Identification
- Summary
Bepotastine is an ophthalmic H1 antagonist used to treat itchiness associated with allergic conjunctivitis.
- Brand Names
- Bepreve
- Generic Name
- Bepotastine
- DrugBank Accession Number
- DB04890
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Bepotastine (DB04890)
- Weight
- Average: 388.888
Monoisotopic: 388.155370383 - Chemical Formula
- C21H25ClN2O3
- Synonyms
- bepotastina
- Bepotastine
- External IDs
- TAU-284DS
Pharmacology
- Indication
For the symptomatic treatment of itchy eyes (caused by IgE-induced mast cell degranulation) due to allergic conjunctivitis.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Itching •••••••••••• - Contraindications & Blackbox Warnings
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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.
Onset of action = 0.25 hours; Duration of action = 12-24 hours;- 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.
Target Actions Organism AHistamine H1 receptor antagonistHumans - Absorption
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.
- Volume of distribution
Not Available
- Protein binding
55.4% mean plasma protein binding with 10 mg oral dose. Extent of protein binding is independent of plasma drug concentration.
- Metabolism
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.
- Half-life
Elimination half life = 2.5 hours
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
Pathway Category Bepotastine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Bepotastine which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Bepotastine which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Bepotastine which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Bepotastine which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Bepotastine which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- Take with or without food. Orally formulated bepotastine bioavailability is not significantly impacted by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Bepotastine besilate 6W18MO1QR3 190786-44-8 UDGHXQPQKQPSBB-BOXHHOBZSA-N - International/Other Brands
- Talion
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bepreve Solution / drops 15 mg/1mL Ophthalmic Ista Pharmaceuticals, Inc 2009-09-08 2014-09-30 US 
Bepreve Solution 1.5 % w/v Ophthalmic Bausch & Lomb Inc 2017-03-23 Not applicable Canada 
Bepreve Solution / drops 15 mg/1mL Ophthalmic Physicians Total Care, Inc. 2011-09-26 Not applicable US Bepreve Solution / drops 15 mg/1mL Ophthalmic Bausch & Lomb Incorporated 2009-09-08 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bepotastine Besilate Solution / drops 15 mg/1mL Ophthalmic Bausch & Lomb Incorporated 2021-05-28 Not applicable US Bepotastine Besilate Solution / drops 15 mg/1mL Ophthalmic Bausch & Lomb Americas Inc. 2021-05-28 Not applicable US Bepotastine Besilate Solution / drops 15 mg/1mL Ophthalmic Mylan Pharmaceuticals Inc. 2021-05-28 Not applicable US Bepotastine Besilate Solution / drops 15 mg/1mL Ophthalmic Apotex Corp. 2021-11-08 2024-08-25 US Bepotastine Besilate Ophthalmic Solution 1.5% Solution / drops 15 mg/1mL Ophthalmic Alembic Pharmaceuticals Inc. 2023-04-05 Not applicable US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzylethers
- Direct Parent
- Benzylethers
- Alternative Parents
- Amino fatty acids / Chlorobenzenes / Pyridines and derivatives / Piperidines / Aryl chlorides / Heteroaromatic compounds / Trialkylamines / Amino acids / Monocarboxylic acids and derivatives / Azacyclic compounds show 7 more
- Substituents
- Amine / Amino acid / Amino acid or derivatives / Amino fatty acid / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzylether / Carbonyl group show 23 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- HYD2U48IAS
- CAS number
- 125602-71-3
- InChI Key
- YWGDOWXRIALTES-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 4-{4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidin-1-yl}butanoic acid
- SMILES
- OC(=O)CCCN1CCC(CC1)OC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1
References
- Synthesis Reference
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- General References
- Ohashi R, Kamikozawa Y, Sugiura M, Fukuda H, Yabuuchi H, Tamai I: Effect of P-glycoprotein on intestinal absorption and brain penetration of antiallergic agent bepotastine besilate. Drug Metab Dispos. 2006 May;34(5):793-9. Epub 2006 Feb 2. [Article]
