Olopatadine

{{Drugbox

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| tradename = Patanol, Pataday, Opatanol

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| DailyMedID = Olopatadine

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| routes_of_administration = Eye drops, nasal spray

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| legal_US = Rx-only

| legal_US_comment = / OTC{{cite web | title=FDA Approves Three Drugs for Nonprescription Use Through Rx-to-OTC Switch Process | website=U.S. Food and Drug Administration (FDA) | date=14 February 2020 | url=https://www.fda.gov/news-events/press-announcements/fda-approves-three-drugs-nonprescription-use-through-rx-otc-switch-process | archive-url=https://web.archive.org/web/20200215012930/https://www.fda.gov/news-events/press-announcements/fda-approves-three-drugs-nonprescription-use-through-rx-otc-switch-process | archive-date=15 February 2020 | url-status=dead | access-date=14 February 2020 }} {{PD-notice}}

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| index2_label = as HCl

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| CAS_number = 113806-05-6

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| IUPAC_name = {(11Z)-11-[3-(dimethylamino)propylidene]-6,11-
dihydrodibenzo[b,e]oxepin-2-yl}acetic acid

| C=21 | H=23 | N=1 | O=3

| SMILES = O=C(O)Cc2ccc1OCc3c(C(\c1c2)=C\CCN(C)C)cccc3

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| StdInChI = 1S/C21H23NO3/c1-22(2)11-5-8-18-17-7-4-3-6-16(17)14-25-20-10-9-15(12-19(18)20)13-21(23)24/h3-4,6-10,12H,5,11,13-14H2,1-2H3,(H,23,24)/b18-8-

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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).{{cite web |title=Olopatadine Hydrochloride Monograph for Professionals |url=https://www.drugs.com/monograph/olopatadine-hydrochloride.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=26 March 2019 |archive-date=27 March 2019 |archive-url=https://web.archive.org/web/20190327091820/https://www.drugs.com/monograph/olopatadine-hydrochloride.html |url-status=live }} It is used as eye drops or as a nasal spray. The eye drops generally result in an improvement within half an hour.

Common side effects include headache, sore throat, eye discomfort, or changes in perception of taste.{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=1126|edition=76}} More significant side effects may include sleepiness. It is unclear if use during pregnancy or breastfeeding is safe.{{cite web |title=Olopatadine ophthalmic Use During Pregnancy |url=https://www.drugs.com/pregnancy/olopatadine-ophthalmic.html |website=Drugs.com |access-date=26 March 2019 |archive-date=26 March 2019 |archive-url=https://web.archive.org/web/20190326155258/https://www.drugs.com/pregnancy/olopatadine-ophthalmic.html |url-status=live }} It is an antihistamine and mast cell stabilizer.{{cite journal | vauthors = Castillo M, Scott NW, Mustafa MZ, Mustafa MS, Azuara-Blanco A | title = Topical antihistamines and mast cell stabilisers for treating seasonal and perennial allergic conjunctivitis | journal = The Cochrane Database of Systematic Reviews | volume = 2015 | issue = 6 | pages = CD009566 | date = June 2015 | pmid = 26028608 | doi = 10.1002/14651858.CD009566.pub2 | pmc = 10616535 | url = http://aura.abdn.ac.uk/bitstream/2164/6048/1/Castillo_et_al_2015_The_Cochrane_Library.pdf | hdl = 2164/6048 | hdl-access = free | access-date = 24 September 2019 | archive-date = 28 August 2021 | archive-url = https://web.archive.org/web/20210828051138/http://aura.abdn.ac.uk/bitstream/handle/2164/6048/Castillo_et_al_2015_The_Cochrane_Library.pdf;jsessionid=D8DC7729A66970DF95B91197B5CFDB6E?sequence=1 | url-status = live }}

Olopatadine was patented in 1986 and came into medical use in 1997.{{cite book |vauthors=Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=549 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA549 |access-date=20 September 2020 |archive-date=10 January 2023 |archive-url=https://web.archive.org/web/20230110005657/https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA549 |url-status=live }} It is available as a generic medication. In 2022, it was the 250th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}{{cite web | title = Olopatadine Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Olopatadine | access-date = 30 August 2024 }}

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.{{cite journal | pmid=32049778 | date=2020 | title=The effectiveness of olopatadine hydrochloride eye drops for allergic conjunctivitis: Protocol for a systematic review | journal=Medicine | volume=99 | issue=7 | pages=e18618 | doi=10.1097/MD.0000000000018618 | pmc=7035116 | vauthors = Zi Y, Deng Y, Ji M, Qin Y, Nong L, Liu Z, Jin M }}

