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
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
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL231 |
5.7 null [pIC50] | ||
Target ID: CHEMBL4794 |
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 |
|||
| 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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| 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 |
|
| 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
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KEP4SBX4D8
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1206695-39-7
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46831286
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PARENT (SALT/SOLVATE)
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
