Chemistry:Levocetirizine

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Short description: Antihistamine drug
Levocetirizine
Levocetirizine structure 2.svg
Ball-and-stick model of the levocetirizine molecule
Clinical data
Trade namesXyzal, Levazyr, others
Other namesLevocetirizine dihydrochloride
AHFS/Drugs.comMonograph
MedlinePlusa607056
License data
Routes of
administration		By mouth
Drug classSecond generation antihistamines
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityHigh
Protein binding91-92% [2]
MetabolismMinimal (less than 14%, primarily CYP3A4) [2]
Elimination half-life8 to 9 hours [2]
ExcretionUrine: 85% [2]
Feces: 12.9% [2]
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
Chemical and physical data
FormulaC21H25ClN2O3
Molar mass388.89 g·mol−1
3D model (JSmol)
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Levocetirizine, sold under the brand name Xyzal, among others, is a second-generation antihistamine used for the treatment of allergic rhinitis (hay fever) and long-term hives of unclear cause.[3] It is less sedating than older antihistamines.[4] It is taken by mouth.[3]

Common side effects include sleepiness, dry mouth, cough, vomiting, and diarrhea.[3] Use in pregnancy appears safe but has not been well studied and use when breastfeeding is of unclear safety.[5] It is classified as a second-generation antihistamine and works by blocking histamine H1-receptors.[6][3]

Levocetirizine was approved for medical use in the United States in 2007.[3] It is available as a generic medication.[4] In 2020, it was the 179th most commonly prescribed medication in the United States, with more than 3 million prescriptions.[7][8]

Medical uses

Levocetirizine is used for allergic rhinitis.[9] This includes allergy symptoms such as watery eyes, runny nose, sneezing, hives, and itching.[10]

Side effects

Levocetirizine is referred to as a non-sedating antihistamine as it does not enter the brain in significant amounts and is therefore unlikely to cause drowsiness. Cardiac safety with repolarization may be better than some other antihistamines, as levocetirizine does not significantly prolong the QT interval in healthy individuals.[11][12][13] However, some people may still experience some slight sleepiness, headache, mouth dryness, lightheadedness, vision problems (mainly blurred vision), palpitations and fatigue.[14]

Pharmacology

Levocetirizine is an antihistamine. It acts as an inverse agonist that decreases activity at histamine H1 receptors. This in turn prevents the release of other allergy chemicals and increases the blood supply to the area, providing relief from the typical symptoms of hay fever. Levocetirizine, (R)-(-)-cetirizine, is essentially a chiral switch of (±)-cetirizine. This enantiomer, the eutomer, is more selective and the (S)-counterpart, the distomer, is inactive.[15][16]

Chemistry

Chemically, levocetirizine is the active levorotary enantiomer of cetirizine, also called the l-enantiomer of cetirizine. It is a member of the diphenylmethylpiperazine group of antihistamines.[citation needed]

History

Levocetirizine was first launched in 2001 by the Belgian pharmaceutical company UCB (Union Chimique Belge).[citation needed]

Society and culture

Availability

In January 2017, the US Food and Drug Administration approved an over-the-counter preparation.[17] Levocetirizine had previously received authorization by the FDA as a prescription drug in 2007, having already been brought to market throughout much of Europe.[citation needed] In India, a prescription-only drug containing levocetirizine hydrochloride and montelukast is sold as Crohist MK.[citation needed]

Brand names

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

Preparations of levocetirizine are sold under the following brand names:

  • Xyzal /ˈzaɪˌzɑːl/ in Australia, Austria, Bulgaria, Croatia, Cyprus, Czech Republic, Finland, France, Hong Kong, Hungary, India, Ireland (also Rinozal), Italy, Japan, Lithuania, Netherlands, Poland, Portugal, Romania, Taiwan, Thailand, Turkey, The Philippines, Serbia, Singapore, Slovakia, Slovenia, South Africa, Switzerland and UK. In May 2007, the US Food and Drug Administration approved Xyzal, where it is co-marketed by Sanofi-Aventis.
  • Xazal in Spain.[18]
  • Zobral in Cyprus.
  • Levobert in India.
  • Xusal in Germany and Mexico.
  • Xozal in Greece.
  • Degraler in Chile.
  • Allevo in Egypt.
  • Zilola, Histisynt, and Xyzal (UCB) in Hungary.
  • Alcet, Curin, and Seasonix in Bangladesh.
  • Vozet and Uvnil in India.
  • T-Day Syrup in Pakistan.
  • Curin in Nepal.[19]
  • Zenaro in the Czech Republic and Slovakia.
  • Xuzal and Zival in Chile.
  • Cezera, Levosetil, Robenan, and Xyzal in Serbia.[20]
  • Rinozal and Xyzal in Ireland.
  • Xycet in Morocco.[21]