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".{{cite journal | doi=10.1016/j.anai.2022.07.029 | title=Efficacy and safety of GSP301 nasal spray in children aged 6 to 11 years with seasonal allergic rhinitis | date=2022 | journal=Annals of Allergy, Asthma & Immunology | volume=129 | issue=5 | pages=618–626.e2 | pmid=35926824 | vauthors = Prenner BM, Amar NJ, Hampel FC, Caracta CF, Wu W | doi-access=free }}{{cite journal | url=https://doi.org/10.1007/s00405-021-07085-w | doi=10.1007/s00405-021-07085-w | title=Efficacy and safety of twice-daily olopatadine–mometasone combination nasal spray (GSP301) in the treatment of allergic rhinitis: A systematic review and meta-analysis | date=2022 | journal=European Archives of Oto-Rhino-Laryngology | volume=279 | issue=4 | pages=1691–1699 | pmid=34591150 | vauthors = Chen R, Zheng D, Zhang Y, Sima G | url-access=subscription }}{{cite journal | url=https://doi.org/10.1016/j.anai.2018.09.199 | doi=10.1016/j.anai.2018.09.199 | title=Long-Term Safety and Efficacy of Olopatadine/Mometasone Combination Nasal Spray in Patients with Perennial Allergic Rhinitis | date=2018 | journal=Annals of Allergy, Asthma & Immunology | volume=121 | issue=5 | pages=S60 | vauthors = Segall N, Lumry W, Prenner B, Caracta C, Tantry S | url-access=subscription }}

Side effects

Known side effects for olopatadine eye drops include headache, eye burning and/or stinging, blurred vision, dry eyes, foreign body sensation, hyperemia, keratitis, eyelid edema, pruritus, asthenia, sore throat (pharyngitis), rhinitis, sinusitis, taste perversion, and vomiting.{{cite web | url=https://www.drugs.com/sfx/olopatadine-ophthalmic-side-effects.html | title=Olopatadine ophthalmic Side Effects: Common, Severe, Long Term | access-date=14 July 2024 | archive-date=19 June 2024 | archive-url=https://web.archive.org/web/20240619234031/https://www.drugs.com/sfx/olopatadine-ophthalmic-side-effects.html | url-status=live }}

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.{{cite web | url=https://www.drugs.com/mtm/olopatadine-nasal.html | title=Olopatadine nasal Uses, Side Effects & Warnings }}{{cite journal | doi=10.1007/s40629-023-00282-5 | title=Efficacy and safety of the combination nasal spray olopatadine hydrochloride-mometasone furoate in the treatment of allergic rhinitis | date=2024 | journal=Allergo Journal International | volume=33 | pages=9–19 | vauthors = Klimek L, Klimek F, Bergmann C, Hagemann J, Cuevas M, Becker S | doi-access=free }}

Chemistry

=Synthesis=

File:Olopatadine synthesis.png

Pharmacology

=Pharmacodynamics=

Olopatadine acts as a selective antagonist of the histamine H₁ receptor, thus stabilizing mast cells and inhibiting histamine release.{{cite journal | vauthors = Gonzalez-Estrada A, Reddy K, Dimov V, Eidelman F | title = Olopatadine hydrochloride ophthalmic solution for the treatment of allergic conjunctivitis | journal = Expert Opinion on Pharmacotherapy | volume = 18 | issue = 11 | pages = 1137–1143 | date = August 2017 | pmid = 28656804 | doi = 10.1080/14656566.2017.1346085 }}

History

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

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). 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. These drugs are mast cell stabilizers, which work by preventing the release of histamine and therefore prevent or control allergic disorders.

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.

Society and culture

= Brand names =

File:Pallada Olopatadinum Olopatadine.jpgBrand names include Pallada, Pazeo, Pataday, Patanol S, Patanol, Opatanol, Olopat, Patanase.{{cite web | url=https://medilib.ir/uptodate/show/9894 | title=Olopatadine (Ophthalmic): Drug information }}{{Cite web |url=https://www.drugs.com/newdrugs/alcon-s-patanase-nasal-approved-fda-nasal-allergy-symptoms-942.html |title=Drugs.com, Alcon's Patanase Nasal Spray Approved by FDA for Treatment of Nasal Allergy Symptoms |access-date=23 January 2018 |archive-date=17 April 2009 |archive-url=https://web.archive.org/web/20090417080723/http://www.drugs.com/newdrugs/alcon-s-patanase-nasal-approved-fda-nasal-allergy-symptoms-942.html |url-status=live }} It is also available as an oral tablet in Japan under the tradename Allelock, manufactured by Kyowa Hakko Kogyo.{{cite web | author = Kyowa Hakko Kogyo Co., Ltd. | year = 2007 | url = http://www.e-search.ne.jp/~jpr/PDF/KYOWA08.PDF | title = Allelock Tablets 2.5 & Allelock Tablets 5 (English) | access-date = 10 August 2008 | archive-url = https://web.archive.org/web/20110722114455/http://www.e-search.ne.jp/~jpr/PDF/KYOWA08.PDF | archive-date = 22 July 2011 | url-status = dead }}

References

External links

{{cite web | title=Olopatadine Nasal Spray | website=MedlinePlus | url=https://medlineplus.gov/druginfo/meds/a615038.html }}

Category:Phenylacetic acids

Category:Drugs developed by Alcon

Category:Dibenzoxepins

Category:Dimethylamino compounds

Category:H1 receptor antagonists

Category:Mast cell stabilizers

Category:Muscarinic antagonists

Category:Drugs developed by Novartis

Category:Oxygen heterocycles

Category:Wikipedia medicine articles ready to translate