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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H25ClN2O3
Molecular Weight 388.888
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEPOTASTINE

SMILES

OC(=O)CCCN1CCC(CC1)O[C@@H](C2=CC=C(Cl)C=C2)C3=CC=CC=N3

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

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

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
The effects of olopatadine hydrochloride on the number of scratching induced by repeated application of oxazolone in mice.
2005 Nov 7
Oral administration of bepotastine besilate suppressed scratching behavior of atopic dermatitis model NC/Nga mice.
2008
Brain histamine H1 receptor occupancy of orally administered antihistamines, bepotastine and diphenhydramine, measured by PET with 11C-doxepin.
2008 Jun
Olopatadine in chronic idiopathic urticaria.
2009
Bepotastine besilate OD tablets suppress nasal symptoms caused by Japanese cedar pollen exposure in an artificial exposure chamber (OHIO Chamber).
2009 Mar
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 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
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 17:35:46 GMT 2023
Edited
by admin
on Fri Dec 15 17:35:46 GMT 2023
Record UNII
HYD2U48IAS
Record Status Validated (UNII)
Record Version
  • Download
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
4-((S)-(4-CHLOROPHENYL)-2-PYRIDINYLMETHOXY)-1-PIPERIDINEBUTANOIC ACID
Systematic Name English
BETOTASTINE
Common Name English
BEPOTASTINE [VANDF]
Common Name English
Bepotastine [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175587
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID90904947
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
WIKIPEDIA
BEPOTASTINE
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
LACTMED
Bepotastine
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
SMS_ID
100000086290
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
DRUG BANK
DB04890
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
DRUG CENTRAL
341
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
CAS
190786-43-7
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
SUPERSEDED
MERCK INDEX
m2421
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY Merck Index
RXCUI
863035
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY RxNorm
IUPHAR
7466
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
MESH
C108476
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
NCI_THESAURUS
C77431
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
USAN
WW-120
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
INN
7648
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
CAS
125602-71-3
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
DAILYMED
HYD2U48IAS
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201758
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
FDA UNII
HYD2U48IAS
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
EVMPD
SUB05778MIG
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
PUBCHEM
164522
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
CHEBI
71204
Created by admin on Fri Dec 15 17:35:46 GMT 2023 , Edited by admin on Fri Dec 15 17:35:46 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC