ANTAZOLINE PHOSPHATE

First approved in 1948

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H19N3.H3O4P
Molecular Weight	363.348
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OP(O)(O)=O.C(N(CC1=CC=CC=C1)C2=CC=CC=C2)C3=NCCN3

InChI

InChIKey=DUIGUKRYYAGJAF-UHFFFAOYSA-N

InChI=1S/C17H19N3.H3O4P/c1-3-7-15(8-4-1)13-20(14-17-18-11-12-19-17)16-9-5-2-6-10-16;1-5(2,3)4/h1-10H,11-14H2,(H,18,19);(H3,1,2,3,4)

HIDE SMILES / InChI

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 316 Target ID: CHEMBL3943 Sources: https://www.drugbank.ca/drugs/DB08799	Antagonist 2849		38.4 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic conjunctivitis 101 Sources: http://www.empr.com/vasocon-a/drug/1227/	Palliative		Approved 8583	VASOCON-A Approved Use Temporary relief of ocular redness and itching. Launch Date 1990

C_max

Value	Dose	Co-administered	Analyte	Population
2.02 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26895496/	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		ANTAZOLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
0.91 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26895496/	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		ANTAZOLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.29 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26895496/	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		ANTAZOLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 drop single, ophthalmic Recommended Dose: 2 drop Route: ophthalmic Route: single Dose: 2 drop Sources: https://pubmed.ncbi.nlm.nih.gov/2693136/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2693136/	Sources: https://pubmed.ncbi.nlm.nih.gov/2693136/
250 mg 1 times / 5 min multiple, intravenous Studied dose Dose: 250 mg, 1 times / 5 min Route: intravenous Route: multiple Dose: 250 mg, 1 times / 5 min Sources: https://pubmed.ncbi.nlm.nih.gov/28339554/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28339554/	Sources: https://pubmed.ncbi.nlm.nih.gov/28339554/

PubMed

Title	Date	PubMed
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011-07-14	21599003
Simultaneous determination of antazoline and naphazoline by the net analyte signal standard addition method and spectrophotometric technique.	2011-02-15	21313830
Evidence for the involvement of the noradrenergic system, dopaminergic and imidazoline receptors in the antidepressant-like effect of tramadol in mice.	2010-05	20184917
Treatment of allergic conjunctivitis: results of a 1-month, single-masked randomized study.	2010-04-13	20383847
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.	2009-10-23	19725810
Demand for food and cocaine in Fischer and Lewis rats.	2009-02	19170441
[Histamine and the convulsive threshold or effectiveness of antiepileptic drugs].	2008	19205365
Evidence for imidazoline receptors involvement in the agmatine antidepressant-like effect in the forced swimming test.	2007-06-22	17445795
Net analyte signal-based simultaneous determination of antazoline and naphazoline using wavelength region selection by experimental design-neural networks.	2006-02-15	18970453
A rapid derivative spectrophotometric method for simultaneous determination of naphazoline and antazoline in eye drops.	2006-01	16394564
Simple HPLC determination of benzalkonium chloride in ophthalmic formulations containing antazoline and tetrahydrozoline.	2005-12-01	16316068
Effect of histamine receptor antagonists on aminophylline-induced seizures and lethality in mice.	2004-10-21	16129921
Influence of antazoline and ketotifen on the anticonvulsant activity of conventional antiepileptics against maximal electroshock in mice.	2004-08	15163441
The thermodynamic dissociation constants of ambroxol, antazoline, naphazoline, oxymetazoline and ranitidine by the regression analysis of spectrophotometric data.	2004-02-27	18969326
The effects of imidazoline agents on the aggregation of human platelets.	2004-02	15005880
Evaluation of the phencyclidine-like discriminative stimulus effects of novel NMDA channel blockers in rats.	2003-11	12851738
Conjunctival allergen challenge: models in the investigation of ocular allergy.	2003-07	12791217
Neuroprotective activity of antazoline against neuronal damage induced by limbic status epilepticus.	2003	12890517
Inhibition of voltage-gated Ca2+ channels by antazoline.	2002-10-07	12395109
Pharmacometric analysis of alpha1-adrenoceptor function in rat tail artery pretreated with lipopolysaccharides.	2002-05-03	11985334
Interactions of ligands at angiotensin II-receptors and imidazoline receptors.	2001-02	11286399

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).

Name

Type

Language

VASOCON-A COMPONENT ANTAZOLINE PHOSPHATE

Preferred Name

English

ANTAZOLINE PHOSPHATE

Common Name

English

Antazoline phosphate [WHO-DD]

Common Name

English

NSC-755865

Code

English

ANTAZOLINE PHOSPHATE [ORANGE BOOK]

Common Name

English

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

Systematic Name

English

ANTAZOLINE PHOSPHATE [USP MONOGRAPH]

Common Name

English

2-[(N-Benzylanilino)methyl]-2-imidazoline phosphate (1:1)

Systematic Name

English

ANTAZOLINE PHOSPHATE [MART.]

Common Name

English

ANTAZOLINE PHOSPHATE [USP-RS]

Common Name

English

ANTAZOLINE PHOSPHATE [MI]

Common Name

English

ANTAZOLINE PHOSPHATE [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29578