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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 15:46:28 UTC
HMDB IDHMDB0014361
Secondary Accession Numbers
  • HMDB14361
Metabolite Identification
Common NameEletriptan
DescriptionEletriptan is only found in individuals that have used or taken this drug. It is a second generation triptan drug developed by Pfizer Inc for the treatment of migraine headaches. [Wikipedia ]Eletriptan binds with high affinity to 5-HT1B, 5-HT1D and 5-HT1F receptors, has modest affinity for 5-HT1A, 5-HT1E, 5-HT2B and 5-HT7 receptors, and little or no affinity for 5-HT2A, 5-HT2C, 5-HT3, 5-HT4, 5-HT5A and 5-HT6 receptors. Eletriptan has no significant affinity or pharmacological activity at adrenergic alpha1, alpha2, or beta; dopaminergic D1 or D2; muscarinic; or opioid receptors. Two theories have been proposed to explain the efficacy of 5-HT receptor agonists in migraine. One theory suggests that activation of 5-HT1 receptors located on intracranial blood vessels, including those on the arteriovenous anastomoses, leads to vasoconstriction, which is correlated with the relief of migraine headache. The other hypothesis suggests that activation of 5-HT1 receptors on sensory nerve endings in the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release.
Structure
Data?1582753169
Synonyms
ValueSource
EletriptanumChEBI
3-(1-Methyl-2-pyrrolidinylmethyl)-5-(2-(phenylsulfonyl)ethyl)-1H-indole hydrobromideHMDB
Eletriptan hydrobromideHMDB
RelpaxHMDB
(R)-3-((1-Methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1H-indoleHMDB
(R)-3-((1-Methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1H-indole monohydrobromideHMDB
Chemical FormulaC22H26N2O2S
Average Molecular Weight382.519
Monoisotopic Molecular Weight382.171498776
IUPAC Name5-[2-(benzenesulfonyl)ethyl]-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole
Traditional Nameeletriptan
CAS Registry Number143322-58-1
SMILES
CN1CCC[C@@H]1CC1=CNC2=C1C=C(CCS(=O)(=O)C1=CC=CC=C1)C=C2
InChI Identifier
InChI=1S/C22H26N2O2S/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20/h2-4,7-10,14,16,19,23H,5-6,11-13,15H2,1H3/t19-/m1/s1
InChI KeyPWVXXGRKLHYWKM-LJQANCHMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Benzenesulfonyl group
  • Aralkylamine
  • Monocyclic benzene moiety
  • Substituted pyrrole
  • N-alkylpyrrolidine
  • Benzenoid
  • Pyrrole
  • Pyrrolidine
  • Sulfone
  • Sulfonyl
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0012 g/LNot Available
LogP3.9Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM186.130932474
[M+H]+Not Available185.234http://allccs.zhulab.cn/database/detail?ID=AllCCS00001522
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP10(3.84) g/LALOGPS
logP10(3.77) g/LChemAxon
logS10(-5.5) g/LALOGPS
pKa (Strongest Acidic)17.11ChemAxon
pKa (Strongest Basic)8.37ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.17 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity110.94 m³·mol⁻¹ChemAxon
Polarizability42.99 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.42831661259
DarkChem[M-H]-190.22831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EletriptanCN1CCC[C@@H]1CC1=CNC2=C1C=C(CCS(=O)(=O)C1=CC=CC=C1)C=C25251.6Standard polar33892256
EletriptanCN1CCC[C@@H]1CC1=CNC2=C1C=C(CCS(=O)(=O)C1=CC=CC=C1)C=C23521.1Standard non polar33892256
EletriptanCN1CCC[C@@H]1CC1=CNC2=C1C=C(CCS(=O)(=O)C1=CC=CC=C1)C=C23565.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Eletriptan,1TMS,isomer #1CN1CCC[C@@H]1CC1=CN([Si](C)(C)C)C2=CC=C(CCS(=O)(=O)C3=CC=CC=C3)C=C123381.9Semi standard non polar33892256
Eletriptan,1TMS,isomer #1CN1CCC[C@@H]1CC1=CN([Si](C)(C)C)C2=CC=C(CCS(=O)(=O)C3=CC=CC=C3)C=C122997.5Standard non polar33892256
Eletriptan,1TMS,isomer #1CN1CCC[C@@H]1CC1=CN([Si](C)(C)C)C2=CC=C(CCS(=O)(=O)C3=CC=CC=C3)C=C124087.5Standard polar33892256
Eletriptan,1TBDMS,isomer #1CN1CCC[C@@H]1CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CCS(=O)(=O)C3=CC=CC=C3)C=C123583.7Semi standard non polar33892256
Eletriptan,1TBDMS,isomer #1CN1CCC[C@@H]1CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CCS(=O)(=O)C3=CC=CC=C3)C=C123211.8Standard non polar33892256
Eletriptan,1TBDMS,isomer #1CN1CCC[C@@H]1CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CCS(=O)(=O)C3=CC=CC=C3)C=C124143.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Eletriptan GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9110000000-bef75cdb82e945554b4a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Eletriptan 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 - Eletriptan 10V, Positive-QTOFsplash10-001i-0309000000-94ede4ac3c6cb8f733c92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eletriptan 20V, Positive-QTOFsplash10-001l-9468000000-0e675066db2cea9eb2782016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eletriptan 40V, Positive-QTOFsplash10-0fr6-9401000000-6ea64b3711b1e34491742016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eletriptan 10V, Negative-QTOFsplash10-001i-0309000000-bca3b55d287b0f646ca02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eletriptan 20V, Negative-QTOFsplash10-000x-2957000000-13868d17d46c97bfd4782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eletriptan 40V, Negative-QTOFsplash10-0006-9820000000-93669003e8f047d1c3d62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eletriptan 10V, Positive-QTOFsplash10-001i-0009000000-bb20fd58f55dd639bd4e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eletriptan 20V, Positive-QTOFsplash10-001i-1149000000-398bda48e8642076254a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eletriptan 40V, Positive-QTOFsplash10-004i-9311000000-a970ee8f51934ad7a8cb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eletriptan 10V, Negative-QTOFsplash10-001i-0009000000-f00e87020d8b2372d4de2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eletriptan 20V, Negative-QTOFsplash10-001i-0549000000-bd448dd0cb94ea9bb8e62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eletriptan 40V, Negative-QTOFsplash10-01ox-4819000000-4c9bae15e3bf79d5fdf92021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00216 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00216 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00216
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID70379
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEletriptan
METLIN IDNot Available
PubChem Compound77993
PDB IDNot Available
ChEBI ID50922
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 ReferencesNot Available