Bilastine

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
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofChronic spontaneous urticaria••••••••••••••••••••• ••••••
Symptomatic treatment ofSeasonal allergic rhinitis••••••••••••••••••••• ••••••
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
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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Toxicity

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
PathwayCategory
Bilastine H1-Antihistamine ActionDrug 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.
DrugInteraction
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Bilastine.
AdenosineThe risk or severity of QTc prolongation can be increased when Bilastine is combined with Adenosine.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Bilastine.
AlbuterolThe risk or severity of QTc prolongation can be increased when Salbutamol is combined with Bilastine.
AlfuzosinThe 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

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International/Other Brands
Bilaxten (Faes Farma)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BlextenTablet20 mgOralAralez Pharmaceuticals Canada Inc2016-12-02Not applicableCanada flag
BlextenTablet, orally disintegrating10 mgOralAralez Pharmaceuticals Canada Inc2022-02-10Not applicableCanada flag
BlextenSolution2.5 mg / mLOralAralez Pharmaceuticals Canada Inc2022-02-10Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-bilastine Oral SolutionSolution2.5 mg / mLOralApotex CorporationNot applicableNot applicableCanada flag
Apo-bilastine Orodispersible TabletsTablet, orally disintegrating10 mgOralApotex CorporationNot applicableNot applicableCanada flag
Apo-bilastine TabletsTablet20 mgOralApotex CorporationNot applicableNot applicableCanada flag

