Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H24ClN3O.ClH |
| Molecular Weight | 418.359 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN1CCC[C@@H](CC1)N2N=C(CC3=CC=C(Cl)C=C3)C4=C(C=CC=C4)C2=O
InChI
InChIKey=YEJAJYAHJQIWNU-FERBBOLQSA-N
InChI=1S/C22H24ClN3O.ClH/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;1H/t18-;/m0./s1
Azelastine (brand names AZEP, ASTEPRO, ASTELIN etc.) a phthalazine derivative, is an antihistamine and mast cell stabilizer available as a nasal spray for hay fever and as eye drops for allergic conjunctivitis. Azelastine is a potent antiallergic compound with histamine H1-receptor antagonist activity and a rapid onset and long duration of action. The major metabolite, desmethylazelastine, also exhibits H1-
receptor antagonist activity. AZEP Nasal Spray is administered as a racemic mixture.
The racemate, R- and S- enantiomers were equally potent at inhibiting eyelid
histamine-induced oedema in rats, however the R-enantiomer was 2-fold less active
at inhibiting eyeball histamine-induced oedema.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 8.9 null [pKi] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | ASTELIN Approved UseAstelin Nasal Spray is indicated for the treatment of the symptoms of seasonal allergic rhinitis such as rhinorrhea, sneezing, and
nasal pruritus in adults and children 5 years and older, and for the treatment of the symptoms of vasomotor rhinitis, such as rhinorrhea,
nasal congestion and postnasal drip in adults and children 12 years and older. Launch Date1996 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of azelastine, montelukast, and their combination on allergen-induced bronchoconstriction in asthma. | 2008 |
|
| Azelastine hydrochloride: a review of pharmacology, pharmacokinetics, clinical efficacy and tolerability. | 2007-10 |
|
| Onset of action of azelastine nasal spray compared with mometasone nasal spray and placebo in subjects with seasonal allergic rhinitis evaluated in an environmental exposure chamber. | 2007-09-22 |
|
| Efficacy and safety of azelastine nasal spray at a dose of 1 spray per nostril twice daily. | 2007-09 |
|
| Duration of action of topical antiallergy drugs in a Guinea pig model of histamine-induced conjunctival vascular permeability. | 2007-08 |
|
| Nasal azelastine for self-medication: modest symptomatic relief from rhinitis. | 2007-08 |
|
| Inhibition of IgE-mediated phosphorylation of FcepsilonRIgamma protein by antiallergic drugs in rat basophilic leukemia (RBL-2H3) cells: a novel action of antiallergic drugs. | 2007-07 |
|
| Antianaphylactic properties of 7-epiclusianone, a tetraprenylated benzophenone isolated from Garcinia brasiliensis. | 2007-06 |
|
| Meta-analysis of azelastine nasal spray for the treatment of allergic rhinitis. | 2007-06 |
|
| Review of azelastine nasal spray in the treatment of allergic and non-allergic rhinitis. | 2007-04 |
|
| Comparative efficacy of steroid nasal spray versus antihistamine nasal spray in allergic rhinitis. | 2007-03 |
|
| Synergistic effects of the anti-cholinergic R,R-glycopyrrolate with anti-inflammatory drugs. | 2006-12-15 |
|
| Long QT syndrome in a patient with allergic rhinoconjunctivitis and auto-immune diabetes: focus on the choice of anti-H1 drugs. | 2006-12 |
|
| Allergic rhinitis: evidence for impact on asthma. | 2006-11-30 |
|
| Antiallergic drugs, azelastine hydrochloride and epinastine hydrochloride, inhibit ongoing IgE secretion of rat IgE-producing hybridoma FE-3 cells. | 2006-10-10 |
|
| Impact of azelastine nasal spray on symptoms and quality of life compared with cetirizine oral tablets in patients with seasonal allergic rhinitis. | 2006-09 |
|
| Pharmacotherapy of allergic eye disease. | 2006-06 |
|
| [Comparison of clinical efficacy and cost-quality of antihistamines in early treatment for Japanese cedar pollinosis]. | 2006-05 |
|
| Expression of urocortin in rat lung and its effect on pulmonary vascular permeability. | 2006-04 |
|
| Azelastine nasal spray and desloratadine tablets in pollen-induced seasonal allergic rhinitis: a pharmacodynamic study of onset of action and efficacy. | 2006-01 |
