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Record Information
Version3.6
Creation Date2013-07-09 16:05:59 UTC
Update Date2016-02-11 08:15:03 UTC
HMDB IDHMDB60898
Secondary Accession NumbersNone
Metabolite Identification
Common NameEletriptan N-oxide
DescriptionEletriptan N-oxide is a metabolite of eletriptan. Eletriptan (also known as eletriptan hydrobromide) is a second generation triptan drug intended for treatment of migraine headaches. It is used as an abortive medication, blocking a migraine attack which is already in progress. Eletriptan is marketed and manufactured by Pfizer Inc. It is sold in the US and Canada under the brand name Relpax, and in several other countries under the brand name Relert. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H26N2O3S
Average Molecular Weight398.518
Monoisotopic Molecular Weight398.166413398
IUPAC Name(2R)-2-({5-[2-(benzenesulfonyl)ethyl]-1H-indol-3-yl}methyl)-1-methylpyrrolidin-1-ium-1-olate
Traditional Name(2R)-2-({5-[2-(benzenesulfonyl)ethyl]-1H-indol-3-yl}methyl)-1-methylpyrrolidin-1-ium-1-olate
CAS Registry NumberNot Available
SMILES
C[N+]1([O-])CCC[C@@H]1CC1=CNC2=C1C=C(CCS(=O)(=O)C1=CC=CC=C1)C=C2
InChI Identifier
InChI=1S/C22H26N2O3S/c1-24(25)12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-28(26,27)20-7-3-2-4-8-20/h2-4,7-10,14,16,19,23H,5-6,11-13,15H2,1H3/t19-,24?/m1/s1
InChI KeyInChIKey=QXXCIRSBRHOOJE-PHSANKKPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • Indole
  • Benzenoid
  • N-alkylpyrrolidine
  • Substituted pyrrole
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Sulfonyl
  • Sulfone
  • Pyrrolidine
  • Pyrrole
  • Azacycle
  • Trisubstituted n-oxide
  • N-oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organosulfur compound
  • Organonitrogen compound
  • Organic zwitterion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 Solubility0.000126 mg/mLALOGPS
logP1.78ALOGPS
logP2.65ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)16.13ChemAxon
pKa (Strongest Basic)3.05ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.81 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity112.99 m3·mol-1ChemAxon
Polarizability43.59 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00089
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60898
Metagene LinkHMDB60898
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available