Identification
- Summary
Azelastine is a histamine H1-receptor antagonist used intranasally to treat allergic and vasomotor rhinitis and in an ophthalmic solution to treat allergic conjunctivitis.
- Brand Names
- Astelin, Astepro, Astepro Allergy, Dymista
- Generic Name
- Azelastine
- DrugBank Accession Number
- DB00972
- Background
Azelastine, a phthalazine derivative, is an antihistamine available as an intranasal spray for the treatment of allergic and vasomotor rhinitis and as an ophthalmic solution for the treatment of allergic conjunctivitis.10,11 It is a racemic mixture, though there is no noted difference in pharmacologic activity between enantiomers, and was first granted FDA approval in 1996.10,11 Azelastine is also available in combination with fluticasone propionate as a nasal spray marketed under the trade name Dymista™, which is indicated for the symptomatic treatment of seasonal allergic rhinitis in patients 6 years of age and older.13
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Azelastine (DB00972)
- Weight
- Average: 381.898
Monoisotopic: 381.160790112 - Chemical Formula
- C22H24ClN3O
- Synonyms
- 4-(p-Chlorobenzyl)-2-(hexahydro-1-methyl-1H-azepin-4-yl)-1-(2H)-phthalazinone
- Azelastina
- Azelastine
- Azélastine
- Azelastinum
Pharmacology
- Indication
Intranasal azelastine is indicated for the symptomatic treatment of seasonal allergic rhinitis in patients 5 years and older and for the symptomatic treatment of vasomotor rhinitis in patients 12 years and older.10 Ophthalmic azelastine solution is indicated for the treatment of itchy eyes associated with allergic conjunctivitis.11
As a 0.15% nasal spray, azelastine hydrochloride is also indicated for over-the-counter treatment of allergies in patients aged six years and older.14
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 Symptomatic treatment of Allergic conjunctivitis •••••••••••• •••••••• • ••••• Symptomatic treatment of Allergic eye disease •••••••••••• Prevention of Allergic eye disease •••••••••••• Symptomatic treatment of Allergic rhinitis (ar) ••• ••• ••••• Symptomatic treatment of Allergic rhinitis (ar) •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Azelastine antagonizes the actions of histamine, resulting in the relief of histamine-mediated allergy symptoms.2,10,11 Onset of action occurs within 15 minutes with intranasal formulations and as quickly as 3 minutes with ophthalmic solutions.1 Intranasal formulations have a relatively long-duration of action, with peak effects observed 4-6 hours after the initial dose and efficacy maintained over the entirety of the standard 12 hour dosing interval.2
- Mechanism of action
Azelastine is primarily a selective antagonist of histamine H1-receptors, with a lesser affinity for H2-receptors, used for the symptomatic treatment of allergies.2,1,10,11 Histamine H1-receptors are G-protein-coupled receptors with 7 transmembrane spanning domains7 that are found on nerve endings, smooth muscle cells, and glandular cells.8 Following allergen exposure in sensitized individuals, IgE-receptor cross-linking on mast cells results in the release of histamine, which binds to H1-receptors and contributes to typical allergic symptoms such as itching, sneezing, and congestion.8
Though its primary mode of action is thought to be via H1-receptor antagonism, azelastine (like other second-generation antihistamines) appears to affect other mediators of allergic symptomatology. Azelastine has mast cell-stabilizing properties that prevent the release of interleukin-6, tryptase, histamine, and TNF-alpha2 from mast cells, and has been shown to reduce mediators of mast cell degranulation such as leukotrienes in the nasal lavage of patients with rhinitis,1 as well as inhibiting their production and release from eosinophils (potentially via inhibition of phospholipase A2 and leukotriene C4 synthase).2,9 Additionally, patients using oral azelastine were observed to have significantly reduced concentrations of substance P and bradykinin in nasal secretions2, both of which may play a role in nasal itching and sneezing in patients with allergic rhinitis.
