Olopatadine
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| Systematic (IUPAC) name |
{(11Z)-11-[3-(dimethylamino)propylidene]-6,11-
dihydrodibenzob,eoxepin-2-yl}acetic acid |
| Clinical data |
| Trade names |
Patanol |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a602025 |
| Pregnancy cat. |
C |
| Legal status |
? |
| Routes |
Ophthalmic, intranasal, oral |
| Pharmacokinetic data |
| Half-life |
3 hours |
| Identifiers |
| CAS number |
113806-05-6 Y |
| ATC code |
S01GX09 R01AC08 |
| PubChem |
CID 5281071 |
| DrugBank |
DB00768 |
| ChemSpider |
4444528 Y |
| UNII |
D27V6190PM Y |
| KEGG |
D08293 Y |
| ChEMBL |
CHEMBL1189432 N |
| Chemical data |
| Formula |
C21H23NO3 |
| Mol. mass |
337.412 g/mol |
| SMILES |
eMolecules & PubChem |
InChI
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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- Y
Key:JBIMVDZLSHOPLA-LSCVHKIXSA-N Y
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N (what is this?) (verify)
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Olopatadine hydrochloride is an antihistamine (as well as anticholinergic) and mast cell stabilizer, sold as a prescription eye drop (0.2% solution, Pataday (or Patanol S in some countries), manufactured by Alcon). It is used to treat itching associated with allergic conjunctivitis (eye allergies). 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, 2008.1 It is also available as an oral tablet in Japan under the tradename Allelock, manufactured by Kyowa Hakko Kogyo.2
It should not be used to treat irritation caused by contact lenses. The usual dose for Patanol is 1 drop in each affected eye 2 times per day, with 6 to 8 hours between doses.
Its side effects may include headaches (7% of occurrence) burning and stinging (5%), dry eye, foreign body sensation, hyperemia, keratitis, lid edema, pruritus, asthenia, cold syndrome, pharyngitis, rhinitis, sinusitis, and taste perversion.
There is potential for Olopatadine as a treatment modality for steroid rebound (red skin syndrome.) 3
Olopatadine was developed by Kyowa Hakko Kogyo.4
References
- ^ 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). http://www.e-search.ne.jp/~jpr/PDF/KYOWA08.PDF. Retrieved 2008-08-10.
- ^ Tamura T, Matsubara M, Hasegawa K, Ohmori K, Karasawa A. (2005). "Olopatadine hydrochloride suppresses the rebound phenomenon after discontinuation of treatment with a topical steroid in mice with chronic contact hypersensitivity.". http://www.ncbi.nlm.nih.gov/pubmed/15649273.
- ^ Kyowa Hakko Kogyo Co., Ltd. (2002). "Company History". Company Information. Kyowa Hakko Kogyo Co., Ltd.. http://www.kyowa-kirin.co.jp/english/company/history/index.html. Retrieved 16 September 2010.
External links
- Pataday website
- Patanase website
- Olopatadine Ophthalmic via MedlinePlus
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Decongestants and other nasal preparations (R01)
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| Topical |
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Sympathomimetics, plain
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- Cyclopentamine
- Ephedrine
- Phenylephrine
- Oxymetazoline
- Tetryzoline
- Xylometazoline
- Naphazoline
- Tramazoline
- Metizoline
- Tuaminoheptane
- Fenoxazoline
- Tymazoline
- Epinephrine
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Antiallergic agents,
excluding corticosteroids
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- histamine antagonists (Levocabastine
- Antazoline
- Thonzylamine)
- mast cell stabilizer (some are also antihistamines) (Cromoglicic acid
- Nedocromil
- Azelastine
- Olopatadine
- Lodoxamide)
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Corticosteroids
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- Beclometasone
- Prednisolone
- Dexamethasone
- Flunisolide
- Budesonide
- Betamethasone
- Tixocortol
- Fluticasone
- Mometasone furoate
- Triamcinolone
- Ciclesonide
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Other nasal preparations
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- Cafaminol
- Calcium hexamine thiocyanate
- Retinol
- Ipratropium bromide
- Ritiometan
- Mupirocin
- Hexamidine
- Framycetin
- Hyaluronic acid
- Eucalyptus oil
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Systemic use:
Sympathomimetics |
- Phenylpropanolamine
- Pseudoephedrine (+loratadine)
- Phenylephrine
- Phenylpropylamine
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anat(n, x, l, c)/phys/devp
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noco(c, p)/cong/tumr, sysi/epon, injr
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Cholinergics
