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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

Description

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

CNS Non-penetrant
1018
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.

Originator

Approval Year

2009
330
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2737
 5.7 null [pIC50]
Agonist
2637
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8307
TALION

Approved Use

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

Launch Date

9.6240959E11
Primary
Approved
8307
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24105252/
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022288s008lbl.pdf
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24105252/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24105252/
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%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24105252/
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%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022288s008lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022288lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Allergic conjunctivitis
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022288lbl.pdf
Page: p.1
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022288lbl.pdf
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1532
inhibitor
1695

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
1410
CYP450
65

P-gp
1491
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C19
1484
 no
CYP2C9
1747
 no
CYP3A4
1857
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP450
65
 minimal
P-gp
1491
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:71204
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:71204
ChemicalBook
CB3102554
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3102554
MolPort
MolPort-020-006-033
https://www.molport.com/shop/molecule-link/MolPort-020-006-033
ZINC
ZINC000000602128
http://zinc15.docking.org/substances/ZINC000000602128
PubMed

PubMed

TitleDatePubMed
Effects of bepotastine, cetirizine, fexofenadine, and olopatadine on histamine-induced wheal-and flare-response, sedation, and psychomotor performance.
2004 Sep
The effects of olopatadine hydrochloride on the number of scratching induced by repeated application of oxazolone in mice.
2005 Nov 7
Effect of P-glycoprotein on intestinal absorption and brain penetration of antiallergic agent bepotastine besilate.
2006 May
Suppression by bepotastine besilate of substance P-induced itch-associated responses through the inhibition of the leukotriene B4 action in mice.
2006 Oct 10
Involvement of histamine released from mast cells in acute radiation dermatitis in mice.
2007 Jun
Analysis of disease-dependent sedative profiles of H(1)-antihistamines by large-scale surveillance using the visual analog scale.
2008 Apr
Brain histamine H1 receptor occupancy of orally administered antihistamines, bepotastine and diphenhydramine, measured by PET with 11C-doxepin.
2008 Jun
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
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 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

Patents

06307052
6
JP2011063619A
6
JP4746318B2
18

Sample Use Guides

In Vivo Use Guide
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 Use Guide
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
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 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
NCI_THESAURUS C29578
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
Code System Code Type Description
EPA CompTox
DTXSID90904947
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY
WIKIPEDIA
BEPOTASTINE
Created by admin on Fri Dec 16 22:34:29 UTC 2022 , Edited by admin on Fri Dec 16 22:34:29 UTC 2022
PRIMARY
LACTMED
Bepotastine
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY
DRUG BANK
DB04890
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY
DRUG CENTRAL
341
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY
CAS
190786-43-7
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
SUPERSEDED
MERCK INDEX
M2421
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY Merck Index
RXCUI
863035
Created by admin on Fri Dec 16 22:34:29 UTC 2022 , Edited by admin on Fri Dec 16 22:34:29 UTC 2022
PRIMARY RxNorm
IUPHAR
7466
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY
MESH
C108476
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY
NCI_THESAURUS
C77431
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY
USAN
WW-120
Created by admin on Fri Dec 16 22:34:29 UTC 2022 , Edited by admin on Fri Dec 16 22:34:29 UTC 2022
PRIMARY
INN
7648
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY
CAS
125602-71-3
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY
DAILYMED
HYD2U48IAS
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY
ChEMBL
CHEMBL1201758
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY
FDA UNII
HYD2U48IAS
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY
EVMPD
SUB05778MIG
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY
PUBCHEM
164522
Created by admin on Fri Dec 16 22:34:29 UTC 2022 , Edited by admin on Fri Dec 16 22:34:29 UTC 2022
PRIMARY
CHEBI
71204
Created by admin on Fri Dec 16 22:34:28 UTC 2022 , Edited by admin on Fri Dec 16 22:34:28 UTC 2022
PRIMARY
ACTIVE MOIETY
Structure of BEPOTASTINE
SALT/SOLVATE (PARENT)
Structure of BEPOTASTINE BESYLATE
SALT/SOLVATE (PARENT)
Structure of BEPOTASTINE CALCIUM
SALT/SOLVATE (PARENT)
Structure of Bepotastine nicotinate
SALT/SOLVATE (PARENT)
Structure of BEPOTASTINE SALICYLATE
NIH
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