Misplaced Pages

Olopatadine: Difference between revisions

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively
Page 1
Page 2
← Previous editContent deleted Content addedVisualWikitext
Revision as of 21:52, 16 March 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user← Previous edit Latest revision as of 05:10, 2 December 2024 edit undoWhywhenwhohow (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers49,324 edits rank 
(139 intermediate revisions by 63 users not shown)
Line 1: Line 1:
{{Short description|Chemical compound}}
{{drugbox
{{Use dmy dates|date=January 2024}}
| verifiedrevid = 411890370
{{cs1 config |name-list-style=vanc |display-authors=6}}
| IUPAC_name = {(11''Z'')-11--6,11-<br/>dihydrodibenzooxepin-2-yl}acetic acid
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 462265189
| image = Olopatadine.svg | image = Olopatadine.svg
| width =
| CASNo_Ref = {{cascite|correct|CAS}}
| alt =
| caption =

<!-- Clinical data -->
| pronounce =
| tradename = Patanol, Pataday, Opatanol
| Drugs.com = {{drugs.com|monograph|olopatadine-hydrochloride}}
| MedlinePlus = a602025
| DailyMedID = Olopatadine
| pregnancy_AU = B1
| pregnancy_AU_comment =
| pregnancy_category=
| routes_of_administration = ], ]
| ATC_prefix = S01
| ATC_suffix = GX09
| ATC_supplemental = {{ATC|R01|AC08}}

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->
| legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled-->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = POM
| legal_UK_comment =
| legal_US = Rx-only
| legal_US_comment = /&nbsp;OTC<ref name="FDA switch">{{cite web | title=FDA Approves Three Drugs for Nonprescription Use Through Rx-to-OTC Switch Process | website=U.S. ] (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=live | access-date=14 February 2020 }} {{PD-notice}}</ref>
| legal_EU = Rx-only
| legal_EU_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN_comment =
| legal_status = <!--For countries not listed above-->

<!-- Pharmacokinetic data -->
| bioavailability =
| protein_bound =
| metabolism =
| metabolites =
| onset =
| elimination_half-life = 3 hours
| duration_of_action =
| excretion =

<!-- Identifiers -->
| index2_label = as HCl
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 113806-05-6
| CAS_supplemental =
| PubChem = 5281071
| IUPHAR_ligand =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00768
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444528 | ChemSpiderID = 4444528
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = D27V6190PM | UNII = D27V6190PM
| KEGG_Ref = {{keggcite|correct|kegg}}
| InChI = 1/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-
| KEGG = D08293
| InChIKey = JBIMVDZLSHOPLA-LSCVHKIXBJ
| KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = D01192
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1189432
| NIAID_ChemDB =
| PDB_ligand =
| synonyms =

<!-- Chemical and physical data -->
| IUPAC_name = {(11''Z'')-11--6,11-<br />dihydrodibenzooxepin-2-yl}acetic acid
| C=21 | H=23 | N=1 | O=3
| SMILES = O=C(O)Cc2ccc1OCc3c(C(\c1c2)=C\CCN(C)C)cccc3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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- | 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-
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JBIMVDZLSHOPLA-LSCVHKIXSA-N | StdInChIKey = JBIMVDZLSHOPLA-LSCVHKIXSA-N
| density =
| CAS_number = 113806-05-6
| density_notes =
| ATC_prefix = S01
| melting_point =
| ATC_suffix = GX09
| melting_high =
| ATC_supplemental = {{ATC|R01|AC08}}
| melting_notes =
| PubChem = 5281071
| boiling_point =
| DrugBank = APRD00310
| boiling_notes =
| KEGG_Ref = {{keggcite|correct|kegg}}
| solubility =
| KEGG = D08293
| C = 21 |H = 23 |N = 1 |O = 3 | sol_units =
| specific_rotation =
| molecular_weight = 337.412 ]/]
| smiles = O=C(O)Cc2ccc1OCc3c(C(\c1c2)=C\CCN(C)C)cccc3
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life = 3 hours
| pregnancy_category = C
| legal_status =
| routes_of_administration = ], intranasal, oral
}} }}


<!-- Definition and medical uses -->
'''Olopatadine hydrochloride''' is an ] (as well as ]) and ] stabilizer, sold as a ] ] (0.2% solution, '''Pataday''' (or '''Patanol S''' in some countries), manufactured by ]). It is used to treat itching associated with allergic ] (eye ]). Olopatadine hydrochloride 0.1% is sold as '''Patanol''' (or '''Opatanol''' in some countries). A nasal spray formulation is sold as '''Patanase''', which was approved by the FDA on April 15, 2008.<ref></ref> It is also available as an oral tablet in Japan under the tradename '''Allelock''', manufactured by Kyowa Hakko Kogyo.<ref name=KYOWA08>{{cite web | author = Kyowa Hakko Kogyo Co., Ltd. | year = 2007 | url = http://www.e-search.ne.jp/~jpr/PDF/KYOWA08.PDF |format=PDF| title = ALLELOCK Tablets 2.5 & ALLELOCK Tablets 5 (English) | accessdate = 2008-08-10}}</ref>
'''Olopatadine''', sold under the brand name '''Patanol''' among others, is an antihistamine medication used to decrease the symptoms of ] and ] (hay fever).<ref name=AHFS2019>{{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 }}</ref> It is used as ] or as a ].<ref name=AHFS2019/> The eye drops generally result in an improvement within half an hour.<ref name=AHFS2019/>