Target Actions Organism AHistamine H1 receptor antagonistHumans UHistamine H2 receptor inhibitorHumans UPhospholipase A2 inhibitorHumans ULeukotriene C4 synthase inhibitorHumans - Absorption
Systemic bioavailability of azelastine hydrochloride following intranasal administration is approximately 40%, reaching Cmax within 2-3 hours.2 When administered at doses greater than the recommended maximum, greater than proportional increases in both Cmax and AUC were observed.
- Volume of distribution
After intravenous and oral administration, the steady-state volume of distribution is 14.5 L/kg.2,10,11
- Protein binding
In-vitro studies in human plasma indicate that the plasma protein binding of azelastine and desmethylazelastine are approximately 88% and 97%, respectively.2,10,11
- Metabolism
Azelastine hydrochloride is oxidatively metabolized to its main, and biologically active, metabolite desmethylazelastine by the cytochrome P450 enzyme system.10,11 Though labels for azelastine state that specific CYP enzyme involvement has not been elucidated, it has been suggested that the N-demethylation of azelastine is primarily catalyzed by CYP3A4, CYP2D6, and CYP1A2.4
Hover over products below to view reaction partners
- Route of elimination
After an oral dose of radio-labeled azelastine hydrochloride, approximately 75% was excreted in the feces, with less than 10% as unchanged azelastine hydrochloride.2,10,11
- Half-life
Based on intravenous and oral administration, azelastine demonstrated an elimination half-life of 22 hours.10,11 Its primary active metabolite, desmethylazelastine, has an elimination half-life of 54 hours.2
- Clearance
Based on intravenous and oral administration, azelastine demonstrated a plasma clearance of 0.5 L/h/kg.10,11,6
- 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
Overdosage of intranasal or ophthalmic azelastine is unlikely to result in clinically significant adverse effects aside from increased drowsiness.10,11 If overdose does occur, employ general supportive measures. Oral ingestion of antihistamines, including non-oral formulations of azelastine, can cause serious adverse effects in children - for this reason, these products should be kept out of the reach of children. The oral LD50 in rats is 580 mg/kg.12
- Pathways
Pathway Category Azelastine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 software1,2-Benzodiazepine 1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Azelastine. Abametapir The serum concentration of Azelastine can be increased when it is combined with Abametapir. Abatacept The metabolism of Azelastine can be increased when combined with Abatacept. Abiraterone The serum concentration of Azelastine can be increased when it is combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Azelastine. - Food Interactions
- Avoid alcohol. Ingesting alcohol may cause additive CNS depressant effects.
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 Azelastine hydrochloride 0L591QR10I 79307-93-0 YEJAJYAHJQIWNU-UHFFFAOYSA-N - International/Other Brands
- Astepro Allergy (Bayer)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Astelin Spray, metered 137 ug/1 Nasal MEDA Pharmaceuticals 1996-11-01 Not applicable US 
Astelin Spray, metered 137 ug/1 Nasal Physicians Total Care, Inc. 2004-05-25 Not applicable US Astepro Spray, metered 205.5 ug/1 Nasal MEDA Pharmaceuticals 2009-10-12 2020-12-31 US Astepro Spray, metered 137 ug/1 Nasal MEDA Pharmaceuticals 2008-11-03 2008-11-03 US Azelastine Hydrochloride Spray, metered 205.5 ug/1 Nasal Perrigo New York Inc. 2015-04-09 2018-03-01 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Azelastine Spray, metered 137 ug/1 Nasal Ascend Laboratories, LLC 2017-08-18 Not applicable US Azelastine HCl Nasal Spray 205.5 ug/1 Nasal Padagis Israel Pharmaceuticals Ltd 2014-05-09 Not applicable US Azelastine HCl