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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H25ClN2O3.C6H5NO2
Molecular Weight 511.997
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Bepotastine nicotinate

SMILES

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

InChI

InChIKey=KMLYDGIAPQGTQZ-BOXHHOBZSA-N
InChI=1S/C21H25ClN2O3.C6H5NO2/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;8-6(9)5-2-1-3-7-4-5/h1-2,4,6-9,12,18,21H,3,5,10-11,13-15H2,(H,25,26);1-4H,(H,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 C6H5NO2
Molecular Weight 123.1094
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
1050
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
334
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2760
 5.7 null [pIC50]
Agonist
2662
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8360
TALION

Approved Use

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

Launch Date

9.6240959E11
Primary
Approved
8360
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
1579
inhibitor
1752

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
1463
CYP450
65

P-gp
1527
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C19
1537
 no
CYP2C9
1803
 no
CYP3A4
1909
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP450
65
 minimal
P-gp
1527
 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
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
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
Olopatadine in chronic idiopathic urticaria.
2009
Oral bepotastine: in allergic disorders.
2010 Aug 20
Bepotastine (bepreve)--an ophthalmic H1-antihistamine.
2010 Feb 8
Non-clinical pharmacology, pharmacokinetics, and safety findings for the antihistamine bepotastine besilate.
2010 Oct
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).
Substance Class Chemical
Created
by admin
on Fri Jul 07 00:27:48 UTC 2023
Edited
by admin
on Fri Jul 07 00:27:48 UTC 2023
Record UNII
KEP4SBX4D8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Bepotastine nicotinate
Common Name English
Bepotastine nicotinate [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
KEP4SBX4D8
Created by admin on Fri Jul 07 00:27:48 UTC 2023 , Edited by admin on Fri Jul 07 00:27:48 UTC 2023
PRIMARY
CAS
1206695-39-7
Created by admin on Fri Jul 07 00:27:48 UTC 2023 , Edited by admin on Fri Jul 07 00:27:48 UTC 2023
PRIMARY
PUBCHEM
46831286
Created by admin on Fri Jul 07 00:27:48 UTC 2023 , Edited by admin on Fri Jul 07 00:27:48 UTC 2023
PRIMARY
Related Record Type Details
Structure of BEPOTASTINE
PARENT -> SALT/SOLVATE
Structure of NIACIN
PARENT -> SALT/SOLVATE
NIH
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