Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H24ClN3O |
| Molecular Weight | 381.898 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCC[C@@H](CC1)N2N=C(CC3=CC=C(Cl)C=C3)C4=C(C=CC=C4)C2=O
InChI
InChIKey=MBUVEWMHONZEQD-SFHVURJKSA-N
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/t18-/m0/s1
| Molecular Formula | C22H24ClN3O |
| Molecular Weight | 381.898 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| Poor sleep and daytime somnolence in allergic rhinitis: significance of nasal congestion. | 2002 |
|
| Interactions of olopatadine and selected antihistamines with model and natural membranes. | 2003 Dec |
|
| 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 Nov |
|
| Histamine skin test reactivity following single and multiple doses of azelastine nasal spray in patients with seasonal allergic rhinitis. | 2003 Sep |
|
| Treatment of nonallergic perennial rhinitis. | 2004 |
|
| Efficacy of azelastine nasal spray in seasonal allergic rhinitis patients who remain symptomatic after treatment with fexofenadine. | 2004 Aug |
|
| Antiallergic activity of hesperidin is activated by intestinal microflora. | 2004 Aug |
|
| Synthesis and potential anti-inflammatory activity of some tetrahydrophthalazinones. | 2004 Dec |
|
| In vitro effects of astaxanthin combined with ginkgolide B on T lymphocyte activation in peripheral blood mononuclear cells from asthmatic subjects. | 2004 Feb |
|
| [Topical H1 antihistaminics in the therapy of acute conjunctival allergic reactions]. | 2004 Jan |
|
| [Respiratory allergies in the child and the adult]. | 2004 Jan 31 |
|
| Nasal saline: placebo or drug? | 2004 Jul |
|
| Intradermal nociceptin elicits itch-associated responses through leukotriene B(4) in mice. | 2004 Jul |
|
| Ocular allergy treatment comparisons: azelastine and olopatadine. | 2004 Jul |
|
| Vasomotor rhinitis update. | 2004 Jun |
|
| Cutaneous drug eruption from cetirizine and hydroxyzine. | 2004 Jun |
|
| Influences of allergic rhinitis on sleep. | 2004 May |
|
| 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 May |
|
| Evidence-based strategies for treatment of allergic rhinitis. | 2004 Nov |
|
| Efficacy and tolerability of newer antihistamines in the treatment of allergic conjunctivitis. | 2005 |
|
| Open-label evaluation of azelastine nasal spray in patients with seasonal allergic rhinitis and nonallergic vasomotor rhinitis. | 2005 Apr |
|
| Passive cutaneous anaphylaxis-inhibitory activity of flavanones from Citrus unshiu and Poncirus trifoliata. | 2005 Jan |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
| Protein kinase C-alpha mediates TNF release process in RBL-2H3 mast cells. | 2005 Jun |
|
| A Japanese patient with familial Mediterranean fever associated with compound heterozygosity for pyrin variant E148Q/M694I. | 2005 Mar |
|
| Effectiveness of azelastine nasal spray compared with oral cetirizine in patients with seasonal allergic rhinitis. | 2005 May |
|
| Nasal obstruction, the airway, and the athlete. | 2005 Oct |
|
| [Azelastine hydrochloride in the treatment of allergic rhinitis]. | 2005 Sep |
|
| Antipruritic effect of ginsenoside rb1 and compound k in scratching behavior mouse models. | 2005 Sep |
|
| The role of antihistamines in asthma management. | 2006 |
|
| Expression of urocortin in rat lung and its effect on pulmonary vascular permeability. | 2006 Apr |
|
| Long QT syndrome in a patient with allergic rhinoconjunctivitis and auto-immune diabetes: focus on the choice of anti-H1 drugs. | 2006 Dec |
|
| Synergistic effects of the anti-cholinergic R,R-glycopyrrolate with anti-inflammatory drugs. | 2006 Dec 15 |
|
| Azelastine nasal spray and desloratadine tablets in pollen-induced seasonal allergic rhinitis: a pharmacodynamic study of onset of action and efficacy. | 2006 Jan |
|
| Pharmacotherapy of allergic eye disease. | 2006 Jun |
|
| [Comparison of clinical efficacy and cost-quality of antihistamines in early treatment for Japanese cedar pollinosis]. | 2006 May |
|
| Allergic rhinitis: evidence for impact on asthma. | 2006 Nov 30 |
|
| Antiallergic drugs, azelastine hydrochloride and epinastine hydrochloride, inhibit ongoing IgE secretion of rat IgE-producing hybridoma FE-3 cells. | 2006 Oct 10 |
|
| Impact of azelastine nasal spray on symptoms and quality of life compared with cetirizine oral tablets in patients with seasonal allergic rhinitis. | 2006 Sep |
|
| Review of azelastine nasal spray in the treatment of allergic and non-allergic rhinitis. | 2007 Apr |
|
| Duration of action of topical antiallergy drugs in a Guinea pig model of histamine-induced conjunctival vascular permeability. | 2007 Aug |
|
| Nasal azelastine for self-medication: modest symptomatic relief from rhinitis. | 2007 Aug |
|
| 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 Jul |
|
| 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 Jul-Aug |
|
| Antianaphylactic properties of 7-epiclusianone, a tetraprenylated benzophenone isolated from Garcinia brasiliensis. | 2007 Jun |
|
| Meta-analysis of azelastine nasal spray for the treatment of allergic rhinitis. | 2007 Jun |
|
| Comparative efficacy of steroid nasal spray versus antihistamine nasal spray in allergic rhinitis. | 2007 Mar |
|
| Azelastine hydrochloride: a review of pharmacology, pharmacokinetics, clinical efficacy and tolerability. | 2007 Oct |
|
| Efficacy and safety of azelastine nasal spray at a dose of 1 spray per nostril twice daily. | 2007 Sep |
|
| Effect of azelastine, montelukast, and their combination on allergen-induced bronchoconstriction in asthma. | 2008 |
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.
| Substance Class |
Chemical
Created
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7Y9YE1DOYQ
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| Related Record | Type | Details | ||
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RACEMATE -> ENANTIOMER |
