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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 of ANTAZOLINE PHOSPHATE

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
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
Molecular Formula H3O4P
Molecular Weight 97.9952
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Pharmacometric analysis of alpha1-adrenoceptor function in rat tail artery pretreated with lipopolysaccharides.
2001 Nov-Dec
The effects of imidazoline agents on the aggregation of human platelets.
2004 Feb
The thermodynamic dissociation constants of ambroxol, antazoline, naphazoline, oxymetazoline and ranitidine by the regression analysis of spectrophotometric data.
2004 Feb 27
Effect of histamine receptor antagonists on aminophylline-induced seizures and lethality in mice.
2005 Jul-Aug
Net analyte signal-based simultaneous determination of antazoline and naphazoline using wavelength region selection by experimental design-neural networks.
2006 Feb 15
[Histamine and the convulsive threshold or effectiveness of antiepileptic drugs].
2008
Demand for food and cocaine in Fischer and Lewis rats.
2009 Feb
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:58:15 GMT 2023
Edited
by admin
on Fri Dec 15 14:58:15 GMT 2023
Record UNII
VPR5FPH326
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANTAZOLINE PHOSPHATE
MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
Antazoline phosphate [WHO-DD]
Common Name English
VASOCON-A COMPONENT ANTAZOLINE PHOSPHATE
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
ANTAZOLINE PHOSPHATE COMPONENT OF VASOCON-A
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
Code System Code Type Description
PUBCHEM
158798
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-831-4
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
PRIMARY
CAS
154-68-7
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
PRIMARY
DRUG BANK
DBSALT001374
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
PRIMARY
ChEMBL
CHEMBL1305
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID00165507
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
PRIMARY
NSC
755865
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
PRIMARY
NCI_THESAURUS
C47399
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
PRIMARY
SMS_ID
100000085166
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
PRIMARY
FDA UNII
VPR5FPH326
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
PRIMARY
MERCK INDEX
m1942
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1038003
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
PRIMARY
RXCUI
866
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
PRIMARY RxNorm
EVMPD
SUB00541MIG
Created by admin on Fri Dec 15 14:58:15 GMT 2023 , Edited by admin on Fri Dec 15 14:58:15 GMT 2023
PRIMARY
Related Record Type Details
Structure of ANTAZOLINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of ACETAMIDE, N-(2-AMINOETHYL)-2-(PHENYL(PHENYLMETHYL)AMINO)-
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of ANTAZOLINE
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