Identification
- Summary
Levocetirizine is an H1-receptor antagonist used to treat symptoms associated with chronic allergic rhinitis and uncomplicated cases of chronic idiopathic urticaria.
- Brand Names
- Xyzal
- Generic Name
- Levocetirizine
- DrugBank Accession Number
- DB06282
- Background
Levocetirizine is a selective histamine H1 antagonist used to treat a variety of allergic symptoms.2,3,4 It is the R enantiomer of cetirizine.4 Levocetirizine has greater affinity for the histamine H1 receptor than cetirizine.4
Levocetirizine was granted FDA approval in 1995.4
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Levocetirizine (DB06282)
- Weight
- Average: 388.89
Monoisotopic: 388.1553704 - Chemical Formula
- C21H25ClN2O3
- Synonyms
- 2-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
- Levocetirizina
- Levocetirizine
Pharmacology
- Indication
Levocetirizine is indicated to treat symptoms of perennial allergic rhinitis and uncomplicated skin manifestations of chronic idiopathic urticaria.4 It is also used over the counter for a variety of mild allergy symptoms.2
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Allergic rhinitis (ar) Combination Product in combination with: Montelukast (DB00471) ••• ••• •••••••• ••••••• •••••• Symptomatic treatment of Chronic idiopathic urticaria •••••••••••• Used in combination for symptomatic treatment of Common cold Combination Product in combination with: Dextromethorphan (DB00514), Ibuprofen (DB01050), Phenylephrine (DB00388) ••• ••• •••••••• •••••• •••••• Used in combination for symptomatic treatment of Nasal congestion Combination Product in combination with: Pseudoephedrine (DB00852) ••• ••• ••••••• Used in combination for symptomatic treatment of Nasal congestion Combination Product in combination with: Pseudoephedrine (DB00852) ••• ••• ••••••• - Contraindications & Blackbox Warnings
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Levocetirizine is a second generation histamine H1 antagonist used to treat various allergic symptoms.2,3,4 It has a long duration of action as it is generally taken once daily, and a wide therapeutic window as animal studies show the maximal nonlethal dose is over 100x a normal dose.4 Patients are cautioned to avoid tasks that require complete alertness, avoid alertness, and use caution in patients with factors predisposing urinary retention.4
- Mechanism of action
Levocetirizine selectively inhibits histamine H1 receptors.4 This action prevents histamine from activating this receptor and causing effects like smooth muscle contraction, increased permeability of vascular endothelium, histidine uptake in basophils, stimulation of cough receptors, and stimulation of flare responses in the nervous system.3
Target Actions Organism AHistamine H1 receptor antagonistinhibitorHumans - Absorption
Following a 5mg oral dose of levocetirizine, a Cmax of 0.27±0.04µg/mL with a Tmax of 0.75±0.50h.1 The AUC of levocetirizine is 2.31±0.50µg*h/mL.1 Taking levocetirizine with food does not affect the AUC but delays Tmax by 1.25 hours and lowers Cmax by 36%.4
- Volume of distribution
The volume of distribution of levocetirizine is 0.33±0.02L/kg.1
- Protein binding
Plasma protein binding of levocetirizine was on average 96.1% 1 hour post dose and 91.9% 6 hours post dose.1
- Metabolism
Levocetirizine is poorly metabolized with 85.8% of an oral dose being excreted as the unchanged drug.1 Levocetirizine can be metabolized to a dihydrodiol (M2), an N-oxide (M3), a hydroxymethoxy derivative (M4), a hydroxy derivative (M5), an O-dealkylated derivative (M6), a taurine conjugate (M8), and an N-dealkylated and aromatic hydroxylated derivative (M9).1 The M5 metabolite can be glucuronidated to form the M1 metabolite and the M9 metabolite can form 4-chloro-4'-hydroxybenzhydryl mercapturates (M10a and M10b).1
Hover over products below to view reaction partners
- Route of elimination
168 hours post dose an average of 85.4% of a radiolabeled dose was recovered with an average of 80.8% in the urine and 9.5% in the feces.1 In the urine, 77% of the dose was recovered as unchanged drug, 0.5% as the M8 and M9 metabolites, 0.4% as the M10a metabolite, 0.4% as the M10b metabolite, 0.3% as the M3 metabolite, 0.3% as the M4 and M5 metabolite, 0.2% as the M2 metabolite, and 0.1% as the M1 metabolite.1 In the feces, 9.0% of the dose was recovered as unchanged drug, 1.0% as the M4 and M5 metabolite, and 0.1% as the M1 metabolite.1
- Half-life
The average half life of levocetirizine is 7.05±1.54 hours.1
- Clearance
The average clearance of levocetirizine is 0.57±0.18mL/min/kg.1
- Adverse Effects
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Patients experiencing an overdose may present with drowsiness.4 Children may become agitated and restless before drowsiness.4 Patients should be treated with supportive measures.4 Dialysis will not assist in removing the drug from the body.4
The maximal nonlethal dose in mice and rats is 240mg/kg.4
- Pathways
Pathway Category Levocetirizine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Levocetirizine is combined with 1,2-Benzodiazepine. Abacavir Abacavir may decrease the excretion rate of Levocetirizine which could result in a higher serum level. Abametapir The serum concentration of Levocetirizine can be increased when it is combined with Abametapir. Aceclofenac Aceclofenac may decrease the excretion rate of Levocetirizine which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Levocetirizine which could result in a higher serum level. - Food Interactions
- Avoid alcohol.
