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Showing metabocard for Sumatriptan (HMDB0005037)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (10) Show 10 proteinsXML
enzymes (10) Show 10 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-10-17 11:10:02 UTC
Update Date2019-01-11 19:18:34 UTC
HMDB IDHMDB0005037
Secondary Accession Numbers
  • HMDB05037
Metabolite Identification
Common 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.
Structure
Data?1547234314
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(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 sumatriptanMeSH
Sumatriptan GSK brandMeSH
GSK Brand OF sumatriptanMeSH
Sumatriptan succinateMeSH
Succinate, sumatriptanMeSH
Chemical FormulaC14H21N3O2S
Average Molecular Weight295.4
Monoisotopic Molecular Weight295.135447621
IUPAC Name1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide
Traditional Namesumatriptan
CAS Registry Number103628-46-2
SMILES
CNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1
InChI Identifier
InChI=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
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tryptamines and derivatives. These 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point169 - 171 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.93ADLARD,M ET AL. (1995)
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-7390000000-5809ad2270f77ffcec79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-0190000000-c12ee3ac5f29c3420996View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-2910000000-8769dc29dcac8fede7d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0390000000-cdddf05865e6d570c337View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-2910000000-8769dc29dcac8fede7d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0090000000-42a6041e68fbb33f3c3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-1290000000-18f63d6714d369042cedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-1910000000-b311f02f2295ff294573View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3090000000-23dacc0baf4eac1e818aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mo-9280000000-45a6f0dbb82744e4f102View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r6-9120000000-ca48d4e064a2f6323651View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-9400000000-93cc7dc7e521f98aa292View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Brain
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00669
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023604
KNApSAcK IDNot Available
Chemspider ID5165
KEGG Compound IDC07319
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSumatriptan
METLIN ID2612
PubChem Compound5358
PDB IDNot Available
ChEBI ID10650
References
Synthesis ReferenceTorner Montoya, Miguel. Process for the synthesis of 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide [sumatriptan]. Span. (1994), 6 pp. CODEN: SPXXAD ES 2059236 A1 19941101 CAN 122:265245 AN 1995:520544
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pascual J, del Arco C, Romon T, del Olmo E, Castro E, Pazos A: Autoradiographic distribution of [3H]sumatriptan-binding sites in post-mortem human brain. Cephalalgia. 1996 Aug;16(5):317-22. [PubMed:8869766 ]
  2. Castro ME, Pascual J, Romon T, del Arco C, del Olmo E, Pazos A: Differential distribution of [3H]sumatriptan binding sites (5-HT1B, 5-HT1D and 5-HT1F receptors) in human brain: focus on brainstem and spinal cord. Neuropharmacology. 1997 Apr-May;36(4-5):535-42. [PubMed:9225278 ]

Enzymes

Enzyme Details
1. Amine oxidase [flavin-containing] A
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Enzyme Details
2. Mitogen-activated protein kinase 1
General function:
Involved in MAP kinase activity
Specific function:
Acts as a transcriptional repressor. Binds to a [GC]AAA[GC] consensus sequence. Repress the expression of interferon gamma-induced genes. Seems to bind to the promoter of CCL5, DMP1, IFIH1, IFITM1, IRF7, IRF9, LAMP3, OAS1, OAS2, OAS3 and STAT1. Transcriptional activity is independent of kinase activity
Gene Name:
MAPK1
Uniprot ID:
P28482
Molecular weight:
41389.3
Enzyme Details
3. Mitogen-activated protein kinase 3
General function:
Involved in MAP kinase activity
Specific function:
Involved in both the initiation and regulation of meiosis, mitosis, and postmitotic functions in differentiated cells by phosphorylating a number of transcription factors such as ELK-1. Phosphorylates EIF4EBP1; required for initiation of translation. Phosphorylates microtubule-associated protein 2 (MAP2). Phosphorylates SPZ1. Phosphorylates heat shock factor protein 4 (HSF4)
Gene Name:
MAPK3
Uniprot ID:
P27361
Molecular weight:
43135.2
Enzyme Details
4. Inhibitor of nuclear factor kappa-B kinase subunit beta
General function:
Involved in protein kinase activity
Specific function:
Acts as part of the IKK complex in the conventional pathway of NF-kappa-B activation and phosphorylates inhibitors of NF-kappa-B thus leading to the dissociation of the inhibitor/NF- kappa-B complex and ultimately the degradation of the inhibitor. Also phosphorylates NCOA3
Gene Name:
IKBKB
Uniprot ID:
O14920
Molecular weight:
86563.2
Enzyme Details
5. RAC-alpha serine/threonine-protein kinase
General function:
Involved in protein serine/threonine kinase activity
Specific function:
Plays a role as a key modulator of the AKT-mTOR signaling pathway controlling the tempo of the process of newborn neurons integration during adult neurogenesis, including correct neuron positioning, dendritic development and synapse formation. General protein kinase capable of phosphorylating several known proteins. Phosphorylates TBC1D4. Signals downstream of phosphatidylinositol 3-kinase (PI(3)K) to mediate the effects of various growth factors such as platelet-derived growth factor (PDGF), epidermal growth factor (EGF), insulin and insulin-like growth factor I (IGF-I). Plays a role in glucose transport by mediating insulin-induced translocation of the GLUT4 glucose transporter to the cell surface. Mediates the antiapoptotic effects of IGF-I. Mediates insulin-stimulated protein synthesis by phosphorylating TSC2 at 'Ser-939' and 'Thr-1462', thereby activating mTORC1 signaling and leading to both phosphorylation of 4E-BP1 and in activation of RPS6KB1. Promotes glycogen synthesis by mediating the insulin-induced activation of glycogen synthase
Gene Name:
AKT1
Uniprot ID:
P31749
Molecular weight:
55686.0
Enzyme Details
6. BR serine/threonine-protein kinase 1
General function:
Involved in protein kinase activity
Specific function:
Required for the polarization of forebrain neurons which endows axons and dendrites with distinct properties, possibly by locally regulating phosphorylation of microtubule-associated proteins. May be involved in the regulation of G2/M arrest in response to UV- or methyl methane sulfonate (MMS)- induced, but not IR-induced, DNA damage. Phosphorylates WEE1 and CDC25B in vitro and CDC25C in vitro and in vivo
Gene Name:
BRSK1
Uniprot ID:
Q8TDC3
Molecular weight:
86752.7
Enzyme Details
7. 5-hydroxytryptamine receptor 2B
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
HTR2B
Uniprot ID:
P41595
Molecular weight:
54297.4
Enzyme Details
8. 5-hydroxytryptamine receptor 1B
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular weight:
43567.5
Enzyme Details
9. 5-hydroxytryptamine receptor 1F
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1F
Uniprot ID:
P30939
Molecular weight:
41708.5
Enzyme Details
10. 5-hydroxytryptamine receptor 1D
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1D
Uniprot ID:
P28221
Molecular weight:
41906.4