Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C21H25ClN2O3.2ClH |
| Molecular Weight | 461.81 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.OC(=O)COCCN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=C(Cl)C=C3
InChI
InChIKey=PGLIUCLTXOYQMV-UHFFFAOYSA-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
| 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 | ( + / - ) |
| 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 |
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 |
|||
| 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 |
|||
| 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 |
|---|---|---|---|---|
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 |
|
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 |
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 |
|---|---|---|---|---|
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 |
|
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 |
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 |
|
270 mg single, oral Overdose |
unhealthy, 18 years |
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 |
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 Health Status: unhealthy Age Group: 23 months Sex: M 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 Health Status: unhealthy Age Group: 39 years Sex: M+F 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 |
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 |
|
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 |
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: |
unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sex: M+F Sources: |
Other AEs: Somnolence, Fatigue... Other AEs: Somnolence (13.7%) Sources: Fatigue (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 Health Status: unhealthy Age Group: adult 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 |
| Metabolic acidosis | grade 5, 1 patient | 270 mg single, oral Overdose |
unhealthy, 18 years |
| 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 |
| 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 |
| 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 Health Status: unhealthy Age Group: 23 months Sex: M Sources: |
| Dysgeusia | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years Health Status: unhealthy Age Group: 39 years Sex: M+F Sources: |
| Dyspepsia | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years Health Status: unhealthy Age Group: 39 years Sex: M+F Sources: |
| Feeling hot | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years Health Status: unhealthy Age Group: 39 years Sex: M+F Sources: |
| Headache | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years Health Status: unhealthy Age Group: 39 years Sex: M+F Sources: |
| Hyperhidrosis | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years Health Status: unhealthy Age Group: 39 years Sex: M+F Sources: |
| Paresthesia | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years Health Status: unhealthy Age Group: 39 years Sex: M+F Sources: |
| Presyncope | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years Health Status: unhealthy Age Group: 39 years Sex: M+F Sources: |
| Sedation | 1 patient | 60 mg single, oral Overdose |
healthy, 4 years |
| Drowsiness | severe, 1 patient | 60 mg single, oral Overdose |
healthy, 4 years |
| 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 |
| 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: |
unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sex: M+F Sources: |
| 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: |
unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sex: M+F Sources: |
| 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: |
unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sex: M+F Sources: |
| 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: |
unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sex: M+F Sources: |
| 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: |
unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sex: M+F Sources: |
| 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 Health Status: unhealthy Age Group: adult 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 Health Status: unhealthy Age Group: adult 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 Health Status: unhealthy Age Group: adult Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cetirizine and loratadine: a comparison using the ED50 in skin reactions. | 2000 Mar-Apr |
|
| Clinical prescribing of allergic rhinitis medication in the preschool and young school-age child: what are the options? | 2001 |
|
| Cetirizine reduces the number of tryptase-positive mast cells in psoriatic patients: a double-blind controlled study. | 2001 |
|
| Treatment of severe seasonal rhinoconjunctivitis by a combination of azelastine nasal spray and eye drops: a double-blind, double-placebo study. | 2001 |
|
| Twenty-four hours of activity of cetirizine and fexofenadine in the skin. | 2001 Apr |
|
| Newer antihistamines. | 2001 Apr 30 |
|
| [The allergic pregnant woman]. | 2001 Dec |
|
| [Prednicarbate and cetirizin dihydrochloride in the treatment of atopic eczema in the acute phase in children]. | 2001 Jan |
|
| Effects of monotherapy with intra-nasal corticosteroid or combined oral histamine and leukotriene receptor antagonists in seasonal allergic rhinitis. | 2001 Jan |
|
| Urticaria induced by cetirizine. | 2001 Jan |
|
| Effect of cetirizine on bronchial hyperresponsiveness in patients with seasonal allergic rhinitis and asthma. | 2001 Jan |