|
| The role of antihistamines in asthma management. | 2006 |
|
| Nasal obstruction, the airway, and the athlete. | 2005-10 |
|
| [Azelastine hydrochloride in the treatment of allergic rhinitis]. | 2005-09 |
|
| Antipruritic effect of ginsenoside rb1 and compound k in scratching behavior mouse models. | 2005-09 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005-06 |
|
| Protein kinase C-alpha mediates TNF release process in RBL-2H3 mast cells. | 2005-06 |
|
| Effectiveness of azelastine nasal spray compared with oral cetirizine in patients with seasonal allergic rhinitis. | 2005-05 |
|
| Open-label evaluation of azelastine nasal spray in patients with seasonal allergic rhinitis and nonallergic vasomotor rhinitis. | 2005-04 |
|
| A Japanese patient with familial Mediterranean fever associated with compound heterozygosity for pyrin variant E148Q/M694I. | 2005-03 |
|
| Passive cutaneous anaphylaxis-inhibitory activity of flavanones from Citrus unshiu and Poncirus trifoliata. | 2005-01 |
|
| Efficacy and tolerability of newer antihistamines in the treatment of allergic conjunctivitis. | 2005 |
|
| Synthesis and potential anti-inflammatory activity of some tetrahydrophthalazinones. | 2004-12 |
|
| Evidence-based strategies for treatment of allergic rhinitis. | 2004-11 |
|
| Efficacy of azelastine nasal spray in seasonal allergic rhinitis patients who remain symptomatic after treatment with fexofenadine. | 2004-08 |
|
| Antiallergic activity of hesperidin is activated by intestinal microflora. | 2004-08 |
|
| Nasal saline: placebo or drug? | 2004-07 |
|
| Intradermal nociceptin elicits itch-associated responses through leukotriene B(4) in mice. | 2004-07 |
|
| Ocular allergy treatment comparisons: azelastine and olopatadine. | 2004-07 |
|
| Vasomotor rhinitis update. | 2004-06 |
|
| Cutaneous drug eruption from cetirizine and hydroxyzine. | 2004-06 |
|
| Influences of allergic rhinitis on sleep. | 2004-05 |
|
| Pharmacokinetic interactions between Japanese traditional medicine (kampo) and modern medicine (III). Effect of Sho-seiryu-to on the pharmacokinetics of azelastine hydrochloride in rats. | 2004-05 |
|
| In vitro effects of astaxanthin combined with ginkgolide B on T lymphocyte activation in peripheral blood mononuclear cells from asthmatic subjects. | 2004-02 |
|
| [Respiratory allergies in the child and the adult]. | 2004-01-31 |
|
| [Topical H1 antihistaminics in the therapy of acute conjunctival allergic reactions]. | 2004-01 |
|
| Treatment of nonallergic perennial rhinitis. | 2004 |
|
| Interactions of olopatadine and selected antihistamines with model and natural membranes. | 2003-12 |
|
| Azelastine inhibits secretion of IL-6, TNF-alpha and IL-8 as well as NF-kappaB activation and intracellular calcium ion levels in normal human mast cells. | 2003-11 |
|
| Histamine skin test reactivity following single and multiple doses of azelastine nasal spray in patients with seasonal allergic rhinitis. | 2003-09 |
|
| Poor sleep and daytime somnolence in allergic rhinitis: significance of nasal congestion. | 2002 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: To male Wistar rats one single dose of 50 mg/kg AZELASTINE, (S)- was
applied orally (by oral gavage): https://www.ncbi.nlm.nih.gov/pubmed/12906914
Adults and children aged 5 years and over:Each spray contains 125 ug of azelastine (as hydrochloride).One spray into each nostril twice daily as necessary (equivalent to a daily dose of 0.50 mg azelastine
Route of Administration:
Nasal
In Vitro Use Guide
Curator's Comment: Sensitized cultured human mast cells (CHMCs) were pretreated with various concentrations of azelastine or olopatadine for 5 minutes. Then, CHMCs were challenged with anti-immunoglobulin E (IgE) and the released mediators were quantitated.
The greatest inhibition of mediator release was seen when cultured human mast cells (CHMCs) were pretreated with 24 uM of azelastine.
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DTXSID50735375
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SUBSTANCE RECORD
