Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C21H25ClN2O3 |
| Molecular Weight | 388.888 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)COCCN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=C(Cl)C=C3
InChI
InChIKey=ZKLPARSLTMPFCP-UHFFFAOYSA-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)
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/cetirizine.html
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/cetirizine.html
Cetirizine, a human metabolite of hydroxyzine, is an antihistamine; its principal effects are mediated via selective inhibition of peripheral H1 receptors. It is indicated for the relief of nasal and non-nasal symptoms associated with seasonal or perennial allergic rhinitis, hay fever and chronic idiopathic urticaria. Commonly reported adverse reactions of cetirizine include headache, dry mouth and drowsiness or fatigue. Pharmacokinetic interaction studies with Cetirizine in adults were conducted with pseudoephedrine, antipyrine, ketoconazole, erythromycin and azithromycin. No interactions were observed.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 8.2 null [pKi] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | ZYRTEC HIVES RELIEF Approved UseTablets should be administered when both the antihistaminic properties of cetirizine hydrochloride and the nasal decongestant properties of pseudoephedrine hydrochloride are desired. Launch Date1995 |
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| Palliative | ZYRTEC HIVES RELIEF Approved UseTablets should be administered when both the antihistaminic properties of cetirizine hydrochloride and the nasal decongestant properties of pseudoephedrine hydrochloride are desired. Launch Date1995 |
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| Palliative | ZYRTEC HIVES RELIEF Approved UseUses temporarily relieves these symptoms due to hay fever or other upper respiratory allergies: •runny nose •sneezing •itchy, watery eyes •itching of the nose or throat Launch Date1995 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
311 ng/mL |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CETIRIZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
978.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2571627/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CETIRIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6375.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2571627/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CETIRIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
8.3 h |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CETIRIZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
6.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2571627/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CETIRIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7% |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CETIRIZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
180 mg single, oral Overdose |
unhealthy, 18 months n = 1 Health Status: unhealthy Age Group: 18 months Sex: M Population Size: 1 Sources: |
|
270 mg single, oral Overdose |
unhealthy, 18 years n = 1 Health Status: unhealthy Age Group: 18 years Sex: F Population Size: 1 Sources: |
Other AEs: Metabolic acidosis, Hypokalemia... Other AEs: Metabolic acidosis (grade 5, 1 patient) Sources: Hypokalemia (grade 5, 1 patient) |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, 18 years n = 1 Health Status: unhealthy Condition: allergic rhinitis Age Group: 18 years Sex: F Population Size: 1 Sources: |
Disc. AE: Delusions, Depression... AEs leading to discontinuation/dose reduction: Delusions (1 patient) Sources: Depression (1 patient) |
2.5 mg 1 times / day multiple, oral Dose: 2.5 mg, 1 times / day Route: oral Route: multiple Dose: 2.5 mg, 1 times / day Sources: |
unhealthy, 23 months n = 1 Health Status: unhealthy Condition: chronic rhinitis Age Group: 23 months Sex: M Population Size: 1 Sources: |
Disc. AE: Insomnia... AEs leading to discontinuation/dose reduction: Insomnia (1 patient) Sources: |
10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
Other AEs: Dyspepsia, Feeling hot... Other AEs: Dyspepsia (1%) Sources: Feeling hot (1%) Dysgeusia (1%) Headache (1%) Paresthesia (1%) Presyncope (1%) Hyperhidrosis (1%) |
60 mg single, oral Overdose |
healthy, 4 years n = 1 Health Status: healthy Age Group: 4 years Sex: M Population Size: 1 Sources: |
Other AEs: Drowsiness, Sedation... Other AEs: Drowsiness (severe, 1 patient) Sources: Sedation (1 patient) |
50 mg 1 times / day multiple, oral Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, 46 years n = 1 Health Status: unhealthy Condition: chronic idiopathic urticaria Age Group: 46 years Sex: M Population Size: 1 Sources: |
|
5 mg 1 times / day multiple, oral Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy, 6 years n = 1 Health Status: unhealthy Condition: allergic rhinitis Age Group: 6 years Sex: M Population Size: 1 Sources: |
