ANTAZOLINE

First approved in 1948

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H19N3
Molecular Weight	265.3529
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(N(CC1=CC=CC=C1)C2=CC=CC=C2)C3=NCCN3

InChI

InChIKey=REYFJDPCWQRWAA-UHFFFAOYSA-N

InChI=1S/C17H19N3/c1-3-7-15(8-4-1)13-20(14-17-18-11-12-19-17)16-9-5-2-6-10-16/h1-10H,11-14H2,(H,18,19)

HIDE SMILES / InChI

Molecular Formula	C17H19N3
Molecular Weight	265.3529
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugbank.ca/drugs/DB08799
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68000865

Antazoline is an antagonist of histamine H1 receptors. It selectively bind to but does not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine. Antazoline in combination with naphazoline (VASOCON-A®) is indicated to relieve the symptoms of allergic conjunctivitis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL3943 Sources: https://www.drugbank.ca/drugs/DB08799	Antagonist 2778		38.4 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic conjunctivitis 100 Sources: http://www.empr.com/vasocon-a/drug/1227/	Palliative		Approved 8429	VASOCON-A Approved Use Temporary relief of ocular redness and itching. Launch Date 6.414336E11

PubMed

Title	Date	PubMed
Interactions of ligands at angiotensin II-receptors and imidazoline receptors.	2001 Feb	11286399
Pharmacometric analysis of alpha1-adrenoceptor function in rat tail artery pretreated with lipopolysaccharides.	2001 Nov-Dec	11985334
Inhibition of voltage-gated Ca2+ channels by antazoline.	2002 Oct 7	12395109
Neuroprotective activity of antazoline against neuronal damage induced by limbic status epilepticus.	2003	12890517
Conjunctival allergen challenge: models in the investigation of ocular allergy.	2003 Jul	12791217
Evaluation of the phencyclidine-like discriminative stimulus effects of novel NMDA channel blockers in rats.	2003 Nov	12851738
Influence of antazoline and ketotifen on the anticonvulsant activity of conventional antiepileptics against maximal electroshock in mice.	2004 Aug	15163441
The effects of imidazoline agents on the aggregation of human platelets.	2004 Feb	15005880
The thermodynamic dissociation constants of ambroxol, antazoline, naphazoline, oxymetazoline and ranitidine by the regression analysis of spectrophotometric data.	2004 Feb 27	18969326
Effect of histamine receptor antagonists on aminophylline-induced seizures and lethality in mice.	2005 Jul-Aug	16129921
Simple HPLC determination of benzalkonium chloride in ophthalmic formulations containing antazoline and tetrahydrozoline.	2005 Sep-Oct	16316068
Net analyte signal-based simultaneous determination of antazoline and naphazoline using wavelength region selection by experimental design-neural networks.	2006 Feb 15	18970453
A rapid derivative spectrophotometric method for simultaneous determination of naphazoline and antazoline in eye drops.	2006 Jan	16394564
Evidence for imidazoline receptors involvement in the agmatine antidepressant-like effect in the forced swimming test.	2007 Jun 22	17445795
[Histamine and the convulsive threshold or effectiveness of antiepileptic drugs].	2008	19205365
Demand for food and cocaine in Fischer and Lewis rats.	2009 Feb	19170441
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.	2009 Oct 23	19725810
Evidence for the involvement of the noradrenergic system, dopaminergic and imidazoline receptors in the antidepressant-like effect of tramadol in mice.	2010 May	20184917
Simultaneous determination of antazoline and naphazoline by the net analyte signal standard addition method and spectrophotometric technique.	2010 Nov-Dec	21313830
Treatment of allergic conjunctivitis: results of a 1-month, single-masked randomized study.	2010 Sep-Oct	20383847
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

Sample Use Guides

In Vivo Use Guide

1-2 drops up to 4 times daily.

Route of Administration: Other

In Vitro Use Guide

The antihistaminic agent, antazoline, was tested for its ability to compete for [3H]pyrilamine, [3H]tiotidine and [3H]N-methyl histamine binding to rodent brain H1, H2 and H3 histamine receptors, respectively. Antazoline exhibited the highest affinity for H1-receptors (dissociation constant, Ki = 38.4 +/- 4.4 nM), and was considerably weaker at H2- (K1 = 44,433 +/- 1,763 nM) and H3-receptors (Ki = 42,400 +/- 7,527 nM).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:05:14 UTC 2023` Edited by `admin` on `Fri Dec 15 15:05:14 UTC 2023`
Record UNII	DHA8014SS1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANTAZOLINE

Official Name

English

ANTAZOLINE [VANDF]

Common Name

English

Antazoline [WHO-DD]

Common Name

English

ANTAZOLINE [MART.]

Common Name

English

antazoline [INN]

Common Name

English

ANTAZOLINE [HSDB]

Common Name

English

ANTAZOLINE [MI]

Common Name

English

ATAZOLINE

Common Name

English

2-((N-BENZYLANILINO)METHYL)-2-IMIDAZOLINE

Systematic Name

English

1H-IMIDAZOLE-2-METHANAMINE, 4,5-DIHYDRO-N-PHENYL-N-(PHENYLMETHYL)-

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

R01AC04