Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:39:12 UTC
Update Date2022-03-07 03:18:14 UTC
HMDB IDHMDB0240232
Secondary Accession NumbersNone
Metabolite Identification
Common NameBilastine
DescriptionBilastine, also known as bilanoa, 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). Bilastine is a drug which is used 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 [fda label]. In humans, bilastine is involved in the bilastine h1-antihistamine action pathway. Bilastine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Bilastine.
Structure
Data?1563892733
Synonyms
ValueSource
BilanoaKegg
BilaxtenHMDB
BilastineHMDB, MeSH
Chemical FormulaC28H37N3O3
Average Molecular Weight463.622
Monoisotopic Molecular Weight463.283492063
IUPAC Name2-[4-(2-{4-[1-(2-ethoxyethyl)-1H-1,3-benzodiazol-2-yl]piperidin-1-yl}ethyl)phenyl]-2-methylpropanoic acid
Traditional Namebilastine
CAS Registry Number202189-78-4
SMILES
CCOCCN1C(=NC2=CC=CC=C12)C1CCN(CCC2=CC=C(C=C2)C(C)(C)C(O)=O)CC1
InChI Identifier
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)
InChI KeyACCMWZWAEFYUGZ-UHFFFAOYSA-N
Chemical Taxonomy
Description 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).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassNot Available
Direct ParentBenzimidazoles
Alternative Parents
Substituents
  • Benzimidazole
  • Phenylpropane
  • Phenethylamine
  • Aralkylamine
  • Monocyclic benzene moiety
  • N-substituted imidazole
  • Benzenoid
  • Piperidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity135.58 m³·mol⁻¹ChemAxon
Polarizability54.96 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M-H]-210.14731661259
AllCCS[M+H]+214.78131661259
DeepCCS[M-2H]-242.63630932474
DeepCCS[M+Na]+218.0630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BilastineCCOCCN1C(=NC2=CC=CC=C12)C1CCN(CCC2=CC=C(C=C2)C(C)(C)C(O)=O)CC14416.7Standard polar33892256
BilastineCCOCCN1C(=NC2=CC=CC=C12)C1CCN(CCC2=CC=C(C=C2)C(C)(C)C(O)=O)CC13262.9Standard non polar33892256
BilastineCCOCCN1C(=NC2=CC=CC=C12)C1CCN(CCC2=CC=C(C=C2)C(C)(C)C(O)=O)CC13710.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bilastine,1TMS,isomer #1CCOCCN1C(C2CCN(CCC3=CC=C(C(C)(C)C(=O)O[Si](C)(C)C)C=C3)CC2)=NC2=CC=CC=C213613.6Semi standard non polar33892256
Bilastine,1TBDMS,isomer #1CCOCCN1C(C2CCN(CCC3=CC=C(C(C)(C)C(=O)O[Si](C)(C)C(C)(C)C)C=C3)CC2)=NC2=CC=CC=C213793.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bilastine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilastine 10V, Positive-QTOFsplash10-03xr-0001900000-24fa1a74b5226ff7c8c32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilastine 20V, Positive-QTOFsplash10-01bm-1437900000-ed03582bf3b0c452bda12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilastine 40V, Positive-QTOFsplash10-0f6w-0749000000-fd0d8dfb1572733b69d22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilastine 10V, Negative-QTOFsplash10-03di-0002900000-ba0adcf1dc395f8879b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilastine 20V, Negative-QTOFsplash10-02fy-2039800000-a81b333cae77d027dabc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilastine 40V, Negative-QTOFsplash10-0007-6395000000-c91521b64232da5f46aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilastine 10V, Positive-QTOFsplash10-03di-0002900000-c25e4569514550544c3b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilastine 20V, Positive-QTOFsplash10-02mr-0009700000-ae68b4ca76e6dac7f2d92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilastine 40V, Positive-QTOFsplash10-0007-5529200000-600ea8468863f6ba176e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilastine 10V, Negative-QTOFsplash10-03di-0001900000-d9d3358fa0f122df6fd52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilastine 20V, Negative-QTOFsplash10-0w29-0004900000-f1d17b67454b97e77af72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bilastine 40V, Negative-QTOFsplash10-0ufs-0592000000-836c1f973bc6c59f74132021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11591
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID161234
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBilastine
METLIN IDNot Available
PubChem Compound185460
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Church MK, Labeaga L: Bilastine: a new H1 -antihistamine with an optimal profile for updosing in urticaria. J Eur Acad Dermatol Venereol. 2017 Sep;31(9):1447-1452. doi: 10.1111/jdv.14305. Epub 2017 Jun 1. [PubMed:28467671 ]