Chemistry:Olopatadine

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Olopatadine, sold under the brand name Patanol among others, is an antihistamine medication used to decrease the symptoms of allergic conjunctivitis and allergic rhinitis (hay fever).[1] It is used as eye drops or as a nasal spray.[1] The eye drops generally result in an improvement within half an hour.[1]

Common side effects include headache, sore throat, eye discomfort, or changes in perception of taste.[2][1] More significant side effects may include sleepiness.[1] It is unclear if use during pregnancy or breastfeeding is safe.[3] It is an antihistamine and mast cell stabilizer.[4][1]

Olopatadine was patented in 1986 and came into medical use in 1997.[5] It is available as a generic medication.[1] In 2023, it was the 269th most commonly prescribed medication in the United States, with more than 900,000 prescriptions.[6][7]

Medical uses

Olopatadine is an active ingredient in eye drops designed to alleviate allergic conjunctivitis, a condition characterized by itchy, red, and watery eyes. It is intended to serve as a superior alternative to eye drops that contain corticosteroids. By utilizing olopatadine, the goal is to minimize the side effects associated with corticosteroids. These side effects include elevated intraocular pressure, which can lead to glaucoma, and an increased susceptibility to infections.[8]

In nasal sprays, olopatadine is used either as a standalone active ingredient, or in a combination with mometasone, a corticosteroid. A fixed-dose combination of olopatadine hydrochloride 665 μg and mometasone furoate 25 μg is called "GSP301".[9][10][11]

Side effects

Known side effects for olopatadine eye drops include headache, eye burning or stinging, blurred vision, dry eyes, foreign body sensation, hyperemia, keratitis, eyelid edema, pruritus, asthenia, sore throat (pharyngitis), rhinitis, sinusitis, taste perversion, and vomiting.[12]

Olopatadine nasal spray may cause side effects such as nosebleeds, painful nasal sores, fever, urinary discomfort, nasal congestion, cough, throat irritation, a bitter taste, drowsiness, headaches, rashes, and repeated instances of painful urination.[13][14]

Chemistry

Synthesis

Olopatadine synthesis:[15]

Pharmacology

Pharmacodynamics

Olopatadine acts as a selective antagonist of the histamine H1 receptor, thus stabilizing mast cells and inhibiting histamine release.[16]

History

Olopatadine was patented in 1986 by Kyowa Hakko Kogyo and came into medical use in 1997.[5]

In the United States, Pataday Twice Daily Relief was first approved by the FDA in 1996, under the name Patanol as a prescription drug and was indicated for the treatment of the signs and symptoms of allergic conjunctivitis (referring to ocular redness and itching due to allergies).[17] Pataday – now Pataday Once Daily Relief – was first approved by the FDA in 2004, as a prescription drug and was indicated for the treatment of ocular itching associated with allergic conjunctivitis.[17] These drugs are mast cell stabilizers, which work by preventing the release of histamine and therefore prevent or control allergic disorders.[17]

In February 2020, Pataday Twice Daily Relief and Pataday Once Daily Relief were switched to be over-the-counter drugs in the United States when the FDA granted the approvals of the nonprescription products to Alcon.[17]

Society and culture

Brand names

A package of generic formulation of olopatadine eye drops sold under the brand name Pallada

Brand names include Pallada, Pazeo, Pataday, Patanol S, Patanol, Opatanol, Olopat, Patanase.[18][19] It is also available as an oral tablet in Japan under the tradename Allelock, manufactured by Kyowa Hakko Kogyo.[20]

