BEPOTASTINE

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 Search

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

Description
Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=35400 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022288lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/24191914

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20735291	Antagonist 2849		5.7 null [pIC50]
Vanilloid receptor 53 Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24980233	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 104 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=35400	Primary		Approved 8583	TALION Approved Use TALION is usually used to treat allergic rhinitis, hives and itch resulting from skin diseases. Launch Date 2000
Allergic conjunctivitis 101 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022288lbl.pdf	Primary		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057	CYP450 59 P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022288s000_ClinPharm.pdf#page=15 Page: 15.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022288s000_ClinPharm.pdf#page=15 Page: 15.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022288s000_ClinPharm.pdf#page=15 Page: 15.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP450 59	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022288s000_ClinPharm.pdf#page=4 Page: 4.0	minimal
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16455807/	yes

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Next-day residual sedative effect after nighttime administration of an over-the-counter antihistamine sleep aid, diphenhydramine, measured by positron emission tomography.	2010-12	21105284
Non-clinical pharmacology, pharmacokinetics, and safety findings for the antihistamine bepotastine besilate.	2010-10	20735291
Azelastine hydrochloride, a dual-acting anti-inflammatory ophthalmic solution, for treatment of allergic conjunctivitis.	2010-09-07	20856595
Oral bepotastine: in allergic disorders.	2010-08-20	20687621
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.	2010-07	20412793
Bepotastine (bepreve)--an ophthalmic H1-antihistamine.	2010-02-08	20216525
Effects of olopatadine hydrochloride, a histamine h(1) receptor antagonist, on histamine-induced skin responses.	2010	20886023
Multiple H1-antihistamine-induced urticaria.	2009-04	19348661
Bepotastine besilate OD tablets suppress nasal symptoms caused by Japanese cedar pollen exposure in an artificial exposure chamber (OHIO Chamber).	2009-03	19216705
Novel functional aspect of antihistamines: the impact of bepotastine besilate on substance p-induced events.	2009	20975801
Olopatadine in chronic idiopathic urticaria.	2009	20101322
Downmodulatory effects of the antihistaminic drug bepotastine on cytokine/chemokine production and CD54 expression in human keratinocytes.	2009	19088500
Evaluation of efficacy and sedative profiles of H(1) antihistamines by large-scale surveillance using the visual analogue scale (VAS).	2008-09	18566547
Mast cells play a critical role in the pathogenesis of viral myocarditis.	2008-07-22	18606918
Brain histamine H1 receptor occupancy of orally administered antihistamines, bepotastine and diphenhydramine, measured by PET with 11C-doxepin.	2008-06	18410464
Intact cell binding for in vitro prediction of sedative and non-sedative histamine H1-receptor antagonists based on receptor internalization.	2008-05	18446005
Analysis of disease-dependent sedative profiles of H(1)-antihistamines by large-scale surveillance using the visual analog scale.	2008-04	18597008
Oral administration of bepotastine besilate suppressed scratching behavior of atopic dermatitis model NC/Nga mice.	2008	18004068
Involvement of histamine released from mast cells in acute radiation dermatitis in mice.	2007-06	17558180
Suppression by bepotastine besilate of substance P-induced itch-associated responses through the inhibition of the leukotriene B4 action in mice.	2006-10-10	16914135
Effect of P-glycoprotein on intestinal absorption and brain penetration of antiallergic agent bepotastine besilate.	2006-05	16455807
The effects of olopatadine hydrochloride on the number of scratching induced by repeated application of oxazolone in mice.	2005-11-07	16259975
Effects of bepotastine, cetirizine, fexofenadine, and olopatadine on histamine-induced wheal-and flare-response, sedation, and psychomotor performance.	2004-09	15347340
Effect of histamine on the permeability of the nasal mucosa in vivo.	2003-04	12737298

Patents

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 `Mon Mar 31 18:49:04 GMT 2025` Edited by `admin` on `Mon Mar 31 18:49:04 GMT 2025`
Record UNII	HYD2U48IAS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BEPOTASTINE [MI]

Preferred Name

English

BEPOTASTINE

Official 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