Human Metabolome Database: Showing metabocard for Antazoline (HMDB15689)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

enzymes (1) Show 1 protein

Record Information

Version

3.6

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2016-02-11 01:34:00 UTC

HMDB ID

HMDB15689

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Antazoline

Description

Antazoline is only found in individuals that have used or taken this drug. It is a 1st generation antihistamine that also anticholinergic properties used to relieve nasal congestion and in eye drops, usually in combination with naphazoline, to relieve the symptoms of allergic conjunctivitis.Antazoline binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2-(N-Benzylanilinomethyl)-2-imidazoline	ChEBI
2-(N-Phenyl-N-benzylaminomethyl)imidazoline	ChEBI
4,5-dihydro-N-Phenyl-N-phenylmethyl-1H-imidazole-2-methanamine	ChEBI
Antazolina	ChEBI
Antazolinum	ChEBI
Phenazolin	HMDB
Phenazoline	HMDB

Chemical Formula

C₁₇H₁₉N₃

Average Molecular Weight

265.3529

Monoisotopic Molecular Weight

265.157897623

IUPAC Name

N-benzyl-N-(4,5-dihydro-1H-imidazol-2-ylmethyl)aniline

Traditional Name

antazoline

CAS Registry Number

91-75-8

SMILES

C(N(CC1=CC=CC=C1)C1=CC=CC=C1)C1=NCCN1

InChI Identifier

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)

InChI Key

InChIKey=REYFJDPCWQRWAA-UHFFFAOYSA-N

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylmethylamines

Alternative Parents

Substituents

Dialkylarylamine
Phenylmethylamine
Benzylamine
Aralkylamine
Aniline
Imidolactam
2-imidazoline
Tertiary amine
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Carboxylic acid amidine
Amidine
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Status

Expected but not Quantified

Origin

Drug

Biofunction

Anti-Allergic Agents
Antihistamines
Histamine Antagonists

Application

Pharmaceutical

Cellular locations

Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.11 mg/mL	ALOGPS
logP	3.22	ALOGPS
logP	2.88	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	27.63 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.89 m³·mol^-1	ChemAxon
Polarizability	30.11 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Biological Properties

Cellular Locations

Membrane

Biofluid Locations

Blood
Urine

Tissue Location

Not Available

Pathways

Not Available

Normal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Applicable	Not Available	Not Available	Taking drug identified by DrugBank entry DB08799	Not Applicable	details
Urine	Expected but not Quantified	Not Applicable	Not Available	Not Available	Taking drug identified by DrugBank entry DB08799	Not Applicable	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08799

DrugBank Metabolite ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2115

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Antazoline

NuGOwiki Link

HMDB15689

Metagene Link

HMDB15689

METLIN ID

Not Available

PubChem Compound

2200

PDB ID

Not Available

ChEBI ID

358709

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Figus M, Fogagnolo P, Lazzeri S, Capizzi F, Romagnoli M, Canovetti A, Iester M, Ferreras A, Rossetti L, Nardi M: Treatment of allergic conjunctivitis: results of a 1-month, single-masked randomized study. Eur J Ophthalmol. 2010 Sep-Oct;20(5):811-8. [20383847 ]

Enzymes

Enzyme Details

1. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular weight:: 55783.6

References

Swiader MJ, Luszczki JJ, Wielosz M, Czuczwar SJ: Effect of histamine receptor antagonists on aminophylline-induced seizures and lethality in mice. Pharmacol Rep. 2005 Jul-Aug;57(4):531-5. [16129921 ]

Showing metabocard for Antazoline (HMDB15689)

Structure for HMDB15689 (Antazoline)

Enzymes

References