U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H25ClN2O3
Molecular Weight 388.8885
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOCETIRIZINE

SMILES

c1ccc(cc1)[C@]([H])(c2ccc(cc2)Cl)N3CCN(CC3)CCOCC(=O)O

InChI

InChIKey=ZKLPARSLTMPFCP-OAQYLSRUSA-N
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

HIDE SMILES / InChI
Levocetirizine dihydrochloride is the R enantiomer of cetirizine hydrochloride, a racemic compound with antihistaminic properties. Levocetirizine is a third-generation non-sedative antihistamine indicated for the relief of symptoms associated with seasonal and perennial allergic rhinitis and uncomplicated skin manifestations of chronic idiopathic urticaria. It was developed from the second-generation antihistamine cetirizine. Levocetirizine was approved by the United States Food and Drug Administration on May 25, 2007 and is marketed under the brand XYZAL. Its principal effects are mediated via selective inhibition of H1 receptors. The antihistaminic activity of levocetirizine has been documented in a variety of animal and human models. In vitro binding studies revealed that levocetirizine has an affinity for the human H1-receptor 2-fold higher than that of cetirizine (Ki = 3 nmol/L vs. 6 nmol/L, respectively). The clinical relevance of this finding is unknown.

CNS Activity

Curator's Comment:: Levocetirizine is highly (91–93%) protein bound. It can cross the blood-brain barrier, but typically occupy only 30–50% of the H1 receptors in the cerebral cortex, compared to more than 90% of peripheral H1 receptors

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
XYZAL

Approved Use

Levocetirizine dihydrochloride tablet is a histamine H1-receptor antagonist indicated for: The relief of symptoms associated with seasonal and perennial allergic rhinitis (1.1, 1.2) The treatment of the uncomplicated skin manifestations of chronic idiopathic urticaria (1.3) 1.1 Seasonal Allergic Rhinitis Levocetirizine dihydrochloride tablets are indicated for the relief of symptoms associated with seasonal allergic rhinitis in adults and children 6 years of age and older. 1.2 Perennial Allergic Rhinitis Levocetirizine dihydrochloride tablets are indicated for the relief of symptoms associated with perennial allergic rhinitis in adults and children 6 years of age and older. 1.3 Chronic Idiopathic Urticaria Levocetirizine dihydrochloride tablets are indicated for the treatment of the uncomplicated skin manifestations of chronic idiopathic urticaria in adults and children 6 years of age and older.

Launch Date

1.18005118E12
Palliative
XYZAL

Approved Use

Levocetirizine dihydrochloride tablet is a histamine H1-receptor antagonist indicated for: The relief of symptoms associated with seasonal and perennial allergic rhinitis (1.1, 1.2) The treatment of the uncomplicated skin manifestations of chronic idiopathic urticaria (1.3) 1.1 Seasonal Allergic Rhinitis Levocetirizine dihydrochloride tablets are indicated for the relief of symptoms associated with seasonal allergic rhinitis in adults and children 6 years of age and older. 1.2 Perennial Allergic Rhinitis Levocetirizine dihydrochloride tablets are indicated for the relief of symptoms associated with perennial allergic rhinitis in adults and children 6 years of age and older. 1.3 Chronic Idiopathic Urticaria Levocetirizine dihydrochloride tablets are indicated for the treatment of the uncomplicated skin manifestations of chronic idiopathic urticaria in adults and children 6 years of age and older.

Launch Date

1.18005118E12
Palliative
XYZAL

Approved Use

Levocetirizine dihydrochloride tablet is a histamine H1-receptor antagonist indicated for: The relief of symptoms associated with seasonal and perennial allergic rhinitis (1.1, 1.2) The treatment of the uncomplicated skin manifestations of chronic idiopathic urticaria (1.3) 1.1 Seasonal Allergic Rhinitis Levocetirizine dihydrochloride tablets are indicated for the relief of symptoms associated with seasonal allergic rhinitis in adults and children 6 years of age and older. 1.2 Perennial Allergic Rhinitis Levocetirizine dihydrochloride tablets are indicated for the relief of symptoms associated with perennial allergic rhinitis in adults and children 6 years of age and older. 1.3 Chronic Idiopathic Urticaria Levocetirizine dihydrochloride tablets are indicated for the treatment of the uncomplicated skin manifestations of chronic idiopathic urticaria in adults and children 6 years of age and older.

Launch Date

1.18005118E12
Primary
XYZAL

Approved Use

For the temporary relief of nasal decongestiom due to the commomn cold, hay fever or other upper respiratpry allergies. Temporarily relieves nasal stuffiness. Decongests nasal passages: shrinks swollen membranes. Temporarily restores freer breathing through the nose. Helps decongest sinus openings and passages; temporarily relieves sinus congestion and pressure. Promotes nasal and/or sinus drainage. temporarily relieves sinus congestion and pressure.

Launch Date

1.1799648E12
Primary
XYZAL

Approved Use

For the temporary relief of nasal decongestiom due to the commomn cold, hay fever or other upper respiratpry allergies. Temporarily relieves nasal stuffiness. Decongests nasal passages: shrinks swollen membranes. Temporarily restores freer breathing through the nose. Helps decongest sinus openings and passages; temporarily relieves sinus congestion and pressure. Promotes nasal and/or sinus drainage. temporarily relieves sinus congestion and pressure.

Launch Date

1.18031044E12
Primary
XYZAL

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.17 μg/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCETIRIZINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.27 μg/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCETIRIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
512.25 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCETIRIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.97 μg × h/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCETIRIZINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.31 μg × h/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCETIRIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4136.4 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCETIRIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.83 h
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCETIRIZINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
7.05 h
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCETIRIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7.76 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCETIRIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
4.5%
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCETIRIZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
20 mg 1 times / day multiple, oral
Highest studied dose
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 18–60 years
n = 13
Health Status: unhealthy
Condition: severe urticaria
Age Group: 18–60 years
Population Size: 13
Sources:
5 mg 1 times / day steady, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: steady
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 48-64 years
n = 2
Health Status: unhealthy
Condition: chronic urticaria
Age Group: 48-64 years
Sex: M
Population Size: 2
Sources:
Disc. AE: Hepatotoxicity...
AEs leading to
discontinuation/dose reduction:
Hepatotoxicity (2 patients)
Sources:
5 mg 1 times / day steady, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: steady
Dose: 5 mg, 1 times / day
Sources:
unhealthy, > 12 years
n = 428
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Population Size: 428
Sources:
Disc. AE: Somnolence, Fatigue...
AEs leading to
discontinuation/dose reduction:
Somnolence (2.3%)
Fatigue (2.3%)
Asthenia (2.3%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hepatotoxicity 2 patients
Disc. AE
5 mg 1 times / day steady, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: steady
Dose: 5 mg, 1 times / day
Sources:
unhealthy, 48-64 years
n = 2
Health Status: unhealthy
Condition: chronic urticaria
Age Group: 48-64 years
Sex: M
Population Size: 2
Sources:
Asthenia 2.3%
Disc. AE
5 mg 1 times / day steady, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: steady
Dose: 5 mg, 1 times / day
Sources:
unhealthy, > 12 years
n = 428
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Population Size: 428
Sources:
Fatigue 2.3%
Disc. AE
5 mg 1 times / day steady, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: steady
Dose: 5 mg, 1 times / day
Sources:
unhealthy, > 12 years
n = 428
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Population Size: 428
Sources:
Somnolence 2.3%
Disc. AE
5 mg 1 times / day steady, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: steady
Dose: 5 mg, 1 times / day
Sources:
unhealthy, > 12 years
n = 428
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Population Size: 428
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The acute and sub-chronic effects of levocetirizine, cetirizine, loratadine, promethazine and placebo on cognitive function, psychomotor performance, and weal and flare.
2001
Efficacy and safety of levocetirizine in seasonal allergic rhinitis.
2001
Effect of cetirizine, levocetirizine, and dextrocetirizine on histamine-induced nasal response in healthy adult volunteers.
2001 Apr
Absorption, distribution, metabolism and excretion of [14C]levocetirizine, the R enantiomer of cetirizine, in healthy volunteers.
2001 Oct
Comparison of the effects of levocetirizine and loratadine on histamine-induced wheal, flare, and itch in human skin.
2001 Oct
The new antihistamines--desloratadine and levocetirizine: a review.
2002 Dec
Comparative pharmacology of H1 antihistamines: clinical relevance.
2002 Dec 16
Lack of effect of single and repeated doses of levocetirizine, a new antihistamine drug, on cognitive and psychomotor functions in healthy volunteers.
2002 Jul
The Rx-to-OTC switch of Claritin, Allegra, and Zyrtec: an unprecedented FDA response to petitioners and the protection of public health.
2002 Jun
Chronic urticaria: a role for newer immunomodulatory drugs?
2003
[H1 histamine antagonists].
2003 Apr
Driving ability after acute and sub-chronic administration of levocetirizine and diphenhydramine: a randomized, double-blind, placebo-controlled trial.
2003 Aug
Assessing satisfaction with desloratadine and fexofenadine in allergy patients who report dissatisfaction with loratadine.
2003 Aug 13
[Safety of new antihistamines].
2003 Jun
[Clinical aspects of anti-inflammatory action of antihistamines].
2003 Jun
Acute and subchronic effects of levocetirizine and diphenhydramine on memory functioning, psychomotor performance, and mood.
2003 Mar
Histamine H1 receptor antagonism by cetirizine in isolated guinea pig tissues: influence of receptor reserve and dissociation kinetics.
2003 May 30
Comparison of the effects of desloratadine and levocetirizine on histamine-induced wheal, flare and itch in human skin.
2003 Oct
Twenty-four-hour activity and consistency of activity of levocetirizine and desloratadine in the skin.
2003 Oct
Compared pharmacological characteristics in humans of racemic cetirizine and levocetirizine, two histamine H1-receptor antagonists.
2003 Oct 1
Levocetirizine is effective for symptom relief including nasal congestion in adolescent and adult (PAR) sensitized to house dust mites.
2003 Sep
Comparison of pharmacokinetics and metabolism of desloratadine, fexofenadine, levocetirizine and mizolastine in humans.
2004 Aug
Antihistamines: do they work? Further well-controlled trials involving larger samples are needed.
2004 Aug
Levocetirizine: the allergist's arsenal grows larger.
2004 Jul
Single and short-term dosing effects of levocetirizine on adenosine monophosphate bronchoprovocation in atopic asthma.
2004 Jul
Levocetirizine: a new selective H1 receptor antagonist for use in allergic disorders.
2004 May
Modern histamine H1-receptor antagonists in the unified airway.
2004 Sep
[Patient report: allergic rhinitis].
2005
Quantitative determination of cetirizine enantiomers in guinea pig plasma, brain tissue and microdialysis samples using liquid chromatography/tandem mass spectrometry.
2005
A new antihistamine levocetirizine inhibits eosinophil adhesion to vascular cell adhesion molecule-1 under flow conditions.
2005 Aug
Retrospective population pharmacokinetics of levocetirizine in atopic children receiving cetirizine: the ETAC study.
2005 Jan
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Potential of levocetirizine in the relief of nasal congestion.
2005 Jun
Costs associated with persistent allergic rhinitis are reduced by levocetirizine.
2005 Jun
Population pharmacokinetics of levocetirizine in very young children: the pediatricians' perspective.
2005 Mar
Fixed drug eruption: a novel side-effect of levocetirizine.
2005 Sep
Effect of levocetirizine on the contraction induced by histamine on isolated rabbit bronchioles from precision-cut lung slices.
2006
Facial thermography is a sensitive tool to determine antihistaminic activity: comparison of levocetirizine and fexofenadine.
2006 Aug
Changes in pH differently affect the binding properties of histamine H1 receptor antagonists.
2006 Jan 20
Gateways to clinical trials.
2006 Jun
Effects of levocetirizine as add-on therapy to fluticasone in seasonal allergic rhinitis.
2006 May
Stereoselective pharmacokinetics of cetirizine in the guinea pig: role of protein binding.
2006 Sep
Patents

