File:Cetirizine_structure.svg · Wikimedia Commons · See Wikimedia Commons
cetirizine
Sign in to saveAlso known as (2-{4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid
Cetirizine is a second-generation peripherally selective antihistamine used to treat allergic rhinitis (hay fever), dermatitis, urticaria (hives), and runny nose. It is taken by mouth. Effects generally begin within thirty minutes and last for about a day. The degree of benefit is similar to other antihistamines such as diphenhydramine, which is a first-generation antihistamine.
OverviewAI-generated
Cetirizine is a chemical compound with the formula C₂₁H₂₅ClN₂O₃. Its IUPAC name is 2-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetic acid. The substance has a mass of 388.15537 and a weight of 388.9. It carries a charge of 0 and features one hydrogen bond donor and five hydrogen bond acceptors. The xlogp value is 1.7, while the tpsa is 53.
The defined daily dose for cetirizine is 10. It is also referred to by the stylized name ZyrTEC. The compound is associated with a Commons category titled "Cetirizine" and is referenced by 567 other encyclopedia articles.
Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
In the Vinony graph
Vinony's link graph records 567 inbound references to cetirizine, and connects out to urticaria, allergic rhinitis and pharmacokinetics.
Vinony files it under Acetic acids, Antihistamines and Belgian inventions.
Vinony links it to 46 Wikipedia language editions.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 460026203
- Drug.image
- Cetirizine structure.svg
- Drug.alt
- A structural diagram of the cetirizine molecule
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.image2
- Cetirizine-ball-and-stick.png
- Drug.alt2
- A ball-and-stick diagram of the cetirizine molecule
- Drug.image_class2
- bg-transparent
- Drug.width2
- 250
- Drug.tradename
- Zyrtec, others
- Drug.MedlinePlus
- a698026
- Drug.DailyMedID
- Cetirizine
- Drug.pregnancy_AU
- B2
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- R06
- Drug.ATC_suffix
- AE07
- Drug.legal_AU
- Unscheduled
via Wikipedia infobox
Chemical data
- Formula
- C21H25ClN2O3
- Molecular weight
- 388.9 g/mol
- IUPAC name
- 2-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]ethoxy]acetic acid
- SMILES
- C1CN(CCN1CCOCC(=O)O)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl
- InChIKey
- ZKLPARSLTMPFCP-UHFFFAOYSA-N
- XLogP
- 1.7
- Polar surface area
- 53 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1995
- Admin. routes
- oral, parenteral, topical
- Indications
- seasonal allergic rhinitis, neuromyelitis optica, allergic rhinitis, Rhinitis, Allergic, Perennial
via ChEMBL · EBI
Research
2,334 papers- Cetirizine/pseudoephedrine.Drugs · 2001
- Topical cetirizine for treating androgenetic alopecia: A systematic review.Journal of cosmetic dermatology · 2022
- [Cetirizine].Deutsche medizinische Wochenschrift (1946) · 1998
- Cetirizine: a new, nonsedating antihistamine.The Annals of pharmacotherapy · 1993
- [Cetirizine].Ceskoslovenska pediatrie · 1993
via PubMed
Wikidata facts
- Mass
- 388.15537
- Has use
- medication
Show 9 more facts
- defined daily dose
- 10
- chemical formula
- C₂₁H₂₅ClN₂O₃
- medical condition treated
- allergic rhinitis
- canonical SMILES
- C1CN(CCN1CCOCC(=O)O)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl
- World Health Organisation international non-proprietary name
- cetirizine
- subject has role
- histamine antagonist
- physically interacts with
- Histamine receptor H1
- Commons category
- Cetirizine
- stylized name
- ZyrTEC
Sources (7)
via Wikidata · CC0
~12 min read
Encyclopedic overview
16 sectionsContents
- Medical uses
- Allergies
- Available forms
- Adverse effects
- Pruritus after discontinuation of cetirizine
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Absorption
- Distribution
- Metabolism
- Elimination
- Chemistry
- Synthesis
- Availability
- References
Cetirizine is a second-generation peripherally selective antihistamine used to treat allergic rhinitis (hay fever), dermatitis, urticaria (hives), and runny nose. It is taken by mouth. Effects generally begin within thirty minutes and last for about a day. The degree of benefit is similar to other antihistamines such as diphenhydramine, which is a first-generation antihistamine.
Common side effects include sleepiness, dry mouth, headache, and abdominal pain. The degree of sleepiness that occurs is generally less than with first-generation antihistamines because second-generation antihistamines are more selective for the H1 receptor. Compared to other second-generation antihistamines, cetirizine can cause drowsiness. Among second-generation antihistamines, cetirizine is more likely than fexofenadine and loratadine to cause drowsiness.
Excerpted from Wikipedia’s “cetirizine” article, available under the CC BY-SA 4.0 licence.