Details
Stereochemistry | RACEMIC |
Molecular Formula | C22H24ClN3O |
Molecular Weight | 381.898 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCCC(CC1)N2N=C(CC3=CC=C(Cl)C=C3)C4=CC=CC=C4C2=O
InChI
InChIKey=MBUVEWMHONZEQD-UHFFFAOYSA-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
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.rxlist.com/astelin-drug.htm | https://www.drugs.com/pro/azelastine.html
Curator's Comment: description was created based on several sources, including:
http://www.rxlist.com/astelin-drug.htm | https://www.drugs.com/pro/azelastine.html
Azelastine, a phthalazine derivative, is an antihistamine and mast cell stabilizer. Azelastine is oxidatively metabolized to the principal active metabolite, desmethylazelastine, by the cytochrome P450 enzyme system. It is indicated for the relief of the symptoms of seasonal allergic rhinitis and perennial allergic rhinitis. The most common adverse reactions are: pyrexia, dysgeusia, nasal discomfort, epistaxis, headache, sneezing, fatigue, somnolence, upper respiratory infection, cough, rhinalgia, vomiting, otitis media, contact dermatitis, and oropharyngeal pain. Concurrent use of Azelastine with alcohol or other central nervous system depressants should be avoided because reductions in alertness and impairment of central nervous system performance may occur.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL231 |
872.0 nM [Kd] | ||
Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10421623 |
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Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10421623 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | ASTELIN Approved UseAzelastine hydrochloride ophthalmic solution is indicated for the treatment of itching of the eye associated with allergic conjunctivitis. Launch Date1996 |
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Palliative | ASTELIN Approved UseAzelastine hydrochloride ophthalmic solution is indicated for the treatment of itching of the eye associated with allergic conjunctivitis. Launch Date1996 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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61.59 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23681835 |
0.28 mg single, nasal dose: 0.28 mg route of administration: Nasal experiment type: SINGLE co-administered: |
AZELASTINE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1526.8 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23681835 |
0.28 mg single, nasal dose: 0.28 mg route of administration: Nasal experiment type: SINGLE co-administered: |
AZELASTINE HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
22 h |
unknown, unknown |
AZELASTINE HYDROCHLORIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12% |
unknown, unknown |
AZELASTINE HYDROCHLORIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
4 mg 1 times / day multiple, oral Dose: 4 mg, 1 times / day Route: oral Route: multiple Dose: 4 mg, 1 times / day Sources: |
unhealthy, 38.5 years (range: 18-64 years) n = 16 Health Status: unhealthy Condition: Chronic Idiopathic Urticaria Age Group: 38.5 years (range: 18-64 years) Sex: M+F Population Size: 16 Sources: |
Disc. AE: Taste perversion, Gastritis... AEs leading to discontinuation/dose reduction: Taste perversion (2 patients) Sources: Gastritis (1 patient) Somnolence (1 patient) |
0.015 mg 2 times / day multiple, ophthalmic Dose: 0.015 mg, 2 times / day Route: ophthalmic Route: multiple Dose: 0.015 mg, 2 times / day Sources: |
unhealthy, 4-12 years n = 51 Health Status: unhealthy Condition: seasonal allergic conjunctiviti Age Group: 4-12 years Sex: M+F Population Size: 51 Sources: |
Disc. AE: Burning sensation, Taste bitter... AEs leading to discontinuation/dose reduction: Burning sensation (1 patient) Sources: Taste bitter (1 patient) |
274 ug 2 times / day multiple, intranasal Recommended Dose: 274 ug, 2 times / day Route: intranasal Route: multiple Dose: 274 ug, 2 times / day Sources: Page: p. 44 |
unhealthy, > 12 years n = 216 Health Status: unhealthy Condition: seasonal allergic rhinitis. Age Group: > 12 years Population Size: 216 Sources: Page: p. 44 |
