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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-08-17 18:00:20 UTC
HMDB IDHMDB0015689
Secondary Accession Numbers
  • HMDB15689
Metabolite Identification
Common NameAntazoline
DescriptionAntazoline 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
Thumb
Synonyms
ValueSource
2-(N-Benzylanilinomethyl)-2-imidazolineChEBI
2-(N-Phenyl-N-benzylaminomethyl)imidazolineChEBI
4,5-dihydro-N-Phenyl-N-phenylmethyl-1H-imidazole-2-methanamineChEBI
AntazolinaChEBI
AntazolinumChEBI
PhenazolinHMDB
PhenazolineHMDB
AntistineMeSH
ArithminMeSH
Lannett brand OF antazoline phosphateMeSH
ImidamineMeSH
AntastenMeSH
Antazoline hydrochlorideMeSH
Antazoline phosphateMeSH
AnalergineMeSH
Antazoline phosphate (1:1)MeSH
Hydrochloride, antazolineMeSH
Phosphate, antazolineMeSH
Chemical FormulaC17H19N3
Average Molecular Weight265.3529
Monoisotopic Molecular Weight265.157897623
IUPAC NameN-benzyl-N-(4,5-dihydro-1H-imidazol-2-ylmethyl)aniline
Traditional Nameantazoline
CAS Registry Number91-75-8
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 KeyREYFJDPCWQRWAA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylbenzamines
Alternative Parents
Substituents
  • Phenylbenzamine
  • Benzylamine
  • Tertiary aliphatic/aromatic amine
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Aralkylamine
  • Imidolactam
  • 2-imidazoline
  • Tertiary amine
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Amidine
  • Carboxylic acid amidine
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Allergic Agents
  • Antihistamines
  • Histamine Antagonists
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 mg/mLALOGPS
logP3.22ALOGPS
logP2.88ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)9.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area27.63 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.89 m3·mol-1ChemAxon
Polarizability30.11 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08799 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08799 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08799
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2115
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAntazoline
NuGOwiki LinkHMDB0015689
METLIN IDNot Available
PubChem Compound2200
PDB IDNot Available
ChEBI ID358709
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:20383847 ]

Enzymes

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
  1. 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. [PubMed:16129921 ]