Nasal Spray 205.5 ug/1 Nasal bryant ranch prepack 2014-05-09 Not applicable US Azelastine Hydrochloride Spray, metered 137 ug/1 Nasal Sun Pharmaceutical Industries, Inc. 2012-05-24 Not applicable US Azelastine Hydrochloride Solution / drops 0.5 mg/1mL Intraocular Fosun Pharma USA Inc 2020-09-08 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Astepro Allergy Spray, metered 205.5 ug/1 Nasal Bayer Healthcare Llc. 2022-06-27 Not applicable US Children Astepro Allergy Spray, metered 205.5 ug/1 Nasal Bayer Healthcare Llc. 2022-06-27 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ALERXY® C Azelastine hydrochloride (137 mcg) + Fluticasone propionate (50 mcg) Suspension Intrasinal; Nasal LABORATORIOS SYNTHESIS S.A.S. 2015-04-21 Not applicable Colombia 
Apo-azelastine/fluticasone Azelastine hydrochloride (137 mcg / act) + Fluticasone propionate (50 mcg / act) Spray, metered Nasal Apotex Corporation 2023-10-31 Not applicable Canada 
AZEC® Azelastine hydrochloride (137 mcg) + Fluticasone propionate (50 mcg) Suspension Intrasinal; Nasal PROCAPS S.A. 2018-12-04 Not applicable Colombia AZEFLU®SUSPENSION SPRAY NASAL Azelastine hydrochloride (100 mg) + Fluticasone propionate (36.5 mg) Suspension Intrasinal; Nasal C.I. FARMACAPSULAS S.A.S. - PLANTA NO. 2 2018-04-05 2023-10-26 Colombia Azelastine Hydrochloride and Fluticasone Propionate Azelastine hydrochloride (137 ug/1) + Fluticasone propionate (50 ug/1) Spray, metered Nasal Padagis Israel Pharmaceuticals Ltd 2021-03-01 Not applicable US
Categories
- ATC Codes
- R06AX19 — Azelastine
- R06AX — Other antihistamines for systemic use
- R06A — ANTIHISTAMINES FOR SYSTEMIC USE
- R06 — ANTIHISTAMINES FOR SYSTEMIC USE
- R — RESPIRATORY SYSTEM
- S01GX — Other antiallergics
- S01G — DECONGESTANTS AND ANTIALLERGICS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- Drug Categories
- Anti-Allergic Agents
- Antiallergic Agents, Excl. Corticosteroids
- Antihistamines for Systemic Use
- Autonomic Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2A6 Inhibitors
- Cytochrome P-450 CYP2A6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2A6 Substrates
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Decongestants and Antiallergics
- Enzyme Inhibitors
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Histamine H1 Antagonists, Non-Sedating
- Nasal Preparations
- Neurotransmitter Agents
- Ophthalmologicals
- P-glycoprotein inhibitors
- Pyridazines
- Respiratory System Agents
- Sensory Organs
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phthalazinones. These are compounds containing a phthalazine bearing a ketone group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazanaphthalenes
- Sub Class
- Benzodiazines
- Direct Parent
- Phthalazinones
- Alternative Parents
- Pyridazinones / Chlorobenzenes / Azepanes / Aryl chlorides / Heteroaromatic compounds / Trialkylamines / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds show 3 more
- Substituents
- Amine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Azepane / Benzenoid / Chlorobenzene / Halobenzene / Heteroaromatic compound show 16 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- tertiary amino compound, monochlorobenzenes, phthalazines (CHEBI:2950)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- ZQI909440X
- CAS number
- 58581-89-8
- InChI Key
- MBUVEWMHONZEQD-UHFFFAOYSA-N
- InChI
- InChI=1S/C22H24ClN3O/c1-25-13-4-5-18(12-14-25)26-22(27)20-7-3-2-6-19(20)21(24-26)15-16-8-10-17(23)11-9-16/h2-3,6-11,18H,4-5,12-15H2,1H3
- IUPAC Name
- 4-[(4-chlorophenyl)methyl]-2-(1-methylazepan-4-yl)-1,2-dihydrophthalazin-1-one
- SMILES
- CN1CCCC(CC1)N1N=C(CC2=CC=C(Cl)C=C2)C2=CC=CC=C2C1=O
References
- Synthesis Reference
Yutaka Morita, Noritoshi Koyama, Shigemitsu Ohsawa, "Methods employing stable preparation containing azelastine hydrochloride." U.S. Patent US6117864, issued December 1990.
