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
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 |
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 Date1.18005118E12 |
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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 Date1.18005118E12 |
|||
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 Date1.18005118E12 |
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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 Date1.1799648E12 |
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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 Date1.18031044E12 |
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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 |
---|---|---|
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
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:23:35 UTC 2023
by
admin
on
Fri Dec 15 16:23:35 UTC 2023
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Record UNII |
SOD6A38AGA
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C29578
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m3291
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