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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H25ClN2O3
Molecular Weight 388.888
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOCETIRIZINE

SMILES

OC(=O)COCCN1CCN(CC1)[C@H](C2=CC=CC=C2)C3=CC=C(Cl)C=C3

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 is the active enantiomer of cetirizine. It is inverse agonist of H1 receptors. Levocetirizine hydrochloride was approved for treatment of Allergic Rhinitis and Chronic Idiopathic Urticaria.

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

2007
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

2007
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

2007
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

2007
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

2007
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
Efficacy and safety of levocetirizine in seasonal allergic rhinitis.
2001
Cetirizine and levocetirizine inhibit eotaxin-induced eosinophil transendothelial migration through human dermal or lung microvascular endothelial cells.
2002 Aug
Comparative pharmacology of H1 antihistamines: clinical relevance.
2002 Dec 16
A double-blind, randomized, single-dose, crossover comparison of levocetirizine with ebastine, fexofenadine, loratadine, mizolastine, and placebo: suppression of histamine-induced wheal-and-flare response during 24 hours in healthy male subjects.
2002 Feb
Antihistamines in late-phase clinical development for allergic disease.
2002 Feb
Binding characteristics of cetirizine and levocetirizine to human H(1) histamine receptors: contribution of Lys(191) and Thr(194).
2002 Feb
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
[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
Compared pharmacological characteristics in humans of racemic cetirizine and levocetirizine, two histamine H1-receptor antagonists.
2003 Oct 1
Recovery of nitric oxide from acetylcholine-mediated vasodilatation in human skin in vivo.
2004 Apr-May
Antihistamines: do they work? Further well-controlled trials involving larger samples are needed.
2004 Aug
Comparative clinical efficacy, onset and duration of action of levocetirizine and desloratadine for symptoms of seasonal allergic rhinitis in subjects evaluated in the Environmental Exposure Unit (EEU).
2004 Feb
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
Gateways to clinical trials.
2004 Mar
Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic.
2004 Mar
Gateways to clinical trials.
2004 Nov
Chronic urticaria: clinical aspects and focus on a new antihistamine, levocetirizine.
2004 Nov-Dec
Levocetirizine improves quality of life and reduces costs in long-term management of persistent allergic rhinitis.
2004 Oct
A new antihistamine levocetirizine inhibits eosinophil adhesion to vascular cell adhesion molecule-1 under flow conditions.
2005 Aug
Levocetirizine: pharmacokinetics and pharmacodynamics in children age 6 to 11 years.
2005 Aug
Desloratadine and levocetirizine improve nasal symptoms, airflow, and allergic inflammation in patients with perennial allergic rhinitis: a pilot study.
2005 Dec
Levocetirizine improves nasal symptoms and airflow in patients with persistent allergic rhinitis: a pilot study.
2005 Jan
A treatment for allergic rhinitis: a view on the role of levocetirizine.
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Population pharmacokinetics of levocetirizine in very young children: the pediatricians' perspective.
2005 Mar
Levocetirizine in children: evidenced efficacy and safety in a 6-week randomized seasonal allergic rhinitis trial.
2005 May
Bacillus clausii effects in children with allergic rhinitis.
2005 May
Histamine H1 receptor occupancy and pharmacodynamics of second generation H1-antihistamines.
2005 Sep
Effect of levocetirizine on the contraction induced by histamine on isolated rabbit bronchioles from precision-cut lung slices.
2006
Levocetirizine as treatment for symptoms of seasonal allergic rhinitis.
2006
Familial aquagenic urticaria and bernard-soulier syndrome.
2006
Facial thermography is a sensitive tool to determine antihistaminic activity: comparison of levocetirizine and fexofenadine.
2006 Aug
Gateways to clinical trials.
2006 Jun
Chiral separation of cetirizine by capillary electrophoresis.
2006 Jun
Levocetirizine in the treatment of chronic idiopathic urticaria: a randomized, double-blind, placebo-controlled study.
2006 Mar
Gateways to clinical trials.
2006 May
Effects of levocetirizine as add-on therapy to fluticasone in seasonal allergic rhinitis.
2006 May
Patents

Sample Use Guides

Adults and children 12 years of age and older: 5 mg once daily in the evening. Children 6 to 11 years of age: 2.5 mg once daily in the evening. Children 6 months to 5 years of age: 1.25 mg (1/2 teaspoon oral solution)[2.5mL] once daily in the evening.
Route of Administration: Oral
Eosinophils isolated from normal subjects were pre-incubated with a concentration range of levocetirizine (10(-6)-10(-10) m) or negative dilution control. Levocetirizine significantly inhibited resting eosinophil adhesion to recombinant human vascular cell adhesion molecule-1 (rhVCAM-1) with maximal effect at 10(-8) M with an EC(50) of 10(-9) m.
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 [WHO-DD]
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
Classification Tree Code System Code
WHO-ATC R06AE09
Created by admin on Fri Dec 15 15:35:23 GMT 2023 , Edited by admin on Fri Dec 15 15:35:23 GMT 2023
WHO-VATC QR06AE09
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NCI_THESAURUS C29578
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NDF-RT N0000175587
Created by admin on Fri Dec 15 15:35:23 GMT 2023 , Edited by admin on Fri Dec 15 15:35:23 GMT 2023
NDF-RT N0000000190
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LIVERTOX 551
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Code System Code Type Description
SMS_ID
100000092505
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PRIMARY
LACTMED
Levocetirizine
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PRIMARY
RXCUI
356887
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PRIMARY RxNorm
CAS
130018-77-8
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PRIMARY
INN
7700
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PRIMARY
DAILYMED
6U5EA9RT2O
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PRIMARY
WIKIPEDIA
LEVOCETIRIZINE
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PRIMARY
NCI_THESAURUS
C66008
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PRIMARY
ChEMBL
CHEMBL1201191
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PRIMARY
DRUG BANK
DB06282
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PRIMARY
USAN
TT-54
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PRIMARY
EVMPD
SUB08467MIG
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PRIMARY
FDA UNII
6U5EA9RT2O
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PRIMARY
MESH
C472067
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PRIMARY
MERCK INDEX
m3291
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PRIMARY Merck Index
IUPHAR
1214
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PRIMARY
PUBCHEM
1549000
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PRIMARY
EPA CompTox
DTXSID60156294
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PRIMARY
DRUG CENTRAL
1566
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PRIMARY