References

  1. ↑ "Xyzal Allergy 24HR- levocetirizine dihydrochloride tablet". 10 March 2023. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8be45c2a-1eca-4a00-81b9-f7babdbdcd41. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "Levocetirizine dihydrochloride- levocetirizine dihydrochloride tablet, film coated". 6 December 2021. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=717eb542-3a05-485e-be76-3930efb40d33. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "Levocetirizine Dihydrochloride Monograph for Professionals" (in en). American Society of Health-System Pharmacists. https://www.drugs.com/monograph/levocetirizine-dihydrochloride.html. 
  4. ↑ 4.0 4.1 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 280–281. ISBN 9780857113382. 
  5. ↑ "Levocetirizine Pregnancy and Breastfeeding Warnings" (in en). https://www.drugs.com/pregnancy/levocetirizine.html. 
  6. ↑ "The diagnosis and management of rhinitis: an updated practice parameter". The Journal of Allergy and Clinical Immunology 122 (2 Suppl): S1-84. August 2008. doi:10.1016/j.jaci.2008.06.003. PMID 18662584. 
  7. ↑ "The Top 300 of 2020". https://clincalc.com/DrugStats/Top300Drugs.aspx. 
  8. ↑ "Levocetirizine - Drug Usage Statistics". https://clincalc.com/DrugStats/Drugs/Levocetirizine. 
  9. ↑ "A treatment for allergic rhinitis: a view on the role of levocetirizine". Current Medical Research and Opinion (Informa Healthcare) 21 (7): 1099–1106. July 2005. doi:10.1185/030079905x53298. PMID 16004679. "The variable efficacy and durability of response of different antihistamines arise from differing modulatory effects on the H(1)-receptor. Conclusion: These findings support both the short-term and long-term use of levocetirizine in the clinical management of allergic rhinitis. The World Health Organization (WHO) ARIA Guidelines (Allergic Rhinitis and its Impact on Asthma), recommend using a combination of a non-sedating antihistamine with a decongestant, or glucocorticosteroids for treating allergic rhinitis - with the order and combination of treatment depending on severity and duration of symptoms.". 
  10. ↑ "Levocetirizine Oral". WebMD. http://www.webmd.com/drugs/2/drug-148989/levocetirizine-oral/details. 
  11. ↑ "Levocetirizine does not prolong the QT/QTc interval in healthy subjects: results from a thorough QT study". European Journal of Clinical Pharmacology 63 (11): 1011–1017. November 2007. doi:10.1007/s00228-007-0366-5. PMID 17891537. 
  12. ↑ "Cetirizine and loratadine: minimal risk of QT prolongation". Prescrire International 19 (105): 26–28. February 2010. PMID 20455340. 
  13. ↑ "Pro-arrhythmic potential of oral antihistamines (H1): combining adverse event reports with drug utilization data across Europe". PLOS ONE 10 (3): e0119551. 2015. doi:10.1371/journal.pone.0119551. PMID 25785934. Bibcode: 2015PLoSO..1019551P. 
  14. ↑ XOZAL technical specifications booklet.
  15. ↑ "Effect of cetirizine, levocetirizine, and dextrocetirizine on histamine-induced nasal response in healthy adult volunteers". Allergy 56 (4): 339–343. April 2001. doi:10.1034/j.1398-9995.2001.00775.x. PMID 11284803. 
  16. ↑ "A randomized, double-blind, crossover comparison among cetirizine, levocetirizine, and ucb 28557 on histamine-induced cutaneous responses in healthy adult volunteers". Allergy 56 (1): 50–57. January 2001. doi:10.1034/j.1398-9995.2001.00726.x. PMID 11167352. 
  17. ↑ "Prescription to Over-the-Counter (OTC) Switch List". https://www.fda.gov/AboutFDA/CentersOffices/OfficeofMedicalProductsandTobacco/CDER/ucm106378.htm. 
  18. ↑ "Xazal 5 mg Comprimidos Recubierno con película". https://www.vademecum.es/medicamento-xazal_25890. 
  19. ↑ "Curin". http://www.beximco-pharma.com/allergic-disorders/147-curin.html. 
  20. ↑ "Medicines and Medical Devices Agency of Serbia". https://www.alims.gov.rs/eng/medicinal-products/search-for-human-medicines/. 
  21. ↑ "XYCET 5MG, Comprimé enrobé". 7 October 2020. https://medicament.ma/medicament/xycet-5-mg-comprime-enrobe/. 



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