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Showing Compound Sumatriptan (FDB023604)

Record Information
Version1.0
Creation date2011-09-21 00:32:17 UTC
Update date2015-07-21 06:57:47 UTC
Primary IDFDB023604
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSumatriptan
DescriptionOftentimes, serotonin levels in the brain become extremely erratic before the onset of a migraine. In an attempt to stabilize this, sumatriptan is administered to help aid in leveling the serotonin levels in the brain. Sumatriptan is structurally similar to serotonin, and is a 5-HT (5-HT1D) agonist, which is one of the receptors that serotonin binds to. The specific receptor subtype it activates is present in the cranial and basilar arteries. Activation of these receptors causes vasoconstriction of those dilated arteries. Sumatriptan is also shown to decrease the activity of the trigeminal nerve.; Sumatriptan is a triptan drug including a sulfonamide group structurally similar to serotonin, and is a 5-HT (5-HT1D) agonist, which is one of the receptors that serotonin binds to. Oftentimes, serotonin levels in the brain become extremely erratic before the onset of a migraine. In an attempt to stabilize this, sumatriptan is administered to help aid in leveling the serotonin levels in the brain.; A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of migraines.; Sumatriptan (Imitrex, Imigran,Imigran Recovery ) is a triptan drug including a sulfonamide group which was originally developed by Glaxo for the treatment of migraine headaches. [HMDB]
CAS Number103628-46-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamideChEBI
1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamideChEBI
3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamideChEBI
3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulfonamideChEBI
ImigranChEBI
ImitrexChEBI
SumatranChEBI
SumatriptanumChEBI
SumaxChEBI
(3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulphonamideGenerator
1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulphonamideGenerator
3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulphonamideGenerator
3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulphonamideGenerator
Imigran recoveryHMDB
Glaxo wellcome brand OF sumatriptanHMDB
Sumatriptan GSK brandHMDB
GSK Brand OF sumatriptanHMDB
Sumatriptan succinateHMDB
Succinate, sumatriptanHMDB
(3-[2-(dimethylamino)Ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamideChEBI
(3-[2-(dimethylamino)Ethyl]-1H-indol-5-yl)-N-methylmethanesulphonamideGenerator
3-(2-(dimethylamino)Ethyl)-N-methyl-1H-indole-5-methanesulfonamideChEBI
3-(2-(dimethylamino)Ethyl)-N-methyl-1H-indole-5-methanesulphonamideGenerator
3-[2-(dimethylamino)Ethyl]-N-methylindole-5-methanesulfonamideChEBI
3-[2-(dimethylamino)Ethyl]-N-methylindole-5-methanesulphonamideGenerator
Imigran Recoveryhmdb
Sumatriptanhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP1.17ALOGPS
logP0.74ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)11.24ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.2 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.08 m³·mol⁻¹ChemAxon
Polarizability32.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H21N3O2S
IUPAC name1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide
InChI IdentifierInChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3
InChI KeyKQKPFRSPSRPDEB-UHFFFAOYSA-N
Isomeric SMILESCNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1
Average Molecular Weight295.4
Monoisotopic Molecular Weight295.135447621
Classification
Description Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentTryptamines and derivatives
Alternative Parents
Substituents
  • Tryptamine
  • 3-alkylindole
  • Indole
  • Aralkylamine
  • Substituted pyrrole
  • Organic sulfonic acid amide
  • Benzenoid
  • Organosulfonic acid amide
  • Pyrrole
  • Organic sulfonic acid or derivatives
  • Heteroaromatic compound
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-9400000000-93cc7dc7e521f98aa2922014-09-20View Spectrum
Predicted GC-MSSumatriptan, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zfr-7390000000-5809ad2270f77ffcec79Spectrum
Predicted GC-MSSumatriptan, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-0190000000-c12ee3ac5f29c34209962017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-2910000000-8769dc29dcac8fede7d12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0390000000-cdddf05865e6d570c3372017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-2910000000-8769dc29dcac8fede7d12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-1090000000-b0360ed354c3c7a761952021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4i-7970000000-4a9c99ffaf927876bb552021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0090000000-42a6041e68fbb33f3c3c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-1290000000-18f63d6714d369042ced2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-1910000000-b311f02f2295ff2945732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3090000000-23dacc0baf4eac1e818a2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mo-9280000000-45a6f0dbb82744e4f1022016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r6-9120000000-ca48d4e064a2f63236512016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-9000000000-a75e9a0167fac95c8ca32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-9530000000-af10011e851a42315cd82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-2900000000-e271d3cf647593f64e672021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-7a6d991d417845eb044c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zg4-2890000000-0b86cdf68f0a940df9672021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9510000000-e92db5fc8036751fb26f2021-09-22View Spectrum
NMR
TypeDescriptionView
ChemSpider ID5165
ChEMBL IDCHEMBL128
KEGG Compound IDC07319
Pubchem Compound ID5358
Pubchem Substance IDNot Available
ChEBI ID10650
Phenol-Explorer IDNot Available
DrugBank IDDB00669
HMDB IDHMDB05037
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSumatriptan
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
5-hydroxytryptamine receptor 1BHTR1BP28222
5-hydroxytryptamine receptor 1DHTR1DP28221
5-hydroxytryptamine receptor 1FHTR1FP30939
Inhibitor of nuclear factor kappa-B kinase subunit betaIKBKBO14920
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference