Chemical compound
Olopatadine Trade names Patanol, Pataday, Opatanol AHFS /Drugs.com Monograph MedlinePlus a602025 License data Pregnancy category Routes of administration Eye drops , nasal spray ATC code Legal status AU : S4 (Prescription only) UK : POM (Prescription only) US : ℞-only / OTC[1] EU : Rx-only Elimination half-life 3 hours {(11Z )-11-[3-(dimethylamino)propylidene]-6,11- dihydrodibenzo[b,e ]oxepin-2-yl}acetic acid
CAS Number PubChem CID DrugBank ChemSpider UNII KEGG ChEMBL CompTox Dashboard (EPA ) Formula C 21 H 23 N O 3 Molar mass 337.419 g·mol−1 3D model (JSmol ) O=C(O)Cc2ccc1OCc3c(C(\c1c2)=C\CCN(C)C)cccc3
InChI=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).[2] It is used as eye drops or as a nasal spray .[2] The eye drops generally result in an improvement within half an hour.[2]
Common side effects include headache, sore throat, eye discomfort, or changes in perception of taste.[3] [2] More significant side effects may include sleepiness.[2] It is unclear if use during pregnancy or breastfeeding is safe.[4] It is an antihistamine and mast cell stabilizer .[5] [2]
Olopatadine was patented in 1986 and came into medical use in 1997.[6] It is available as a generic medication .[2] In 2021, it was the 263rd most commonly prescribed medication in the United States, with more than 1 million prescriptions.[7] [8]
Side effects [ edit ] Some known side effects include headache (7% of occurrence), eye burning and/or stinging (5%), blurred vision, dry eyes, foreign body sensation, hyperemia , keratitis , eyelid edema , pruritus , asthenia , sore throat (pharyngitis ), rhinitis , sinusitis , taste perversion, and vomiting.
Chemistry [ edit ] Synthesis [ edit ] Olopatadine synthesis:[9] Pharmacology [ edit ] Pharmacodynamics [ edit ] Olopatadine acts as a selective antagonist of the histamine H1 receptor , thus stabilizing mast cells and inhibiting histamine release.
History [ edit ] Olopatadine was patented in 1986 by Kyowa Hakko Kogyo and came into medical use in 1997.[6]
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).[1] 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.[1] These drugs are mast cell stabilizers, which work by preventing the release of histamine and therefore prevent or control allergic disorders.[1]
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 .[1]
Society and culture [ edit ] Brand names [ edit ] Brand names include Pazeo, Pataday, Patanol S, Patanol, Opatanol, Olopat, Patanase.[10] It is also available as an oral tablet in Japan under the tradename Allelock, manufactured by Kyowa Hakko Kogyo.[11]
References [ edit ] ^ a b c d e "FDA Approves Three Drugs for Nonprescription Use Through Rx-to-OTC Switch Process" . U.S. Food and Drug Administration (FDA) . 14 February 2020. Archived from the original on 15 February 2020. Retrieved 14 February 2020 . This article incorporates text from this source, which is in the public domain . ^ a b c d e f g "Olopatadine Hydrochloride Monograph for Professionals" . Drugs.com . American Society of Health-System Pharmacists. Retrieved 26 March 2019 . ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 1126. ISBN 9780857113382 . ^ "Olopatadine ophthalmic Use During Pregnancy" . Drugs.com . Retrieved 26 March 2019 . ^ Castillo M, Scott NW, Mustafa MZ, Mustafa MS, Azuara-Blanco A (June 2015). "Topical antihistamines and mast cell stabilisers for treating seasonal and perennial allergic conjunctivitis" (PDF) . The Cochrane Database of Systematic Reviews . 2015 (6): CD009566. doi :10.1002/14651858.CD009566.pub2 . hdl :2164/6048 . PMC 10616535 . PMID 26028608 . ^ a b Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery . John Wiley & Sons. p. 549. ISBN 9783527607495 . ^ "The Top 300 of 2021" . ClinCalc . Archived from the original on 15 January 2024. Retrieved 14 January 2024 . ^ "Olopatadine - Drug Usage Statistics" . ClinCalc . Retrieved 14 January 2024 . ^ Ueno K, Kubo S, Tagawa H, Yoshioka T, Tsukada W (July 1976). "6,11-Dihydro-11-oxodibenz [b,e] oxepinacetic acids with potent antiinflammatory activity". Journal of Medicinal Chemistry . 19 (7): 941–6. doi :10.1021/jm00229a017 . PMID 940112 . ^ Drugs.com, Alcon's Patanase Nasal Spray Approved by FDA for Treatment of Nasal Allergy Symptoms ^ Kyowa Hakko Kogyo Co., Ltd. (2007). "Allelock Tablets 2.5 & Allelock Tablets 5 (English)" (PDF) . Archived from the original (PDF) on 22 July 2011. Retrieved 10 August 2008 . External links [ edit ]
mAChRs Tooltip Muscarinic acetylcholine receptors
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Precursors (and prodrugs )
nAChRs Tooltip Nicotinic acetylcholine receptors
Agonists (and PAMs Tooltip positive allosteric modulators ) 5-HIAA 6-Chloronicotine A-84,543 A-366,833 A-582,941 A-867,744 ABT-202 ABT-418 ABT-560 ABT-894 Acetylcholine Altinicline Anabasine Anatabine Anatoxin-a AR-R17779 Bephenium hydroxynaphthoate Butinoline Butyrylcholine Carbachol Choline Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol (alcohol) Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Ivermectin JNJ-39393406 Levamisole Lobeline MEM-63,908 (RG-3487) Morantel Nicotine (tobacco ) NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Pyrantel Rivanicline RJR-2429 Sazetidine A SB-206553 Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberyldicholine Suxamethonium (succinylcholine) Suxethonium (succinyldicholine) TC-1698 TC-1734 TC-1827 TC-2216 TC-5214 TC-5619 TC-6683 Tebanicline Tribendimidine Tropisetron UB-165 Varenicline WAY-317,538 XY-4083 Antagonists (and NAMs Tooltip negative allosteric modulators )
Precursors (and prodrugs )
H1
Agonists Antagonists Others: Atypical antipsychotics (e.g., aripiprazole , asenapine , brexpiprazole , brilaroxazine , clozapine , iloperidone , olanzapine , paliperidone , quetiapine , risperidone , ziprasidone , zotepine ) Phenylpiperazine antidepressants (e.g., hydroxynefazodone , nefazodone , trazodone , triazoledione ) Tetracyclic antidepressants (e.g., amoxapine , loxapine , maprotiline , mianserin , mirtazapine , oxaprotiline ) Tricyclic antidepressants (e.g., amitriptyline , butriptyline , clomipramine , desipramine , dosulepin (dothiepin) , doxepin , imipramine , iprindole , lofepramine , nortriptyline , protriptyline , trimipramine ) Typical antipsychotics (e.g., chlorpromazine , flupenthixol , fluphenazine , loxapine , perphenazine , prochlorperazine , thioridazine , thiothixene )
H2
H3
H4