Disc. AE: Dystonic reaction... AEs leading to discontinuation/dose reduction: Dystonic reaction (1 patient) Sources: |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 24 |
unhealthy, > 12 years n = 2034 Health Status: unhealthy Age Group: > 12 years Sex: M+F Population Size: 2034 Sources: Page: p. 24 |
Other AEs: Somnolence, Fatigue... Other AEs: Somnolence (13.7%) Sources: Page: p. 24Fatigue (5.9%) Dry mouth (5%) Dizziness (2%) Pharyngitis (2%) |
0.24 % 2 times / day multiple, ophthalmic Recommended Dose: 0.24 %, 2 times / day Route: ophthalmic Route: multiple Dose: 0.24 %, 2 times / day Sources: |
unhealthy, adult n = 511 Health Status: unhealthy Condition: ocular itching Age Group: adult Population Size: 511 Sources: |
Other AEs: Ocular hyperemia, Visual acuity reduced... Other AEs: Ocular hyperemia (2%) Sources: Visual acuity reduced (0.6%) Conjunctival hyperemia (5.3%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Hypokalemia | grade 5, 1 patient | 270 mg single, oral Overdose |
unhealthy, 18 years n = 1 Health Status: unhealthy Age Group: 18 years Sex: F Population Size: 1 Sources: |
| Metabolic acidosis | grade 5, 1 patient | 270 mg single, oral Overdose |
unhealthy, 18 years n = 1 Health Status: unhealthy Age Group: 18 years Sex: F Population Size: 1 Sources: |
| Delusions | 1 patient Disc. AE |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, 18 years n = 1 Health Status: unhealthy Condition: allergic rhinitis Age Group: 18 years Sex: F Population Size: 1 Sources: |
| Depression | 1 patient Disc. AE |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, 18 years n = 1 Health Status: unhealthy Condition: allergic rhinitis Age Group: 18 years Sex: F Population Size: 1 Sources: |
| Insomnia | 1 patient Disc. AE |
2.5 mg 1 times / day multiple, oral Dose: 2.5 mg, 1 times / day Route: oral Route: multiple Dose: 2.5 mg, 1 times / day Sources: |
unhealthy, 23 months n = 1 Health Status: unhealthy Condition: chronic rhinitis Age Group: 23 months Sex: M Population Size: 1 Sources: |
| Dysgeusia | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
| Dyspepsia | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
| Feeling hot | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
| Headache | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
| Hyperhidrosis | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
| Paresthesia | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
| Presyncope | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
| Sedation | 1 patient | 60 mg single, oral Overdose |
healthy, 4 years n = 1 Health Status: healthy Age Group: 4 years Sex: M Population Size: 1 Sources: |
| Drowsiness | severe, 1 patient | 60 mg single, oral Overdose |
healthy, 4 years n = 1 Health Status: healthy Age Group: 4 years Sex: M Population Size: 1 Sources: |
| Dystonic reaction | 1 patient Disc. AE |
5 mg 1 times / day multiple, oral Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy, 6 years n = 1 Health Status: unhealthy Condition: allergic rhinitis Age Group: 6 years Sex: M Population Size: 1 Sources: |
| Somnolence | 13.7% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 24 |
unhealthy, > 12 years n = 2034 Health Status: unhealthy Age Group: > 12 years Sex: M+F Population Size: 2034 Sources: Page: p. 24 |
| Dizziness | 2% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 24 |
unhealthy, > 12 years n = 2034 Health Status: unhealthy Age Group: > 12 years Sex: M+F Population Size: 2034 Sources: Page: p. 24 |
| Pharyngitis | 2% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 24 |
unhealthy, > 12 years n = 2034 Health Status: unhealthy Age Group: > 12 years Sex: M+F Population Size: 2034 Sources: Page: p. 24 |
| Dry mouth | 5% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 24 |
unhealthy, > 12 years n = 2034 Health Status: unhealthy Age Group: > 12 years Sex: M+F Population Size: 2034 Sources: Page: p. 24 |
| Fatigue | 5.9% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 24 |
unhealthy, > 12 years n = 2034 Health Status: unhealthy Age Group: > 12 years Sex: M+F Population Size: 2034 Sources: Page: p. 24 |
| Visual acuity reduced | 0.6% | 0.24 % 2 times / day multiple, ophthalmic Recommended Dose: 0.24 %, 2 times / day Route: ophthalmic Route: multiple Dose: 0.24 %, 2 times / day Sources: |
unhealthy, adult n = 511 Health Status: unhealthy Condition: ocular itching Age Group: adult Population Size: 511 Sources: |
| Ocular hyperemia | 2% | 0.24 % 2 times / day multiple, ophthalmic Recommended Dose: 0.24 %, 2 times / day Route: ophthalmic Route: multiple Dose: 0.24 %, 2 times / day Sources: |
unhealthy, adult n = 511 Health Status: unhealthy Condition: ocular itching Age Group: adult Population Size: 511 Sources: |
| Conjunctival hyperemia | 5.3% | 0.24 % 2 times / day multiple, ophthalmic Recommended Dose: 0.24 %, 2 times / day Route: ophthalmic Route: multiple Dose: 0.24 %, 2 times / day Sources: |
unhealthy, adult n = 511 Health Status: unhealthy Condition: ocular itching Age Group: adult Population Size: 511 Sources: |
