BEPOTASTINE BESILATE CAS 190786-44-8
Introduction：Basic information about BEPOTASTINE BESILATE CAS 190786-44-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
BEPOTASTINE BESILATE Basic information
| Product Name: | BEPOTASTINE BESILATE |
| Synonyms: | BEPOTASTINE BESILATE;(+)-(S)-4-(4-((4-Chlorophenyl)(2-pyridyl)methoxy)piperidino)butyric acid monobenzenesulfonate;4-((4-Chlorophenyl)-2-pyridinylmethoxy)- (S)-1-piperidinebutanoic acid monobenzenesulfonate;Talion (TN);Bepotastine Beslilat;Bepotastine Besylate;1-Piperidinebutanoic acid, 4-[(4-chlorophenyl)-2-pyridinylmethoxy]-, (S)-, monobenzenesulfonate;1-Piperidinebutanoic acid, 4-[(S)-(4-chlorophenyl)-2-pyridinylmethoxy]-, monobenzenesulfonate |
| CAS: | 190786-44-8 |
| MF: | C27H31ClN2O6S |
| MW: | 547.06 |
| EINECS: | 1806241-263-5 |
| Product Categories: | Inhibitors;Other APIs;Aromatics;Drug Analogues;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;API;Amino Acids & Derivatives;Coronavirus |
| Mol File: | 190786-44-8.mol |
BEPOTASTINE BESILATE Chemical Properties
| Melting point | 161-163° |
| alpha | D20 +6.0° (c = 5 in methanol) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | DMSO (Slightly, Heated), Methanol (Slightly, Heated) |
| form | Solid |
| color | White to Light Beige |
| Optical Rotation | [α]/D 4.5 to 6.5°, c =1 in methanol |
| Stability: | Hygroscopic |
| InChIKey | UDGHXQPQKQPSBB-ZMBIFBSDSA-N |
| SMILES | [S](=O)(=O)(O)c4ccccc4.Clc1ccc(cc1)[C@@H](OC3CCN(CC3)CCCC(=O)O)c2ncccc2 |
Safety Information
| WGK Germany | WGK 3 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Repr. 2 |
| Description | Betotastine was introduced in Japan for the treatment of allergic rhinitis. Thisstructurally-related derivative of chlorpheniramine and ebastine is prepared bycondensation of optically-resolved 4-[1-(4-chlorophenyl)-1-(2-pyridyl)-methoxy]piperidinewith ethyl 4-bromobutyrate followed by ester hydrolysis. Betotastine is the seventhmarketed non-sedating histamine H1 antagonist. Its very low sedative side effect is due tovery poor penetration in the central nervous system. Besides its potent and long-actingactivity in models of allergic rhinitis, betotastine was also shown to act as a PAF antagonist and inhibit LTD4 in tracheal smooth muscle and ileum, IL-5 production by human peripheralblood mononuclear cells as well as eosinophil infiltration in the airway and peripheralblood. As a consequence, it is currently being developed against other allergic andrespiratory disorders. |
| Description | Bepotastine is an antagonist of the histamine H1 receptor that is selective over H3, α1-, α2-, and β-adrenergic, dopamine D2long, serotonin 5-HT2, muscarinic acetylcholine, and benzodiazepine receptors. It reduces dye leakage from the nasal passages of rats acutely sensitized to an antigen (ED50 = 0.03 mg/kg) and inhibits histamine-induced bronchoconstriction in the anesthetized dog (ED50 = 3.2 μg/kg). Bepotastine prevents conjunctival vascular hyperpermeability in a guinea pig model of conjunctivitis in a dose-dependent manner. Formulations containing bepotastine have been used in the treatment of itching associated with allergic conjunctivitis. |
| Chemical Properties | Off-White to Light Beige Solid |
| Originator | UBE (Japan) |
| Uses | Bepotastine is a non-sedating, selective antagonist of histamine 1 (H1) receptor with pIC50 of 5.7 |
| Uses | Bepotastine is a histamine H1 receptor anatagonist. Bepotastine suppresses some allergic inflammatory processes such as allergic rhinitis, chronic urticaria or pruritus associated with skin conditions (eczema/dermatitis, prurigo or pruritus cutaneus). |
