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{{Short description|Antihistamine drug}}
{{Short description|Antihistamine drug}}
{{Use dmy dates|date=July 2023}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
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| alt2 = Ball-and-stick model of the levocetirizine molecule
| alt2 = Ball-and-stick model of the levocetirizine molecule


<!--Clinical data-->
<!-- Clinical data -->
| tradename = Xyzal, Levazyr, others
| tradename = Xyzal, Levazyr, others
| Drugs.com = {{drugs.com|monograph|levocetirizine-dihydrochloride}}
| Drugs.com = {{drugs.com|monograph|levocetirizine-dihydrochloride}}
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| pregnancy_AU =
| pregnancy_AU =
| pregnancy_category =
| pregnancy_category =
⚫
| legal_AU =
⚫
| legal_UK = POM
⚫
| legal_US = OTC
| legal_US_comment = /&nbsp;Rx-only
| routes_of_administration = [[Oral administration|By mouth]]
| routes_of_administration = [[Oral administration|By mouth]]
| class = [[Second generation antihistamines]]
| class = [[Second generation antihistamines]]
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| ATC_suffix = AE09
| ATC_suffix = AE09


⚫
| legal_AU =
⚫
<!--Pharmacokinetic data-->
⚫
| legal_UK = POM
⚫
| legal_US = OTC
| legal_US_comment = /&nbsp;Rx-only<ref name="Xyzal FDA label">{{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 }}</ref><ref name="FDA prescribing information" />

⚫
<!-- Pharmacokinetic data -->
| bioavailability = High
| bioavailability = High
| protein_bound = 91–92%<ref name="FDA prescribing information">{{cite web | title=Levocetirizine dihydrochloride- levocetirizine dihydrochloride tablet, film coated | website=DailyMed | date=6 December 2021 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=717eb542-3a05-485e-be76-3930efb40d33 | access-date=9 July 2023}}</ref>
| protein_bound = 90%
| metabolism = [[Liver]] 14% [[CYP3A4]]
| metabolism = Minimal (less than 14%, primarily [[CYP3A4]])<ref name="FDA prescribing information" />
| elimination_half-life = 6 to 10 hours
| elimination_half-life = 8 to 9 hours<ref name="FDA prescribing information" />
| excretion = [[Urine]]: 85%<ref name="FDA prescribing information" /><br />[[Feces]]: 12.9%<ref name="FDA prescribing information" />
| excretion = [[Kidney]] and [[feces|fecal]]


<!--Identifiers-->
<!-- Identifiers -->
| index2_label = as salt
| index2_label = as salt
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number_Ref = {{cascite|changed|??}}
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| synonyms = Levocetirizine dihydrochloride
| synonyms = Levocetirizine dihydrochloride


<!--Chemical data-->
<!-- Chemical data -->
| IUPAC_name = 2-(2-<nowiki>{</nowiki>4-[(''R'')-(4-Chlorophenyl)(phenyl)methyl]piperazin-1-yl<nowiki>}</nowiki>ethoxy)acetic acid
| IUPAC_name = 2-(2-<nowiki>{</nowiki>4-[(''R'')-(4-Chlorophenyl)(phenyl)methyl]piperazin-1-yl<nowiki>}</nowiki>ethoxy)acetic acid
| C=21 | H=25 | Cl=1 | N=2 | O=3
| C=21 | H=25 | Cl=1 | N=2 | O=3
Line 62: Line 64:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZKLPARSLTMPFCP-OAQYLSRUSA-N
| StdInChIKey = ZKLPARSLTMPFCP-OAQYLSRUSA-N
}}
⚫
}}<!-- Definition and medical uses -->


⚫
<!-- Definition and medical uses -->
'''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.<ref name=AHFS2019>{{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}}</ref> It is less sedating than older antihistamines.<ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=280–281|edition=76}}</ref> It is taken by mouth.<ref name=AHFS2019/>
'''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.<ref name=AHFS2019>{{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 }}</ref> It is less sedating than older antihistamines.<ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=280–281|edition=76}}</ref> It is taken [[by mouth]].<ref name=AHFS2019/>