US6117864- General References
- Horak F: Effectiveness of twice daily azelastine nasal spray in patients with seasonal allergic rhinitis. Ther Clin Risk Manag. 2008 Oct;4(5):1009-22. [Article]
- Bernstein JA: Azelastine hydrochloride: a review of pharmacology, pharmacokinetics, clinical efficacy and tolerability. Curr Med Res Opin. 2007 Oct;23(10):2441-52. [Article]
- Zha W, Shum L: Simultaneous determination of azelastine and its major metabolite desmethylazelastine in human plasma using high performance liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Oct 1;906:69-74. doi: 10.1016/j.jchromb.2012.08.023. Epub 2012 Aug 24. [Article]
- Nakajima M, Nakamura S, Tokudome S, Shimada N, Yamazaki H, Yokoi T: Azelastine N-demethylation by cytochrome P-450 (CYP)3A4, CYP2D6, and CYP1A2 in human liver microsomes: evaluation of approach to predict the contribution of multiple CYPs. Drug Metab Dispos. 1999 Dec;27(12):1381-91. [Article]
- Nakajima M, Ohyama K, Nakamura S, Shimada N, Yamazaki H, Yokoi T: Inhibitory effects of azelastine and its metabolites on drug oxidation catalyzed by human cytochrome P-450 enzymes. Drug Metab Dispos. 1999 Jul;27(7):792-7. [Article]
- Williams PB, Crandall E, Sheppard JD: Azelastine hydrochloride, a dual-acting anti-inflammatory ophthalmic solution, for treatment of allergic conjunctivitis. Clin Ophthalmol. 2010 Sep 7;4:993-1001. doi: 10.2147/opth.s13479. [Article]
- Fukui H, Mizuguchi H, Nemoto H, Kitamura Y, Kashiwada Y, Takeda N: Histamine H1 Receptor Gene Expression and Drug Action of Antihistamines. Handb Exp Pharmacol. 2017;241:161-169. doi: 10.1007/164_2016_14. [Article]
- Baroody FM, Naclerio RM: Antiallergic effects of H1-receptor antagonists. Allergy. 2000;55 Suppl 64:17-27. [Article]
- Hamasaki Y, Shafigeh M, Yamamoto S, Sato R, Zaitu M, Muro E, Kobayashi I, Ichimaru T, Tasaki H, Miyazaki S: Inhibition of leukotriene synthesis by azelastine. Ann Allergy Asthma Immunol. 1996 May;76(5):469-75. doi: 10.1016/S1081-1206(10)63465-5. [Article]
- FDA Approved Drug Product: Azelastine nasal spray [Link]
- FDA Approved Drugs: Azelastine ophthalmic solution [Link]
- CaymenChem: Azelastine MSDS [Link]
- FDA Approved Drugs: Dymista nasal spray [Link]
- FDA News Release: Astepro OTC Approval [Link]
- External Links
- Human Metabolome Database
- HMDB0015107
- KEGG Drug
- D07483
- KEGG Compound
- C07768
- PubChem Compound
- 2267
- PubChem Substance
- 46507582
- ChemSpider
- 2180
- BindingDB
- 50341448
- 18603
- ChEBI
- 2950
- ChEMBL
- CHEMBL639
- Therapeutic Targets Database
- DNC000270
- PharmGKB
- PA448517
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Azelastine
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Allergic Rhinitis (AR) 2 4 Completed Treatment Perennial Allergic Rhinitis (PAR) 1 4 Completed Treatment Seasonal Allergic Rhinitis 3 4 Completed Treatment Vasomotor Rhinitis 1 4 Recruiting Supportive Care Coronavirus Disease 2019 (COVID‑19) 1
Pharmacoeconomics
- Manufacturers
- Apotex inc richmond hill
- Sun pharma global fze
- Meda pharmaceuticals inc
- Meda pharmaceuticals meda pharmaceuticals inc
- Apotex inc
- Meda pharmaceuticals
- Packagers
- Apotex Inc.