| Definition | ChEBI: An organosulfonate salt obtained by combining equimolar amounts of bepotastine and benzenesulfonic acid. A topical, selective and non-sedating histamine (H1) receptor antagonist used for treatment of itching associated with allergic cojunctivitis. |
| Manufacturing Process | Manufacturing process for BEPOTASTINE BESILATE includes these steps as follows: Step A: Synthesis of Methyl 2-endo-hydroxy-1-exo-hydroxymethyl-3a,8b-cis-2,3,3a,8b-tetrahydro-1H-5-cyclopenta[b]benzofurancarboxylate,Step B: Synthesis of Methyl 3-methyl-trans-4a-cisoid-4a,5a-cis-5a-1,4a,5,5a,10b,10c-hexahydro-7-dioxin o[5,4-a]cyclopenta[b]benzofurancarboxylate,Step C: Synthesis of 3-Methyl-trans-4a-cosoid-4a,5a-cis-5a-1,4a,5,5a,10b,10c-hexahydro-7-dioxino[5,4-a]cyclopenta[b]benzofuranylmethanol,Step D: Synthesis of 7-Chloromethyl-3-methyl-trans-4a-cisoid-4a,5a-cis-5a-1,4a,5,5a,10b,10chexahydrodioxino[5,4-a]cyclopenta[b]benzofuran,Step E: Synthesis of 4-[3-Methyl-trans-4a-cisoid-4a,5a-cis-5a-1,4a,5,5a,10b,10c-hexahydro-7-dioxino[5,4-a]cyclopenta[b]benzofuranyl]butyric acid, Step F: Synthesis of Methyl 4-[2-endo-hydroxy-1-exo-hydroxymethyl-3a,8b-cis-2,3,3a,8btetrahydro-1H-5- cyclopenta[b]benzofuranyl]butyrate, Step G: Synthesis of Methyl 4-[2-endo-acetoxy-1-exo-hydroxymethyl-3a,8b-cis-2,3,3a,8btetrahydro-1H-5-cyclopenta[b]benzofuranyl]butyrate, Step H: Synthesis of Methyl ester of 11,15-dideoxy-11-acetoxy-16-methyl-15-oxo-18,19-tetradehydro-5,6,7-trinor-4,8-inter-m-phenylene PGI2,Step I: Synthesis of 11-Deoxy-11-acetoxy-16-methyl-18,19-tetradehydro-5,6,7-trinor-4,8-inter-mphenylene PGI2.To a solution of 54 mg of methyl ester of 11-deoxy-11-acetoxy-16-methyl-18,19-tetradehydro-5,6,7-trinor-4,8-inter-m-phenylene PGI2 in 4.5 ml ofanhydrous methanol was added 0.001 ml of 4.8 N sodium methoxide underargon, and the reaction mixture was stirred for 1.5 hours at roomtemperature.After addition of acetic acid to the reaction mixture and concentration of themixture, the residue was dissolved in 20 ml of ethyl acetate, and the solutionwas washed with aqueous saturated solution of sodium hydrogen carbonate,water and aqueous saturated solution of sodium chloride, dried andconcentrated to afford 55 mg of an oily material.This oily material was purified by column chromatography using ethyl acetateand cyclohexane (3:1) as eluent to give 48 mg of the methyl ester of 16-methyl-18,19-tetradehydro-5,6,7-trinor-4,8-inter-m-phenylene PGI2. |
| Brand name | Talion |
| Therapeutic Function | Antiallergic |
| References | [1] M KATO. Pharmacokinetic and pharmacodynamic evaluation of central effect of the novel antiallergic agent betotastine besilate.[J]. Arzneimittel-Forschung-Drug Research, 1997, 47 10: 1116-1124. [2] T MURATA. [Effect of betotastine besilate (TAU-284), a novel anti-allergic agent, on experimental allergic rhinitis].[J]. Arerugi = [Allergy], 1997, 46 7: 576-584. [3] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras. [4] TETSUO KIDA. Bepotastine besilate, a highly selective histamine H1 receptor antagonist, suppresses vascular hyperpermeability and eosinophil recruitment in in vitro and in vivo experimental allergic conjunctivitis models[J]. Experimental eye research, 2010, 91 1: Pages 85-91. DOI: 10.1016/j.exer.2010.04.006 |
BEPOTASTINE BESILATE Preparation Products And Raw materials
| Raw materials | Phosphonic acid,(3-methyl-2-oxo-5-heptynyl)-, dimethyl ester-->Thionyl chloride-->BENZOFURANCARBOXYLIC ACID-->Sodium bicarbonate-->Lithium Aluminum Hydride-->Sodium Methoxide-->CERIUM(III) CHLORIDE HEPTAHYDRATE-->p-Toluenesulfonic acid monohydrate |
