Azelastine

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Azelastine
Azelastine.svg
Azelastine-based-on-xtal-3D-bs-17.png
Clinical data
Trade names Astelin, others
AHFS/Drugs.com Monograph
MedlinePlus a603009
License data
Pregnancy
category
  • AU:B3
Routes of
administration 		Eye drops, nasal spray, by mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 40% (intranasal) [4]
Metabolites desmethylazelastine (active) [4]
Onset of action Within 1 hour [4]
Elimination half-life 22 hours [4]
Duration of action 12 hours [4]
Identifiers
  • (RS)-4-[(4-Chlorophenyl)methyl]-2-(1-methylazepan-4-yl)-phthalazin-1-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.133.278 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C22H24ClN3O
Molar mass 381.90 g·mol−1
3D model (JSmol)
  • Clc1ccc(cc1)CC\3=N\N(C(=O)c2ccccc2/3)C4CCCN(C)CC4
  • 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 Yes check.svgY
  • Key:MBUVEWMHONZEQD-UHFFFAOYSA-N Yes check.svgY
   (verify)

Azelastine, sold under the brand name Astelin among others, is a H1 receptor-blocking medication primarily used as a nasal spray to treat allergic rhinitis (hay fever) and as eye drops for allergic conjunctivitis. [5] [6] Other uses may include asthma and skin rashes for which it is taken by mouth. [7] Onset of effects is within minutes when used in the eyes and within an hour when used in the nose. [8] Effects last for up to 12 hours. [8]

Contents

Common side effects include headache, sleepiness, change in taste, and sore throat. [8] It is unclear if use is safe during pregnancy or breastfeeding. [9] It is a second-generation antihistamine and works by blocking the release of a number of inflammatory mediators including histamine. [7] [8]

Azelastine was patented in 1971 and came into medical use in 1986. [10] It is available as a generic medication. [3] [11] In 2021, it was the 145th most commonly prescribed medication in the United States, with more than 4 million prescriptions. [12] [13]

Medical uses

Azelastine nasal spray is indicated for the local treatment of the symptoms of seasonal allergic rhinitis and perennial allergic rhinitis, such as rhinorrhea, sneezing and nasal pruritus in people five years of age and older. [14] [15] [1] In some countries, it is also indicated for the treatment of vasomotor rhinitis in adults and children ≥ 12 years old. [1] Azelastine eye drops are indicated for the local treatment of seasonal and perennial allergic conjunctivitis. [16] [2]

Side effects

Azelastine is safe and well tolerated in both adults and children with allergic rhinitis. [17] [18] [19] Bitter taste, headache, nasal burning and somnolence are the most frequently reported adverse events. US prescribing recommendations warn against the concurrent use of alcohol and/or other central nervous system depressants, but to date there have been no studies to assess the effects of azelastine nasal spray on the CNS in humans[ needs update? ]. More recent studies [20] [21] have shown similar degrees of somnolence (approx. 2%) compared with placebo treatment.

The most common side effect is a bitter taste (about 20% of people). Due to this, the manufacturer has produced another formulation of azelastine with sucralose. [22] The problem of bitter taste may also be reduced by correct application of the nasal spray (i.e. slightly tipping the head forward and not inhaling the medication too deeply), or alternatively using the azelastine/sucralose formulation. [23]

In addition, anosmia (loss in the ability to smell) can occur with nasal spray antihistamines (including both formulations of azelastine). [8]

Pharmacology

Pharmacodynamics

Azelastine has a triple mode of action: [24]

  1. Anti-histamine effect,
  2. Mast-cell stabilizing effect and
  3. Anti-inflammatory effect.

Pharmacokinetics

The systemic bioavailability of azelastine is approximately 40% when administered intranasally. [4] Maximum plasma concentrations (Cmax) are observed within 2–3 hours. [4] The elimination half life, steady-state volume of distribution and plasma clearance are 22 h, 14.5 L/kg and 0.5 L/h/kg respectively (based on intravenous and oral administration data). Approximately 75% of an oral dose is excreted in feces. Pharmacokinetics of orally administered azelastine is not affected by age, gender, or hepatic impairment. [24]

Metabolism

Azelastine is oxidatively metabolized by the cytochrome P450 family into its active metabolite, desmethylazelastine, and two inactive carboxylic acid metabolites. [24]

Chemical properties

The chemical nomenclature of azelastine is (±)-1-(2H)-phthalazinone, 4-[(4-chlorophenyl) methyl]-2-(hexahydro-1-methyl-1H-azepin-4-yl)-monohydrochloride. It is white, almost odorless with a bitter taste. [25]

Related Research Articles

An allergen is an otherwise harmless substance that triggers an allergic reaction in sensitive individuals by stimulating an immune response.

