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Bepotastine Besylate

CAS No:
190786-44-8 Categories: , , , ,
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Product Details:

  • Product Name: Bepotastine Besylate
  • CAS #: 190786-44-8
  • Mode of Action:

    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.

  • Pharmacodynamics:

    Bepotastine is a non-sedating, selective antagonist of the histamine 1 (H1) receptor. It belongs to the second-generation piperidine chemical class. It is a mast cell stabilizer and suppresses the migration of eosinophils into inflamed tissues. Furthermore, bepotastine does not interact with serotonin, muscarinic, benzodiazepine, and beta-adrenergic receptor that would otherwise result in adverse reactions such as dry mouth or sonmolence. Onset of action = 0.25 hours; Duration of action = 12-24 hours;

  • Metabolism:

    Minimal metabolism via CYP enzymes

  • IUPAC: 1-Piperidinebutanoic acid, 4-((4-chlorophenyl)-2-pyridinylmethoxy)- (S)-, monobenzenesulfonate
  • DrugBank: DB04890
  • Formula: C21-H25-Cl-N2-O3.C6-H6-O3-S
  • Molecular Mass: 547.0689
  • Synonyms: (+)-(S)-4-(4-((4-Chlorophenyl)(2-pyridyl)methoxy)piperidino)butyric acid monobenzenesulfonate, 4-((4-Chlorophenyl)-2-pyridinylmethoxy)- (S)-1-piperidinebutanoic acid monobenzenesulfonate, BB, Bepotastine benzenesulfonate, Bepotastine besilate, Bepotastine besylate, Bepreve, Betotastine besilate, Talion, TAU-284, UNII-6W18MO1QR3
  • SMILES: N1(CCC(CC1)O[C@H](c1ccccn1)c1ccc(cc1)Cl)CCCC(=O)O.c1(ccccc1)S(=O)(=O)O
  • InChl: 1S/C21H25ClN2O3.C6H6O3S/c22-17-8-6-16(7-9-17)21(19-4-1-2-12-23-19)27-18-10-14-24(15-11-18)13-3-5-20(25)26;7-10(8,9)6-4-2-1-3-5-6/h1-2,4,6-9,12,18,21H,3,5,10-11,13-15H2,(H,25,26);1-5H,(H,7,8,9)/t21-;/m0./s1
  • General Reference:

     

    1. Ohashi R, Kamikozawa Y, Sugiura M, Fukuda H, Yabuuchi H, Tamai I: Effect of P-glycoprotein on intestinal absorption and brain penetration of antiallergic agent bepotastine besilate. Drug Metab Dispos. 2006 May;34(5):793-9. Epub 2006 Feb 2. Pubmed
    2. Andoh T, Kuraishi Y: Suppression by bepotastine besilate of substance P-induced itch-associated responses through the inhibition of the leukotriene B4 action in mice. Eur J Pharmacol. 2006 Oct 10;547(1-3):59-64. Epub 2006 Jul 25. Pubmed
    3. Simons FE, Simons KJ: Histamine and H1-antihistamines: celebrating a century of progress. J Allergy Clin Immunol. 2011 Dec;128(6):1139-1150.e4. doi: 10.1016/j.jaci.2011.09.005. Epub 2011 Oct 27. Pubmed
    4. Wingard JB, Mah FS: Critical appraisal of bepotastine in the treatment of ocular itching associated with allergic conjunctivitis. Clin Ophthalmol. 2011;5:201-7. doi: 10.2147/OPTH.S8665. Epub 2011 Feb 15. Pubmed
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