antazoline

Also known as 4,5-Dihydro-N-phenyl-N-phenylmethyl-1H-imidazole-2-methanamine, 2-(N-Benzylanilinomethyl)-2-imidazoline, 2-(N-Phenyl-N-benzylaminomethyl)imidazoline

Antazoline is a 1st generation antihistamine with anticholinergic properties used to relieve nasal congestion and in eye drops, usually in combination with naphazoline, to relieve the symptoms of allergic conjunctivitis. To treat allergic conjunctivitis, antazoline can be combined in a solution with tetryzoline. The drug is a Histamine H1 receptor antagonist: selectively binding to but not activating the receptor, thereby blocking the actions of endogenous histamine and subsequently leading to the temporary relief of the negative symptoms brought on by histamine.

In the Vinony graph

Vinony's link graph records 408 inbound references to antazoline, and connects out to atropine, histamine antagonist and nicotinic acetylcholine receptor.

It sits within the topics ECHA InfoCard ID from Wikidata, H1 receptor antagonists and Imidazolines.

Vinony links it to 14 Wikipedia language editions.

Key facts

Drug.image: Antazoline.svg
Drug.image_class: skin-invert-image
Drug.width: 215
Drug.tradename: Vasocon-a
Drug.routes_of_administration: Topical (nasal, eye drops)
Drug.ATC_prefix: R01
Drug.ATC_suffix: AC04
Drug.legal_AU: S4
Drug.legal_AU_comment: /Schedule 2
Drug.CAS_number: 91-75-8
Drug.PubChem: 2200
Drug.IUPHAR_ligand: 7116
Drug.DrugBank: DB08799
Drug.ChemSpiderID: 2115
Drug.UNII: DHA8014SS1
Drug.KEGG: D07458
Drug.ChEBI: 84115
Drug.ChEMBL: 1305

via Wikipedia infobox

Chemical data

Formula: C17H19N3
Molecular weight: 265.35 g/mol
IUPAC name: N-benzyl-N-(4,5-dihydro-1H-imidazol-2-ylmethyl)aniline
SMILES: C1CN=C(N1)CN(CC2=CC=CC=C2)C3=CC=CC=C3
InChIKey: REYFJDPCWQRWAA-UHFFFAOYSA-N
XLogP: 2.6
Polar surface area: 27.6 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1994
Admin. routes: topical
Indications: Nasal congestion, allergic disease

via ChEMBL · EBI

Research

325 papers

Antazoline: the Lazarus of antiarrhythmic drugs?Polish archives of internal medicine · 2022
Effectiveness of antazoline versus amiodarone, flecainide and propafenone in restoring sinus rhythm at the emergency department.Advances in medical sciences · 2024
Intravenous antazoline, a first-generation antihistaminic drug with antiarrhythmic properties, is a suitable agent for pharmacological cardioversion of atrial fibrillation induced during pulmonary vein isolation due to the lack of influence on atrio-venous conduction and high clinical effectiveness (AntaEP Study).British journal of clinical pharmacology · 2019
Antazoline for pharmacologic cardioversion of atrial fibrillation: teaching an old drug new tricks.Polish archives of internal medicine · 2024
Efficacy and safety of antazoline vs propafenone for conversion of paroxysmal atrial fibrillation to sinus rhythm: a randomized, double-blind study (AnProAF).Polish archives of internal medicine · 2024

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 265.157898
Has use: medication

Show 4 more facts

chemical formula: C₁₇H₁₉N₃
canonical SMILES: C1CN=C(N1)CN(CC2=CC=CC=C2)C3=CC=CC=C3
World Health Organisation international non-proprietary name: antazoline
Commons category: Antazoline

Sources (2)

via Wikidata · CC0

~1 min read

Encyclopedic overview

2 sections

Contents

Research
References

== Research == A 2015 study on people aged 65 years of age or older linked the development of Alzheimer's disease and other forms of dementia to the "higher cumulative" use of first-generation antihistamines, due to their anticholinergic properties.

Excerpted from Wikipedia’s “antazoline” article, available under the CC BY-SA 4.0 licence.