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 |
|
| Efficacy and safety of levocetirizine in seasonal allergic rhinitis. | 2001 |
|
| Cetirizine/pseudoephedrine. | 2001 |
|
| [The effect of second generation histamine antagonists on the heart]. | 2001 |
|
| Is it Crohn's disease? A severe systemic granulomatous reaction to sulfasalazine in patient with rheumatoid arthritis. | 2001 |
|
| Absorption and disposition of levocetirizine, the eutomer of cetirizine, administered alone or as cetirizine to healthy volunteers. | 2001 Aug |
|
| [The allergic pregnant woman]. | 2001 Dec |
|
| Comparative onset of action and symptom relief with cetirizine, loratadine, or placebo in an environmental exposure unit in subjects with seasonal allergic rhinitis: confirmation of a test system. | 2001 Dec |
|
| A double-blinded, randomized, placebo-controlled trial of cetirizine in preventing the onset of asthma in children with atopic dermatitis: 18 months' treatment and 18 months' posttreatment follow-up. | 2001 Dec |
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| Antihistamines and the torsade de point in children with allergic rhinitis. | 2001 Jul-Aug |
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| Efficacy and safety of an oral formulation of cetirizine and prolonged-release pseudoephedrine versus xylometazoline nasal spray in nasal congestion. | 2001 Nov |
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| Inhibition of depolarization-induced [3H]noradrenaline release from SH-SY5Y human neuroblastoma cells by some second-generation H(1) receptor antagonists through blockade of store-operated Ca(2+) channels (SOCs). | 2001 Nov 1 |
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| [Efficacy and safety of fexofenadine and cetirizine in the treatment of allergic rhinitis]. | 2001 Nov-Dec |
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| Multiwavelength spectrophotometric resolution of the micro-equilibria of cetirizine. | 2001 Oct |
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| Preclinical comparison of ebastine and other second generation H1-antihistamines. | 2001 Oct |
|
| Absorption, distribution, metabolism and excretion of [14C]levocetirizine, the R enantiomer of cetirizine, in healthy volunteers. | 2001 Oct |
|
| Effects of topical corticosteroid and combined mediator blockade on domiciliary and laboratory measurements of nasal function in seasonal allergic rhinitis. | 2001 Oct |
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| The costs of nonsedating antihistamine therapy for allergic rhinitis in managed care: an updated analysis. | 2001 Oct |
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| Comparison of the effects of levocetirizine and loratadine on histamine-induced wheal, flare, and itch in human skin. | 2001 Oct |
|
| Dissociable effects of histamine H1 antagonists on reaction-time performance in rats. | 2001 Oct-Nov |
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| Antiallergic/antiasthmatic effect of novel antiallergic hexapeptide-95/220 in various experimental models. | 2001 Sep |
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| Cetirizine inhibits skin reactions but not mediator release in immediate and developing late-phase allergic cutaneous reactions. A double-blind, placebo-controlled study. | 2001 Sep |
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| Long-term cetirizine treatment reduces allergic symptoms and drug prescriptions in children with mite allergy. | 2001 Sep |
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| Serum tryptase in allergic rhinitis: effect of cetirizine and fluticasone propionate treatment. | 2001 Sep-Oct |
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| Photosensitivity disorders: cause, effect and management. | 2002 |
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| [Comparative antihistamine and anti-allergic effects of various antihistamine preparations]. | 2002 |
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| Displacement of histamine from liver cells and cell components by ligands for cytochromes P450. | 2002 |
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| Effects of antihistamines on leukotriene and cytokine release from dispersed nasal polyp cells. | 2002 |
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| [The first case of lasting pigmented toxidermia induced by cetirizine (Zyrtec, Virlix) and ticlopidine]. | 2002 Apr |
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| Major role for the carboxylic function of cetirizine and levocetirizine in their binding characteristics to human H1-histamine-receptors. | 2002 Apr |
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| Binding characteristics of [3H]levocetirizine to cloned human H1-histamine-receptors expressed in CHO cells. | 2002 Apr |
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| Acute hepatitis associated with cetirizine intake. | 2002 Apr |
