Accession NumberDB04890
TypeSmall Molecule

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.

External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Bepotastine Besilate6W18MO1QR3 190786-44-8UDGHXQPQKQPSBB-BOXHHOBZSA-NDetails
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BepreveSolution / drops15 mg/mLOphthalmicPhysicians Total Care, Inc.2011-09-26Not applicableUs
BepreveSolution / drops15 mg/mLOphthalmicBauch & Lomb Incorporated2009-09-08Not applicableUs
BepreveSolution1.5 %OphthalmicBausch & Lomb Inc2017-03-23Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
TalionNot Available
Brand mixturesNot Available
CAS number125602-71-3
WeightAverage: 388.888
Monoisotopic: 388.155370383
Chemical FormulaC21H25ClN2O3
4-{4-[(4-chlorophenyl)(pyridin-2-yl)methoxy]piperidin-1-yl}butanoic acid

For the symptomatic treatment of itchy eyes (caused by IgE-induced mast cell degranulation) due to allergic conjunctivitis.

Structured Indications

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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Histamine H1 receptorProteinyes
HumanP35367 details
Related Articles

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 distributionNot Available
Protein binding

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.

Half life

Elimination half life = 2.5 hours

ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Drug Interactions No interactions found.
Food InteractionsNot Available
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.

General References
  1. 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. [PubMed:16455807 ]
  2. 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 ]
  3. 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. [PubMed:22035879 ]
  4. 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. [PubMed:21386912 ]
External Links
ATC CodesNot Available
AHFS Codes
  • 52:02
PDB EntriesNot Available
FDA labelDownload (161 KB)
MSDSNot Available
Clinical Trials
Clinical Trials
1CompletedNot AvailableHealthy Volunteers1
1RecruitingTreatmentHealthy Volunteers1
2CompletedTreatmentConjunctivitis, Seasonal Allergic1
2CompletedTreatmentSeasonal Allergic Rhinitis (SAR)1
2, 3CompletedTreatmentConjunctivitis, Seasonal Allergic1
3CompletedTreatmentAtopics / Skin Inflammation1
3CompletedTreatmentConjunctivitis, Seasonal Allergic2
3CompletedTreatmentPerennial Allergic Rhinitis (PAR)3
4CompletedNot AvailableHistamine Responsive Allergy Patients1
4CompletedTreatmentConjunctivitis, Seasonal Allergic1
4Unknown StatusTreatmentConjunctivitis, Seasonal Allergic2
Not AvailableCompletedTreatmentEye Allergies1
ManufacturersNot Available
Dosage forms
SolutionOphthalmic1.5 %
Solution / dropsOphthalmic15 mg/mL
Unit descriptionCostUnit
Bepreve 1.5% eye drops10.8USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6780877 No1999-09-192019-09-19Us
US8784789 No2004-09-052024-09-05Us
US8877168 No2003-07-302023-07-30Us
Experimental PropertiesNot Available
Predicted Properties
Water Solubility0.0503 mg/mLALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area62.66 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity105.1 m3·mol-1ChemAxon
Polarizability42.18 Å3ChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Human Intestinal Absorption+0.9205
Blood Brain Barrier-0.5488
Caco-2 permeable-0.5304
P-glycoprotein substrateSubstrate0.6552
P-glycoprotein inhibitor IInhibitor0.8159
P-glycoprotein inhibitor IIInhibitor0.7308
Renal organic cation transporterInhibitor0.5948
CYP450 2C9 substrateNon-substrate0.7907
CYP450 2D6 substrateNon-substrate0.7496
CYP450 3A4 substrateNon-substrate0.5729
CYP450 1A2 substrateNon-inhibitor0.8235
CYP450 2C9 inhibitorNon-inhibitor0.8817
CYP450 2D6 inhibitorNon-inhibitor0.8289
CYP450 2C19 inhibitorNon-inhibitor0.8369
CYP450 3A4 inhibitorNon-inhibitor0.8711
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6461
Ames testNon AMES toxic0.8246
BiodegradationNot ready biodegradable0.9929
Rat acute toxicity2.7211 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6558
hERG inhibition (predictor II)Inhibitor0.6222
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Mass Spec (NIST)Not Available
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
DescriptionThis 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).
KingdomChemical entities
Super ClassOrganic compounds
Sub ClassBenzene and substituted derivatives
Direct ParentBenzylethers
Alternative ParentsAmino fatty acids / Chlorobenzenes / Pyridines and derivatives / Piperidines / Aryl chlorides / Heteroaromatic compounds / Trialkylamines / Amino acids / Monocarboxylic acids and derivatives / Azacyclic compounds
SubstituentsBenzylether / Amino fatty acid / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Fatty acyl / Pyridine / Piperidine / Heteroaromatic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot 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
  1. 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 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Drug created on October 21, 2007 10:29 / Updated on July 27, 2017 16:03