Identification
- Summary
Antazoline is an antihistamine agent used for the symptomatic treatment of nasal congestion and allergic conjunctivitis.
- Generic Name
- Antazoline
- DrugBank Accession Number
- DB08799
- Background
Antazoline is a 1st generation antihistamine with anticholinergic activity. It is used to relieve nasal congestion. It is also formulated as eye drops with naphazoline to relieve allergic conjunctivitis.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Antazoline (DB08799)
- Weight
- Average: 265.3529
Monoisotopic: 265.157897623 - Chemical Formula
- C17H19N3
- Synonyms
- 2-(N-Benzylanilinomethyl)-2-imidazoline
- 2-(N-Phenyl-N-benzylaminomethyl)imidazoline
- 4,5-Dihydro-N-phenyl-N-phenylmethyl-1H-imidazole-2-methanamine
- Antazolina
- Antazoline
- Antazolinum
Pharmacology
- Indication
Used to relieve nasal congestion and in eye drops, usually in combination with naphazoline, to relieve the symptoms of allergic conjunctivitis.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Eye allergy Combination Product in combination with: Naphazoline (DB06711) ••• ••• •••••••• - Contraindications & Blackbox Warnings
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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.
Target Actions Organism AHistamine H1 receptor antagonistHumans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Antazoline H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Antazoline. Adenosine The risk or severity of QTc prolongation can be increased when Adenosine is combined with Antazoline. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Antazoline. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Antazoline. Alimemazine The risk or severity of QTc prolongation can be increased when Alimemazine is combined with Antazoline. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Antazoline hydrochloride FP8Q8F72JH 2508-72-7 SWKDMSRRIBZZAY-UHFFFAOYSA-N Antazoline phosphate VPR5FPH326 154-68-7 DUIGUKRYYAGJAF-UHFFFAOYSA-N Antazoline sulfate 6T74I07212 24359-81-7 UWOSJBSLQYMGDL-UHFFFAOYSA-N - International/Other Brands
- Vasocon-a
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Albalon A Antazoline phosphate (.5 %) + Naphazoline hydrochloride (.05 %) Liquid Ophthalmic Allergan 1978-12-31 2017-07-26 Canada 
ALOSYN EYE DROPS Antazoline hydrochloride (0.50 MG/ML) + Tetrahydrozoline hydrochloride (0.40 MG/ML) Solution Ophthalmic PETER CHIA MARKETING PTE LTD 2008-01-24 Not applicable Singapore 
ANTISTIN PRIVINA Antazoline (0.5 %) + Naphazoline (0.025 %) Solution / drops Conjunctival Laboratoires Thea 2014-07-08 2022-02-16 Italy 
Cooper A.R. Antazoline phosphate (5 mg / mL) + Naphazoline hydrochloride (.5 mg / mL) Solution / drops Ophthalmic Coopervision, Inc. 1996-08-14 1998-03-12 Canada Ophtrivin A Ophthalmic Dps Antazoline sulfate (.5 %) + Xylometazoline hydrochloride (.05 %) Solution / drops Ophthalmic Ciba Vision 1992-12-31 2000-11-08 Canada
Categories
- ATC Codes
- R06AX05 — Antazoline
- R06AX — Other antihistamines for systemic use
- R06A — ANTIHISTAMINES FOR SYSTEMIC USE
- R06 — ANTIHISTAMINES FOR SYSTEMIC USE
- R — RESPIRATORY SYSTEM
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 2-imidazoline / Amidine / Amine / Aniline or substituted anilines / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzylamine / Carboximidamide / Carboxylic acid amidine show 12 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- tertiary amino compound, aromatic amine, imidazolines (CHEBI:84115)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- DHA8014SS1
- CAS number
- 91-75-8
- 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-yl)methyl]aniline
- SMILES
- C(N(CC1=CC=CC=C1)C1=CC=CC=C1)C1=NCCN1
References
- Synthesis Reference
Miescher, K. and Klarer, W.; US. Patent 2,449,241; September 14,1948: assigned to Ciba Pharmaceutical Products, Inc.
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0015689
- KEGG Drug
- D07458
- PubChem Compound
- 2200
- PubChem Substance
- 99445269
- ChemSpider
- 2115
- BindingDB
- 76862
- 865
- ChEBI
- 84115
- ChEMBL
- CHEMBL1305
- ZINC
- ZINC000000057204
- PharmGKB
- PA165958418
- Wikipedia
- Antazoline
- MSDS
- Download (70.7 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Paroxysmal Atrial Fibrillation (PAF) 1 4 Recruiting Treatment Atrial Fibrillation 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution / drops Conjunctival Solution / drops Ophthalmic Solution Ophthalmic Solution / drops Intraocular Liquid Ophthalmic - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 227-229 Miescher, K. and Klarer, W.; US. Patent 2,449,241; September 14,1948: assigned to Ciba Pharmaceutical Products, Inc. water solubility 663 mg/L (at 30 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) - Predicted Properties
Property Value Source Water Solubility 0.114 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 No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9699 Blood Brain Barrier + 0.9578 Caco-2 permeable - 0.5076 P-glycoprotein substrate Substrate 0.7167 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Inhibitor 0.59 Renal organic cation transporter Inhibitor 0.8403 CYP450 2C9 substrate Non-substrate 0.798 CYP450 2D6 substrate Substrate 0.6581 CYP450 3A4 substrate Non-substrate 0.6963 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.919 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9644 CYP450 3A4 inhibitor Non-inhibitor 0.952 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8681 Ames test Non AMES toxic 0.788 Carcinogenicity Non-carcinogens 0.896 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4576 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5401 hERG inhibition (predictor II) Inhibitor 0.5709
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 174.7369326 predictedDarkChem Lite v0.1.0 [M-H]- 157.3321 predictedDeepCCS 1.0 (2019) [M+H]+ 174.7501326 predictedDarkChem Lite v0.1.0 [M+H]+ 159.72766 predictedDeepCCS 1.0 (2019) [M+Na]+ 174.7038326 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.77373 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
Drug created at October 14, 2010 20:06 / Updated at February 02, 2024 22:53