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "Olopatadine Hydrochloride Monograph for Professionals". American Society of Health-System Pharmacists. https://www.drugs.com/monograph/olopatadine-hydrochloride.html. 
  2. ↑ British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 1126. ISBN 978-0-85711-338-2. 
  3. ↑ "Olopatadine ophthalmic Use During Pregnancy". https://www.drugs.com/pregnancy/olopatadine-ophthalmic.html. 
  4. ↑ "Topical antihistamines and mast cell stabilisers for treating seasonal and perennial allergic conjunctivitis". The Cochrane Database of Systematic Reviews 2015 (6). June 2015. doi:10.1002/14651858.CD009566.pub2. PMID 26028608. PMC 10616535. http://aura.abdn.ac.uk/bitstream/2164/6048/1/Castillo_et_al_2015_The_Cochrane_Library.pdf. Retrieved 24 September 2019. 
  5. ↑ 5.0 5.1 Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 549. ISBN 978-3-527-60749-5. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA549. Retrieved 20 September 2020. 
  6. ↑ "The Top 300 of 2023". https://clincalc.com/DrugStats/Top300Drugs.aspx. 
  7. ↑ "Olopatadine Drug Usage Statistics, United States, 2014 - 2023". https://clincalc.com/DrugStats/Drugs/Olopatadine. 
  8. ↑ "The effectiveness of olopatadine hydrochloride eye drops for allergic conjunctivitis: Protocol for a systematic review". Medicine 99 (7). 2020. doi:10.1097/MD.0000000000018618. PMID 32049778. 
  9. ↑ "Efficacy and safety of GSP301 nasal spray in children aged 6 to 11 years with seasonal allergic rhinitis". Annals of Allergy, Asthma & Immunology 129 (5): 618–626.e2. 2022. doi:10.1016/j.anai.2022.07.029. PMID 35926824. 
  10. ↑ "Efficacy and safety of twice-daily olopatadine–mometasone combination nasal spray (GSP301) in the treatment of allergic rhinitis: A systematic review and meta-analysis". European Archives of Oto-Rhino-Laryngology 279 (4): 1691–1699. 2022. doi:10.1007/s00405-021-07085-w. PMID 34591150. 
  11. ↑ "Long-Term Safety and Efficacy of Olopatadine/Mometasone Combination Nasal Spray in Patients with Perennial Allergic Rhinitis". Annals of Allergy, Asthma & Immunology 121 (5): S60. 2018. doi:10.1016/j.anai.2018.09.199. 
  12. ↑ "Olopatadine ophthalmic Side Effects: Common, Severe, Long Term". https://www.drugs.com/sfx/olopatadine-ophthalmic-side-effects.html. 
  13. ↑ "Olopatadine nasal Uses, Side Effects & Warnings". https://www.drugs.com/mtm/olopatadine-nasal.html. 
  14. ↑ "Efficacy and safety of the combination nasal spray olopatadine hydrochloride-mometasone furoate in the treatment of allergic rhinitis". Allergo Journal International 33: 9–19. 2024. doi:10.1007/s40629-023-00282-5. 
  15. ↑ "6,11-Dihydro-11-oxodibenz [b,e] oxepinacetic acids with potent antiinflammatory activity". Journal of Medicinal Chemistry 19 (7): 941–6. July 1976. doi:10.1021/jm00229a017. PMID 940112. 
  16. ↑ "Olopatadine hydrochloride ophthalmic solution for the treatment of allergic conjunctivitis". Expert Opinion on Pharmacotherapy 18 (11): 1137–1143. August 2017. doi:10.1080/14656566.2017.1346085. PMID 28656804. 
  17. ↑ 17.0 17.1 17.2 17.3 Cite error: Invalid <ref> tag; no text was provided for refs named FDA switch
  18. ↑ "Olopatadine (Ophthalmic): Drug information". https://medilib.ir/uptodate/show/9894. 
  19. ↑ "Drugs.com, Alcon's Patanase Nasal Spray Approved by FDA for Treatment of Nasal Allergy Symptoms". https://www.drugs.com/newdrugs/alcon-s-patanase-nasal-approved-fda-nasal-allergy-symptoms-942.html. 
  20. ↑ Kyowa Hakko Kogyo Co., Ltd. (2007). "Allelock Tablets 2.5 & Allelock Tablets 5 (English)". http://www.e-search.ne.jp/~jpr/PDF/KYOWA08.PDF. 



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