Disc. AE: Somnolence, Back pain... AEs leading to discontinuation/dose reduction: Somnolence (2 patients) Sources: Page: p. 44Back pain (1 patient) Taste perversion (1 patient) Sinusitis (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Gastritis | 1 patient Disc. AE |
4 mg 1 times / day multiple, oral Dose: 4 mg, 1 times / day Route: oral Route: multiple Dose: 4 mg, 1 times / day Sources: |
unhealthy, 38.5 years (range: 18-64 years) n = 16 Health Status: unhealthy Condition: Chronic Idiopathic Urticaria Age Group: 38.5 years (range: 18-64 years) Sex: M+F Population Size: 16 Sources: |
Somnolence | 1 patient Disc. AE |
4 mg 1 times / day multiple, oral Dose: 4 mg, 1 times / day Route: oral Route: multiple Dose: 4 mg, 1 times / day Sources: |
unhealthy, 38.5 years (range: 18-64 years) n = 16 Health Status: unhealthy Condition: Chronic Idiopathic Urticaria Age Group: 38.5 years (range: 18-64 years) Sex: M+F Population Size: 16 Sources: |
Taste perversion | 2 patients Disc. AE |
4 mg 1 times / day multiple, oral Dose: 4 mg, 1 times / day Route: oral Route: multiple Dose: 4 mg, 1 times / day Sources: |
unhealthy, 38.5 years (range: 18-64 years) n = 16 Health Status: unhealthy Condition: Chronic Idiopathic Urticaria Age Group: 38.5 years (range: 18-64 years) Sex: M+F Population Size: 16 Sources: |
Burning sensation | 1 patient Disc. AE |
0.015 mg 2 times / day multiple, ophthalmic Dose: 0.015 mg, 2 times / day Route: ophthalmic Route: multiple Dose: 0.015 mg, 2 times / day Sources: |
unhealthy, 4-12 years n = 51 Health Status: unhealthy Condition: seasonal allergic conjunctiviti Age Group: 4-12 years Sex: M+F Population Size: 51 Sources: |
Taste bitter | 1 patient Disc. AE |
0.015 mg 2 times / day multiple, ophthalmic Dose: 0.015 mg, 2 times / day Route: ophthalmic Route: multiple Dose: 0.015 mg, 2 times / day Sources: |
unhealthy, 4-12 years n = 51 Health Status: unhealthy Condition: seasonal allergic conjunctiviti Age Group: 4-12 years Sex: M+F Population Size: 51 Sources: |
Back pain | 1 patient Disc. AE |
274 ug 2 times / day multiple, intranasal Recommended Dose: 274 ug, 2 times / day Route: intranasal Route: multiple Dose: 274 ug, 2 times / day Sources: Page: p. 44 |
unhealthy, > 12 years n = 216 Health Status: unhealthy Condition: seasonal allergic rhinitis. Age Group: > 12 years Population Size: 216 Sources: Page: p. 44 |
Sinusitis | 1 patient Disc. AE |
274 ug 2 times / day multiple, intranasal Recommended Dose: 274 ug, 2 times / day Route: intranasal Route: multiple Dose: 274 ug, 2 times / day Sources: Page: p. 44 |
unhealthy, > 12 years n = 216 Health Status: unhealthy Condition: seasonal allergic rhinitis. Age Group: > 12 years Population Size: 216 Sources: Page: p. 44 |
Taste perversion | 1 patient Disc. AE |
274 ug 2 times / day multiple, intranasal Recommended Dose: 274 ug, 2 times / day Route: intranasal Route: multiple Dose: 274 ug, 2 times / day Sources: Page: p. 44 |
unhealthy, > 12 years n = 216 Health Status: unhealthy Condition: seasonal allergic rhinitis. Age Group: > 12 years Population Size: 216 Sources: Page: p. 44 |
Somnolence | 2 patients Disc. AE |
274 ug 2 times / day multiple, intranasal Recommended Dose: 274 ug, 2 times / day Route: intranasal Route: multiple Dose: 274 ug, 2 times / day Sources: Page: p. 44 |
unhealthy, > 12 years n = 216 Health Status: unhealthy Condition: seasonal allergic rhinitis. Age Group: > 12 years Population Size: 216 Sources: Page: p. 44 |
PubMed
Title | Date | PubMed |
---|---|---|
Evaluation of the efficacy of olopatadine hydrochloride 0.1% ophthalmic solution and azelastine hydrochloride 0.05% ophthalmic solution in the conjunctival allergen challenge model. | 2001 Aug |
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[Influence of peplomycin on pulmonary function (PaO2, %DLco) in patients with oral carcinoma]. | 2001 Sep |
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Mechanism of the antitussive effect of azelastine in guinea pigs. | 2002 |
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Azelastine is more potent than olopatadine n inhibiting interleukin-6 and tryptase release from human umbilical cord blood-derived cultured mast cells. | 2002 May |
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A study of intranasal distribution of azelastine hydrochloride aqueous nasal spray with different spray techniques. | 2002 Oct |
