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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-09 20:59:27 UTC
Update Date2019-07-23 07:13:42 UTC
HMDB IDHMDB0060159
Secondary Accession Numbers
  • HMDB60159
Metabolite Identification
Common NameEbastine
DescriptionEbastine, also known as kestine or ebastel, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Ebastine is a drug. Ebastine is a H1 antihistamine with low potential for causing drowsiness. Ebastine is a very strong basic compound (based on its pKa). After oral administration, ebastine undergoes extensive first-pass metabolism by hepatic cytochrome P450 3A4 into its active carboxylic acid metabolite, carebastine. In humans, ebastine is involved in ebastine h1-antihistamine action. It is available in 10 and 20 mg tablets and as fast-dissolving tablets, as well as in pediatric syrup. The substance is often provided in micronised form due to poor water solubility. While experiments in pregnant animals showed no risk for the unborn, no such data are available in humans. Ebastine has shown overall safety and tolerability profile with no cognitive/psychomotor impairment and no sedation worse than placebo, and cardiac safety, that is, no QT prolongation. Ebastine is available in different formulations (tablets, fast dissolving tablets and syrup) and commercialized under different brand names around the world, Ebatrol, Atmos, Ebet, Ebastel FLAS, Kestine, KestineLIO, KestinLYO, EstivanLYO, Evastel Z, Ebasten (ACI), etc. This conversion is practically complete.
Structure
Data?1563866022
Synonyms
ValueSource
KestineKegg
KestinHMDB
4-Diphenylmethoxy-1-(3-(4-tert-butylbenzoyl)propyl)piperidineHMDB
BactilHMDB
BusidrilHMDB
EbastelHMDB
EvastelHMDB
LAS W-090HMDB
1-[4-(1,1-Dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanoneHMDB
AlevaHMDB
BastelHMDB
EbastinHMDB
EbatrolHMDB
ErostinHMDB
EvastinHMDB
LAS-W 090HMDB
RP 64305HMDB
EbastineSMPDB
Chemical FormulaC32H39NO2
Average Molecular Weight469.6576
Monoisotopic Molecular Weight469.298079497
IUPAC Name1-(4-tert-butylphenyl)-4-[4-(diphenylmethoxy)piperidin-1-yl]butan-1-one
Traditional Namekestin
CAS Registry Number90729-43-4
SMILES
CC(C)(C)C1=CC=C(C=C1)C(=O)CCCN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C32H39NO2/c1-32(2,3)28-18-16-25(17-19-28)30(34)15-10-22-33-23-20-29(21-24-33)35-31(26-11-6-4-7-12-26)27-13-8-5-9-14-27/h4-9,11-14,16-19,29,31H,10,15,20-24H2,1-3H3
InChI KeyMJJALKDDGIKVBE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Alkyl-phenylketone
  • Butyrophenone
  • Phenylbutylamine
  • Benzylether
  • Phenylketone
  • Phenylpropane
  • Benzoyl
  • Aryl alkyl ketone
  • Aryl ketone
  • Gamma-aminoketone
  • Piperidine
  • Ketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Dialkyl ether
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.5e-05 g/LALOGPS
logP6.89ALOGPS
logP6.96ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)16.45ChemAxon
pKa (Strongest Basic)8.43ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity145.38 m³·mol⁻¹ChemAxon
Polarizability55.41 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1941000000-bcc59998a2c37520b0d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gi0-0930400000-a3b7001dd8bec489cf92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0130900000-d87c3180806d2efe676eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gi9-0983500000-a76fa5e83260410a5814Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-3940000000-492eb62bc79baf0463e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0110900000-6ae36965d1edc6b0f2aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-0622900000-e92cb58fb2500c21490fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-6910000000-b7147b6ba5db0334baabSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDDB11742
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEbastine
METLIN IDNot Available
PubChem Compound3191
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  2. Lee CA, Jones JP 3rd, Katayama J, Kaspera R, Jiang Y, Freiwald S, Smith E, Walker GS, Totah RA: Identifying a selective substrate and inhibitor pair for the evaluation of CYP2J2 activity. Drug Metab Dispos. 2012 May;40(5):943-51. doi: 10.1124/dmd.111.043505. Epub 2012 Feb 10. [PubMed:22328583 ]