Identification

Name
Antazoline
Accession Number
DB08799
Type
Small Molecule
Groups
Approved
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
Product Ingredients
IngredientUNIICASInChI Key
Antazoline phosphateVPR5FPH326154-68-7DUIGUKRYYAGJAF-UHFFFAOYSA-N
Antazoline sulfate6T74I0721224359-81-7UWOSJBSLQYMGDL-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Albalon AAntazoline phosphate (.5 %) + Naphazoline hydrochloride (.05 %)LiquidOphthalmicAllergan1978-12-31Not applicableCanada
Cooper A.R.Antazoline phosphate (5 mg) + Naphazoline hydrochloride (.5 mg)Solution / dropsOphthalmicCoopervision, Inc.1996-08-141998-03-12Canada
Ophtrivin A Ophthalmic DpsAntazoline sulfate (.5 %) + Xylometazoline hydrochloride (.05 %)Solution / dropsOphthalmicCiba Vision1992-12-312000-11-08Canada
Refresh Eye Allergy ReliefAntazoline phosphate (0.51 %) + Naphazoline hydrochloride (0.051 %)SolutionOphthalmicAllergan2009-02-09Not applicableCanada
Steritears ArAntazoline phosphate (0.5 %) + Naphazoline hydrochloride (0.05 %)Solution / dropsOphthalmicLaboratoires Sterigen IncNot applicableNot applicableCanada
Vasocon A Eye DropsAntazoline phosphate (5 mg) + Naphazoline hydrochloride (.5 mg)Solution / dropsOphthalmicNovartis Ophthalmics Novartis Pharmaceuticals (Canada) Inc1996-12-312005-03-01Canada
Vasocon A Oph SolnAntazoline phosphate (5 mg) + Naphazoline hydrochloride (.5 mg)Solution / dropsOphthalmicIolab Pharmaceuticals1988-12-311996-09-09Canada
Zincfrin AAntazoline phosphate (0.5 %) + Naphazoline hydrochloride (0.05 %) + Zinc sulfate (0.125 %)Solution / dropsOphthalmicAlcon, Inc.1969-12-312009-04-24Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Nestabs ONEAntazoline (225 mg/1) + Calcium ascorbate dihydrate (18 mg/1) + Cholecalciferol (6.25 ug/1) + Cyanocobalamin (15 ug/1) + Folic Acid (1 mg/1) + Iron (38 mg/1) + Magnesium oxide (15 mg/1) + Pyridoxine hydrochloride (30 mg/1) + Tocopherol (10 mg/1) + Zinc oxide (1 mg/1)Capsule, gelatin coatedOralWomens Choice Pharmaceuticals, Llc2017-07-20Not applicableUs
International/Other Brands
Vasocon-a
Categories
UNII
DHA8014SS1
CAS number
91-75-8
Weight
Average: 265.3529
Monoisotopic: 265.157897623
Chemical Formula
C17H19N3
InChI Key
REYFJDPCWQRWAA-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.

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.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Antazoline H1-Antihistamine ActionDrug action
Antazoline H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Antazoline.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative activities of Antazoline.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Antazoline.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Antazoline.
AlfuzosinThe risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Antazoline.
AlimemazineThe risk or severity of QTc prolongation can be increased when Alimemazine is combined with Antazoline.
AmiodaroneThe risk or severity of QTc prolongation can be increased when Antazoline is combined with Amiodarone.
AmitriptylineThe risk or severity of QTc prolongation can be increased when Amitriptyline is combined with Antazoline.
AmphetamineAmphetamine may decrease the sedative and stimulatory activities of Antazoline.
AnagrelideThe risk or severity of QTc prolongation can be increased when Antazoline is combined with Anagrelide.
Food Interactions
Not 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
Human Metabolome Database
HMDB0015689
KEGG Drug
D07458
PubChem Compound
2200
PubChem Substance
99445269
ChemSpider
2115
BindingDB
76862
ChEBI
84115
ChEMBL
CHEMBL1305
PharmGKB
PA165958418
Wikipedia
Antazoline
ATC Codes
R01AC04 — AntazolineR06AX05 — Antazoline
MSDS
Download (70.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentParoxysmal Atrial Fibrillation (PAF)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidOphthalmic
Capsule, gelatin coatedOral
Solution / dropsOphthalmic
SolutionOphthalmic
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9000000000-1eb3fa441bd25a0e41a3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylmethylamines
Direct Parent
Phenylbenzamines
Alternative Parents
Dialkylarylamines / Benzylamines / Aniline and substituted anilines / Aralkylamines / Imidolactams / Imidazolines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds
show 2 more
Substituents
Phenylbenzamine / Benzylamine / Tertiary aliphatic/aromatic amine / Aniline or substituted anilines / Dialkylarylamine / Aralkylamine / Imidolactam / 2-imidazoline / Tertiary amine / Organoheterocyclic compound
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
tertiary 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 catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
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 August 02, 2018 07:53