<span class="mw-page-title-main">Allergic rhinitis</span> Nasal inflammation due to allergens in the air

Allergic rhinitis, of which the seasonal type is called hay fever, is a type of inflammation in the nose that occurs when the immune system overreacts to allergens in the air. Signs and symptoms include a runny or stuffy nose, sneezing, red, itchy, and watery eyes, and swelling around the eyes. The fluid from the nose is usually clear. Symptom onset is often within minutes following allergen exposure, and can affect sleep and the ability to work or study. Some people may develop symptoms only during specific times of the year, often as a result of pollen exposure. Many people with allergic rhinitis also have asthma, allergic conjunctivitis, or atopic dermatitis.

<span class="mw-page-title-main">Rhinitis</span> Irritation and inflammation of the mucous membrane inside the nose

Rhinitis, also known as coryza, is irritation and inflammation of the mucous membrane inside the nose. Common symptoms are a stuffy nose, runny nose, sneezing, and post-nasal drip.

<span class="mw-page-title-main">Cetirizine</span> Antihistamine medication

Cetirizine is a second-generation antihistamine used to treat allergic rhinitis, dermatitis, and urticaria (hives). It is taken by mouth. Effects generally begin within thirty minutes and last for about a day. The degree of benefit is similar to other antihistamines such as diphenhydramine, which is a first-generation antihistamine.

<span class="mw-page-title-main">Fexofenadine</span> Antihistamine medication

Fexofenadine, sold under the brand name Allegra among others, is an antihistamine pharmaceutical drug used in the treatment of allergy symptoms, such as hay fever and urticaria.

<span class="mw-page-title-main">Nasal spray</span> Spray that delivers medications locally in the nasal cavities or systemically

Nasal sprays are used to deliver medications locally in the nasal cavities or systemically. They are used locally for conditions such as nasal congestion and allergic rhinitis. In some situations, the nasal delivery route is preferred for systemic therapy because it provides an agreeable alternative to injection or pills. Substances can be assimilated extremely quickly and directly through the nose. Many pharmaceutical drugs exist as nasal sprays for systemic administration. Other applications include hormone replacement therapy, treatment of Alzheimer's disease and Parkinson's disease. Nasal sprays are seen as a more efficient way of transporting drugs with potential use in crossing the blood–brain barrier.

<span class="mw-page-title-main">Allergen immunotherapy</span> Medical treatment for environmental allergies

Allergen immunotherapy, also known as desensitization or hypo-sensitization, is a medical treatment for environmental allergies and asthma. Immunotherapy involves exposing people to larger and larger amounts of allergens in an attempt to change the immune system's response.

<span class="mw-page-title-main">Olopatadine</span> Chemical compound

Olopatadine, sold under the brand name Patanol among others, is an antihistamine medication used to decrease the symptoms of allergic conjunctivitis and allergic rhinitis. It is used as eye drops or as a nasal spray. The eye drops generally result in an improvement within half an hour.

<span class="mw-page-title-main">Post-nasal drip</span> Medical condition

Post-nasal drip (PND), also known as upper airway cough syndrome (UACS), occurs when excessive mucus is produced by the nasal mucosa. The excess mucus accumulates in the back of the nose, and eventually in the throat once it drips down the back of the throat. It can be caused by rhinitis, sinusitis, gastroesophageal reflux disease (GERD), or by a disorder of swallowing. Other causes can be allergy, cold, flu, and side effects from medications.

<span class="mw-page-title-main">Levocetirizine</span> Antihistamine drug

Levocetirizine, sold under the brand name Xyzal, among others, is a second-generation antihistamine used for the treatment of allergic rhinitis and long-term hives of unclear cause. It is less sedating than older antihistamines. It is taken by mouth.

<span class="mw-page-title-main">Ketotifen</span> Antihistamine medication

Ketotifen is an antihistamine medication and a mast cell stabilizer used to treat allergic conditions such as conjunctivitis, asthma, and urticaria (hives). Ketotifen is available in ophthalmic and oral forms: the ophthalmic form relieves eye itchiness and irritation associated with seasonal allergies, while the oral form helps prevent systemic conditions such as asthma attacks and allergic reactions. In addition to treating allergies, ketotifen has shown efficacy in managing systemic mast cell diseases such as mastocytosis and mast cell activation syndrome (MCAS), which involve abnormal accumulation or activation of mast cells throughout the body. Ketotifen is also used for other allergic-type conditions like atopic dermatitis (eczema) and food allergies.

