Bepotastine is a non-sedating, selective antagonist of the histamine 1 (H1) receptor. 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.
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|Weight||Average: 388.888 |
For the symptomatic treatment of itchy eyes (caused by IgE-induced mast cell degranulation) due to allergic conjunctivitis.
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. Furthermore, bepotastine does not interact with serotonin, muscarinic, benzodiazepine, and beta-adrenergic receptor that would otherwise result in adverse reactions such as dry mouth or sonmolence.
|Mechanism of action|
Because of a type 1 hypersensitivity reaction cascade that is triggered by antigen exposure, allergic conjunctivitis occurs. Allergen exposure is followed by conjunctival mast cell degranulation and histamine released as a result of the formation of complementary IgE cross-links on the conjunctiva. Due to the release of histamine, symptoms such as itching can be observed. Bepotastine works to relieve itchy eyes by three primary mechanisms of action. It is a non-sedating, selective antagonist of the histamine 1 (H1) receptor, a mast cell stabilizer, and it suppresses the migration of eosinophils into inflamed tissues to prevent tissue damage and worsening of allergic inflammation of the conjunctiva.
Tmax, after single dose, opthalmic = 1.2 hours; Cmax, 1.5%, opthalmic dose = 7.3 ±1.9 ng/mL; After 24 hours post-installation, levels of bepotastine are below quantifiable limit of 2 ng/mL. Minimal systemic absorption with opthalmic dosage form.
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55.4% mean plasma protein binding with 10 mg oral dose. Extent of protein binding is independent of plasma drug concentration.
Minimal metabolism via CYP enzymes
|Route of elimination|
When a oral dose of 2.5 - 40 mg bepotastine is given, 75%-90% of the dose was excreted unchanged in the urine by 24 hours.
Elimination half life = 2.5 hours
|Pharmacogenomic Effects/ADRs||Not Available|
|Drug Interactions||No interactions found.|
|Food Interactions||Not Available|
Tae Hee Ha, Chang Hee Park, Won Jeoung Kim, Soohwa Cho, Han Kyong Kim, Kwee Hyun Suh, "PROCESS FOR PREPARING BEPOTASTINE AND INTERMEDIATES USED THEREIN." U.S. Patent US20100168433, issued July 01, 2010.US20100168433
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|FDA label||Download (161 KB)|
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|Experimental Properties||Not Available|
|Predicted ADMET features|
|Mass Spec (NIST)||Not Available|
|Description||This compound belongs to the class of chemical entities known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).|
|Super Class||Organic compounds|
|Sub Class||Benzene and substituted derivatives|
|Alternative Parents||Amino fatty acids / Chlorobenzenes / Pyridines and derivatives / Piperidines / Aryl chlorides / Heteroaromatic compounds / Trialkylamines / Amino acids / Monocarboxylic acids and derivatives / Azacyclic compounds / Dialkyl ethers / Carboxylic acids / Carbonyl compounds / Hydrocarbon derivatives / Organic oxides / Organochlorides / Organopnictogen compounds|
|Substituents||Benzylether / Amino fatty acid / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Fatty acyl / Pyridine / Piperidine / Heteroaromatic compound/ Amino acid or derivatives / Amino acid / Tertiary aliphatic amine / Tertiary amine / Carboxylic acid derivative / Carboxylic acid / Azacycle / Dialkyl ether / Ether / Organoheterocyclic compound / Monocarboxylic acid or derivatives / Organic oxygen compound / Organic nitrogen compound / Amine / Carbonyl group / Organopnictogen compound / Organic oxide / Hydrocarbon derivative / Organohalogen compound / Organochloride / Organonitrogen compound / Organooxygen compound / Aromatic heteromonocyclic compound|
|Molecular Framework||Aromatic heteromonocyclic compounds|
|External Descriptors||Not Available|
- Pharmacological action
- General Function:
- Histamine receptor activity
- Specific Function:
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
- Gene Name:
- Uniprot ID:
- Uniprot Name:
- Histamine H1 receptor
- Molecular Weight:
- 55783.61 Da
- Andoh T, Kuraishi Y: Suppression by bepotastine besilate of substance P-induced itch-associated responses through the inhibition of the leukotriene B4 action in mice. Eur J Pharmacol. 2006 Oct 10;547(1-3):59-64. Epub 2006 Jul 25. [PubMed:16914135 ]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]