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Levocetirizine dihydrochloride SOD6A38AGA 130018-87-0 PGLIUCLTXOYQMV-GHVWMZMZSA-N - Product Images
- International/Other Brands
- Xusal
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Levocetirizine Dihydrochloride Solution 0.5 mg/1mL Oral Winthrop U.S. 2008-04-02 2017-01-31 US 
Levocetirizine Dihydrochloride Tablet, film coated 5 mg/1 Oral Winthrop U.S. 2007-08-09 2015-10-31 US Xyzal Tablet 5 mg/1 Oral Physicians Total Care, Inc. 2007-11-06 Not applicable US 
Xyzal Tablet, film coated 5 mg/1 Oral Ucb Inc 2007-08-09 2019-01-19 US 
Xyzal Tablet, film coated 5 mg/1 Oral sanofi-aventis U.S. LLC 2007-08-09 2016-05-31 US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Levocetirizine Dihydrochloride Tablet 5 mg/1 Oral A-S Medication Solutions 2015-02-13 Not applicable US Levocetirizine Dihydrochloride Tablet, film coated 5 mg/1 Oral REMEDYREPACK INC. 2020-06-24 Not applicable US Levocetirizine Dihydrochloride Tablet 5 mg/1 Oral bryant ranch prepack 2015-02-13 Not applicable US Levocetirizine Dihydrochloride Tablet 5 mg/1 Oral Perrigo New York Inc 2010-11-26 Not applicable US 
Levocetirizine Dihydrochloride Tablet 5 mg/1 Oral Northwind Pharmaceuticals 2021-01-25 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image 24HR Allergy Relief Tablet, coated 5 mg/1 Oral LEADER/ Cardinal Health 110, Inc. 2018-03-12 Not applicable US ALERINIT FILM-COATED TABLET 5MG Tablet, film coated 5.00 mg Oral GOLDPLUS UNIVERSAL PTE LTD 2021-08-31 Not applicable Singapore 
Allergy Relief Tablet 5 mg/1 Oral YYBA CORP 2020-06-30 Not applicable US Allergy Relief Tablet, coated 5 mg/1 Oral AmerisourceBergen Drug Corporation 2018-04-20 Not applicable US Allergy Relief Tablet, film coated 5 mg/1 Oral Meijer Distribution Inc 2020-02-06 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image AIRPASS 5/10 MG FILM KAPLI TABLET, 30 ADET Levocetirizine dihydrochloride (5 mg) + Montelukast (10 mg) Tablet, coated Oral CELTİS İLAÇ SAN. VE TİC. A.Ş. 2011-02-23 Not applicable Turkey 
AIRPASS 5/10 MG FILM KAPLI TABLET, 90 ADET Levocetirizine dihydrochloride (5 mg) + Montelukast (10 mg) Tablet, coated Oral CELTİS İLAÇ SAN. VE TİC. A.Ş. 2011-02-23 Not applicable Turkey ALERNESS M Levocetirizine dihydrochloride (2.5 mg) + Montelukast sodium (5 mg) Tablet, chewable Oral TECNOQUIMICAS S.A. 2023-10-09 Not applicable Colombia 
ANTISS® D Levocetirizine dihydrochloride (0.05 g) + Phenylephrine hydrochloride (0.1 g) Solution Oral LABORATORIO FRANCO COLOMBIANO - LAFRANCOL S.A.S. 2010-01-25 Not applicable Colombia BREATHEZY - L Levocetirizine dihydrochloride (5 mg) + Montelukast sodium (10 mg) Tablet, coated Oral Msn Laboratories Private Limited 2020-05-19 Not applicable Colombia - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image AlloPAX Levocetirizine dihydrochloride (3 g/3g) + Loratadine (3 g/3g) Kit Transdermal PharmaGenetico LLC 2015-06-30 Not applicable US Clobetasol Propionate 0.05% / Levocetirizine Dihydrochloride 2% Levocetirizine dihydrochloride (2 g/100g) + Clobetasol propionate (0.05 g/100g) Shampoo Topical Sincerus Florida, LLC 2019-05-17 Not applicable US Hydrocortisone 2.5% / Levocetirizine Dihydrochloride 2% Levocetirizine dihydrochloride (2 g/100g) + Hydrocortisone (2.5 g/100g) Cream Topical Sincerus Florida, LLC 2019-05-15 Not applicable US Imiquimod 5% / Levocetirizine Dihydrochloride 1% / Niacinamide 2% Levocetirizine dihydrochloride (1 g/100g) + Imiquimod (5 g/100g) + Nicotinamide (2 g/100g) Gel Topical Sincerus Florida, LLC 2019-05-01 Not applicable US Imiquimod 5% / Levocetirizine Dihydrochloride 1% / Tretinoin 0.05% Levocetirizine dihydrochloride (1 g/100g) + Imiquimod (5 g/100g) + Tretinoin (0.05 g/100g) Gel Topical Sincerus Florida, LLC 2019-05-01 Not applicable US
