare it to cetirizine.

History

Levocetirizine was first launched in 2001 by Belgian pharmaceutical company UCB.

Brand names

It is sold under the brand names:

• Xyzal /ˈzaɪzæl/ in Australia, Austria, Croatia, Czech Republic, Finland, France, India, Ireland (also Rinozal), Lithuania, Netherlands, Portugal, Romania, Taiwan, Turkey, The Philippines, Serbia, Slovakia, Slovenia, South Africa and UK. On May 25, 2007, the United States Food and Drug Administration approved Xyzal, where it is co-marketed by Sanofi-Aventis.
• Xusal in Germany;
• Xozal in Greece;
• Cezera in Poland;
• Xazal in Spain;
• Xuzal in Mexico;
• In Hungary it is marketed as Zilola (made by Richter Gedeon) and Histisynt (Actavis).
• In India, levocetirizine is marketed by GlaxoSmithKline under the brand name Vozet. Torrent Pharma launched UVNIL for the rural market.
• In Pakistan levocetirizine was first launched in a liquid formulation by Novartis Consumer Health Division under the name of T-Day Syrup.
• In Nepal levocetirizine is available in tablet with brand name Curin manufactured by Beximco Pharma.
• In Chile, it is marketed as Zival and made by Laboratorio Saval.

Side effects

Levocetirizine is called a non-sedating antihistamine as it does not enter the brain in significant amounts, and is therefore unlikely to cause drowsiness. However, some people may experience some slight sleepiness, headache, mouth dryness, lightheadedness, vision problems (mainly blurred vision), palpitations and fatigue.

Research

Latest research shows levocetirizine reduces asthma attacks by 70% in children.

Availability

The drug is currently available by prescription in the United States. Although the drug was only authorized by the FDA on 25 May 2007, it was already available in most European countries. Like many new drugs it entered the market at a higher price than currently available third and second generation antihistamines. In India, one form of the drug is available as Crohist MK tablets and syrup, a formulation of levocetirizine hydrochloride and montelukast. In India, Crohist MK is a Schedule 'H' drug and may only be prescribed by a registered medical practitioner. In Finland, Hungary, China, and Kuwait the drug is sold over-the-counter.

Different brands (Actavis, Glenmark, UCB) Levocetirizine tablets and oral solution.

External links

• Full US prescribing information Xyzal® (levocetirizine dihydrochloride) tablets and oral solution (provided by UCB, December 2010, pdf file)