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Suplatast tosilate inhibits eosinophil production and recruitment into the skin in murine contact sensitivity. | 2003 Sep |
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Review of the pharmacology, clinical efficacy, and safety of azelastine hydrochloride. | 2005 Jul |
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Antiallergic drugs, azelastine hydrochloride and epinastine hydrochloride, inhibit ongoing IgE secretion of rat IgE-producing hybridoma FE-3 cells. | 2006 Oct 10 |
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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 |
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Comparison of the conjunctival toxicity of topical ocular antiallergic agents. | 2008 Dec |
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Effectiveness of twice daily azelastine nasal spray in patients with seasonal allergic rhinitis. | 2008 Oct |
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Treatment of allergic conjunctivitis with olopatadine hydrochloride eye drops. | 2008 Sep |
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Contact allergic dermatitis and periocular depigmentation after using olapatidine eye drops. | 2008 Sep-Oct |
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Management of allergic conjunctivitis: an evaluation of the perceived comfort and therapeutic efficacy of olopatadine 0.2% and azelastine 0.05% from two prospective studies. | 2009 |
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Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines. | 2009 Aug 31 |
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Effects of olopatadine hydrochloride nasal spray 0.6% in the treatment of seasonal allergic rhinitis: a phase III, multicenter, randomized, double-blind, active- and placebo-controlled study in adolescents and adults. | 2009 Jan |
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Allergen-induced airway inflammation and its therapeutic intervention. | 2009 Oct |
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Advanced taste sensors based on artificial lipids with global selectivity to basic taste qualities and high correlation to sensory scores. | 2010 |
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Double-blind, placebo-controlled study of azelastine and fluticasone in a single nasal spray delivery device. | 2010 Aug |
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Prevention and management of antineoplastic therapy induced oral mucositis. | 2010 Jul |
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Azelastine hydrochloride, a dual-acting anti-inflammatory ophthalmic solution, for treatment of allergic conjunctivitis. | 2010 Sep 7 |
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The discovery of phthalazinone-based human H1 and H3 single-ligand antagonists suitable for intranasal administration for the treatment of allergic rhinitis. | 2011 Apr 14 |
Sample Use Guides
0.1% or 0.15% azelastine hydrochloride: 1 or 2 sprays per nostril once or twice daily.
Route of Administration:
Nasal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9300717
In a rat mast RBL-2H3 cell line, azelastine inhibited Ag- and ionomycin-induced TNF-alpha release with IC50 values of 25.7 +/- 3.4 uM and 1.66 +/- 0.45 uM, respectively.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000000190
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QS01GX07
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NCI_THESAURUS |
C29578
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S01GX07
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R06AX19
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QR06AX19
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WHO-ATC |
R01AC03
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QR01AC03
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NDF-RT |
N0000175519
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NDF-RT |
N0000175587
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AZELASTINE
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Azelastine
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100000086100
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
SALT/SOLVATE (PARENT)