Categories
- ATC Codes
- R06AE09 — Levocetirizine
- Drug Categories
- Antihistamines for Systemic Use
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Histamine H1 Antagonists, Non-Sedating
- Neurotransmitter Agents
- Piperazine Derivatives
- Piperazines
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- N-alkylpiperazines / Chlorobenzenes / Aralkylamines / Aryl chlorides / Trialkylamines / Amino acids / Monocarboxylic acids and derivatives / Dialkyl ethers / Carboxylic acids / Azacyclic compounds show 5 more
- Substituents
- 1,4-diazinane / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Carbonyl group show 22 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 6U5EA9RT2O
- CAS number
- 130018-77-8
- InChI Key
- ZKLPARSLTMPFCP-OAQYLSRUSA-N
- InChI
- 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
- IUPAC Name
- 2-(2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
- SMILES
- OC(=O)COCCN1CCN(CC1)[C@H](C1=CC=CC=C1)C1=CC=C(Cl)C=C1
References
- General References
- Benedetti MS, Plisnier M, Kaise J, Maier L, Baltes E, Arendt C, McCracken N: Absorption, distribution, metabolism and excretion of [14C]levocetirizine, the R enantiomer of cetirizine, in healthy volunteers. Eur J Clin Pharmacol. 2001 Oct;57(8):571-82. [Article]
- Mosges R, Konig V, Koberlein J: The effectiveness of levocetirizine in comparison with loratadine in treatment of allergic rhinitis--a meta-analysis. Allergol Int. 2011 Dec;60(4):541-6. doi: 10.2332/allergolint.10-OA-0300. Epub 2011 Sep 25. [Article]
- Desager JP, Horsmans Y: Pharmacokinetic-pharmacodynamic relationships of H1-antihistamines. Clin Pharmacokinet. 1995 May;28(5):419-32. doi: 10.2165/00003088-199528050-00006. [Article]
- FDA Approved Drug Products: Levocetirizine Dihydrochloride Tablets and Oral Solution [Link]
- External Links
- Human Metabolome Database
- HMDB0240226
- KEGG Drug
- D07402
- PubChem Compound
- 1549000
- PubChem Substance
- 310264866
- ChemSpider
- 1266001
- BindingDB
- 85030
- 356887
- ChEBI
- 94559
- ChEMBL
- CHEMBL1201191
- ZINC
- ZINC000019364230
- PDBe Ligand
- LCR
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Levocetirizine
- PDB Entries
- 5dqf
- FDA label
- Download (167 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Anti-allergic Agents 1 4 Completed Not Available Perennial Allergic Rhinitis (PAR) 1 4 Completed Not Available Seasonal Allergic Rhinitis 1 4 Completed Basic Science Healthy Subjects (HS) 1 4 Completed Treatment Allergic Reaction 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral 5.00 mg Tablet, chewable Oral 2.5 mg Kit Transdermal Tablet, orally disintegrating Oral 5 mg Solution Oral 0.5 g Solution Oral Syrup Oral 0.05 g Capsule Oral Tablet 5 mg Tablet, film coated Oral Shampoo Topical Capsule Oral 5.00 mg Tablet, coated Oral Tablet Oral Syrup Oral Tablet Gel Topical Solution Oral 0.050 g Solution Oral 0.505 g Tablet Oral 5.00 mg Tablet, effervescent Oral Solution Oral 50.000 mg