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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H25ClN2O3.C6H6O3S
Molecular Weight 547.063
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEPOTASTINE BESYLATE

SMILES

OS(=O)(=O)C1=CC=CC=C1.OC(=O)CCCN2CCC(CC2)O[C@@H](C3=CC=C(Cl)C=C3)C4=CC=CC=N4

InChI

InChIKey=UDGHXQPQKQPSBB-BOXHHOBZSA-N
InChI=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

HIDE SMILES / InChI

Molecular Formula C21H25ClN2O3
Molecular Weight 388.888
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C6H6O3S
Molecular Weight 158.175
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

2000
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

2009
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
Suppression by bepotastine besilate of substance P-induced itch-associated responses through the inhibition of the leukotriene B4 action in mice.
2006 Oct 10
Analysis of disease-dependent sedative profiles of H(1)-antihistamines by large-scale surveillance using the visual analog scale.
2008 Apr
Mast cells play a critical role in the pathogenesis of viral myocarditis.
2008 Jul 22
Evaluation of efficacy and sedative profiles of H(1) antihistamines by large-scale surveillance using the visual analogue scale (VAS).
2008 Sep
Novel functional aspect of antihistamines: the impact of bepotastine besilate on substance p-induced events.
2009
Downmodulatory effects of the antihistaminic drug bepotastine on cytokine/chemokine production and CD54 expression in human keratinocytes.
2009
Effects of olopatadine hydrochloride, a histamine h(1) receptor antagonist, on histamine-induced skin responses.
2010
Oral bepotastine: in allergic disorders.
2010 Aug 20
Next-day residual sedative effect after nighttime administration of an over-the-counter antihistamine sleep aid, diphenhydramine, measured by positron emission tomography.
2010 Dec
Bepotastine (bepreve)--an ophthalmic H1-antihistamine.
2010 Feb 8
Bepotastine besilate, a highly selective histamine H(1) receptor antagonist, suppresses vascular hyperpermeability and eosinophil recruitment in in vitro and in vivo experimental allergic conjunctivitis models.
2010 Jul
Non-clinical pharmacology, pharmacokinetics, and safety findings for the antihistamine bepotastine besilate.
2010 Oct
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:04:20 GMT 2023
Edited
by admin
on Fri Dec 15 16:04:20 GMT 2023
Record UNII
6W18MO1QR3
Record Status Validated (UNII)
Record Version
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Name Type Language
BEPOTASTINE BESILATE
DASH   JAN   MART.   ORANGE BOOK   VANDF   WHO-DD  
Preferred Name English
BEPOTASTINE BESYLATE
USAN  
USAN  
Official Name English
BEPOTASTINE BENZENESULPHONATE SALT
Common Name English
TALION
Brand Name English
1-PIPERIDINEBUTANOIC ACID, 4-((S)-(4-CHLOROPHENYL)-2-PYRIDINYLMETHOXY)-, BENZENESULPHONATE (1:1)
Common Name English
(+)-4-(4-((S)-(4-CHLOROPHENYL)(PYRIDIN-2-YL)METHOXY)PIPERIDIN-1-YL)BUTANOIC ACID MONOBENZENESULFONATE
Systematic Name English
Bepotastine besilate [WHO-DD]
Common Name English
BEPOTASTINE BENZENESULFONATE SALT
MI  
Common Name English
1-PIPERIDINEBUTANOIC ACID, 4-((S)-(4-CHLOROPHENYL)-2-PYRIDINYLMETHOXY)-, BENZENESULFONATE (1:1)
Common Name English
BEPOTASTINE BESILATE [MART.]
Common Name English
BEPOTASTINE BESYLATE [USAN]
Common Name English
BEPOTASTINE BENZENESULFONATE SALT [MI]
Common Name English
4-((S)-(4-CHLOROPHENYL)-2-PYRIDINYLMETHOXY)-1-PIPERIDINEBUTANOIC ACID BENZENESULPHONATE SALT
Common Name English
BEPOTASTINE BESILATE [ORANGE BOOK]
Common Name English
4-((S)-(4-CHLOROPHENYL)-2-PYRIDINYLMETHOXY)-1-PIPERIDINEBUTANOIC ACID BENZENESULFONATE SALT
Common Name English
BEPREVE
Brand Name English
TAU-284
Code English
BEPOTASTINE BESILATE [VANDF]
Common Name English
(+)-4-(4-((S)-(4-CHLOROPHENYL)(PYRIDIN-2-YL)METHOXY)PIPERIDIN-1-YL)BUTANOIC ACID MONOBENZENESULPHONATE
Systematic Name English
BEPOTASTINE BESILATE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
Code System Code Type Description
USAN
WW-121
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID80172577
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY
MESH
C511534
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY
DRUG BANK
DBSALT000017
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY
RXCUI
658552
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY RxNorm
CAS
190786-44-8
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY
PUBCHEM
164521
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY
EVMPD
SUB22587
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY
FDA UNII
6W18MO1QR3
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY
CHEBI
31281
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201758
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY
DAILYMED
6W18MO1QR3
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY
SMS_ID
100000086310
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY
NCI_THESAURUS
C83550
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY
MERCK INDEX
m2421
Created by admin on Fri Dec 15 16:04:20 GMT 2023 , Edited by admin on Fri Dec 15 16:04:20 GMT 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY