Bepotastine besilate

Base Information

• Chemical Name: Bepotastine besilate
• CAS No.: 190786-44-8
• Molecular Formula: C₆H₆O₃S*C₂₁H₂₅ClN₂O₃
• Molecular Weight: 547.072
• European Community (EC) Number: 878-395-1
• UNII: 6W18MO1QR3
• DSSTox Substance ID: DTXSID80172577
• Wikidata: Q27114261
• NCI Thesaurus Code: C83550
• RXCUI: 658552
• ChEMBL ID: CHEMBL1201759
• Mol file: 190786-44-8.mol

Synonyms:bepotastine besilate

Chemical Property of Bepotastine besilate

Chemical Property:

• Appearance/Colour: Brown Viscous liquid
• Vapor Pressure: 8.63E-13mmHg at 25°C
• Melting Point: 161-163°
• Boiling Point: 546.8 °C at 760 mmHg
• Flash Point: 284.5 °C
• PSA: 125.41000
• LogP: 6.12220
• Storage Temp.: -196°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 546.1591356
• Heavy Atom Count: 37
• Complexity: 632

Purity/Quality:

99% ^*data from raw suppliers

Bepotastine Besylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCC1OC(C2=CC=C(C=C2)Cl)C3=CC=CC=N3)CCCC(=O)O.C1=CC=C(C=C1)S(=O)(=O)O
• Isomeric SMILES: C1CN(CCC1O[C@@H](C2=CC=C(C=C2)Cl)C3=CC=CC=N3)CCCC(=O)O.C1=CC=C(C=C1)S(=O)(=O)O
• Recent ClinicalTrials: Clinical Study for the Evaluation of Safety and Tolerability of PRO-172 Ophthalmic Solution+
• Recent NIPH Clinical Trials: Efficacy of bepotastine besilate for seasonal allergic rhinitis patients - about laryngeal symptoms, olfactory disorder, sleep disorder, QOL and symptoms caused by Asian sand dust
• Description: 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. 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.
• Uses: Bepotastine is a non-sedating, selective antagonist of histamine 1 (H1) receptor with pIC50 of 5.7 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).
• Therapeutic Function: Antiallergic

Technology Process of Bepotastine besilate

There total 42 articles about Bepotastine besilate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.9%

benzenesulfonic acid (98-11-3) + Bepotastine (125602-71-3,190786-43-7,190730-41-7) → [14C]-Bepotastine besilate (125602-71-3,190786-44-8,190730-42-8)

Guidance literature:

In ethanol; at 50 ℃;

DOI:10.1080/00304948.2020.1868930

Reference yield: 75.0%

(S)-(-)-2-((4-chlorophenyl)(piperidin-4-yloxy)methyl)pyridine (210095-55-9) + Ethyl 4-bromobutyrate (2969-81-5) + benzenesulfonic acid (98-11-3) → [14C]-Bepotastine besilate (125602-71-3,190786-44-8,190730-42-8)

Guidance literature:

(S)-(-)-2-((4-chlorophenyl)(piperidin-4-yloxy)methyl)pyridine; Ethyl 4-bromobutyrate; With potassium carbonate; In acetonitrile; at 60 ℃; for 6h; Large scale;

With sodium hydroxide; In acetonitrile; at 20 ℃; for 2h; Large scale;

benzenesulfonic acid; In acetonitrile; at 70 ℃; Solvent; Temperature; Large scale;

Reference yield: 67.3%

benzene-sulfonic acid monohydrate (26158-00-9,5928-72-3) + Bepotastine (125602-71-3,190786-43-7,190730-41-7) → [14C]-Bepotastine besilate (125602-71-3,190786-44-8,190730-42-8)

Guidance literature:

In ethyl acetate;

upstream raw materials:

benzenesulfonic acid

Bepotastine

bepotastine besilate

4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidine

Downstream raw materials:

[14C]-Bepotastine besilate

Refernces

• 1、 -. "Total synthesis method of bestatin". Paragraph 0020; 0050; 0064-0066; 0066; 0080-0081. . Retrieved 2021/10/11.
• 2、 -. "A stable besylate bepotastine crystal and its preparation method". Paragraph 0054-0055. . Retrieved 2018/02/04.