Tablet, effervescent 5 mg Tablet, chewable Oral Powder Oral Tablet Buccal 5 mg Solution Oral 0.05 g Syrup Oral Solution Oral 0.1 g Tablet Oral 5 mg Tablet, film coated Oral Solution Oral 2.5 mg/5mL Tablet, coated Oral 5 mg/1 Tablet, film coated Oral 5 mg/1 Cream Topical Capsule Oral 5 mg Tablet Oral 500000 mg Tablet, film coated Oral 5 mg/10mg Solution Oral 500 mg Solution Oral 5 mg Capsule, liquid filled Oral 5 mg Syrup Oral 50 mg Syrup Oral 2.5 mg/5ml Solution Oral 50 mg Solution Oral 500000 mg Tablet Oral Kit Topical Syrup Oral 0.1 g Powder, for solution Oral Capsule, liquid filled Oral Capsule, coated Oral Solution Oral 500.000 mg Syrup Oral 50.000 mg Solution Oral 5.000 mg Tablet Oral 5.000 mg Solution Oral 0.5 MG/ML Solution Oral 0.5 mg/1mL Solution / drops Oral 5 MG/ML Tablet Oral 5 mg/1 Solution Oral 5 mg/ml Solution Oral 0.50 mg/ml Solution Oral 500.00 mg Tablet, film coated Oral 5 mg Tablet, coated Oral 5 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5698558 No 1997-12-16 2013-03-24 US US8633194 No 2014-01-21 2027-10-16 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 205-208 http://www.chemspider.com/Chemical-Structure.1266001.html boiling point (°C) 542.1 http://www.chemspider.com/Chemical-Structure.1266001.html - Predicted Properties
Property Value Source Water Solubility 0.0658 mg/mL ALOGPS logP 2.98 ALOGPS logP 0.87 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 3.59 Chemaxon pKa (Strongest Basic) 7.42 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 53.01 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 106.87 m3·mol-1 Chemaxon Polarizability 41.93 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 199.3624895 predictedDarkChem Lite v0.1.0 [M-H]- 186.19106 predictedDeepCCS 1.0 (2019) [M+H]+ 199.6626895 predictedDarkChem Lite v0.1.0 [M+H]+ 188.54904 predictedDeepCCS 1.0 (2019) [M+Na]+ 199.5563895 predictedDarkChem Lite v0.1.0 [M+Na]+ 195.66512 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AntagonistInhibitor
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Ferrer M: Pharmacokinetic evaluation of levocetirizine. Expert Opin Drug Metab Toxicol. 2011 Aug;7(8):1035-47. doi: 10.1517/17425255.2011.590131. Epub 2011 Jun 4. [Article]
- Devillier P, Roche N, Faisy C: Clinical pharmacokinetics and pharmacodynamics of desloratadine, fexofenadine and levocetirizine : a comparative review. Clin Pharmacokinet. 2008;47(4):217-30. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- FDA Approved Drug Products: Levocetirizine Dihydrochloride Tablets and Oral Solution [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Liu X, Du Y, Sun W, Kou J, Yu B: Study on the interaction of levocetirizine dihydrochloride with human serum albumin by molecular spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc. 2009 Dec;74(5):1189-96. doi: 10.1016/j.saa.2009.09.033. Epub 2009 Oct 4. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
- Gene Name
- SLC22A11
- Uniprot ID
- Q9NSA0
- Uniprot Name
- Solute carrier family 22 member 11
- Molecular Weight
- 59970.945 Da
References
- Noguchi S, Nishimura T, Mukaida S, Benet LZ, Nakashima E, Tomi M: Cellular Uptake of Levocetirizine by Organic Anion Transporter 4. J Pharm Sci. 2017 Sep;106(9):2895-2898. doi: 10.1016/j.xphs.2017.03.026. Epub 2017 Apr 4. [Article]
Drug created at March 19, 2008 16:21 / Updated at February 02, 2024 22:53