<span class="mw-page-title-main">Flunisolide</span> Chemical compound

Flunisolide is a corticosteroid often prescribed as treatment for allergic rhinitis. Intranasal corticosteroids are the most effective medication for controlling symptoms.

<span class="mw-page-title-main">Rhinitis medicamentosa</span> Medical condition

Rhinitis medicamentosa is a condition of rebound nasal congestion suspected to be brought on by extended use of topical decongestants and certain oral medications that constrict blood vessels in the lining of the nose, although evidence has been contradictory.

<span class="mw-page-title-main">Mometasone</span> Steroid medication

Mometasone, also known as mometasone y 3 s, is a steroid medication used to treat certain skin conditions, hay fever, and asthma. Specifically it is used to prevent rather than treat asthma attacks. It can be applied to the skin, inhaled, or used in the nose. Mometasone furoate, not mometasone, is used in medical products.

<span class="mw-page-title-main">Mast cell stabilizer</span> Category of pharmaceutical drugs

Mast cell stabilizers are medications used to prevent or treat certain allergic disorders. They block mast cell degranulation, stabilizing the cell and thereby preventing the release of histamine and related mediators. One suspected pharmacodynamic mechanism is the blocking of IgE-regulated calcium channels. Without intracellular calcium, the histamine vesicles cannot fuse to the cell membrane and degranulate.

<span class="mw-page-title-main">Ebastine</span> Antihistamine drug

Ebastine is a H1 antihistamine with low potential for causing drowsiness.

<span class="mw-page-title-main">Bilastine</span> Antihistamine medication

Bilastine is an antihistamine medication used to treat hives (urticaria), allergic rhinitis and itchy inflamed eyes (allergic conjunctivitis) caused by an allergy. It is a second-generation antihistamine and takes effect by selectively inhibiting the histamine H1 receptor, preventing these allergic reactions. Bilastine has an effectiveness similar to cetirizine, fexofenadine, and desloratadine.

Nonallergic rhinitis is rhinitis—inflammation of the inner part of the nose—not caused by an allergy. Nonallergic rhinitis displays symptoms including chronic sneezing or having a congested, drippy nose, without an identified allergic reaction. Other common terms for nonallergic rhinitis are vasomotor rhinitis and perennial rhinitis. The prevalence of nonallergic rhinitis in otolaryngology is 40%. Allergic rhinitis is more common than nonallergic rhinitis; however, both conditions have similar presentation, manifestation and treatment. Nasal itching and paroxysmal sneezing are usually associated with nonallergic rhinitis rather than allergic rhinitis.

Olopatadine/mometasone, sold under the brand name Ryaltris, is a fixed-dose combination medication for the treatment of allergic rhinitis and rhinoconjunctivitis in adults and adolescents twelve years of age and older. It contains olopatadine hydrochloride and mometasone furoate monohydrate. It is sprayed into the nose.

Anti-allergic agents are medications used to treat allergic reactions. Anti-allergic agents have existed since 3000 B.C in countries such as China and Egypt. It was not until 1933 when antihistamines, the first type of anti-allergic agents, were developed. Common allergic diseases include allergic rhinitis, allergic asthma and atopic dermatitis with varying symptoms, including runny nose, watery eyes, itchiness, coughing, and shortness of breath. More than one-third of the world's population is currently being affected by one or more allergic conditions.