- A-S Medication Solutions LLC
- Catalent Pharma Solutions
- Meda AB
- Patheon Inc.
- Physicians Total Care Inc.
- Redpharm Drug
- Wallace Pharmaceuticals Inc.
- Dosage Forms
Form Route Strength Solution Intrasinal; Nasal 0.1 g Suspension Intrasinal; Nasal Spray Nasal 1 MG/1ML Tablet, film coated Oral Solution / drops Ophthalmic 0.05 % Spray Nasal 0.14 mg/0.4mL Solution / drops Ophthalmic Spray, metered Nasal 137 ug/1 Spray Nasal 1.5 MG/ML Spray Nasal 0.15 % Solution Ophthalmic 0.5 mg Spray Nasal 205.5 ug/1 Solution / drops Ophthalmic 0.5 mg/1mL Spray Nasal 137 ug/0.137mL Spray, metered Nasal 1 mg/1mL Spray, metered Nasal 1.5 mg/1mL Spray, metered Nasal 137 ug/0.137mL Spray, metered Nasal 205.5 ug/1 Spray Nasal 0.14 mg Solution Ophthalmic 0.05 % w/v Spray Nasal 1 mg/ml Suspension Nasal 0.050 g Solution Nasal 1.000 mg Spray Nasal 137 MICROGRAMMI/50MICROGRAMMI Spray, metered Nasal Spray, suspension Respiratory (inhalation) Spray, suspension Respiratory (inhalation) 50 mcg Suspension Nasal Spray, suspension Nasal Solution / drops Conjunctival 0.5 MG/ML Tablet 2.2 MG Solution Conjunctival; Ophthalmic 0.5 mg Spray Nasal 0.14 mg/spray Solution Nasal 0.14 mg/spray Spray Nasal Solution / drops Intraocular 0.5 mg/1mL Spray Nasal Solution / drops Ophthalmic 0.5 MG/ML - Prices
Unit description Cost Unit Optivar 0.05% Solution 6ml Bottle 120.26USD bottle Astelin 137 mcg/spray Solution 30ml Bottle 117.27USD bottle Azelastine HCl 0.05% Solution 6ml Bottle 108.23USD bottle Optivar 0.05% drops 19.27USD ml Azelastine hcl 0.05% drops 17.35USD ml Astelin 137 mcg nasal spray 3.71USD ml Astepro 137 mcg nasal spray 3.61USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5164194 No 1992-11-17 2011-05-01 US US8518919 No 2013-08-27 2025-11-22 US US8071073 No 2011-12-06 2028-06-04 US US8163723 Yes 2012-04-24 2024-02-29 US US9259428 Yes 2016-02-16 2023-12-13 US US8168620 Yes 2012-05-01 2026-08-24 US US9901585 No 2018-02-27 2023-06-13 US US9919050 No 2018-03-20 2025-11-22 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 225 °C (hydrochloride salt) FDA Label (intranasal azelastine) water solubility Sparingly soluble (hydrochloride salt) FDA Label (intranasal azelastine) - Predicted Properties
Property Value Source Water Solubility 0.0092 mg/mL ALOGPS logP 3.81 ALOGPS logP 4.04 Chemaxon logS -4.6 ALOGPS pKa (Strongest Basic) 8.88 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 35.91 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 110.52 m3·mol-1 Chemaxon Polarizability 41.54 Å3 Chemaxon Number of Rings 4 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 + 1.0 Blood Brain Barrier + 0.982 Caco-2 permeable - 0.5102 P-glycoprotein substrate Substrate 0.7034 P-glycoprotein inhibitor I Inhibitor 0.8563 P-glycoprotein inhibitor II Inhibitor 0.9563 Renal organic cation transporter Inhibitor 0.6812 CYP450 2C9 substrate Non-substrate 0.7501 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Substrate 0.8204 CYP450 1A2 substrate Inhibitor 0.6371 CYP450 2C9 inhibitor Non-inhibitor 0.8114 CYP450 2D6 inhibitor Non-inhibitor 0.568 CYP450 2C19 inhibitor Non-inhibitor 0.6934 CYP450 3A4 inhibitor Non-inhibitor 0.5902 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7266 Ames test Non AMES toxic 0.6567 Carcinogenicity Non-carcinogens 0.878 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 3.0597 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7885 hERG inhibition (predictor II) Inhibitor 0.7391