Sample Use Guides

Allergic Rhinitis: 5 mg once daily; alternatively, 2.5 mg once daily may be adequate for some patients. Chronic Idiopathic Urticaria: 5 mg once daily; alternatively, 2.5 mg once daily may be adequate for some patients.
Route of Administration: Oral
Equilibrium binding experiments on CHO cells expressing H1 receptor were performed using [3H]mepyramine as a radiolabel ligand.
Name Type Language
LEVOCETIRIZINE
INN   MART.   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
(R)-CETIRIZINE
Common Name English
CETIRIZINE (R)-FORM
MI  
Common Name English
XAZAL
Brand Name English
CETIRIZINE, (R)-
Common Name English
LEVOCETIRIZINE [VANDF]
Common Name English
LEVOCETIRIZINE [USAN]
Common Name English
(-)-CETIRIZINE
Common Name English
ACETIC ACID, (2-(4-((R)-(4-CHLOROPHENYL)PHENYLMETHYL)-1-PIPERAZINYL)ETHOXY)-
Common Name English
LEVOCETIRIZINE [MART.]
Common Name English
CETIRIZINE (R)-FORM [MI]
Common Name English
ACETIC ACID, (2-(4-((R)-(4-CHLOROPHENYL)PHENYLMETHYL)-1-PIPERAZINYL)ETHOXY)
Common Name English
CETIRIZINE, (-)-
Common Name English
LEVOCETIRIZINE [INN]
Common Name English
(2-(4-((R)-(4-CHLOROPHENYL)PHENYLMETHYL)PIPERAZIN-1-YL)ETHOXY)ACETIC ACID
Systematic Name English
LEVOCETIRIZINE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC R06AE09
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
WHO-VATC QR06AE09
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
NCI_THESAURUS C29578
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
NDF-RT N0000175587
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
NDF-RT N0000000190
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
LIVERTOX 551
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
Code System Code Type Description
LACTMED
Levocetirizine
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
RXCUI
356887
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY RxNorm
CAS
130018-77-8
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
INN
7700
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
WIKIPEDIA
LEVOCETIRIZINE
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
NCI_THESAURUS
C66008
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201191
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
DRUG BANK
DB06282
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
EVMPD
SUB08467MIG
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
FDA UNII
6U5EA9RT2O
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
MESH
C472067
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
MERCK INDEX
M3291
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY Merck Index
IUPHAR
1214
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
PUBCHEM
1549000
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
EPA CompTox
130018-77-8
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
DRUG CENTRAL
1566
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY