CAS 190786-44-8|Talion|bepotastine|TAU-284DS|Bepotastine besilate|@bepotastine|4-{4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidin-1-yl}butanoic acid|Betotastine besilate|Bepotastine

General Information

Structure

Molecular Formula

C₂₁H₂₅ClN₂O₃

Molecular Mass

388.8878

Exact Mass

388.15537035

Charge

0

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

Canonic Smiles

OC(=O)CCCN1CCC(CC1)OC(c1ccccn1)c1ccc(cc1)Cl

Isomeric Smiles

Clc1ccc(C(OC2CCN(CC2)CCCC(=O)O)c2ncccc2)cc1

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

Polarizability

41.298424

Polar Surface Area

62.66

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

Data Source

Academic Data

Data Source

Names and Identifiers

Brand Name

Talion

Synonyms

bepotastineTAU-284DSBepotastine besilateBetotastine besilateBepotastine

IUPAC Traditional name

@bepotastine

IUPAC name

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

Names and Identifiers

Registration numbers

PubChem SID

16096782846504940

PubChem CID

2350

CAS Number

190786-44-8

Registration numbers

Properties

No Data Available

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Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:4396