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 200.9283568 predictedDarkChem Lite v0.1.0 [M-H]- 185.36775 predictedDeepCCS 1.0 (2019) [M+H]+ 201.7355568 predictedDarkChem Lite v0.1.0 [M+H]+ 187.75728 predictedDeepCCS 1.0 (2019) [M+Na]+ 201.6715568 predictedDarkChem Lite v0.1.0 [M+Na]+ 195.84378 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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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
- Casale TB: The interaction of azelastine with human lung histamine H1, beta, and muscarinic receptor-binding sites. J Allergy Clin Immunol. 1989 Apr;83(4):771-6. [Article]
- Conde Hernandez DJ, Palma Aqilar JL, Delgado Romero J: Comparison of azelastine nasal spray and oral ebastine in treating seasonal allergic rhinitis. Curr Med Res Opin. 1995;13(6):299-304. [Article]
- Antepara I, Jauregui I, Basomba A, Cadahia A, Feo F, Garcia JJ, Gonzalo MA, Luna I, Rubio M, Vazquez M: [Investigation of the efficacy and tolerability of azelastine nasal spray versus ebastine tablets in patients with seasonal allergic rhinitis]. Allergol Immunopathol (Madr). 1998 Jan-Feb;26(1):9-16. [Article]
- Horak F: Effectiveness of twice daily azelastine nasal spray in patients with seasonal allergic rhinitis. Ther Clin Risk Manag. 2008 Oct;4(5):1009-22. [Article]
- Bernstein JA: Azelastine hydrochloride: a review of pharmacology, pharmacokinetics, clinical efficacy and tolerability. Curr Med Res Opin. 2007 Oct;23(10):2441-52. [Article]
- Golden SJ, Craig TJ: Efficacy and safety of azelastine nasal spray for the treatment of allergic rhinitis. J Am Osteopath Assoc. 1999 Jul;99(7 Suppl):S7-12. [Article]
- FDA Approved Drug Product: Azelastine nasal spray [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Histamine receptor activity
- Specific Function
- The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and diff...
- Gene Name
- HRH2
- Uniprot ID
- P25021
- Uniprot Name
- Histamine H2 receptor
- Molecular Weight
- 40097.65 Da
References
- Bernstein JA: Azelastine hydrochloride: a review of pharmacology, pharmacokinetics, clinical efficacy and tolerability. Curr Med Res Opin. 2007 Oct;23(10):2441-52. [Article]
- Williams PB, Crandall E, Sheppard JD: Azelastine hydrochloride, a dual-acting anti-inflammatory ophthalmic solution, for treatment of allergic conjunctivitis. Clin Ophthalmol. 2010 Sep 7;4:993-1001. doi: 10.2147/opth.s13479. [Article]
- Horak F: Effectiveness of twice daily azelastine nasal spray in patients with seasonal allergic rhinitis. Ther Clin Risk Manag. 2008 Oct;4(5):1009-22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Receptor binding
- Specific Function
- PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides, this releases glycerophospholipids and arachidonic acid that serve as the precursors of signal molecules.
- Gene Name
- PLA2G1B
- Uniprot ID
- P04054
- Uniprot Name
- Phospholipase A2
- Molecular Weight
- 16359.535 Da
References
- Hamasaki Y, Shafigeh M, Yamamoto S, Sato R, Zaitu M, Muro E, Kobayashi I, Ichimaru T, Tasaki H, Miyazaki S: Inhibition of leukotriene synthesis by azelastine. Ann Allergy Asthma Immunol. 1996 May;76(5):469-75. doi: 10.1016/S1081-1206(10)63465-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Lipid binding
- Specific Function
- Catalyzes the conjugation of leukotriene A4 with reduced glutathione to form leukotriene C4.
- Gene Name
- LTC4S
- Uniprot ID
- Q16873
- Uniprot Name
- Leukotriene C4 synthase
- Molecular Weight
- 16566.465 Da
References
- Hamasaki Y, Shafigeh M, Yamamoto S, Sato R, Zaitu M, Muro E, Kobayashi I, Ichimaru T, Tasaki H, Miyazaki S: Inhibition of leukotriene synthesis by azelastine. Ann Allergy Asthma Immunol. 1996 May;76(5):469-75. doi: 10.1016/S1081-1206(10)63465-5. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Nakajima M, Nakamura S, Tokudome S, Shimada N, Yamazaki H, Yokoi T: Azelastine N-demethylation by cytochrome P-450 (CYP)3A4, CYP2D6, and CYP1A2 in human liver microsomes: evaluation of approach to predict the contribution of multiple CYPs. Drug Metab Dispos. 1999 Dec;27(12):1381-91. [Article]
- Nakajima M, Ohyama K, Nakamura S, Shimada N, Yamazaki H, Yokoi T: Inhibitory effects of azelastine and its metabolites on drug oxidation catalyzed by human cytochrome P-450 enzymes. Drug Metab Dispos. 1999 Jul;27(7):792-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Nakajima M, Nakamura S, Tokudome S, Shimada N, Yamazaki H, Yokoi T: Azelastine N-demethylation by cytochrome P-450 (CYP)3A4, CYP2D6, and CYP1A2 in human liver microsomes: evaluation of approach to predict the contribution of multiple CYPs. Drug Metab Dispos. 1999 Dec;27(12):1381-91. [Article]
- Nakajima M, Ohyama K, Nakamura S, Shimada N, Yamazaki H, Yokoi T: Inhibitory effects of azelastine and its metabolites on drug oxidation catalyzed by human cytochrome P-450 enzymes. Drug Metab Dispos. 1999 Jul;27(7):792-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- Curator comments
- Data supporting this enzyme action is limited to in vitro studies.
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Nakajima M, Nakamura S, Tokudome S, Shimada N, Yamazaki H, Yokoi T: Azelastine N-demethylation by cytochrome P-450 (CYP)3A4, CYP2D6, and CYP1A2 in human liver microsomes: evaluation of approach to predict the contribution of multiple CYPs. Drug Metab Dispos. 1999 Dec;27(12):1381-91. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Nakajima M, Ohyama K, Nakamura S, Shimada N, Yamazaki H, Yokoi T: Inhibitory effects of azelastine and its metabolites on drug oxidation catalyzed by human cytochrome P-450 enzymes. Drug Metab Dispos. 1999 Jul;27(7):792-7. [Article]
- Nakajima M, Nakamura S, Tokudome S, Shimada N, Yamazaki H, Yokoi T: Azelastine N-demethylation by cytochrome P-450 (CYP)3A4, CYP2D6, and CYP1A2 in human liver microsomes: evaluation of approach to predict the contribution of multiple CYPs. Drug Metab Dispos. 1999 Dec;27(12):1381-91. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Vitamin d 24-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Nakajima M, Ohyama K, Nakamura S, Shimada N, Yamazaki H, Yokoi T: Inhibitory effects of azelastine and its metabolites on drug oxidation catalyzed by human cytochrome P-450 enzymes. Drug Metab Dispos. 1999 Jul;27(7):792-7. [Article]
- Nakajima M, Nakamura S, Tokudome S, Shimada N, Yamazaki H, Yokoi T: Azelastine N-demethylation by cytochrome P-450 (CYP)3A4, CYP2D6, and CYP1A2 in human liver microsomes: evaluation of approach to predict the contribution of multiple CYPs. Drug Metab Dispos. 1999 Dec;27(12):1381-91. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Nakajima M, Nakamura S, Tokudome S, Shimada N, Yamazaki H, Yokoi T: Azelastine N-demethylation by cytochrome P-450 (CYP)3A4, CYP2D6, and CYP1A2 in human liver microsomes: evaluation of approach to predict the contribution of multiple CYPs. Drug Metab Dispos. 1999 Dec;27(12):1381-91. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- Data are limited to the findings of one in vitro study.
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Nakajima M, Ohyama K, Nakamura S, Shimada N, Yamazaki H, Yokoi T: Inhibitory effects of azelastine and its metabolites on drug oxidation catalyzed by human cytochrome P-450 enzymes. Drug Metab Dispos. 1999 Jul;27(7):792-7. [Article]
- Nakajima M, Nakamura S, Tokudome S, Shimada N, Yamazaki H, Yokoi T: Azelastine N-demethylation by cytochrome P-450 (CYP)3A4, CYP2D6, and CYP1A2 in human liver microsomes: evaluation of approach to predict the contribution of multiple CYPs. Drug Metab Dispos. 1999 Dec;27(12):1381-91. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Nakajima M, Nakamura S, Tokudome S, Shimada N, Yamazaki H, Yokoi T: Azelastine N-demethylation by cytochrome P-450 (CYP)3A4, CYP2D6, and CYP1A2 in human liver microsomes: evaluation of approach to predict the contribution of multiple CYPs. Drug Metab Dispos. 1999 Dec;27(12):1381-91. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56501.005 Da
References
- Nakajima M, Ohyama K, Nakamura S, Shimada N, Yamazaki H, Yokoi T: Inhibitory effects of azelastine and its metabolites on drug oxidation catalyzed by human cytochrome P-450 enzymes. Drug Metab Dispos. 1999 Jul;27(7):792-7. [Article]
- Nakajima M, Nakamura S, Tokudome S, Shimada N, Yamazaki H, Yokoi T: Azelastine N-demethylation by cytochrome P-450 (CYP)3A4, CYP2D6, and CYP1A2 in human liver microsomes: evaluation of approach to predict the contribution of multiple CYPs. Drug Metab Dispos. 1999 Dec;27(12):1381-91. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Nakajima M, Ohyama K, Nakamura S, Shimada N, Yamazaki H, Yokoi T: Inhibitory effects of azelastine and its metabolites on drug oxidation catalyzed by human cytochrome P-450 enzymes. Drug Metab Dispos. 1999 Jul;27(7):792-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Inhibition of CYP2B6 is via azelastine's active metabolite, desmethylazelastine, rather than the parent drug itself.
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Nakajima M, Ohyama K, Nakamura S, Shimada N, Yamazaki H, Yokoi T: Inhibitory effects of azelastine and its metabolites on drug oxidation catalyzed by human cytochrome P-450 enzymes. Drug Metab Dispos. 1999 Jul;27(7):792-7. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Katoh M, Nakajima M, Yamazaki H, Yokoi T: Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport. Eur J Pharm Sci. 2001 Feb;12(4):505-13. [Article]
- Hu YP, Robert J: Azelastine and flezelastine as reversing agents of multidrug resistance: pharmacological and molecular studies. Biochem Pharmacol. 1995 Jul 17;50(2):169-75. [Article]
- Kim JY, Kim KS, Kim IS, Yoon S: Histamine Receptor Antagonists, Loratadine and Azelastine, Sensitize P-gp-overexpressing Antimitotic Drug-resistant KBV20C Cells Through Different Molecular Mechanisms. Anticancer Res. 2019 Jul;39(7):3767-3775. doi: 10.21873/anticanres.13525. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:46