Bepotastine Besilate
BB · Bepotastine Besylate · CS-645 · CS-487 · Talion · Bepreve · TAU 284 · Talion (TN)
Identifikatoren & physikalische Daten
| CAS No. | 190786-44-8 |
|---|---|
| Summenformel | C27H31ClN2O6S |
| Durchschnittliche Molmasse | 547,1 g/mol |
| Monoisotopische Masse | 546,15913539 g/mol |
| SMILES | O=C(O)CCCN1CCC(O[C@@H](c2ccc(Cl)cc2)c2ccccn2)CC1.O=S(=O)(O)c1ccccc1 |
| InChIKey | UDGHXQPQKQPSBB-BOXHHOBZSA-N |
| PubChem CID | 164521 |
| ChEMBL | CHEMBL1201759 |
| ChEBI | CHEBI:31281 |
| EC No. | 878-395-1 |
| DTXSID | DTXSID80172577 |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 125 |
|---|---|
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 8 |
| Frei drehbare Bindungen | 9 |
| Schwere Atome | 37 |
| Formalladung | 0 |
| Komplexität | 632 |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-Allergic AgentsAntihistaminesFDA approved drugs -> Active ingredient |
| Schmelzpunkt | 161-163° |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Löslichkeit | DMSO (Slightly, Heated), Methanol (Slightly, Heated) |
| Aggregatzustand | Solid |
| Farbe | White to Light Beige |
| Stabilität | Hygroscopic |
| InChIKey | UDGHXQPQKQPSBB-ZMBIFBSDSA-N |
| SMILES | [S](=O)(=O)(O)c4ccccc4.Clc1ccc(cc1)[C@@H](OC3CCN(CC3)CCCC(=O)O)c2ncccc2 |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.WarningH361 (33.3%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Repr. 2 (33.3%) |
| Expositionspfade | Oral, Ophthalmic. Tmax, after single dose, opthalmic = 1.2 hoursCmax, 1.5%, opthalmic dose = 7.3 ۫.9 ng/mLAfter 24 hours post-installation, levels of bepotastine are below quantifiable limit of 2 ng/mL. Minimal systemic absorption with opthalmic dosage form. |
| Toxizitätsübersicht | Because of a type 1 hypersensitivity reaction cascade that is triggered by antigen exposure, allergic conjunctivitis occurs. Allergen exposure is followed by conjunctival mast cell degranulation and histamine released as a result of the formation of complementary IgE cross-links on the conjunctiva. Due to the release of histamine, symptoms such as itching can be observed. Bepotastine works to relieve itchy eyes by three primary mechanisms of action. It is a non-sedating, selective antagonist of the histamine 1 (H1) receptor, a mast cell stabilizer, and it suppresses the migration of eosinophils into inflamed tissues to prevent tissue damage and worsening of allergic inflammation of the conjunctiva. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Wassergefährdungsklasse (WGK) | WGK 3 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Repr. 2 |
Anwendungen & Verwendung
Beschreibung
Betotastine was introduced in Japan for the treatment of allergic rhinitis. This structurally-related derivative of chlorpheniramine and ebastine is prepared by condensation of optically-resolved 4-[1-(4-chlorophenyl)-1-(2-pyridyl)-methoxy]piperidine with ethyl 4-bromobutyrate followed by ester hydrolysis. Betotastine is the seventh marketed non-sedating histamine H1 antagonist. Its very low sedative side effect is due to very poor penetration in the central nervous system. Besides its potent and long-acting activity 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 peripheral blood mononuclear cells as well as eosinophil infiltration in the airway and peripheral blood. As a consequence, it is currently being developed against other allergic and respiratory disorders.
Verwenden
Bepotastine is a non-sedating, selective antagonist of histamine 1 (H1) receptor with pIC50 of 5.7