Identification
- Summary
Bilastine is a peripheral histamine H1-antagonist used to treat seasonal allergic rhinitis and chronic spontaneous urticaria.
- Brand Names
- Blexten
- Generic Name
- Bilastine
- DrugBank Accession Number
- DB11591
- Background
Bilastine is a novel new-generation antihistamine that is highly selective for the H1 histamine receptor, has a rapid onset and prolonged duration of action.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Bilastine (DB11591)
- Weight
- Average: 463.622
Monoisotopic: 463.283492063 - Chemical Formula
- C28H37N3O3
- Synonyms
- Bilastina
- Bilastine
Pharmacology
- Indication
For symptomatic relief of nasal and non-nasal symptoms of seasonal rhinitis in patients 12 years of age and older and for symptomatic relief in chronic spontaneous urticaria in patients 18 years of age and older Label.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Chronic spontaneous urticaria •••••••••••• ••••••••• •••••• Symptomatic treatment of Seasonal allergic rhinitis •••••••••••• ••••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Bilastine is an antiallergenic and acts to reduce allergic symptoms such as nasal congestion and urticaria Label.
- Mechanism of action
Bilastine is a selective histamine H1 receptor antagonist (Ki = 64nM) Label. During allergic response mast cells undergo degranulation which releases histamine and other subastances. By binding to and preventing activation of the H1 receptor, bilastine reduces the development of allergic symptoms due to the release of histamine from mast cells.
Target Actions Organism AHistamine H1 receptor antagonistHumans - Absorption
Bilastine has a Tmax of 1.13 h Label. The absolute bioavailability is 61%. No accumulation observed with daily dosing of 20-100 mg after 14 days. Cmax decreased by 25 % and 33% when taken with a low fat and high fat meal compared to fasted state. Administration with grapefruit juice decreased Cmax by 30%.
- Volume of distribution
Not Available
- Protein binding
Bilastine is 84-90% bound to human plasma proteins Label.
- Metabolism
Bilastine does not interact with the cytochrome P450 system and does not undergo significant metabolism in humans Label.
- Route of elimination
Bilastine is mainly excreted in the feces (66.5%) with some excreted in the urine (28.3%) Label. Nearly all is excreted as the parent compound.
- Half-life
The mean half life of elimination is 14.5h Label.
- Clearance
Bilastine has a total clearance is 9.20 L/h and a renal clearance of 8.7 L/h Label.
- Adverse Effects
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The most common adverse effects experienced during clinical trials were abdominal pain, dizziness, headache, and somnolence Label. Bilastine is associated with Q/T prolongation. The no observed adverse effect level of bilastine is 1200 mg/kg/day in rats and 125 mg/kg/day in dogs 2.
- Pathways
Pathway Category Bilastine 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 softwareAcrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Bilastine. Adenosine The risk or severity of QTc prolongation can be increased when Bilastine is combined with Adenosine. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Bilastine. Albuterol The risk or severity of QTc prolongation can be increased when Salbutamol is combined with Bilastine. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Bilastine. - Food Interactions
- Avoid grapefruit products. Avoid other fruit juice as well for optimal absorption.
- Take on an empty stomach. Take at least two hours before or one hour after eating.
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.- International/Other Brands
- Bilaxten (Faes Farma)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Blexten Solution 2.5 mg / mL Oral Aralez Pharmaceuticals Canada Inc 2022-02-10 Not applicable Canada 
Blexten Tablet 20 mg Oral Aralez Pharmaceuticals Canada Inc 2016-12-02 Not applicable Canada Blexten Tablet, orally disintegrating 10 mg Oral Aralez Pharmaceuticals Canada Inc 2022-02-10 Not applicable Canada
Categories
- ATC Codes
- S01GX13 — Bilastine
- S01GX — Other antiallergics
- S01G — DECONGESTANTS AND ANTIALLERGICS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- Drug Categories
- Antihistamines for Systemic Use
- Decongestants and Antiallergics
- Heterocyclic Compounds, Fused-Ring
- Histamine Antagonists
- Histamine H1 Antagonists
- Histamine H1 Antagonists, Non-Sedating
- Ophthalmologicals
- Organic Anion Transporting Polypeptide 2B1 Inhibitors
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Sensory Organs
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzimidazoles
- Sub Class
- Not Available
- Direct Parent
- Benzimidazoles
- Alternative Parents
- Phenylpropanes / Phenethylamines / Aralkylamines / Piperidines / N-substituted imidazoles / Heteroaromatic compounds / Trialkylamines / Amino acids / Azacyclic compounds / Carboxylic acids show 6 more
