levocetirizine
{{Short description|Antihistamine drug}}
{{Use dmy dates|date=July 2023}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 464192413
| image = Levocetirizine structure 2.svg
| width = 200
| image2 = Levocetirizine 3D ball.png
| alt2 = Ball-and-stick model of the levocetirizine molecule
| tradename = Xyzal, Levazyr, others
| Drugs.com = {{drugs.com|monograph|levocetirizine-dihydrochloride}}
| MedlinePlus = a607056
| DailyMedID = Levocetirizine
| pregnancy_AU =
| pregnancy_category =
| routes_of_administration = By mouth
| class = Second generation antihistamines
| ATC_prefix = R06
| ATC_suffix = AE09
| legal_AU =
| legal_UK = POM
| legal_US = OTC
| legal_US_comment = / Rx-only{{cite web | title=Xyzal Allergy 24HR- levocetirizine dihydrochloride tablet | website=DailyMed | date=10 March 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8be45c2a-1eca-4a00-81b9-f7babdbdcd41 | access-date=6 July 2023 | archive-date=30 June 2023 | archive-url=https://web.archive.org/web/20230630132124/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8be45c2a-1eca-4a00-81b9-f7babdbdcd41 | url-status=live }}
| bioavailability = High
| metabolism = Minimal (less than 14%, primarily CYP3A4)
| elimination_half-life = 8 to 9 hours
| excretion = Urine: 85%
Feces: 12.9%
| index2_label = as salt
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 130018-77-8
| PubChem = 1549000
| IUPHAR_ligand = 1214
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB06282
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1266001
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6U5EA9RT2O
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07402
| KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = D08118
| ChEBI = 94559
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1201191
| NIAID_ChemDB =
| PDB_ligand = LCR
| synonyms = Levocetirizine dihydrochloride
| IUPAC_name = 2-(2-
| C=21 | H=25 | Cl=1 | N=2 | O=3
| SMILES = Clc1ccc(cc1)[C@H](N2CCN(CCOCC(=O)O)CC2)c3ccccc3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZKLPARSLTMPFCP-OAQYLSRUSA-N
}}
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.{{cite web |title=Levocetirizine Dihydrochloride Monograph for Professionals |url=https://www.drugs.com/monograph/levocetirizine-dihydrochloride.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=22 March 2019 |language=en |archive-date=1 April 2019 |archive-url=https://web.archive.org/web/20190401035935/https://www.drugs.com/monograph/levocetirizine-dihydrochloride.html |url-status=live }} It is less sedating than older antihistamines.{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=280–281|edition=76}} It is taken by mouth.
Common side effects include sleepiness, dry mouth, cough, vomiting, and diarrhea. Use in pregnancy appears safe but has not been well studied and use when breastfeeding is of unclear safety.{{cite web |title=Levocetirizine Pregnancy and Breastfeeding Warnings |url=https://www.drugs.com/pregnancy/levocetirizine.html |website=Drugs.com |access-date=3 March 2019 |language=en |archive-date=22 March 2019 |archive-url=https://web.archive.org/web/20190322164020/https://www.drugs.com/pregnancy/levocetirizine.html |url-status=live }} It is classified as a second-generation antihistamine and works by blocking histamine H1-receptors.{{cite journal | vauthors = Wallace DV, Dykewicz MS, Bernstein DI, Blessing-Moore J, Cox L, Khan DA, Lang DM, Nicklas RA, Oppenheimer J, Portnoy JM, Randolph CC, Schuller D, Spector SL, Tilles SA | display-authors = 6 | title = The diagnosis and management of rhinitis: an updated practice parameter | journal = The Journal of Allergy and Clinical Immunology | volume = 122 | issue = 2 Suppl | pages = S1-84 | date = August 2008 | pmid = 18662584 | doi = 10.1016/j.jaci.2008.06.003 | doi-access = free }}
Levocetirizine was approved for medical use in the United States in 2007, and is available as a generic medication. In 2022, it was the 152nd most commonly prescribed medication in the United States, with more than 3{{nbsp}}million prescriptions.{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}{{cite web | title = Levocetirizine Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Levocetirizine | access-date = 30 August 2024 }}
Medical uses
Levocetirizine is used for allergic rhinitis.{{cite journal | vauthors = Holgate S, Powell R, Jenkins M, Ali O | title = A treatment for allergic rhinitis: a view on the role of levocetirizine | journal = Current Medical Research and Opinion | volume = 21 | issue = 7 | pages = 1099–1106 | date = July 2005 | pmid = 16004679 | doi = 10.1185/030079905x53298 | publisher = Informa Healthcare | quote = 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. | s2cid = 26620889 }} This includes allergy symptoms such as watery eyes, runny nose, sneezing, hives, and itching.{{cite web | url = http://www.webmd.com/drugs/2/drug-148989/levocetirizine-oral/details | title = Levocetirizine Oral | publisher = WebMD | access-date = 21 August 2017 | archive-date = 16 August 2019 | archive-url = https://web.archive.org/web/20190816020150/https://www.webmd.com/drugs/2/drug-148989/levocetirizine-oral/details | url-status = live }}
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.{{cite journal | vauthors = Hulhoven R, Rosillon D, Letiexhe M, Meeus MA, Daoust A, Stockis A | title = Levocetirizine does not prolong the QT/QTc interval in healthy subjects: results from a thorough QT study | journal = European Journal of Clinical Pharmacology | volume = 63 | issue = 11 | pages = 1011–1017 | date = November 2007 | pmid = 17891537 | doi = 10.1007/s00228-007-0366-5 | s2cid = 36218027 }}{{cite journal | vauthors = | title = Cetirizine and loratadine: minimal risk of QT prolongation | journal = Prescrire International | volume = 19 | issue = 105 | pages = 26–28 | date = February 2010 | pmid = 20455340 }}{{cite journal | vauthors = Poluzzi E, Raschi E, Godman B, Koci A, Moretti U, Kalaba M, Wettermark B, Sturkenboom M, De Ponti F | display-authors = 6 | title = Pro-arrhythmic potential of oral antihistamines (H1): combining adverse event reports with drug utilization data across Europe | journal = PLOS ONE | volume = 10 | issue = 3 | pages = e0119551 | date = 2015 | pmid = 25785934 | pmc = 4364720 | doi = 10.1371/journal.pone.0119551 | doi-access = free | bibcode = 2015PLoSO..1019551P }} However, some people may still experience some slight sleepiness, headache, mouth dryness, lightheadedness, vision problems (mainly blurred vision), palpitations and fatigue.XOZAL technical specifications booklet.
