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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H25ClN2O3.C7H6O3
Molecular Weight 527.0095
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEPOTASTINE SALICYLATE

SMILES

c1ccnc(c1)[C@]([H])(c2ccc(cc2)Cl)OC3CCN(CCCC(=O)O)CC3.c1ccc(c(c1)C(=O)O)O

InChI

InChIKey=YUVMVRKHFRSJKQ-BOXHHOBZSA-N
InChI=1S/C21H25ClN2O3.C7H6O3/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;8-6-4-2-1-3-5(6)7(9)10/h1-2,4,6-9,12,18,21H,3,5,10-11,13-15H2,(H,25,26);1-4,8H,(H,9,10)/t21-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C21H25ClN2O3
Molecular Weight 388.8885
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C7H6O3
Molecular Weight 138.121
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

9.6240959E11
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

1.25236806E12
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
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

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 Jun 25 23:11:26 UTC 2021
Edited
by admin
on Fri Jun 25 23:11:26 UTC 2021
Record UNII
MQA2OA5SYH
Record Status Validated (UNII)
Record Version
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Name Type Language
BEPOTASTINE SALICYLATE
Common Name English
BERION
Brand Name English
BEPOTASTINE SALICYLATE [WHO-DD]
Common Name English
BENZOIC ACID, 2-HYDROXY-, COMPD. WITH 4-((S)-(4-CHLOROPHENYL)-2-PYRIDINYLMETHOXY)-1-PIPERIDINEBUTANOATE (1:1)
Common Name English
Code System Code Type Description
FDA UNII
MQA2OA5SYH
Created by admin on Fri Jun 25 23:11:26 UTC 2021 , Edited by admin on Fri Jun 25 23:11:26 UTC 2021
PRIMARY
CAS
1206695-40-0
Created by admin on Fri Jun 25 23:11:26 UTC 2021 , Edited by admin on Fri Jun 25 23:11:26 UTC 2021
PRIMARY
PUBCHEM
46831287
Created by admin on Fri Jun 25 23:11:26 UTC 2021 , Edited by admin on Fri Jun 25 23:11:26 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE