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
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
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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24191914 | https://www.ncbi.nlm.nih.gov/pubmed/9368705
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20735291 |
5.7 null [pIC50] | ||
Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24980233 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | TALION Approved UseTALION is usually used to treat allergic rhinitis, hives and itch resulting from skin diseases. Launch Date2000 |
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Primary | BEPREVE Approved UseBEPREVE® (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 Date2009 |
Cmax
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 |
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 |
T1/2
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 |
Funbound
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% |
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 |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022288s000_ClinPharm.pdf#page=15 Page: 15.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022288s000_ClinPharm.pdf#page=15 Page: 15.0 |
no | |||
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 |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022288s000_ClinPharm.pdf#page=4 Page: 4.0 |
minimal | |||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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
Substance Class |
Chemical
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Record UNII |
HYD2U48IAS
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Validated (UNII)
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NDF-RT |
N0000175587
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NCI_THESAURUS |
C29578
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DTXSID90904947
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BEPOTASTINE
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Bepotastine
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100000086290
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190786-43-7
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m2421
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863035
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7466
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C108476
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CHEMBL1201758
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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