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 Date8.183808E11 |
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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 Date8.183808E11 |
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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 Date8.183808E11 |
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 |
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| Cetirizine/pseudoephedrine. | 2001 |
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| Treatment of urticaria. An evidence-based evaluation of antihistamines. | 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 |
|
| Cetirizine reduces the number of tryptase-positive mast cells in psoriatic patients: a double-blind controlled study. | 2001 |
|
| Absorption and disposition of levocetirizine, the eutomer of cetirizine, administered alone or as cetirizine to healthy volunteers. | 2001 Aug |
|
| [Eosinophilic pustular folliculitis in childhood]. | 2001 Aug |
|
| 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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| Efficacy and safety of an oral formulation of cetirizine and prolonged-release pseudoephedrine versus xylometazoline nasal spray in nasal congestion. | 2001 Nov |
|
| Multiwavelength spectrophotometric resolution of the micro-equilibria of cetirizine. | 2001 Oct |
|
| Preclinical comparison of ebastine and other second generation H1-antihistamines. | 2001 Oct |
|
| Effects of topical corticosteroid and combined mediator blockade on domiciliary and laboratory measurements of nasal function in seasonal allergic rhinitis. | 2001 Oct |
|
| The costs of nonsedating antihistamine therapy for allergic rhinitis in managed care: an updated analysis. | 2001 Oct |
|
| Efficacy of leukotriene receptor antagonist in chronic urticaria. A double-blind, placebo-controlled comparison of treatment with montelukast and cetirizine in patients with chronic urticaria with intolerance to food additive and/or acetylsalicylic acid. | 2001 Oct |
|
| 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 |
|
| 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 |
|
| Long-term cetirizine treatment reduces allergic symptoms and drug prescriptions in children with mite allergy. | 2001 Sep |
|
| Pharmacokinetics of cetirizine in chronic hemodialysis patients: multiple-dose study. | 2001 Sep |
|
| Serum tryptase in allergic rhinitis: effect of cetirizine and fluticasone propionate treatment. | 2001 Sep-Oct |
|
| Potential cardiac toxicity of H1-antihistamines. | 2002 |
|
| Pharmacokinetics of cetirizine in tear fluid after a single oral dose. | 2002 |
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| Photosensitivity disorders: cause, effect and management. | 2002 |
|
| [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 |
|
| [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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| Acute hepatitis associated with cetirizine intake. | 2002 Apr |
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| Comparison of five new antihistamines (H1-receptor antagonists) in patients with allergic rhinitis using nasal provocation studies and skin tests. | 2002 Apr |
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| Are antihistamines useful in managing asthma? | 2002 Feb |
|
| 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 |
|
| 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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| 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 |
|
| Cetirizine decreases interleukin-4, interleukin-5, and interferon-gamma gene expressions in nasal-associated lymphoid tissue of sensitized mice. | 2002 Jan-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 |
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| Immune changes in patients with advanced breast cancer undergoing chemotherapy with taxanes. | 2002 Jul 1 |
|
| Extractionless and sensitive method for high-throughput quantitation of cetirizine in human plasma samples by liquid chromatography-tandem mass spectrometry. | 2002 Jun 25 |
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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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| [Already allergic to pollen in early childhood. Can future asthma still be prevented?]. | 2002 Mar 7 |
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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 |
|
| 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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| Classification Tree | Code System | Code | ||
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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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5520
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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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SUB07451MIG
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581
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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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1222
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7739
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YO7261ME24
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ACTIVE MOIETY
PARENT (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