|
| Double-blind multicenter study on the efficacy and tolerability of cetirizine compared with oxatomide in chronic idiopathic urticaria in preschool children. | 2001 Jul |
|
| Severe hepatitis in a patient taking cetirizine. | 2001 Jul 17 |
|
| Antihistamines and the torsade de point in children with allergic rhinitis. | 2001 Jul-Aug |
|
| Burn wound itch control using H1 and H2 antagonists. | 2001 Jul-Aug |
|
| Stanozolol in chronic urticaria: a double blind, placebo controlled trial. | 2001 Jun |
|
| [Co-administration of histamine H1 antagonist and oral anticoagulants]. | 2001 Jun-Jul |
|
| Local safety of intranasal triamcinolone acetonide: clinical and histological aspects of nasal mucosa in the long-term treatment of perennial allergic rhinitis. | 2001 Mar |
|
| An investigation into the effects of cetirizine on cognitive function and psychomotor performance in healthy volunteers. | 2001 Mar |
|
| Lipophilicity behaviour of the Zwitterionic antihistamine cetirizine in phosphatidylcholine liposomes/water systems. | 2001 May |
|
| Acute urticaria with elevated circulating interleukin-6 is resistant to anti-histamine treatment. | 2001 May |
|
| [The course of allergy: principles for early diagnosis, prevention and early therapy of allergic diseases]. | 2001 May |
|
| Preclinical comparison of ebastine and other second generation H1-antihistamines. | 2001 Oct |
|
| Antiallergic/antiasthmatic effect of novel antiallergic hexapeptide-95/220 in various experimental models. | 2001 Sep |
|
| 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 |
|
| Potential cardiac toxicity of H1-antihistamines. | 2002 |
|
| Pharmacokinetics of cetirizine in tear fluid after a single oral dose. | 2002 |
|
| Photosensitivity disorders: cause, effect and management. | 2002 |
|
| Effects of antihistamines on leukotriene and cytokine release from dispersed nasal polyp cells. | 2002 |
|
| [The first case of lasting pigmented toxidermia induced by cetirizine (Zyrtec, Virlix) and ticlopidine]. | 2002 Apr |
|
| Major role for the carboxylic function of cetirizine and levocetirizine in their binding characteristics to human H1-histamine-receptors. | 2002 Apr |
|
| Binding characteristics of [3H]levocetirizine to cloned human H1-histamine-receptors expressed in CHO cells. | 2002 Apr |
|
| 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 |
|
| Cardiotoxicity of new antihistamines and cisapride. | 2002 Feb 28 |
|
| Titrimetric and spectrophotometric assay of some antihistamines through the determination of the chloride of their hydrochlorides. | 2002 Jan |
|
| Randomised controlled trial of butterbur and cetirizine for treating seasonal allergic rhinitis. | 2002 Jan 19 |
|
| Gateways to clinical trials. | 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 |
|
| 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 |
|
| Comparative activity of cetirizine and mizolastine on histamine-induced skin wheal and flare responses at 24 h. | 2002 Mar |
|
| Gateways to clinical trials. | 2002 May |
|
| Urticarial intolerance reaction to cetirizine. | 2002 May |
|
| 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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:49:09 GMT 2025
by
admin
on
Mon Mar 31 18:49:09 GMT 2025
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| Record UNII |
64O047KTOA
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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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203150
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SUB11803MIG
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64O047KTOA
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DTXSID2044268
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1102929
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100000091468
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m3291
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83881-52-1
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C28920
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759102
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CHEMBL1000
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| Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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PARENT -> SALT/SOLVATE |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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| Related Record | Type | Details | ||
|---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
For the calculation of content, multiply the peak areas by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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|
IMPURITY -> PARENT |
For the calculation of content, multiply the peak areas by 0.6
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
For the calculation of content, multiply the peak areas by 1.9
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
For the calculation of content, multiply the peak areas by 1.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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![Structure of 2-[2-[2-[4-[(4-Chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]ethoxy]acetic acid](/img/ab8ffc0a-3e0e-493b-92ef-911e5a7049b4.svg "Structure of 2-[2-[2-[4-[(4-Chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]ethoxy]acetic acid")
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ACTIVE MOIETY |
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