- 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. [Article]
- Simons FE, Simons KJ: Histamine and H1-antihistamines: celebrating a century of progress. J Allergy Clin Immunol. 2011 Dec;128(6):1139-1150.e4. doi: 10.1016/j.jaci.2011.09.005. Epub 2011 Oct 27. [Article]
- Wingard JB, Mah FS: Critical appraisal of bepotastine in the treatment of ocular itching associated with allergic conjunctivitis. Clin Ophthalmol. 2011;5:201-7. doi: 10.2147/OPTH.S8665. Epub 2011 Feb 15. [Article]
- FDA Approved Drug Products: Bepreve (bepotastine besilat) ophthalmic solution [Link]
- External Links
- Human Metabolome Database
- HMDB0015600
- KEGG Drug
- D01654
- PubChem Compound
- 2350
- PubChem Substance
- 46504940
- ChemSpider
- 2260
- 863035
- ChEBI
- 71204
- ChEMBL
- CHEMBL1201758
- Therapeutic Targets Database
- DCL000719
- PharmGKB
- PA164781356
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Bepotastine
- FDA label
- Download (161 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Not Available Histamine Responsive Allergy Patients 1 4 Completed Treatment Allergic Conjunctivitis (AC) 3 4 Completed Treatment Allergic Rhinitis (AR) / Cough 1 4 Unknown Status Treatment Allergic Conjunctivitis (AC) 1 3 Completed Treatment Allergic Conjunctivitis (AC) 2
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- ISTA Pharmaceuticals
- Dosage Forms
Form Route Strength Solution Ophthalmic 1.5 % w/v Solution / drops Ophthalmic 15 mg/1mL Solution Ophthalmic 15.000 mg Solution Conjunctival; Ophthalmic 15 mg Tablet, film coated Oral Tablet, film coated Oral 10 MG Solution Ophthalmic 15 mg Tablet, coated Oral 10 mg - Prices
Unit description Cost Unit Bepreve 1.5% eye drops 10.8USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8784789 No 2014-07-22 2024-09-05 US US6780877 No 2004-08-24 2019-09-19 US US8877168 No 2014-11-04 2023-07-30 US
Properties
- State
- Liquid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0503 mg/mL ALOGPS logP 3.64 ALOGPS logP 0.55 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 4.1 Chemaxon pKa (Strongest Basic) 9.39 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 62.66 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 105.1 m3·mol-1 Chemaxon Polarizability 42.18 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9205 Blood Brain Barrier - 0.5488 Caco-2 permeable - 0.5304 P-glycoprotein substrate Substrate 0.6552 P-glycoprotein inhibitor I Inhibitor 0.8159 P-glycoprotein inhibitor II Inhibitor 0.7308 Renal organic cation transporter Inhibitor 0.5948 CYP450 2C9 substrate Non-substrate 0.7907 CYP450 2D6 substrate Non-substrate 0.7496 CYP450 3A4 substrate Non-substrate 0.5729 CYP450 1A2 substrate Non-inhibitor 0.8235 CYP450 2C9 inhibitor Non-inhibitor 0.8817 CYP450 2D6 inhibitor Non-inhibitor 0.8289 CYP450 2C19 inhibitor Non-inhibitor 0.8369 CYP450 3A4 inhibitor Non-inhibitor 0.8711 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6461 Ames test Non AMES toxic 0.8246 Carcinogenicity Non-carcinogens 0.9647 Biodegradation Not ready biodegradable 0.9929 Rat acute toxicity 2.7211 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6558 hERG inhibition (predictor II) Inhibitor 0.6222
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0udi-2292000000-5b45fd7805bbbd416e7f Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00dr-0009000000-7781850f7e715ddd0036 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-2009000000-f6982a1671a660277fed Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0uk9-0109000000-c6765dc6b3f3f6b46a6f Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0f7o-7789000000-5d8ebf9e4350cd2121db Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00dr-2914000000-e048374ffe97b74f7714 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9521000000-bc27b9cd4a62e929b839 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 199.2633895 predictedDarkChem Lite v0.1.0 [M-H]- 183.59439 predictedDeepCCS 1.0 (2019) [M+H]+ 199.3239895 predictedDarkChem Lite v0.1.0 [M+H]+ 186.01315 predictedDeepCCS 1.0 (2019) [M+Na]+ 200.1332895 predictedDarkChem Lite v0.1.0 [M+Na]+ 192.97462 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- 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 catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created at October 21, 2007 16:29 / Updated at April 18, 2024 09:15