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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 of ANTAZOLINE

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

Description
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

1948
95
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 38.4 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
VASOCON-A

Approved Use

Temporary relief of ocular redness and itching.

Launch Date

1990
PubMed

PubMed

TitleDatePubMed
Interactions of ligands at angiotensin II-receptors and imidazoline receptors.
2001 Feb
The thermodynamic dissociation constants of ambroxol, antazoline, naphazoline, oxymetazoline and ranitidine by the regression analysis of spectrophotometric data.
2004 Feb 27
Simple HPLC determination of benzalkonium chloride in ophthalmic formulations containing antazoline and tetrahydrozoline.
2005 Sep-Oct
Net analyte signal-based simultaneous determination of antazoline and naphazoline using wavelength region selection by experimental design-neural networks.
2006 Feb 15
A rapid derivative spectrophotometric method for simultaneous determination of naphazoline and antazoline in eye drops.
2006 Jan
[Histamine and the convulsive threshold or effectiveness of antiepileptic drugs].
2008
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.
2009 Oct 23
Evidence for the involvement of the noradrenergic system, dopaminergic and imidazoline receptors in the antidepressant-like effect of tramadol in mice.
2010 May
Simultaneous determination of antazoline and naphazoline by the net analyte signal standard addition method and spectrophotometric technique.
2010 Nov-Dec
Treatment of allergic conjunctivitis: results of a 1-month, single-masked randomized study.
2010 Sep-Oct
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

20010006677
50
JP2009530408A
51
US2449241
6

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
ANTAZOLINE
HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
WHO-ATC R06AX05
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
WHO-VATC QR01AC04
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
WHO-VATC QR06AX05
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
Code System Code Type Description
PUBCHEM
2200
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PRIMARY
DAILYMED
DHA8014SS1
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID3022613
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL1305
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PRIMARY
RXCUI
865
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
PRIMARY RxNorm
CHEBI
84115
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PRIMARY
ECHA (EC/EINECS)
202-094-0
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PRIMARY
MERCK INDEX
m1942
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PRIMARY Merck Index
WIKIPEDIA
ANTAZOLINE
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
PRIMARY
DRUG CENTRAL
224
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PRIMARY
DRUG BANK
DB08799
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PRIMARY
SMS_ID
100000086951
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
PRIMARY
FDA UNII
DHA8014SS1
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
PRIMARY
EVMPD
SUB05526MIG
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
PRIMARY
INN
1142
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
PRIMARY
MESH
D000865
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
PRIMARY
CAS
91-75-8
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
PRIMARY
IUPHAR
7116
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
PRIMARY
HSDB
6506
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
PRIMARY
NCI_THESAURUS
C61638
Created by admin on Fri Dec 15 15:05:14 GMT 2023 , Edited by admin on Fri Dec 15 15:05:14 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of ANTAZOLINE
METABOLITE (PARENT)
Structure of BENZYLANILINE
SALT/SOLVATE (PARENT)
Structure of ANTAZOLINE PHOSPHATE
SALT/SOLVATE (PARENT)
Structure of ANTAZOLINE MESYLATE
SALT/SOLVATE (PARENT)
Structure of ANTAZOLINE HEMISULFATE
SALT/SOLVATE (PARENT)
Structure of ANTAZOLINE SULFATE
SALT/SOLVATE (PARENT)
Structure of ANTAZOLINE HYDROCHLORIDE
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