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.{{cite journal | vauthors = Wang DY, Hanotte F, De Vos C, Clement P | title = Effect of cetirizine, levocetirizine, and dextrocetirizine on histamine-induced nasal response in healthy adult volunteers | journal = Allergy | volume = 56 | issue = 4 | pages = 339–343 | date = April 2001 | pmid = 11284803 | doi = 10.1034/j.1398-9995.2001.00775.x | s2cid = 11304832 }}{{cite journal | vauthors = Devalia JL, De Vos C, Hanotte F, Baltes E | title = A randomized, double-blind, crossover comparison among cetirizine, levocetirizine, and ucb 28557 on histamine-induced cutaneous responses in healthy adult volunteers | journal = Allergy | volume = 56 | issue = 1 | pages = 50–57 | date = January 2001 | pmid = 11167352 | doi = 10.1034/j.1398-9995.2001.00726.x | s2cid = 40716352 }}
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.{{cn|date=July 2023}}
History
Levocetirizine was first launched in 2001 by the Belgian pharmaceutical company UCB (Union Chimique Belge).{{cn|date=July 2023}}
Society and culture
= Availability =
In January 2017, the US Food and Drug Administration approved an over-the-counter preparation.{{cite web|url=https://www.fda.gov/AboutFDA/CentersOffices/OfficeofMedicalProductsandTobacco/CDER/ucm106378.htm|access-date=9 February 2017|title=Prescription to Over-the-Counter (OTC) Switch List|website=Food and Drug Administration|archive-date=24 April 2019|archive-url=https://web.archive.org/web/20190424044424/https://www.fda.gov/AboutFDA/CentersOffices/OfficeofMedicalProductsandTobacco/CDER/ucm106378.htm|url-status=live}} Levocetirizine had previously received authorization by the FDA as a prescription drug in 2007, having already been brought to market throughout much of Europe.{{cn|date=July 2023}} In India, a prescription-only drug containing levocetirizine hydrochloride and montelukast is sold as Crohist MK.{{cn|date=July 2023}}
= Brand names =
{{more citations needed section|date=July 2020}}
File:Levocetirizine.png, Glenmark, UCB) Levocetirizine tablets and oral solution]]
File:2020-05-20 Levocetirizine Hydrochloride レボセチリジン塩酸塩錠 ザイザル.jpg]]
Preparations of levocetirizine are sold under the following brand names:
- Xyzal {{IPAc-en|ˈ|z|aɪ|ˌ|z|ɑː|l}} 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.{{Cite web |title=Xazal 5 mg Comprimidos Recubierno con película |url=https://www.vademecum.es/medicamento-xazal_25890}}
- Avocel, Histrine Levo, and Xybat in Indonesia
- 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.{{cite web|url=http://www.beximco-pharma.com/allergic-disorders/147-curin.html |title=Curin |access-date=29 August 2012 |url-status=dead |archive-url=https://web.archive.org/web/20121022184859/http://beximco-pharma.com/allergic-disorders/147-curin.html |archive-date=22 October 2012 }}
- Zenaro in the Czech Republic and Slovakia.
- Xuzal and Zival in Chile.
- Cezera, Levosetil, Robenan, and Xyzal in Serbia.{{cite web |url=https://www.alims.gov.rs/eng/medicinal-products/search-for-human-medicines/ |title=Medicines and Medical Devices Agency of Serbia |access-date=23 August 2020 |archive-date=21 September 2020 |archive-url=https://web.archive.org/web/20200921062638/https://www.alims.gov.rs/eng/medicinal-products/search-for-human-medicines/ |url-status=live }}
- Rinozal and Xyzal in Ireland.
- Xycet in Morocco.{{Cite web |date=7 October 2020 |title=XYCET 5MG, Comprimé enrobé |url=https://medicament.ma/medicament/xycet-5-mg-comprime-enrobe/ |access-date=2023-09-12 |website=Medicament.ma }}
References
{{Reflist}}
{{Antihistamines}}
{{Histamine receptor modulators}}
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