Levocetirizine

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Levocetirizine
Levocetirizine structure 2.svg
Levocetirizine 3D ball.png
Clinical data
Trade names Xyzal, Levazyr, others
Other namesLevocetirizine dihydrochloride
AHFS/Drugs.com Monograph
MedlinePlus a607056
License data
Routes of
administration 		By mouth
Drug class Second generation antihistamines
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability High
Protein binding 91–92% [2]
Metabolism Minimal (less than 14%, primarily CYP3A4) [2]
Elimination half-life 8 to 9 hours [2]
Excretion Urine: 85% [2]
Feces: 12.9% [2]
Identifiers
  • 2-(2-{4-[(R)-(4-Chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
Chemical and physical data
Formula C21H25ClN2O3
Molar mass 388.89 g·mol−1
3D model (JSmol)
  • Clc1ccc(cc1)[C@H](N2CCN(CCOCC(=O)O)CC2)c3ccccc3
  • 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 Yes check.svgY
  • Key:ZKLPARSLTMPFCP-OAQYLSRUSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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]

Contents

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] and is available as a generic medication. [4] In 2022, it was the 152nd 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 Levocetirizine.png
Different brands (Actavis, Glenmark, UCB) Levocetirizine tablets and oral solution
Xyzal Tablets 5mg in Japan 2020-05-20 Levocetirizine Hydrochloride rebosechirizinYan Suan Yan Ding zaizaru.jpg
Xyzal Tablets 5mg in Japan

Preparations of levocetirizine are sold under the following brand names:

Related Research Articles

H1 antagonists, also called H1 blockers, are a class of medications that block the action of histamine at the H1 receptor, helping to relieve allergic reactions. Agents where the main therapeutic effect is mediated by negative modulation of histamine receptors are termed antihistamines; other agents may have antihistaminergic action but are not true antihistamines.

<span class="mw-page-title-main">Loratadine</span> Antihistamine medication

Loratadine, sold under the brand name Claritin among others, is a medication used to treat allergies. This includes allergic rhinitis and hives. It is also available in drug combinations such as loratadine/pseudoephedrine, in which it is combined with pseudoephedrine, a nasal decongestant. It is taken orally.

<span class="mw-page-title-main">Brompheniramine</span> Chemical compound

Brompheniramine, sold under the brand name Dimetapp among others, is a first-generation antihistamine drug of the propylamine (alkylamine) class. It is indicated for the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing. Like the other first-generation drugs of its class, it is considered a sedating antihistamine.

<span class="mw-page-title-main">Hydroxyzine</span> Antihistamine drug

Hydroxyzine, sold under the brand names Atarax and Vistaril among others, is an antihistamine medication. It is used in the treatment of itchiness, anxiety, insomnia, and nausea. It is used either by mouth or injection into a muscle.

<span class="mw-page-title-main">Desloratadine</span> Allergy medication

Desloratadine sold under the brand name Clarinex among others, is a tricyclic H1 inverse agonist that is used to treat allergies. It is an active metabolite of loratadine.

<span class="mw-page-title-main">Hives</span> Skin disease characterized by red, raised, and itchy bumps

Hives, also known as urticaria, is a kind of skin rash with red and/or flesh-colored, raised, itchy bumps. Hives may burn or sting. The patches of rash may appear on different body parts, with variable duration from minutes to days, and do not leave any long-lasting skin change. Fewer than 5% of cases last for more than six weeks. The condition frequently recurs.

<span class="mw-page-title-main">Cetirizine</span> Antihistamine medication

Cetirizine is a second-generation antihistamine used to treat allergic rhinitis, dermatitis, and urticaria (hives). It is taken by mouth. Effects generally begin within thirty minutes and last for about a day. The degree of benefit is similar to other antihistamines such as diphenhydramine, which is a first-generation antihistamine.

<span class="mw-page-title-main">Fexofenadine</span> Antihistamine medication

Fexofenadine, sold under the brand name Allegra among others, is an antihistamine pharmaceutical drug used in the treatment of allergy symptoms, such as hay fever and urticaria.

