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)
Molecular Formula | C21H25ClN2O3 |
Molecular Weight | 388.888 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdfCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/cetirizine.html
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf
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 |
---|---|---|---|
Target ID: CHEMBL231 |
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 |
---|---|---|
Cetirizine and loratadine: a comparison using the ED50 in skin reactions. | 2000 Mar-Apr |
|
Efficacy and safety of levocetirizine in seasonal allergic rhinitis. | 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 |
|
Treatment of severe seasonal rhinoconjunctivitis by a combination of azelastine nasal spray and eye drops: a double-blind, double-placebo study. | 2001 |
|
Newer antihistamines. | 2001 Apr 30 |
|
Severe hepatitis in a patient taking cetirizine. | 2001 Jul 17 |
|
Acute urticaria with elevated circulating interleukin-6 is resistant to anti-histamine treatment. | 2001 May |
|
Preclinical comparison of ebastine and other second generation H1-antihistamines. | 2001 Oct |
|
Pharmacokinetics of cetirizine in tear fluid after a single oral dose. | 2002 |
|
Effects of antihistamines on leukotriene and cytokine release from dispersed nasal polyp cells. | 2002 |
|
Comparison of five new antihistamines (H1-receptor antagonists) in patients with allergic rhinitis using nasal provocation studies and skin tests. | 2002 Apr |
|
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 |
|
Randomised controlled trial of butterbur and cetirizine for treating seasonal allergic rhinitis. | 2002 Jan 19 |
|
Applications of derivative UV spectrophotometry for the determinations of cetirizine dihydrochloride in pharmaceutical preparations. | 2002 Jan-Feb |
|
Comparison of cetirizine, ebastine and loratadine in the treatment of immediate mosquito-bite allergy. | 2002 Jun |
|
[Skin prick test results in snoring and sleep apnea patients]. | 2002 Mar |
|
Comparative activity of cetirizine and mizolastine on histamine-induced skin wheal and flare responses at 24 h. | 2002 Mar |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7741033
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 20:11:57 UTC 2022
by
admin
on
Fri Dec 16 20:11:57 UTC 2022
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Record UNII |
YO7261ME24
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Record Status |
Validated (UNII)
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Record Version |
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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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Code System | Code | Type | Description | ||
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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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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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7739
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YO7261ME24
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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BINDER->LIGAND |
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TRANSPORTER -> INHIBITOR | |||
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ENANTIOMER -> RACEMATE | |||
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TRANSPORTER -> SUBSTRATE | |||
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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