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| Are antihistamines useful in managing asthma? | 2002 Feb |
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| 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 |
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| Binding characteristics of cetirizine and levocetirizine to human H(1) histamine receptors: contribution of Lys(191) and Thr(194). | 2002 Feb |
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| Cardiotoxicity of new antihistamines and cisapride. | 2002 Feb 28 |
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| Titrimetric and spectrophotometric assay of some antihistamines through the determination of the chloride of their hydrochlorides. | 2002 Jan |
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| Randomised controlled trial of butterbur and cetirizine for treating seasonal allergic rhinitis. | 2002 Jan 19 |
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| Applications of derivative UV spectrophotometry for the determinations of cetirizine dihydrochloride in pharmaceutical preparations. | 2002 Jan-Feb |
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| Gateways to clinical trials. | 2002 Jan-Feb |
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| Lack of effect of single and repeated doses of levocetirizine, a new antihistamine drug, on cognitive and psychomotor functions in healthy volunteers. | 2002 Jul |
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| Comparison of cetirizine, ebastine and loratadine in the treatment of immediate mosquito-bite allergy. | 2002 Jun |
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| [Skin prick test results in snoring and sleep apnea patients]. | 2002 Mar |
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| Effects of emedastine and cetirizine, alone and with alcohol, on actual driving of males and females. | 2002 Mar |
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| Early treatment of perennial rhinitis with budesonide or cetirizine and its effect on long-term outcome. | 2002 Mar |
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| Comparative activity of cetirizine and mizolastine on histamine-induced skin wheal and flare responses at 24 h. | 2002 Mar |
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| Gateways to clinical trials. | 2002 May |
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| Urticarial intolerance reaction to cetirizine. | 2002 May |
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| Development and validation of a HPLC method for the determination of cetirizine in pharmaceutical dosage forms. | 2002 May |
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| Treating seasonal allergic rhinitis. Trial does not show that there is no difference between butterbur and cetirizine. | 2002 May 25 |
Sample Use Guides
1 to 2 tablets once daily depending upon severity of symptoms; do not take more than 2 tablets in 24 hours
Route of Administration:
Oral
Cetirizine (10 micrograms/ml) significantly enhanced IL-1 release by human monocytes stimulated by a weak LPS concentration (1 microgram/ml) but could not modify the maximal increase of IL-1 release induced by 10 micrograms/ml of LPS. It did not exert any effect on resting cells. Cetirizine (0.1-10 micrograms/ml) enhanced PGE2 release by resting human monocytes. Concentrations of 1 and 10 micrograms/ml enhanced PGE2 release by LPS-stimulated monocytes, and by healthy and inflamed rat macrophages.
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LIVERTOX |
180
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NCI_THESAURUS |
C29578
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NDF-RT |
N0000175587
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WHO-VATC |
QR06AE07
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NDF-RT |
N0000000190
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WHO-ATC |
R06AE07
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CHEMBL1000
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CETIRIZINE
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Cetirizine
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DTXSID4022787
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DB00341
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m3291
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100000081513
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20610
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2678
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YO7261ME24
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3561
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83881-51-0
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C1042
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D017332
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7739
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YO7261ME24
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ACTIVE MOIETY
PARENT (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