References

  1. 1 2 3 "Astelin- azelastine hydrochloride spray, metered".
  2. 1 2 "Optivar- azelastine hydrochloride solution/ drops".
  3. 1 2 "FDA Approves a Nasal Antihistamine for Nonprescription Use". U.S. Food and Drug Administration (FDA) (Press release). 17 June 2021. Retrieved 21 June 2021.
  4. 1 2 3 4 5 6 7 Lieberman P, Hernandez-Trujillo V, Lieberman J, Frew AJ (2008). "Antihistamines". Clinical Immunology. Elsevier. pp. 1317–1329. doi:10.1016/b978-0-323-04404-2.10089-2. ISBN   9780323044042. After intranasal administration, its systemic bioavailability is approximately 40%. Azelastine has an onset of action within the first hour of administration and reaches peak activity at 1–3 hours after administration. Duration of activity is about 12 hours. Intranasal administration results in maximal plasma concentrations in 2–3 hours. ... The half-life of the parent compound is 22 hours ...
  5. ↑ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 1169. ISBN   9780857113382.
  6. ↑ Al-Ahmad M, Hassab M, Al Ansari A (21 December 2020). "Allergic and Non-allergic Rhinitis". Textbook of Clinical Otolaryngology. Cham: Springer International Publishing. pp. 241–252. doi:10.1007/978-3-030-54088-3_22. ISBN   978-3-030-54087-6. S2CID   234142758.
  7. 1 2 Aronson JK (2015). Meyler's Side Effects of Drugs: The International Encyclopedia of Adverse Drug Reactions and Interactions. Elsevier. p. 782. ISBN   9780444537164.
  8. 1 2 3 4 5 "Azelastine Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists.
  9. ↑ "Azelastine ophthalmic (Optivar) Use During Pregnancy". Drugs.com. Retrieved 26 March 2019.
  10. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 548. ISBN   9783527607495.
  11. ↑ "First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). 8 July 2024. Retrieved 9 July 2024.
  12. ↑ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  13. ↑ "Azelastine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  14. ↑ Bousquet J, Schünemann HJ, Togias A, Bachert C, Erhola M, Hellings PW, et al. (January 2020). "Next-generation Allergic Rhinitis and Its Impact on Asthma (ARIA) guidelines for allergic rhinitis based on Grading of Recommendations Assessment, Development and Evaluation (GRADE) and real-world evidence". The Journal of Allergy and Clinical Immunology. 145 (1): 70–80.e3. doi:10.1016/j.jaci.2019.06.049. hdl: 10400.17/3723 . PMID   31627910.
  15. ↑ "Rhinolast Nasal Spray Summary of Product Characteristics". October 2009. Retrieved 27 April 2010.
  16. ↑ "Optilast Eye Drops Summary of Product Characteristics". January 2010. Retrieved 27 April 2010.
  17. ↑ McNeely W, Wiseman LR (July 1998). "Intranasal azelastine. A review of its efficacy in the management of allergic rhinitis". Drugs. 56 (1): 91–114. doi:10.2165/00003495-199856010-00011. PMID   9664202. S2CID   46956783.
  18. ↑ Ratner PH, Findlay SR, Hampel F, van Bavel J, Widlitz MD, Freitag JJ (November 1994). "A double-blind, controlled trial to assess the safety and efficacy of azelastine nasal spray in seasonal allergic rhinitis". The Journal of Allergy and Clinical Immunology. 94 (5): 818–25. doi:10.1016/0091-6749(94)90148-1. PMID   7963150.
  19. ↑ LaForce C, Dockhorn RJ, Prenner BM, et al. (February 1996). "Safety and efficacy of azelastine nasal spray (Astelin NS) for seasonal allergic rhinitis: a 4-week comparative multicenter trial". Annals of Allergy, Asthma & Immunology. 76 (2): 181–8. doi:10.1016/S1081-1206(10)63420-5. PMID   8595539.
  20. ↑ Corren J, Storms W, Bernstein J, Berger W, Nayak A, Sacks H (May 2005). "Effectiveness of azelastine nasal spray compared with oral cetirizine in patients with seasonal allergic rhinitis". Clinical Therapeutics. 27 (5): 543–53. doi:10.1016/j.clinthera.2005.04.012. PMID   15978303.
  21. ↑ Berger W, Hampel F, Bernstein J, Shah S, Sacks H, Meltzer EO (September 2006). "Impact of azelastine nasal spray on symptoms and quality of life compared with cetirizine oral tablets in patients with seasonal allergic rhinitis". Annals of Allergy, Asthma & Immunology. 97 (3): 375–81. doi:10.1016/S1081-1206(10)60804-6. PMID   17042145.
  22. ↑ Kalpaklioglu AF, Kavut AB (2010). "Comparison of azelastine versus triamcinolone nasal spray in allergic and nonallergic rhinitis". American Journal of Rhinology & Allergy. 24 (1): 29–33. doi:10.2500/ajra.2010.24.3423. PMID   20109317. S2CID   24449860.
  23. ↑ Bernstein JA (October 2007). "Azelastine hydrochloride: a review of pharmacology, pharmacokinetics, clinical efficacy and tolerability". Current Medical Research and Opinion. 23 (10): 2441–52. doi:10.1185/030079907X226302. PMID   17723160. S2CID   25827650.
  24. 1 2 3 Horak F, Zieglmayer UP (November 2009). "Azelastine nasal spray for the treatment of allergic and nonallergic rhinitis". Expert Review of Clinical Immunology. 5 (6): 659–669. doi:10.1586/eci.09.38. PMID   20477689. S2CID   32512061.
  25. ↑ drugs.com Azelastine Page accessed 28 June 2015
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