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

Molecular Formula C21H25ClN2O3
Molecular Weight 388.888
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
A randomized, double-blind, crossover comparison among cetirizine, levocetirizine, and ucb 28557 on histamine-induced cutaneous responses in healthy adult volunteers.
2001 Jan
Major role for the carboxylic function of cetirizine and levocetirizine in their binding characteristics to human H1-histamine-receptors.
2002 Apr
Cetirizine and levocetirizine inhibit eotaxin-induced eosinophil transendothelial migration through human dermal or lung microvascular endothelial cells.
2002 Aug
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
The Rx-to-OTC switch of Claritin, Allegra, and Zyrtec: an unprecedented FDA response to petitioners and the protection of public health.
2002 Jun
Gateways to Clinical Trials. June 2002.
2002 Jun
Acute allergy reaction after posterior sub-Tenon's triamcinolone injection in the treatment of intermediate uveitis in the asthmatic patient.
2003
Chronic urticaria: a role for newer immunomodulatory drugs?
2003
Levocetirizine: new preparation. Me-too: simply the active enantiomer of cetirizine.
2003 Oct
Comparison of pharmacokinetics and metabolism of desloratadine, fexofenadine, levocetirizine and mizolastine in humans.
2004 Aug
Levocetirizine: the allergist's arsenal grows larger.
2004 Jul
Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic.
2004 Mar
H1 histamine receptor mediates inflammatory responses in human keratinocytes.
2004 Nov
Chronic urticaria: clinical aspects and focus on a new antihistamine, levocetirizine.
2004 Nov-Dec
Comparison of the effects in the nose and skin of a single dose of desloratadine and levocetirizine over 24 hours.
2004 Oct
[Patient report: allergic rhinitis].
2005
Pharmacological management of allergic rhinitis in the elderly: safety issues with oral antihistamines.
2005
Gateways to clinical trials.
2005 Dec
Desloratadine and levocetirizine improve nasal symptoms, airflow, and allergic inflammation in patients with perennial allergic rhinitis: a pilot study.
2005 Dec
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Levocetirizine as treatment for symptoms of seasonal allergic rhinitis.
2006
Familial aquagenic urticaria and bernard-soulier syndrome.
2006
Effects of levocetirizine as add-on therapy to fluticasone in seasonal allergic rhinitis.
2006 May
Lichenoid eruption associated with the use of nebivolol.
2006 Sep
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:23:35 UTC 2023
Edited
by admin
on Fri Dec 15 16:23:35 UTC 2023
Record UNII
SOD6A38AGA
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
Code System Code Type Description
MERCK INDEX
m3291
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY Merck Index
NSC
758898
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY
CAS
130018-87-0
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY
RXCUI
402349
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY RxNorm
USAN
TT-55
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY
EVMPD
SUB20474
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY
FDA UNII
SOD6A38AGA
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201191
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY
NCI_THESAURUS
C72814
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY
PUBCHEM
9955977
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY
DAILYMED
SOD6A38AGA
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY
EPA CompTox
DTXSID30926567
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY
RS_ITEM_NUM
1359969
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY
DRUG BANK
DBSALT001370
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY
SMS_ID
100000092571
Created by admin on Fri Dec 15 16:23:35 UTC 2023 , Edited by admin on Fri Dec 15 16:23:35 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY