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
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
CNS Activity
Sources: http://www.medscape.com/viewarticle/724851_3https://www.ncbi.nlm.nih.gov/pubmed/18781943
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18336052 |
3.0 nM [Ki] | ||
Target ID: CHEMBL231 |
6.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | XYZAL Approved UseLevocetirizine 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 Date2007 |
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Palliative | XYZAL Approved UseLevocetirizine 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 Date2007 |
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Palliative | XYZAL Approved UseLevocetirizine 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 Date2007 |
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Primary | XYZAL Approved UseFor 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 Date2007 |
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Primary | XYZAL Approved UseFor 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 Date2007 |
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Primary | XYZAL Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.17 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11758635 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11758635 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11564134 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.97 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11758635 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11758635 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11564134 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.83 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11758635 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11758635 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11564134 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11758635 |
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
Dose | Population | Adverse 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%) Sources: Fatigue (2.3%) Asthenia (2.3%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022064s000_ClinPharmR.pdf#page=20 Page: 20.0 |
likely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022064s000_ClinPharmR.pdf#page=20 Page: 20.0 |
likely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022064s000_ClinPharmR.pdf#page=20 Page: 20.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022064s000_ClinPharmR.pdf#page=20 Page: 20.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022064s000_ClinPharmR.pdf#page=20 Page: 20.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022064s000_ClinPharmR.pdf#page=20 Page: 20.0 |
weak | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/022064s000_ClinPharmR.pdf#page=19 Page: 19.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 107.0 |
PubMed
Title | Date | PubMed |
---|---|---|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16120090
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29578
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m3291
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758898
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130018-87-0
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402349
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TT-55
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SUB20474
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100000092571
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ACTIVE MOIETY
SUBSTANCE RECORD