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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H25ClN2O3.2ClH
Molecular Weight 461.81
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOCETIRIZINE DIHYDROCHLORIDE

SMILES

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

InChI

InChIKey=PGLIUCLTXOYQMV-GHVWMZMZSA-N
InChI=1S/C21H25ClN2O3.2ClH/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);2*1H/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
The acute and sub-chronic effects of levocetirizine, cetirizine, loratadine, promethazine and placebo on cognitive function, psychomotor performance, and weal and flare.
2001
Absorption and disposition of levocetirizine, the eutomer of cetirizine, administered alone or as cetirizine to healthy volunteers.
2001 Aug
Comparison of the effects of levocetirizine and loratadine on histamine-induced wheal, flare, and itch in human skin.
2001 Oct
Major role for the carboxylic function of cetirizine and levocetirizine in their binding characteristics to human H1-histamine-receptors.
2002 Apr
24-hour efficacy of once-daily desloratadine therapy in patients with seasonal allergic rhinitis [ISRCTN32042139].
2002 Aug 5
The new antihistamines--desloratadine and levocetirizine: a review.
2002 Dec
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
Binding characteristics of cetirizine and levocetirizine to human H(1) histamine receptors: contribution of Lys(191) and Thr(194).
2002 Feb
Lack of effect of single and repeated doses of levocetirizine, a new antihistamine drug, on cognitive and psychomotor functions in healthy volunteers.
2002 Jul
[Safety of new antihistamines].
2003 Jun
Acute and subchronic effects of levocetirizine and diphenhydramine on memory functioning, psychomotor performance, and mood.
2003 Mar
Levocetirizine: new preparation. Me-too: simply the active enantiomer of cetirizine.
2003 Oct
Gateways to clinical trials.
2003 Sep
Chronic urticaria: aetiology, management and current and future treatment options.
2004
Comparative effects of desloratadine, fexofenadine, and levocetirizine on nasal adenosine monophosphate challenge in patients with perennial allergic rhinitis.
2004 Apr
A direct comparison of the efficacy of antihistamines in SAR and PAR: randomised, placebo-controlled studies with levocetirizine and loratadine using an environmental exposure unit - the Vienna Challenge Chamber (VCC).
2004 Jun
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
Pharmacological management of allergic rhinitis in the elderly: safety issues with oral antihistamines.
2005
Efficacy and safety of levocetirizine on symptoms and health-related quality of life of children with perennial allergic rhinitis: a double-blind, placebo-controlled randomized clinical trial.
2005 Aug
A new antihistamine levocetirizine inhibits eosinophil adhesion to vascular cell adhesion molecule-1 under flow conditions.
2005 Aug
Gateways to clinical trials.
2005 Dec
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Bacillus clausii effects in children with allergic rhinitis.
2005 May
Fixed drug eruption: a novel side-effect of levocetirizine.
2005 Sep
Fixed drug eruption due to levocetirizine.
2005 Sep-Oct
Effect of levocetirizine on the contraction induced by histamine on isolated rabbit bronchioles from precision-cut lung slices.
2006
Levocetirizine for treatment of immediate and delayed mosquito bite reactions.
2006
Familial aquagenic urticaria and bernard-soulier syndrome.
2006
Pathophysiology of nasal obstruction and meta-analysis of early and late effects of levocetirizine.
2006 Aug
Facial thermography is a sensitive tool to determine antihistaminic activity: comparison of levocetirizine and fexofenadine.
2006 Aug
Gateways to clinical trials.
2006 Jan-Feb
Levocetirizine improves health-related quality of life and health status in persistent allergic rhinitis.
2006 Oct
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 DIHYDROCHLORIDE
ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
Levocetirizine dihydrochloride [WHO-DD]
Common Name English
LEVOCETIRIZINE DIHYDROCHLORIDE [USAN]
Common Name English
LEVOCETIRIZINE HYDROCHLORIDE [MART.]
Common Name English
CETIRIZINE (R)-FORM DIHYDROCHLORIDE
MI  
Common Name English
LEVOCETIRIZINE DIHYDROCHLORIDE [ORANGE BOOK]
Common Name English
LEVOCETIRIZINE DIHYDROCHLORIDE [VANDF]
Common Name English
ACETIC ACID, (2-(4-((R)-(4-CHLOROPHENYL)PHENYLMETHYL)-1-PIPERAZINYL)ETHOXY)-, DIHYDROCHLORIDE
Common Name English
CETIRIZINE (R)-FORM DIHYDROCHLORIDE [MI]
Common Name English
LEVOCETIRIZINE HYDROCHLORIDE [JAN]
Common Name English
LEVOCETIRIZINE DIHYDROCHLORIDE [USP MONOGRAPH]
Common Name English
UCB-28556
Code English
XYZAL
Brand Name English
LEVOCETIRIZINE DIHYDROCHLORIDE [USP-RS]
Common Name English
(2-{4-[(R)-(4-Chlorophenyl)phenylmethyl]piperazin-1-yl}ethoxy)acetic acid dihydrochloride
Systematic Name English
NSC-758898
Code English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 16:23:35 GMT 2023 , Edited by admin on Fri Dec 15 16:23:35 GMT 2023
Code System Code Type Description
MERCK INDEX
m3291
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PRIMARY Merck Index
NSC
758898
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PRIMARY
CAS
130018-87-0
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PRIMARY
RXCUI
402349
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PRIMARY RxNorm
USAN
TT-55
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PRIMARY
EVMPD
SUB20474
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PRIMARY
FDA UNII
SOD6A38AGA
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PRIMARY
ChEMBL
CHEMBL1201191
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PRIMARY
NCI_THESAURUS
C72814
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PRIMARY
PUBCHEM
9955977
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PRIMARY
DAILYMED
SOD6A38AGA
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PRIMARY
EPA CompTox
DTXSID30926567
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PRIMARY
RS_ITEM_NUM
1359969
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PRIMARY
DRUG BANK
DBSALT001370
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PRIMARY
SMS_ID
100000092571
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PRIMARY