Levocetirizine

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Levocetirizine
Systematic (IUPAC) name
2-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
Clinical data
Trade namesXyzal
AHFS/Drugs.commonograph
MedlinePlusa607056
Pregnancy cat.B (US)
Legal statusPOM (UK) -only (US)
RoutesOral
Pharmacokinetic data
BioavailabilityHigh
Protein binding90%
MetabolismHepatic 14% CYP3A4
Half-life6 to 10 hours
ExcretionRenal and fecal
Identifiers
CAS number130018-77-8 N
ATC codeR06AE09
PubChemCID 1549000
IUPHAR ligand1214
ChemSpider1266001 YesY
UNII6U5EA9RT2O YesY
KEGGD07402 YesY
ChEMBLCHEMBL1201191 N
Chemical data
FormulaC21H25ClN2O3 
Mol. mass388.888 g/mol
 N (what is this?)  (verify)
 
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Levocetirizine
Systematic (IUPAC) name
2-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
Clinical data
Trade namesXyzal
AHFS/Drugs.commonograph
MedlinePlusa607056
Pregnancy cat.B (US)
Legal statusPOM (UK) -only (US)
RoutesOral
Pharmacokinetic data
BioavailabilityHigh
Protein binding90%
MetabolismHepatic 14% CYP3A4
Half-life6 to 10 hours
ExcretionRenal and fecal
Identifiers
CAS number130018-77-8 N
ATC codeR06AE09
PubChemCID 1549000
IUPHAR ligand1214
ChemSpider1266001 YesY
UNII6U5EA9RT2O YesY
KEGGD07402 YesY
ChEMBLCHEMBL1201191 N
Chemical data
FormulaC21H25ClN2O3 
Mol. mass388.888 g/mol
 N (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 works by blocking histamine receptors. It does not prevent the actual release of histamine from mast cells, but prevents it binding to its 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.

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, although other studies have concluded it may be more effective.[1]

Contents

History and formulations

Levocetirizine was first launched in 2001 by Belgian pharmaceutical company UCB. It is sold under the brand name Xyzal (play /ˈzzæl/) in Australia, Czech Republic, Austria, Finland, France, Ireland, Netherlands, Portugal, Romania, United States, South Africa and UK; Xuzal in Mexico; Xusal in Germany; and Xozal in Greece. In Hungary it is marketed by Richter Gedeon under the Zilola brand name.

In India, levocetirizine is marketed by GlaxoSmithKline under the brand name Vozet and Xyzal. On May 25, 2007, the United States Food and Drug Administration approved Xyzal, where it is co-marketed by Sanofi-Aventis. Torrent Pharma launched UVNIL in rural market of India. It is also available as LEZYNCET 5 mg tablets through Unichem in India. In India, generic name of Lev-Cit 5 mg is manufactured by VIP Pharmaceuticals. Also marketed in India by Croslands (Ranbaxy Laboratories Ltd.) under the brand name Teczine. In Brazil it is marketed under the brand name 'Zyxem' by Farmalab. It is marketed in Egypt by BORG Pharma under the brand name 'Xaltec', Allear by western pharmaceuticals and levcet by marcryl.

In Pakistan levocetirizine was first launched in liquid formulation by Novartis Consumer Health Division by the name of T-Day Syrup. It is available as 5 mg-strength tablets and a 0.5 mg/mL oral solution. In Pakistan levocetirizine is available in liquid formulation as well with the name of OCITRA and T-Day 2.5 mg/5 mL. In Bangladesh levocetirizine is available in 5 mg tablet & 2.5 mg/5 mL oral liquid formulation with the brand name of Alcet marketed by Healthcare Pharmaceuticals and Seasonix marketed by Incepta Pharmaceuticals. In Nepal levocetirizine is availabe in 5 mg tablet with brand name of Curin manufactured by Beximco Pharma.[2]

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.[3]

Research

Latest research shows levocetirizine reduces asthma attacks by 70% in children.[4]

Availability

The drug is currently available on 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 LevoKast tablets, a formulation of levocetirizine hydrochloride and montelukast. In India, LevoKast is a Schedule 'H' drug and can be taken on the prescription by a registered medical practitioner only. In Finland, the drug is sold over-the-counter.

References

  1. ^ Grant, JA; Riethuisen, JM; Moulaert, B; DeVos, C; Gamalero, C.; Descalzi, D.; Folli, C.; Passalacqua, G. et al. (2002-02). "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.". Ann Allergy Asthma Immunol 88 (2): 190–197. doi:10.1016/S1081-1206(10)61995-3. PMID 11868924. 
  2. ^ http://www.beximco-pharma.com/allergic-disorders/147-curin.html
  3. ^ XOZAL technical specifications booklet.
  4. ^ Pasquali, M; Baiardini, I; Rogkakou, A; Riccio, AM; Gamalero, C; Descalzi, D; Folli, C; Passalacqua, G et al. (2006-09). "Levocetirizine in persistent allergic rhinitis and asthma: effects on symptoms, quality of life and inflammatory parameters.". Clinical & Experimental Allergy 36 (9): 1161–7. doi:10.1111/j.1365-2222.2006.02548.x. PMID 16961716. http://www.ncbi.nlm.nih.gov/pubmed/16961716. 

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