Identification
NameAntazoline
Accession NumberDB08799
TypeSmall Molecule
GroupsApproved
Description

Antazoline 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.

Structure
Thumb
Synonyms
Antazoline
Vasocon-a
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Antazoline phosphateVPR5FPH326 154-68-7DUIGUKRYYAGJAF-UHFFFAOYSA-NDetails
Antazoline sulfate6T74I07212 24359-81-7UWOSJBSLQYMGDL-UHFFFAOYSA-NDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Albalon AAllergan
Cooper A.R.Coopervision, Inc.
Ophtrivin A Ophthalmic DpsCiba Vision
Refresh Eye Allergy ReliefAllergan
Steritears ArLaboratoires Sterigen Inc
Vasocon A Eye DropsNovartis Ophthalmics Novartis Pharmaceuticals (Canada) Inc
Vasocon A Oph SolnIolab Pharmaceuticals
Zincfrin AAlcon, Inc.
Categories
UNIIDHA8014SS1
CAS number91-75-8
WeightAverage: 265.3529
Monoisotopic: 265.157897623
Chemical FormulaC17H19N3
InChI KeyREYFJDPCWQRWAA-UHFFFAOYSA-N
InChI
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)
IUPAC Name
N-benzyl-N-(4,5-dihydro-1H-imidazol-2-ylmethyl)aniline
SMILES
C(N(CC1=CC=CC=C1)C1=CC=CC=C1)C1=NCCN1
Pharmacology
Indication

Used to relieve nasal congestion and in eye drops, usually in combination with naphazoline, to relieve the symptoms of allergic conjunctivitis.

Structured Indications Not Available
Pharmacodynamics

Antazoline is a histamine H1 receptor antagonist. It selectively bind to but does not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.

Mechanism of action

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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Histamine H1 receptorProteinyes
antagonist
HumanP35367 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Antazoline.Experimental, Illicit
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Antazoline.Experimental, Illicit
3,4-Methylenedioxymethamphetamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Antazoline.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Antazoline.Experimental, Illicit
AmphetamineAmphetamine may decrease the sedative activities of Antazoline.Approved, Illicit
BenzphetamineBenzphetamine may decrease the sedative activities of Antazoline.Approved, Illicit
Benzylpenicilloyl PolylysineAntazoline may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Antazoline.Approved
ChlorphentermineChlorphentermine may decrease the sedative activities of Antazoline.Illicit, Withdrawn
DextroamphetamineDextroamphetamine may decrease the sedative activities of Antazoline.Approved, Illicit
DiethylpropionDiethylpropion may decrease the sedative activities of Antazoline.Approved, Illicit
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Antazoline.Approved, Investigational
HydroxyamphetamineHydroxyamphetamine hydrobromide may decrease the sedative activities of Antazoline.Approved
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Antazoline.Approved, Investigational
MephedroneMephedrone may decrease the sedative activities of Antazoline.Investigational
MephentermineMephentermine may decrease the sedative activities of Antazoline.Approved
MethamphetamineMethamphetamine may decrease the sedative activities of Antazoline.Approved, Illicit
MMDAMMDA may decrease the sedative activities of Antazoline.Experimental, Illicit
PhenterminePhentermine may decrease the sedative activities of Antazoline.Approved, Illicit
PseudoephedrinePseudoephedrine may decrease the sedative activities of Antazoline.Approved
RitobegronRitobegron may decrease the sedative activities of Antazoline.Investigational
Food InteractionsNot Available
References
Synthesis Reference

Miescher, K. and Klarer, W.; US. Patent 2,449,241; September 14,1948: assigned to Ciba Pharmaceutical Products, Inc.

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 ]
External Links
ATC CodesR01AC04 — AntazolineR06AX05 — Antazoline
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (70.7 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentParoxysmal Atrial Fibrillation (PAF)1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
LiquidOphthalmic
Solution / dropsOphthalmic
SolutionOphthalmic
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)227-229Miescher, K. and Klarer, W.; US. Patent 2,449,241; September 14,1948: assigned to Ciba Pharmaceutical Products, Inc.
water solubility663 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility0.114 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 RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9699
Blood Brain Barrier+0.9578
Caco-2 permeable-0.5076
P-glycoprotein substrateSubstrate0.7167
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IIInhibitor0.59
Renal organic cation transporterInhibitor0.8403
CYP450 2C9 substrateNon-substrate0.798
CYP450 2D6 substrateSubstrate0.6581
CYP450 3A4 substrateNon-substrate0.6963
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.919
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9644
CYP450 3A4 inhibitorNon-inhibitor0.952
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8681
Ames testNon AMES toxic0.788
CarcinogenicityNon-carcinogens0.896
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4576 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5401
hERG inhibition (predictor II)Inhibitor0.5709
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
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
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 ParentsDialkylarylamines / Benzylamines / Aniline and substituted anilines / Aralkylamines / Imidolactams / Imidazolines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds
SubstituentsPhenylbenzamine / Benzylamine / Tertiary aliphatic/aromatic amine / Aniline or substituted anilines / Dialkylarylamine / Aralkylamine / Imidolactam / 2-imidazoline / Tertiary amine / Organoheterocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptorstertiary amino compound, aromatic amine, imidazolines (CHEBI:84115 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Histamine receptor activity
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:
55783.61 Da
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 ]
Drug created on October 14, 2010 14:06 / Updated on June 11, 2017 17:11