4-{4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidin-1-yl}butanoic acid

• ChemBase ID: 4396
• Molecular Formular: C21H25ClN2O3
• Molecular Mass: 388.8878
• Monoisotopic Mass: 388.15537035
• SMILES: Clc1ccc(C(OC2CCN(CC2)CCCC(=O)O)c2ncccc2)cc1
• Canonical SMILES: OC(=O)CCCN1CCC(CC1)OC(c1ccccn1)c1ccc(cc1)Cl
• InChI: InChI=1S/C21H25ClN2O3/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/h1-2,4,6-9,12,18,21H,3,5,10-11,13-15H2,(H,25,26)
• InChIKey: YWGDOWXRIALTES-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidin-1-yl}butanoic acid
• IUPAC Traditional name: @bepotastine
• Brand Name: Talion
• Synonyms: Bepotastine besilate; Betotastine besilate; TAU-284DS; bepotastine; Bepotastine

Database IDs

• CAS Number: 190786-44-8
• PubChem SID: 160967828; 46504940
• PubChem CID: 2350

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.1016054
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.5400221
• LogD (pH = 7.4): 0.5506054
• Log P: 0.55255556
• Molar Refractivity: 105.0988 cm^3
• Polarizability: 41.298424 Å^3
• Polar Surface Area: 62.66 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.64
• LOG S: -3.89
• Solubility (Water): 5.03e-02 g/l

DETAILS

DrugBank - DB04890

• Drug Groups: approved; investigational
• Description: Bepotastine is a non-sedating, selective antagonist of the histamine 1 (H1) receptor. Bepotastine was approved in Japan for use in the treatment of allergic rhinitis and uriticaria/puritus in July 2000 and January 2002, respectively, and is marketed by Tanabe Seiyaku Co., Ltd. under the brand name Talion®. It is currently undergoing trials in the U.S.
• Indication: For the treatment of allergic conjunctivitis and uriticaria/puritus.
• Pharmacology: Bepotastine is a non-sedating, selective antagonist of the histamine 1 (H1) receptor. It has a stabilizing effect on mast cells, and it suppresses the migration of eosinophils into inflamed tissues. Bepotastine is under investigation in an eye drop formulation by Ista for the treatment of allergic conjunctivitis. An oral formulation of this drug is approved in Japan for the treatment of allergic conjunctivitis and uriticaria/puritus. Ista Pharm. filed an IND with the FDA for bepotastine in December of 2006.
• Affected Organisms: Humans and other mammals
• Absorption: High oral absorption
• References: 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] ; 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]
• External Links: Drugs.com

REFERENCES

• 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
• 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