<span class="mw-page-title-main">Clemastine</span> Allergy medication

Clemastine, also known as meclastin, is a first-generation H1 histamine antagonist (antihistamine) with anticholinergic properties (drying) and sedative side effects. Like all first-generation antihistamines, it is sedating.

<span class="mw-page-title-main">Olopatadine</span> Chemical compound

Olopatadine, sold under the brand name Patanol among others, is an antihistamine medication used to decrease the symptoms of allergic conjunctivitis and allergic rhinitis. It is used as eye drops or as a nasal spray. The eye drops generally result in an improvement within half an hour.

<span class="mw-page-title-main">Dermatographic urticaria</span> Skin disorder

Dermatographic urticaria is a skin disorder and one of the most common types of urticaria, affecting 2–5% of the population.

<span class="mw-page-title-main">Terfenadine</span> Chemical compound

Terfenadine is an antihistamine formerly used for the treatment of allergic conditions. It was brought to market by Hoechst Marion Roussel and was marketed under various brand names, including Seldane in the United States, Triludan in the United Kingdom, and Teldane in Australia. It was superseded by fexofenadine in the 1990s due to the risk of a particular type of disruption of the electrical rhythms of the heart and has been withdrawn from markets worldwide.

<span class="mw-page-title-main">Ketotifen</span> Antihistamine medication

Ketotifen is an antihistamine medication and a mast cell stabilizer used to treat allergic conditions such as conjunctivitis, asthma, and urticaria (hives). Ketotifen is available in ophthalmic and oral forms: the ophthalmic form relieves eye itchiness and irritation associated with seasonal allergies, while the oral form helps prevent systemic conditions such as asthma attacks and allergic reactions. In addition to treating allergies, ketotifen has shown efficacy in managing systemic mast cell diseases such as mastocytosis and mast cell activation syndrome (MCAS), which involve abnormal accumulation or activation of mast cells throughout the body. Ketotifen is also used for other allergic-type conditions like atopic dermatitis (eczema) and food allergies.

<span class="mw-page-title-main">Azelastine</span> Chemical compound

Azelastine, sold under the brand name Astelin among others, is a H1 receptor-blocking medication primarily used as a nasal spray to treat allergic rhinitis (hay fever) and as eye drops for allergic conjunctivitis. Other uses may include asthma and skin rashes for which it is taken by mouth. Onset of effects is within minutes when used in the eyes and within an hour when used in the nose. Effects last for up to 12 hours.

<span class="mw-page-title-main">Acrivastine</span> Chemical compound

Acrivastine is a medication used for the treatment of allergies and hay fever. It is a second-generation H1-receptor antagonist antihistamine and works by blocking histamine H1 receptors.

<span class="mw-page-title-main">Mequitazine</span> Chemical compound

Mequitazine (trade name Primalan) is an H1 antagonist and anticholinergic of the phenothiazine chemical class. It is used to treat allergies and rhinitis.

<span class="mw-page-title-main">Ebastine</span> Antihistamine drug

Ebastine is a H1 antihistamine with low potential for causing drowsiness.

<span class="mw-page-title-main">Rupatadine</span> Second generation H1-antihistamine

Rupatadine is a second generation antihistamine and platelet-activating factor antagonist used to treat allergies. It was discovered and developed by Uriach and is marketed as Rupafin and under several other trade names.

<span class="mw-page-title-main">Antihistamine</span> Drug that blocks histamine or histamine agonists

Antihistamines are drugs which treat allergic rhinitis, common cold, influenza, and other allergies. Typically, people take antihistamines as an inexpensive, generic drug that can be bought without a prescription and provides relief from nasal congestion, sneezing, or hives caused by pollen, dust mites, or animal allergy with few side effects. Antihistamines are usually for short-term treatment. Chronic allergies increase the risk of health problems which antihistamines might not treat, including asthma, sinusitis, and lower respiratory tract infection. Consultation of a medical professional is recommended for those who intend to take antihistamines for longer-term use.