Categories

ATC Codes
S01GX13 — BilastineR06AX29 — Bilastine
Drug Categories
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
  1. 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]
  2. 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]
  3. Health Canada Approved Drug Products: Blexten (Bilastine) Tablets [Link]
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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
4CompletedSupportive CareAllergic Rhinitis (AR) / Urticaria1somestatusstop reasonjust information to hide
4CompletedTreatmentAllergic Rhinitis (AR)1somestatusstop reasonjust information to hide
4CompletedTreatmentAsthma / Seasonal Allergic Rhinoconjunctivitis1somestatusstop reasonjust information to hide
4CompletedTreatmentUrticaria1somestatusstop reasonjust information to hide
4Unknown StatusTreatmentSeasonal Allergic Rhinitis1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral10 mg
SolutionOral2.5 MG/ML
Tablet, orally disintegratingOral10 MG/TABLET
TabletOral20.00 mg
SolutionOral2.5 mg
SolutionOral250.000 mg
SolutionOral2.5 mg / mL
Tablet, orally disintegratingOral10 mg
TabletOral
TabletOral20.000 mg
TabletOral10.000 mg
Tablet, orally disintegratingOral
SolutionOral
Tablet, orally disintegratingOral20 mg
Solution / dropsOphthalmic6 mg/ml
TabletOral20 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00203 mg/mLALOGPS
logP5.02ALOGPS
logP2.41Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.06Chemaxon
pKa (Strongest Basic)9.43Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area67.59 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity135.58 m3·mol-1Chemaxon
Polarizability54.96 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03xr-0002900000-6bc60b661be664624664
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0229-1009700000-034ae486ba02478367af
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0009200000-dff0e4186d010c5d389b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0009400000-9d318b011b3aee08d52e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0219200000-47dd43cec02f7178cf47
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0007-0259000000-b7b553021a19a4ec55cd
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-230.3646933
predicted
DarkChem Lite v0.1.0
[M-H]-235.5863933
predicted
DarkChem Lite v0.1.0
[M-H]-209.75226
predicted
DeepCCS 1.0 (2019)
[M+H]+230.7126933
predicted
DarkChem Lite v0.1.0
[M+H]+235.4754933
predicted
DarkChem Lite v0.1.0
[M+H]+212.14781
predicted
DeepCCS 1.0 (2019)
[M+Na]+230.3453933
predicted
DarkChem Lite v0.1.0
[M+Na]+235.8458933
predicted
DarkChem Lite v0.1.0
[M+Na]+218.06035
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein-coupled receptor for histamine, a biogenic amine that functions as an immune modulator and a neurotransmitter (PubMed:33828102, PubMed:8280179). Through the H1 receptor, histamine mediates the contraction of smooth muscles and increases capillary permeability due to contraction of terminal venules. Also mediates neurotransmission in the central nervous system and thereby regulates circadian rhythms, emotional and locomotor activities as well as cognitive functions (By similarity)
Specific Function
G protein-coupled serotonin receptor activity
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. 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
Substrate
Inhibitor
General Function
Energy-dependent efflux transporter responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:12960149, PubMed:15205344, PubMed:15899824, PubMed:22306008). Specifically present in limbal stem cells, where it plays a key role in corneal development and repair (By similarity)
Specific Function
ABC-type xenobiotic transporter activity
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
Na(+)-independent transporter that mediates the cellular uptake of a broad range of organic anions such as the endogenous bile salts cholate and deoxycholate, either in their unconjugated or conjugated forms (taurocholate and glycocholate), at the plasmam membrane (PubMed:19129463, PubMed:7557095). Responsible for intestinal absorption of bile acids (By similarity). Transports dehydroepiandrosterone 3-sulfate (DHEAS), a major circulating steroid secreted by the adrenal cortex, as well as estrone 3-sulfate and 17beta-estradiol 17-O-(beta-D-glucuronate) (PubMed:11159893, PubMed:12568656, PubMed:19129463, PubMed:23918469, PubMed:25560245, PubMed:9539145). Mediates apical uptake of all-trans-retinol (atROL) across human retinal pigment epithelium, which is essential to maintaining the integrity of the visual cycle and thus vision (PubMed:25560245). Involved in the uptake of clinically used drugs (PubMed:17301733, PubMed:20686826, PubMed:27777271). Capable of thyroid hormone transport (both T3 or 3,3',5'-triiodo-L-thyronine, and T4 or L-tyroxine) (PubMed:19129463, PubMed:20358049). Also transports prostaglandin E2 (PubMed:19129463). Plays roles in blood-brain and -cerebrospinal fluid barrier transport of organic anions and signal mediators, and in hormone uptake by neural cells (By similarity). May also play a role in the reuptake of neuropeptides such as substance P/TAC1 and vasoactive intestinal peptide/VIP released from retinal neurons (PubMed:25132355). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drugs methotrexate and paclitaxel (PubMed:23243220). Shows a pH-sensitive substrate specificity which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
Specific Function
bile acid transmembrane transporter activity
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
Mediates the Na(+)-independent transport of steroid sulfate conjugates and other specific organic anions (PubMed:10873595, PubMed:11159893, PubMed:11932330, PubMed:12724351, PubMed:14610227, PubMed:16908597, PubMed:18501590, PubMed:20507927, PubMed:22201122, PubMed:23531488, PubMed:25132355, PubMed:26383540, PubMed:27576593, PubMed:28408210, PubMed:29871943, PubMed:34628357). Responsible for the transport of estrone 3-sulfate (E1S) through the basal membrane of syncytiotrophoblast, highlighting a potential role in the placental absorption of fetal-derived sulfated steroids including the steroid hormone precursor dehydroepiandrosterone sulfate (DHEA-S) (PubMed:11932330, PubMed:12409283). Also facilitates the uptake of sulfated steroids at the basal/sinusoidal membrane of hepatocytes, therefore accounting for the major part of organic anions clearance of liver (PubMed:11159893). Mediates the intestinal uptake of sulfated steroids (PubMed:12724351, PubMed:28408210). Mediates the uptake of the neurosteroids DHEA-S and pregnenolone sulfate (PregS) into the endothelial cells of the blood-brain barrier as the first step to enter the brain (PubMed:16908597, PubMed:25132355). Also plays a role in the reuptake of neuropeptides such as substance P/TAC1 and vasoactive intestinal peptide/VIP released from retinal neurons (PubMed:25132355). May act as a heme transporter that promotes cellular iron availability via heme oxygenase/HMOX2 and independently of TFRC (PubMed:35714613). Also transports heme by-product coproporphyrin III (CPIII), and may be involved in their hepatic disposition (PubMed:26383540). Mediates the uptake of other substrates such as prostaglandins D2 (PGD2), E1 (PGE1) and E2 (PGE2), taurocholate, L-thyroxine, leukotriene C4 and thromboxane B2 (PubMed:10873595, PubMed:14610227, PubMed:19129463, PubMed:29871943, Ref.25). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable). Shows a pH-sensitive substrate specificity which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:14610227, PubMed:19129463, PubMed:22201122). The exact transport mechanism has not been yet deciphered but most likely involves an anion exchange, coupling the cellular uptake of organic substrate with the efflux of an anionic compound (PubMed:19129463, PubMed:20507927, PubMed:26277985). Hydrogencarbonate/HCO3(-) acts as a probable counteranion that exchanges for organic anions (PubMed:19129463). Cytoplasmic glutamate may also act as counteranion in the placenta (PubMed:26277985). An inwardly directed proton gradient has also been proposed as the driving force of E1S uptake with a (H(+):E1S) stoichiometry of (1:1) (PubMed:20507927)
Specific Function
bile acid transmembrane transporter activity
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76697.93 Da

Drug created at May 06, 2016 18:33 / Updated at April 23, 2024 11:38