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Receptor ligands
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mAChR
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- Agonists: 77-LH-28-1
- AC-42
- AC-260,584
- Aceclidine
- Acetylcholine
- AF30
- AF150(S)
- AF267B
- AFDX-384
- Alvameline
- AQRA-741
- Arecoline
- Bethanechol
- Butyrylcholine
- Carbachol
- CDD-0034
- CDD-0078
- CDD-0097
- CDD-0098
- CDD-0102
- Cevimeline
- cis-Dioxolane
- Ethoxysebacylcholine
- LY-593,039
- L-689,660
- LY-2,033,298
- McNA343
- Methacholine
- Milameline
- Muscarine
- NGX-267
- Ocvimeline
- Oxotremorine
- PD-151,832
- Pilocarpine
- RS86
- Sabcomeline
- SDZ 210-086
- Sebacylcholine
- Suberylcholine
- Talsaclidine
- Tazomeline
- Thiopilocarpine
- Vedaclidine
- VU-0029767
- VU-0090157
- VU-0152099
- VU-0152100
- VU-0238429
- WAY-132,983
- Xanomeline
- YM-796
Antagonists: 3-Quinuclidinyl Benzilate
- 4-DAMP
- Aclidinium Bromide
- Anisodamine
- Anisodine
- Atropine
- Atropine Methonitrate
- Benactyzine
- Benzatropine (Benztropine)
- Benzydamine
- BIBN 99
- Biperiden
- Bornaprine
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,368
- CAR-302,537
- CAR-302,668
- CS-27349
- Cyclobenzaprine
- Cyclopentolate
- Darifenacin
- DAU-5884
- Dimethindene
- Dexetimide
- DIBD
- Dicyclomine (Dicycloverine)
- Ditran
- EA-3167
- EA-3443
- EA-3580
- EA-3834
- Etanautine
- Etybenzatropine (Ethylbenztropine)
- Flavoxate
- Himbacine
- HL-031,120
- Ipratropium bromide
- J-104,129
- Hyoscyamine
- Mamba Toxin 3
- Mamba Toxin 7
- Mazaticol
- Mebeverine
- Methoctramine
- Metixene
- N-Ethyl-3-Piperidyl Benzilate
- N-Methyl-3-Piperidyl Benzilate
- Orphenadrine
- Otenzepad
- Oxybutynin
- PBID
- PD-102,807
- PD-0298029
- Phenglutarimide
- Phenyltoloxamine
- Pirenzepine
- Piroheptine
- Procyclidine
- Profenamine
- RU-47,213
- SCH-57,790
- SCH-72,788
- SCH-217,443
- Scopolamine (Hyoscine)
- Solifenacin
- Telenzepine
- Tiotropium bromide
- Tolterodine
- Trihexyphenidyl
- Tripitamine
- Tropatepine
- Tropicamide
- WIN-2299
- Xanomeline
- Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine
- chlorphenamine
- cyproheptadine
- dimenhydrinate
- diphenhydramine
- doxylamine
- mepyramine/pyrilamine
- phenindamine
- pheniramine
- tripelennamine
- triprolidine, etc)
- Tricyclic Antidepressants (Amitriptyline
- doxepin
- trimipramine, etc)
- Tetracyclic Antidepressants (Amoxapine
- maprotiline, etc)
- Typical Antipsychotics (Chlorpromazine
- thioridazine, etc)
- Atypical Antipsychotics (Clozapine
- olanzapine
- quetiapine, etc)
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nAChR
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- Agonists: 5-HIAA
- A-84,543
- A-366,833
- A-582,941
- A-867,744
- ABT-202
- ABT-418
- ABT-560
- ABT-894
- Acetylcholine
- Altinicline
- Anabasine
- Anatoxin-a
- AR-R17779
- Butinoline
- Butyrylcholine
- Carbachol
- Cotinine
- Cytisine
- Decamethonium
- Desformylflustrabromine
- Dianicline
- Dimethylphenylpiperazinium
- Epibatidine
- Epiboxidine
- Ethanol
- Ethoxysebacylcholine
- EVP-4473
- EVP-6124
- Galantamine
- GTS-21
- Ispronicline
- Lobeline
- MEM-63,908 (RG-3487)
- Nicotine
- NS-1738
- PHA-543,613
- PHA-709,829
- PNU-120,596
- PNU-282,987
- Pozanicline
- Rivanicline
- Sazetidine A
- Sebacylcholine
- SIB-1508Y
- SIB-1553A
- SSR-180,711
- Suberylcholine
- TC-1698
- TC-1734
- TC-1827
- TC-2216
- TC-5214
- TC-5619
- TC-6683
- Tebanicline
- Tropisetron
- UB-165
- Varenicline
- WAY-317,538
- XY-4083
Antagonists: 18-Methoxycoronaridine
- α-Bungarotoxin
- α-Conotoxin
- Alcuronium
- Amantadine
- Anatruxonium
- Atracurium
- Bupropion (Amfebutamone)
- Chandonium
- Chlorisondamine
- Cisatracurium
- Coclaurine
- Coronaridine
- Dacuronium
- Decamethonium
- Dextromethorphan
- Dextropropoxyphene
- Dextrorphan
- Diadonium
- DHβE
- Dimethyltubocurarine (Metocurine)
- Dipyrandium
- Dizocilpine (MK-801)
- Doxacurium
- Duador
- Esketamine
- Fazadinium
- Gallamine
- Hexafluronium
- Hexamethonium (Benzohexonium)
- Ibogaine
- Isoflurane
- Ketamine
- Kynurenic acid
- Laudexium (Laudolissin)
- Levacetylmethadol
- Malouetine
- Mecamylamine
- Memantine
- Methadone
- Methorphan (Racemethorphan)
- Methyllycaconitine
- Metocurine
- Mivacurium
- Morphanol (Racemorphanol)
- Neramexane
- Nitrous Oxide
- Pancuronium
- Pempidine
- Pentamine
- Pentolinium
- Phencyclidine
- Pipecuronium
- Radafaxine
- Rapacuronium
- Rocuronium
- Surugatoxin
- Suxamethonium (Succinylcholine)
- Thiocolchicoside
- Toxiferine
- Trimethaphan
- Tropeinium
- Tubocurarine
- Vecuronium
- Xenon
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Reuptake inhibitors
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Plasmalemmal
