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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C21H24ClN2O3.Ca
Molecular Weight 815.838
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEPOTASTINE CALCIUM

SMILES

[Ca++].[O-]C(=O)CCCN1CCC(CC1)O[C@@H](C2=CC=C(Cl)C=C2)C3=CC=CC=N3.[O-]C(=O)CCCN4CCC(CC4)O[C@@H](C5=CC=C(Cl)C=C5)C6=CC=CC=N6

InChI

InChIKey=MPLSUWHSFVECNH-HRQBZJEISA-L
InChI=1S/2C21H25ClN2O3.Ca/c2*22-17-8-6-16(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;/h2*1-2,4,6-9,12,18,21H,3,5,10-11,13-15H2,(H,25,26);/q;;+2/p-2/t2*21-;/m00./s1

HIDE SMILES / InChI
Molecular Formula C21H24ClN2O3
Molecular Weight 387.88
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula Ca
Molecular Weight 40.078
Charge 2
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
1014
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
359
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 5.7 null [pIC50]
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
TALION

Approved Use

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

Launch Date

2000
Primary
Approved
8429
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
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
1587
inhibitor
1767

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
1478
CYP450
65

P-gp
1537
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C19
1553
 no
CYP2C9
1819
 no
CYP3A4
1925
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP450
65
 minimal
P-gp
1537
 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
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
Oral administration of bepotastine besilate suppressed scratching behavior of atopic dermatitis model NC/Nga mice.
2008
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
Brain histamine H1 receptor occupancy of orally administered antihistamines, bepotastine and diphenhydramine, measured by PET with 11C-doxepin.
2008 Jun
Intact cell binding for in vitro prediction of sedative and non-sedative histamine H1-receptor antagonists based on receptor internalization.
2008 May
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
Downmodulatory effects of the antihistaminic drug bepotastine on cytokine/chemokine production and CD54 expression in human keratinocytes.
2009
Multiple H1-antihistamine-induced urticaria.
2009 Apr
Bepotastine besilate OD tablets suppress nasal symptoms caused by Japanese cedar pollen exposure in an artificial exposure chamber (OHIO Chamber).
2009 Mar
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

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 Sat Dec 16 19:00:20 GMT 2023
Edited
by admin
on Sat Dec 16 19:00:20 GMT 2023
Record UNII
NTA656KRK2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BEPOTASTINE CALCIUM
Common Name English
BEPOTASTINE CALCIUM SALT
Common Name English
1-PIPERIDINEBUTANOIC ACID, 4-((S)-(4-CHLOROPHENYL)-2-PYRIDINYLMETHOXY)-, CALCIUM SALT (2:1)
Systematic Name English
Code System Code Type Description
FDA UNII
NTA656KRK2
Created by admin on Sat Dec 16 19:00:20 GMT 2023 , Edited by admin on Sat Dec 16 19:00:20 GMT 2023
PRIMARY
CAS
1092936-91-8
Created by admin on Sat Dec 16 19:00:20 GMT 2023 , Edited by admin on Sat Dec 16 19:00:20 GMT 2023
PRIMARY
SMS_ID
100000180059
Created by admin on Sat Dec 16 19:00:20 GMT 2023 , Edited by admin on Sat Dec 16 19:00:20 GMT 2023
PRIMARY
PUBCHEM
162623673
Created by admin on Sat Dec 16 19:00:20 GMT 2023 , Edited by admin on Sat Dec 16 19:00:20 GMT 2023
PRIMARY
Related Record Type Details
Structure of BEPOTASTINE CALCIUM DIHYDRATE
SOLVATE->ANHYDROUS
Structure of BEPOTASTINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of BEPOTASTINE
ACTIVE MOIETY
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