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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:42:03 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
Data?1582753323
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
AntistineHMDB
ArithminHMDB
Lannett brand OF antazoline phosphateHMDB
ImidamineHMDB
AntastenHMDB
Antazoline hydrochlorideHMDB
Antazoline phosphateHMDB
AnalergineHMDB
Antazoline phosphate (1:1)HMDB
Hydrochloride, antazolineHMDB
Phosphate, antazolineHMDB
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
Description belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
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
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 g/LALOGPS
logP3.22ALOGPS
logP2.88ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)9.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area27.63 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.89 m³·mol⁻¹ChemAxon
Polarizability30.11 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-1eb3fa441bd25a0e41a3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-1eb3fa441bd25a0e41a3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9520000000-acee1c2b85e17e49b750Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4290000000-4ac08a84ab740fb2f33eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9310000000-cdc9ceb7906b163a7989Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-aeb9552d124a58684bc2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0190000000-2a0590deb8d02d0510f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03k9-2590000000-294ec8879dd0fa5e4b8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kcu-7900000000-a5218dce1e2e912dd19eSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2115
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAntazoline
METLIN IDNot Available
PubChem Compound2200
PDB IDNot Available
ChEBI ID84115
Food Biomarker OntologyNot Available
VMH IDNot Available
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 ]