U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H25ClN2O3
Molecular Weight 388.8885
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEPOTASTINE

SMILES

c1ccnc(c1)[C@]([H])(c2ccc(cc2)Cl)OC3CCN(CCCC(=O)O)CC3

InChI

InChIKey=YWGDOWXRIALTES-NRFANRHFSA-N
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)/t21-/m0/s1

HIDE SMILES / InChI
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. 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 available in oral and opthalmic dosage forms in Japan. The opthalmic solution is FDA approved since Sept 8, 2009 and is under the brand name Bepreve.

CNS Activity

Curator's Comment:: Because of limited systemic absorption and poor blood-brain barrier penetration, the incidence of drowsiness with oral bepotastine besilate is low in comparison with other oral antihistamine products such as loratadine and cetirizine.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.7 null [pIC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TALION

Approved Use

TALION is usually used to treat allergic rhinitis, hives and itch resulting from skin diseases.

Launch Date

9.6240959E11
Primary
BEPREVE

Approved Use

BEPREVE® (bepotastine besilate ophthalmic solution) 1.5% is a histamine H1 receptor antagonist indicated for the treatment of itching associated with signs and symptoms of allergic conjunctivitis. BEPREVE ® is a histamine H1 receptor antagonist indicated for the treatment of itching associated with allergic conjunctivitis. (1)

Launch Date

1.25236806E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
99.9 ng/mL
19 mg single, oral
dose: 19 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BEPOTASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7.3 ng/mL
0.75 μg 1 times / day multiple, ocular
dose: 0.75 μg
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
BEPOTASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
392.4 ng × h/mL
19 mg single, oral
dose: 19 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BEPOTASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.9 h
19 mg single, oral
dose: 19 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BEPOTASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
45%
19 mg single, oral
dose: 19 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BEPOTASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
45%
0.75 μg 1 times / day multiple, ocular
dose: 0.75 μg
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
BEPOTASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 drop 2 times / day multiple, topical
Recommended
Dose: 1 drop, 2 times / day
Route: topical
Route: multiple
Dose: 1 drop, 2 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Allergic conjunctivitis
Sources: Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Effect of histamine on the permeability of the nasal mucosa in vivo.
2003 Apr
Effects of bepotastine, cetirizine, fexofenadine, and olopatadine on histamine-induced wheal-and flare-response, sedation, and psychomotor performance.
2004 Sep
Effect of P-glycoprotein on intestinal absorption and brain penetration of antiallergic agent bepotastine besilate.
2006 May
Involvement of histamine released from mast cells in acute radiation dermatitis in mice.
2007 Jun
Oral administration of bepotastine besilate suppressed scratching behavior of atopic dermatitis model NC/Nga mice.
2008
Mast cells play a critical role in the pathogenesis of viral myocarditis.
2008 Jul 22
Intact cell binding for in vitro prediction of sedative and non-sedative histamine H1-receptor antagonists based on receptor internalization.
2008 May
Multiple H1-antihistamine-induced urticaria.
2009 Apr
Effects of olopatadine hydrochloride, a histamine h(1) receptor antagonist, on histamine-induced skin responses.
2010
Next-day residual sedative effect after nighttime administration of an over-the-counter antihistamine sleep aid, diphenhydramine, measured by positron emission tomography.
2010 Dec
Azelastine hydrochloride, a dual-acting anti-inflammatory ophthalmic solution, for treatment of allergic conjunctivitis.
2010 Sep 7
Patents

Sample Use Guides

For adults: In general, take 1 tablet (10 mg of the active ingredient) at a time, twice a day. The dose may be adjusted according to your disease, age and symptom. For children aged 7 years and older: In general, take 1 tablet (10 mg of the active ingredient) at a time, twice a day.
Route of Administration: Oral
In vitro radioligand binding assays have demonstrated that bepotastine has strong affinity for the histamine H1 receptor (IC50 = 101 nM).
Name Type Language
BEPOTASTINE
INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
BEPOTASTINE [MI]
Common Name English
(+)-4-(((S)-P-CHLORO-.ALPHA.-2-PYRIDYLBENZYL)OXY)-1-PIPERIDINEBUTYRIC ACID
Common Name English
BEPOTASTINE [MART.]
Common Name English
BEPOTASTINE [INN]
Common Name English
BEPOTASTINE [USAN]
Common Name English
BEPOTASTINE [WHO-DD]
Common Name English
4-((S)-(4-CHLOROPHENYL)-2-PYRIDINYLMETHOXY)-1-PIPERIDINEBUTANOIC ACID
Systematic Name English
BETOTASTINE
Common Name English
BEPOTASTINE [VANDF]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175587
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
NCI_THESAURUS C29578
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
Code System Code Type Description
WIKIPEDIA
BEPOTASTINE
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY
LACTMED
Bepotastine
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY
DRUG BANK
DB04890
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY
DRUG CENTRAL
341
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY
CAS
190786-43-7
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
SUPERSEDED
MERCK INDEX
M2421
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY Merck Index
RXCUI
863035
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY RxNorm
IUPHAR
7466
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY
MESH
C108476
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY
NCI_THESAURUS
C77431
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY
INN
7648
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY
CAS
125602-71-3
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201758
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY
FDA UNII
HYD2U48IAS
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY
EVMPD
SUB05778MIG
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY
PUBCHEM
164522
Created by admin on Fri Jun 25 23:09:23 UTC 2021 , Edited by admin on Fri Jun 25 23:09:23 UTC 2021
PRIMARY