Olopatadine CAS 113806-05-6
Introduction：Basic information about Olopatadine CAS 113806-05-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Olopatadine Basic information
| Product Name: | Olopatadine |
| Synonyms: | 11-((z)-3-(dimethyl-amino)propylidene)-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid;Olopatatadine;KW 4679;Dibenz[b,e]oxepin-2-acetic acid, 11-[3-(dimethylamino)propylidene]-6,11-dihydro-, (11Z)-;Olopatadine & Olopatadine Hydrochloride;a-Hydroxy-Olopatadine;OLOPATADINE;-2-(11-(3-(Dimethylamino) |
| CAS: | 113806-05-6 |
| MF: | C21H23NO3 |
| MW: | 337.41 |
| EINECS: | 810-050-2 |
| Product Categories: | API;Olopatadine |
| Mol File: | 113806-05-6.mol |
Olopatadine Chemical Properties
| Melting point | 188-189.5° |
| Boiling point | 523.0±50.0 °C(Predicted) |
| density | 1?+-.0.06 g/cm3(Predicted) |
| storage temp. | Amber Vial, Refrigerator |
| solubility | Chloroform (Slightly, Heated), DMSO (Slightly) |
| form | Solid |
| pka | 4.29±0.10(Predicted) |
| color | Pale Yellow to Pale Beige |
| Stability: | Light Sensitive |
| InChI | 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- |
| InChIKey | JBIMVDZLSHOPLA-LSCVHKIXSA-N |
| SMILES | O1CC2=CC=CC=C2/C(=C/CCN(C)C)/C2=CC(CC(O)=O)=CC=C12 |
| CAS DataBase Reference | 113806-05-6(CAS DataBase Reference) |
Safety Information
| Description | Olopatadine belongs to a kind of antihistamine reagent. It is a relatively selective H1-receptor antagonist and can inhibit the histamine release process from the mast cell, subsequently leading to temporary relief on the negative symptoms associated with histamine. It is devoid of effects on alpha-adrenergic, dopamine and muscarinic type I and II receptors. Its 0.1% solution can be used for topical administration to the eyes. It is indicated for the treatment of itching associated with allergic conjunctivitis. |
| Originator | Patanol,Alcon,UK |
| Uses | Olopatadine is a dual acting histamine H1-receptor antagonist and mast cell stabilizer. Antiallergic; antihistaminic. |
| Uses | Anti-allergic. |
| Definition | ChEBI: 2-[11-[3-(dimethylamino)propylidene]-6H-benzo[c][1]benzoxepin-2-yl]acetic acid is a heterotricyclic compound. |
| Manufacturing Process | 402.4 g of phthalide and 200 g of sodium chloride and equal molecularquantity of p-hydroxyphenyl acetic acid are mixed with one another andstirred at 150°C for 6 hours. After completion of the reaction, the mixture iscooled until the temperature is brought back to room temperature, 4 L ofaqueous 10% acetic acid solution is added thereto and the mixture is allowedto stand at room temperature overnight. After stirring the mixture at roomtemperature for 3 hours, deposited crystals are separated by filtration, and 6L of water is added thereto. After stirring the mixture at room temperature for30 minutes, the deposited crystals are separated by filtration. After theaddition of 3 L of toluene to the crystals, the mixture is stirred at roomtemperature for one hour. The crystals are separated by filtration and driedover heating under reduced pressure to yield of 2-(4-acetoxyphenoxy)benzoicacid. 266.0 g of trifluoroacetic anhydride is added to the equal molecular quantityof 2-(4-acetoxyphenoxy)benzoic acid suspended in 5.0 L of methylene chlorideand thereto. After stirring the mixture at room temperature for one hour, 19.4g of boron trifluoride-ethylether complex is added thereto and the mixture isstirred at room temperature for two hours. The reaction solution is pouredinto ice water. After an organic solvent layer is separated from the mixture,the organic layer is washed with diluted aqueous sodium hydroxide solutionand water, dried over anhydrous magnesium sulfate and concentrated underreduced pressure to obtain 335.3 g of methyl 11-oxodibenz[b,e]oxepin-2-carboxylate as a white crystal melting point 130°-132°CMethyl 11-methylene-6,11-dihydrodibenz-[b,e]oxepin-2-acetate. In 100 ml of tetrahydrofuran is suspended 25 g ofmethyltriphenylphosphonium bromide and 40 ml of 1.6 N n-butyl lithiumhexane solution is dropwise added thereto under a nitrogen atmosphere andice-cooling. After stirring the mixture under ice-cooling for 30 minutes, asolution obtained by dissolving equal molar quantity of 11-oxo-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid in 250 ml of tetrahydrofuran isdropwise added thereto and the mixture is stirred at room temperature fortwo hours. The solvent is distilled away under reduced pressure and theresidue is purified by column chromatography on silica gel (eluent:hexane:ethyl acetate = 3:1) to obtain the desired product as a colorless oily matter. |
| Brand name | Patanol (Alcon). |
| Therapeutic Function | Antiallergic |
| References | https://www.drugbank.ca/drugs/DB00768 http://www.rxlist.com/patanol-drug/clinical-pharmacology.htm https://en.wikipedia.org/wiki/Olopatadine |
Olopatadine Preparation Products And Raw materials
| Raw materials | n-Butyllithium-->Trifluoroacetic anhydride-->1,2-Dibromoethane-->4-Hydroxyphenylacetic acid-->Boron trifluoride diethyl etherate-->SODIUM PERMANGANATE-->Phosphorus oxitrichloride-->Phthalide-->3-Chloro-1-(N,N-dimethyl)propylamine-->Methyltriphenylphosphonium bromide-->METHYL 2-(4-((2-BROMOBENZYL)OXY)PHENYL)ACETATE-->Benzeneacetic acid, 4-[(2-bromophenyl)methoxy]-3-iodo-, methyl ester-->Benzeneacetic acid, 4-[(2-bromophenyl)methoxy]-3-(4-hydroxy-1-butyn-1-yl)-, methyl ester-->Dibenz[b,e]oxepin-2-acetamide, 11-[3-(dimethylamino)propylidene]-6,11-dihydro-, (11Z)-, 4-methylbenzenesulfonate (1:1)-->UGDFSHGFPJSALM-OCKHKDLRSA-N-->Isoxepac-->(Z)-11-(3-dimethylaminopropylidene)-6,11-dihydro-dibenz-[b,e]oxepine-2-acetic acid hydrobromide |