<span class="mw-page-title-main">Bilastine</span> Antihistamine medication

Bilastine is an antihistamine medication used to treat hives (urticaria), allergic rhinitis and itchy inflamed eyes (allergic conjunctivitis) caused by an allergy. It is a second-generation antihistamine and takes effect by selectively inhibiting the histamine H1 receptor, preventing these allergic reactions. Bilastine has an effectiveness similar to cetirizine, fexofenadine, and desloratadine.

References

  1. ↑ "Xyzal Allergy 24HR- levocetirizine dihydrochloride tablet". DailyMed. 10 March 2023. Archived from the original on 30 June 2023. Retrieved 6 July 2023.
  2. 1 2 3 4 5 6 "Levocetirizine dihydrochloride- levocetirizine dihydrochloride tablet, film coated". DailyMed. 6 December 2021. Retrieved 9 July 2023.
  3. 1 2 3 4 5 "Levocetirizine Dihydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 1 April 2019. Retrieved 22 March 2019.
  4. 1 2 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 280–281. ISBN   9780857113382.
  5. ↑ "Levocetirizine Pregnancy and Breastfeeding Warnings". Drugs.com. Archived from the original on 22 March 2019. Retrieved 3 March 2019.
  6. ↑ Wallace DV, Dykewicz MS, Bernstein DI, Blessing-Moore J, Cox L, Khan DA, et al. (August 2008). "The diagnosis and management of rhinitis: an updated practice parameter". The Journal of Allergy and Clinical Immunology. 122 (2 Suppl): S1-84. doi: 10.1016/j.jaci.2008.06.003 . PMID   18662584.
  7. ↑ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  8. ↑ "Levocetirizine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  9. ↑ Holgate S, Powell R, Jenkins M, Ali O (July 2005). "A treatment for allergic rhinitis: a view on the role of levocetirizine". Current Medical Research and Opinion. 21 (7). Informa Healthcare: 1099–1106. doi:10.1185/030079905x53298. PMID   16004679. S2CID   26620889. 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. Archived from the original on 16 August 2019. Retrieved 21 August 2017.
  11. ↑ Hulhoven R, Rosillon D, Letiexhe M, Meeus MA, Daoust A, Stockis A (November 2007). "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. doi:10.1007/s00228-007-0366-5. PMID   17891537. S2CID   36218027.
  12. ↑ "Cetirizine and loratadine: minimal risk of QT prolongation". Prescrire International. 19 (105): 26–28. February 2010. PMID   20455340.
  13. ↑ Poluzzi E, Raschi E, Godman B, Koci A, Moretti U, Kalaba M, et al. (2015). "Pro-arrhythmic potential of oral antihistamines (H1): combining adverse event reports with drug utilization data across Europe". PLOS ONE. 10 (3): e0119551. Bibcode:2015PLoSO..1019551P. doi: 10.1371/journal.pone.0119551 . PMC   4364720 . PMID   25785934.
  14. ↑ XOZAL technical specifications booklet.
  15. ↑ Wang DY, Hanotte F, De Vos C, Clement P (April 2001). "Effect of cetirizine, levocetirizine, and dextrocetirizine on histamine-induced nasal response in healthy adult volunteers". Allergy. 56 (4): 339–343. doi:10.1034/j.1398-9995.2001.00775.x. PMID   11284803. S2CID   11304832.
  16. ↑ Devalia JL, De Vos C, Hanotte F, Baltes E (January 2001). "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. doi:10.1034/j.1398-9995.2001.00726.x. PMID   11167352. S2CID   40716352.
  17. ↑ "Prescription to Over-the-Counter (OTC) Switch List". Food and Drug Administration . Archived from the original on 24 April 2019. Retrieved 9 February 2017.
  18. ↑ "Xazal 5 mg Comprimidos Recubierno con película".
  19. ↑ "Curin". Archived from the original on 22 October 2012. Retrieved 29 August 2012.
  20. ↑ "Medicines and Medical Devices Agency of Serbia". Archived from the original on 21 September 2020. Retrieved 23 August 2020.
  21. ↑ "XYCET 5MG, Comprimé enrobé". Medicament.ma. 7 October 2020. Retrieved 12 September 2023.
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