- Substituents
- Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzimidazole / Carbonyl group show 21 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- PA1123N395
- CAS number
- 202189-78-4
- InChI Key
- ACCMWZWAEFYUGZ-UHFFFAOYSA-N
- InChI
- InChI=1S/C28H37N3O3/c1-4-34-20-19-31-25-8-6-5-7-24(25)29-26(31)22-14-17-30(18-15-22)16-13-21-9-11-23(12-10-21)28(2,3)27(32)33/h5-12,22H,4,13-20H2,1-3H3,(H,32,33)
- IUPAC Name
- 2-[4-(2-{4-[1-(2-ethoxyethyl)-1H-1,3-benzodiazol-2-yl]piperidin-1-yl}ethyl)phenyl]-2-methylpropanoic acid
- SMILES
- CCOCCN1C(=NC2=CC=CC=C12)C1CCN(CCC2=CC=C(C=C2)C(C)(C)C(O)=O)CC1
References
- General References
- Wang XY, Lim-Jurado M, Prepageran N, Tantilipikorn P, Wang de Y: Treatment of allergic rhinitis and urticaria: a review of the newest antihistamine drug bilastine. Ther Clin Risk Manag. 2016 Apr 13;12:585-97. doi: 10.2147/TCRM.S105189. eCollection 2016. [Article]
- Lucero ML, Arteche JK, Sommer EW, Casadesus A: Preclinical toxicity profile of oral bilastine. Drug Chem Toxicol. 2012 Jun;35 Suppl 1:25-33. doi: 10.3109/01480545.2012.682652. [Article]
- Health Canada Approved Drug Products: Blexten (Bilastine) Tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0240232
- PubChem Compound
- 185460
- PubChem Substance
- 347827998
- ChemSpider
- 161234
- ChEBI
- 135954
- ChEMBL
- CHEMBL1742423
- ZINC
- ZINC000003822702
- Wikipedia
- Bilastine
- FDA label
- Download (550 KB)
- MSDS
- Download (200 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Supportive Care Allergic Rhinitis (AR) / Urticaria 1 4 Completed Treatment Allergic Rhinitis (AR) 1 4 Completed Treatment Asthma / Seasonal Allergic Rhinoconjunctivitis 1 4 Completed Treatment Urticaria 1 4 Unknown Status Treatment Seasonal Allergic Rhinitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 10 mg Solution Oral 2.5 MG/ML Tablet, orally disintegrating Oral 10 MG/TABLET Tablet Oral 20.00 mg Solution Oral 2.5 mg Solution Oral 250.000 mg Tablet Oral 20.000 mg Solution Oral 2.5 mg / mL Tablet, orally disintegrating Oral 10 mg Tablet Oral Tablet Oral 10.000 mg Tablet, orally disintegrating Oral Solution Oral Tablet, orally disintegrating Oral 20 mg Solution / drops Ophthalmic 6 mg/ml Tablet Oral 20 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00203 mg/mL ALOGPS logP 5.02 ALOGPS logP 2.41 Chemaxon logS -5.4 ALOGPS pKa (Strongest Acidic) 4.06 Chemaxon pKa (Strongest Basic) 9.43 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 67.59 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 135.58 m3·mol-1 Chemaxon Polarizability 54.96 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03xr-0002900000-6bc60b661be664624664 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0229-1009700000-034ae486ba02478367af Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0009200000-dff0e4186d010c5d389b Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0009400000-9d318b011b3aee08d52e Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0219200000-47dd43cec02f7178cf47 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0007-0259000000-b7b553021a19a4ec55cd 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]- 230.3646933 predictedDarkChem Lite v0.1.0 [M-H]- 235.5863933 predictedDarkChem Lite v0.1.0 [M-H]- 209.75226 predictedDeepCCS 1.0 (2019) [M+H]+ 230.7126933 predictedDarkChem Lite v0.1.0 [M+H]+ 235.4754933 predictedDarkChem Lite v0.1.0 [M+H]+ 212.14781 predictedDeepCCS 1.0 (2019) [M+Na]+ 230.3453933 predictedDarkChem Lite v0.1.0 [M+Na]+ 235.8458933 predictedDarkChem Lite v0.1.0 [M+Na]+ 218.06035 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
- Wang XY, Lim-Jurado M, Prepageran N, Tantilipikorn P, Wang de Y: Treatment of allergic rhinitis and urticaria: a review of the newest antihistamine drug bilastine. Ther Clin Risk Manag. 2016 Apr 13;12:585-97. doi: 10.2147/TCRM.S105189. eCollection 2016. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Efflux transmembrane transporter activity
- Specific Function
- Drug efflux transporter present in a number of stem cells that acts as a regulator of cellular differentiation. Able to mediate efflux from cells of the rhodamine dye and of the therapeutic drug do...
- Gene Name
- ABCB5
- Uniprot ID
- Q2M3G0
- Uniprot Name
- ATP-binding cassette sub-family B member 5
- Molecular Weight
- 138639.48 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
- Gene Name
- SLCO1A2
- Uniprot ID
- P46721
- Uniprot Name
- Solute carrier organic anion transporter family member 1A2
- Molecular Weight
- 74144.105 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
- Gene Name
- SLCO2B1
- Uniprot ID
- O94956
- Uniprot Name
- Solute carrier organic anion transporter family member 2B1
- Molecular Weight
- 76709.98 Da
Drug created at May 06, 2016 18:33 / Updated at April 19, 2024 20:55