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-GOSISDBHSA-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-/m1/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 |
|---|---|---|
| Simultaneous enantioselective separation of azelastine and three of its metabolites for the investigation of the enantiomeric metabolism in rats. I. Liquid chromatography-ionspray tandem mass spectrometry and electrokinetic capillary chromatography. | 2003 Aug 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: To male Wistar rats one single dose of 50 mg/kg AZELASTINE, (R)- 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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SUBSTANCE RECORD