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CHT Inhibitors
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- Hemicholinium-3 (Hemicholine; HC3)
- Triethylcholine
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Vesicular
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Enzyme inhibitors
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Anabolism
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ChAT inhibitors
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- 1-(-Benzoylethyl)pyridinium
- 2-(α-Naphthoyl)ethyltrimethylammonium
- 3-Chloro-4-stillbazole
- 4-(1-Naphthylvinyl)pyridine
- Acetylseco hemicholinium-3
- Acryloylcholine
- AF64A
- B115
- BETA
- CM-54,903
- N,N-Dimethylaminoethylacrylate
- N,N-Dimethylaminoethylchloroacetate
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Catabolism
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AChE inhibitors
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BChE inhibitors
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- Cymserine * Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.
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Others
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Precursors
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- Choline (Lecithin)
- Citicoline
- Cyprodenate
- Dimethylethanolamine (DMAE, deanol)
- Glycerophosphocholine
- Meclofenoxate (Centrophenoxine)
- Phosphatidylcholine
- Phosphatidylethanolamine
- Phosphorylcholine
- Pirisudanol
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Cofactors
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- Acetic acid
- Acetylcarnitine
- Acetyl-coA
- Vitamin B5 (Pantethine
- Pantetheine
- Panthenol)
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Others
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- Acetylcholine releasing agents: α-Latrotoxin
- β-Bungarotoxin; Acetylcholine release inhibitors: Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime
- Obidoxime
- Pralidoxime
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Histaminergics
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Receptor
ligands |
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H1
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H2
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- Agonists: Amthamine
- Betazole
- Dimaprit
- Histamine
- HTMT
- Impromidine
- UR-AK49
Antagonists: Burimamide
- Cimetidine
- Ebrotidine
- Famotidine
- Lafutidine
- Lavoltidine/Loxtidine
- Lupitidine
- Metiamide
- Niperotidine
- Nizatidine
- Oxmetidine
- Ranitidine
- Roxatidine
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H3
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- Agonists: α-Methylhistamine
- Cipralisant
- Histamine
- Imetit
- Immepip
- Immethridine
- Methimepip
- Proxyfan
Antagonists: A-349,821
- A-423,579
- ABT-239
- Betahistine
- Burimamide
- Ciproxifan
- Clobenpropit
- Conessine
- GSK-189,254
- Impentamine
- Iodophenpropit
- JNJ-5,207,852
- MK-0249
- NNC-38-1,049
- PF-03654746
- Pitolisant
- SCH-79,687
- Thioperamide
- VUF-5,681
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H4
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- Agonists: 4-Methylhistamine
- Histamine
- VUF-8,430
Antagonists: JNJ-7,777,120
- Thioperamide
- VUF-6,002
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Reuptake
inhibitors |
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Vesicular
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VMAT inhibitors
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- Ibogaine
- Reserpine
- Tetrabenazine
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Enzyme
inhibitors |
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Anabolism
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HDC inhibitors
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- Catechin
- Meciadanol
- Naringenin
- Tritoqualine
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Catabolism
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HNMT inhibitors
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- Amodiaquine
- Diphenhydramine
- Harmaline
- Metoprine
- Quinacrine
- SKF-91,488
- Tacrine
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DAO inhibitors
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| Others |
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Precursors
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Cofactors
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- Vitamin B6 (pyridoxine
- pyridoxamine
- pyridoxal → Pyridoxal phosphate)
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