<!-- Side effects and mechanisms -->
It should not be used to treat irritation caused by ]. The usual dose for Patanol is 1 drop in each affected eye 2 times per day, with 6 to 8 hours between doses.
Common side effects include headache, sore throat, eye discomfort, or changes in perception of taste.<ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=1126|edition=76}}</ref><ref name=AHFS2019/> More significant side effects may include sleepiness.<ref name=AHFS2019/> It is unclear if use during ] or ] is safe.<ref>{{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 }}</ref> It is an ] and ].<ref name=Cas2015>{{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 }}</ref><ref name=AHFS2019/>


<!-- Society and culture -->
Its ] may include ]s (7% of occurrence) burning and stinging (5%), ], ] sensation, ], ], ] ], ], ], cold syndrome, ], ], ], and taste perversion.
Olopatadine was patented in 1986 and came into medical use in 1997.<ref name=Fis2006>{{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 }}</ref> It is available as a ].<ref name=AHFS2019/> In 2022, it was the 250th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{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 }}</ref><ref>{{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 }}</ref>


==Medical uses==
Olopatadine was developed by Kyowa Hakko Kogyo.<ref>{{cite web
Olopatadine is an active ingredient in eye drops designed to alleviate ], a condition characterized by itchy, red, and watery eyes. It is intended to serve as a superior alternative to eye drops that contain ]s. By utilizing olopatadine, the goal is to minimize the side effects associated with corticosteroids. These side effects include elevated ], which can lead to ], and an increased susceptibility to infections.<ref>{{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 }}</ref>
| author=Kyowa Hakko Kogyo Co., Ltd.

| year=2002 | title=Company History | work=Company Information
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".<ref>{{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 }}</ref><ref>{{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 }}</ref><ref>{{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 }}</ref>
| publisher=Kyowa Hakko Kogyo Co., Ltd. | url=http://www.kyowa-kirin.co.jp/english/company/history/index.html

| accessdate=16 September 2010 }}</ref>
==Side effects==
Known side effects for olopatadine eye drops include headache, eye burning and/or stinging, blurred vision, dry eyes, foreign body sensation, ], ], eyelid ], ], ], sore throat (]), ], ], taste perversion, and vomiting.<ref>{{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 }}</ref>

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.<ref>{{cite web | url=https://www.drugs.com/mtm/olopatadine-nasal.html | title=Olopatadine nasal Uses, Side Effects & Warnings }}</ref><ref>{{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 }}</ref>

==Chemistry==

===Synthesis===
oxepinacetic acids with potent antiinflammatory activity | journal = Journal of Medicinal Chemistry | volume = 19 | issue = 7 | pages = 941–6 | date = July 1976 | pmid = 940112 | doi = 10.1021/jm00229a017 }}</ref>]]

==Pharmacology==

===Pharmacodynamics===
Olopatadine acts as a ] ] of the ] ], thus stabilizing mast cells and inhibiting histamine release.<ref>{{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 }}</ref>

==History==
Olopatadine was patented in 1986 by ] and came into medical use in 1997.<ref name=Fis2006/>

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).<ref name="FDA switch" /> 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.<ref name="FDA switch" /> These drugs are mast cell stabilizers, which work by preventing the release of histamine and therefore prevent or control allergic disorders.<ref name="FDA switch" />

In February 2020, Pataday Twice Daily Relief and Pataday Once Daily Relief were switched to be ]s in the United States when the FDA granted the approvals of the nonprescription products to ].<ref name="FDA switch" />

== Society and culture ==
=== Brand names ===
]Brand names include Pallada, Pazeo, Pataday, Patanol S, Patanol, Opatanol, Olopat, Patanase.<ref>{{cite web | url=https://medilib.ir/uptodate/show/9894 | title=Olopatadine (Ophthalmic): Drug information }}</ref><ref>{{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 }}</ref> It is also available as an oral tablet in Japan under the tradename Allelock, manufactured by ].<ref name=KYOWA08>{{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 }}</ref>


== References == == References ==
{{Reflist|2}} {{Reflist}}


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


{{Antihistamines}}
{{Nasal preparations}} {{Nasal preparations}}
{{Acetylcholine receptor modulators}}
{{Cholinergics}}
{{Histamine receptor modulators}}
{{Histaminergics}}
{{Tricyclics}} {{Tricyclics}}
{{Portal bar | Medicine}}
{{Authority control}}


] ]
] ]
]
]
] ]
] ]
]

]

]
{{respiratory-system-drug-stub}}
]

]
Olopatadine: Difference between revisions Add topic