<!-- Side effects and mechanisms -->
<!-- Side effects and mechanisms -->
Common side effects include sleepiness, dry mouth, cough, vomiting, and diarrhea.<ref name=AHFS2019/> Use in [[pregnancy]] appears safe but has not been well studied and use when [[breastfeeding]] is of unclear safety.<ref name=Preg2019>{{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}}</ref> It is classified as a second-generation antihistamine and works by blocking [[histamine H1-receptor|histamine H<sub>1</sub>-receptors]].<ref name=AA2008>{{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 }}</ref><ref name=AHFS2019/>
Common side effects include sleepiness, dry mouth, cough, vomiting, and diarrhea.<ref name=AHFS2019/> Use in [[pregnancy]] appears safe but has not been well studied and use when [[breastfeeding]] is of unclear safety.<ref name=Preg2019>{{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 }}</ref> It is classified as a second-generation antihistamine and works by blocking [[histamine H1-receptor|histamine H<sub>1</sub>-receptors]].<ref name=AA2008>{{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 }}</ref><ref name=AHFS2019/>


<!-- Society and culture -->
<!-- Society and culture -->
Levocetirizine was approved for medical use in the United States in 2007.<ref name=AHFS2019/> It is available as a [[generic medication]].<ref name=BNF76/> In 2020, it was the 179th most commonly prescribed medication in the United States, with more than 3{{nbsp}}million prescriptions.<ref>{{cite web | title = The Top 300 of 2020 | url = https://clincalc.com/DrugStats/Top300Drugs.aspx | website = ClinCalc | access-date = 7 October 2022}}</ref><ref>{{cite web | title = Levocetirizine - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Levocetirizine | access-date = 7 October 2022}}</ref>
Levocetirizine was approved for medical use in the United States in 2007,<ref name=AHFS2019/> and is available as a [[generic medication]].<ref name=BNF76/> In 2022, it was the 152nd most commonly prescribed medication in the United States, with more than 3{{nbsp}}million prescriptions.<ref>{{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 }}</ref><ref>{{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 }}</ref>


== Medical uses ==
== Medical uses ==
Levocetirizine is used for allergic rhinitis.<ref name="Holgate Powell Jenkins Ali 2005 pp. 1099–1106">{{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 }}</ref> This includes allergy symptoms such as watery eyes, runny nose, sneezing, hives, and itching.<ref>{{cite web | url = http://www.webmd.com/drugs/2/drug-148989/levocetirizine-oral/details | title = Levocetirizine Oral | publisher = [[WebMD]]}}</ref>
Levocetirizine is used for allergic rhinitis.<ref name="Holgate Powell Jenkins Ali 2005 pp. 1099–1106">{{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 }}</ref> This includes allergy symptoms such as watery eyes, runny nose, sneezing, hives, and itching.<ref>{{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 }}</ref>


== Side effects ==
== Side effects ==
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== Pharmacology ==
== Pharmacology ==
Levocetirizine is an [[antihistamine]]. It acts as an [[inverse agonist]] that decreases activity at [[histamine H1 receptor]]s. 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 [[Eudysmic ratio|eutomer]], is more selective and less sedative and the (''S'')-counterpart, the [[distomer]], is inactive.<ref>{{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 }}</ref><ref>{{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 }}</ref>
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 [[Eudysmic ratio|eutomer]], is more selective and the (''S'')-counterpart, the [[distomer]], is inactive.<ref>{{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 }}</ref><ref>{{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 }}</ref>


== Chemistry ==
== 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.
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 ==
== History ==
Levocetirizine was first launched in 2001 by the Belgian pharmaceutical company [[UCB (company)|UCB]] (''Union Chimique Belge'').
Levocetirizine was first launched in 2001 by the Belgian pharmaceutical company [[UCB (company)|UCB]] (''Union Chimique Belge'').{{cn|date=July 2023}}


== Society and culture ==
== Society and culture ==


=== Availability ===
=== Availability ===
On 31 January 2017, the [[Food and Drug Administration]] approved an over-the-counter preparation.<ref>{{cite web|url=https://www.fda.gov/AboutFDA/CentersOffices/OfficeofMedicalProductsandTobacco/CDER/ucm106378.htm|access-date=February 9, 2017|title=Prescription to Over-the-Counter (OTC) Switch List|website=[[Food and Drug Administration]]}}</ref> Levocetirizine had previously received authorization by the FDA as a prescription drug in 2007, having already been brought to market throughout much of Europe. In India, a prescription-only drug containing levocetirizine hydrochloride and [[montelukast]] is sold as Crohist MK.
In January 2017, the US [[Food and Drug Administration]] approved an over-the-counter preparation.<ref>{{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}}</ref> 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 ===
=== Brand names ===
{{more citations needed section|date=July 2020}}
{{more citations needed section|date=July 2020}}
[[File:Levocetirizine.png|300px|right|thumb|Different brands ([[Actavis]], [[Glenmark Pharmaceuticals|Glenmark]], [[UCB (company)|UCB]]) Levocetirizine tablets and oral solution.]]
[[File:Levocetirizine.png|260px|right|thumb|Different brands ([[Actavis]], [[Glenmark Pharmaceuticals|Glenmark]], [[UCB (company)|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|thumb|260px|right|Xyzal Tablets 5mg in [[Japan]]]]


Preparations of levocetirizine are sold under the following brand names:
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, Hungary, India, Ireland (also Rinozal), Italy, Japan, Lithuania, Netherlands, Poland, Portugal, Romania, Taiwan, Thailand, Turkey, The Philippines, Serbia, Singapore, Slovakia, Slovenia, South Africa, Spain, Switzerland and UK. On May 25, 2007, the [[United States Food and Drug Administration]] approved Xyzal, where it is co-marketed by [[Sanofi-Aventis]].
* 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.<ref>{{Cite web |title=Xazal 5 mg Comprimidos Recubierno con película |url=https://www.vademecum.es/medicamento-xazal_25890}}</ref>
* Zobral in Cyprus
* Levobert in India
* Zobral in Cyprus.
* Levobert in India.
* Xusal in Germany and Mexico
* Xusal in Germany and Mexico.
* Xozal in Greece
* Degraler in Chile
* Xozal in Greece.
* Allevo in Egypt
* Degraler in Chile.
* Zilola, Histisynt, and Xyzal (UCB) in Hungary
* Allevo in Egypt.
* Zilola, Histisynt, and Xyzal (UCB) in Hungary.
* Alcet, Curin, and Seasonix in Bangladesh
* Alcet, Curin, and Seasonix in Bangladesh.
* Vozet and Uvnil in India
* Vozet and Uvnil in India.
* T-Day Syrup in Pakistan
* T-Day Syrup in Pakistan.
* Curin in Nepal.<ref>{{cite web|url=http://www.beximco-pharma.com/allergic-disorders/147-curin.html |title=Curin |access-date=August 29, 2012 |url-status=dead |archive-url=https://web.archive.org/web/20121022184859/http://beximco-pharma.com/allergic-disorders/147-curin.html |archive-date=October 22, 2012 }}</ref>
* Curin in Nepal.<ref>{{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 }}</ref>
* Zenaro in the Czech Republic and [[Slovak Republic|Slovakia]]
* Zenaro in the Czech Republic and [[Slovak Republic|Slovakia]].
* Xuzal and Zival in Chile
* Xuzal and Zival in Chile.
* Cezera, Levosetil, Robenan, and Xyzal in Serbia.<ref>{{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=August 23, 2020 }}</ref>
* Cezera, Levosetil, Robenan, and Xyzal in Serbia.<ref>{{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 }}</ref>
* Rinozal and Xyzal in Ireland
* Rinozal and Xyzal in Ireland.
* Xycet in Morocco.<ref>{{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 }}</ref>


== References ==
== References ==
{{Reflist}}
{{Reflist}}

== External links ==
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/levocetirizine | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Levocetirizine }}
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/levocetirizine%20dihydrochloride | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Levocetirizine dihydrochloride }}


{{Antihistamines}}
{{Antihistamines}}
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[[Category:Acetic acids]]
[[Category:Acetic acids]]
[[Category:Belgian inventions]]
[[Category:Belgian inventions]]
[[Category:Benzene derivatives]]
[[Category:Chlorobenzene compounds]]
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[[Category:Chloroarenes]]
[[Category:Enantiopure drugs]]
[[Category:Enantiopure drugs]]
[[Category:Ethers]]
[[Category:Ethers]]
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[[Category:Piperazines]]
[[Category:Piperazines]]
[[Category:Wikipedia medicine articles ready to translate]]
[[Category:Wikipedia medicine articles ready to translate]]
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[[Category:Ethanolamines]]

Latest revision as of 10:34, 13 December 2024

Levocetirizine
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
  • 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
FormulaC21H25ClN2O3
Molar mass388.89 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 checkY
  • Key:ZKLPARSLTMPFCP-OAQYLSRUSA-N checkY
 ☒NcheckY (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]

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

[edit]

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

Side effects

[edit]

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

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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

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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

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

Society and culture

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Availability

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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

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Different brands (Actavis, Glenmark, UCB) Levocetirizine tablets and oral solution
Xyzal Tablets 5mg in Japan

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

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  1. ^ "Xyzal Allergy 24HR- levocetirizine dihydrochloride tablet". DailyMed. 10 March 2023. Archived from the original on 30 June 2023. Retrieved 6 July 2023.
  2. ^ a b c d e f "Levocetirizine dihydrochloride- levocetirizine dihydrochloride tablet, film coated". DailyMed. 6 December 2021. Retrieved 9 July 2023.
  3. ^ a b c d e "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. ^ a b 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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