Human Metabolome Database Version 3.5

Showing metabocard for Sumatriptan (HMDB05037)

Record Information
Version 3.5
Creation Date 2006-10-17 05:10:02 -0600
Update Date 2013-03-26 14:52:33 -0600
HMDB ID HMDB05037
Secondary Accession Numbers None
Metabolite Identification
Common Name Sumatriptan
Description 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. 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 Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Imigran
  2. Imigran Recovery
  3. Imitrex
  4. Sumatriptan
Chemical Formula C14H21N3O2S
Average Molecular Weight 295.4
Monoisotopic Molecular Weight 295.135447621
IUPAC Name 1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide
Traditional IUPAC Name sumatriptan
CAS Registry Number 103628-46-2
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 Key KQKPFRSPSRPDEB-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Indoles
Sub Class Tryptamines and Derivatives
Other Descriptors
  • Indoles
  • sulfonamide(ChEBI)
  • tryptamines(ChEBI)
Substituents
  • Pyrrole
  • Sulfonamide
  • Sulfonyl
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct Parent Tryptamines and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 169 - 171 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 0.93 ADLARD,M ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.13 g/L ALOGPS
LogP 1.17 ALOGPS
LogP 0.74 ChemAxon
LogS -3.37 ALOGPS
pKa (strongest acidic) 11.24 ChemAxon
pKa (strongest basic) 9.54 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 65.2 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 82.08 ChemAxon
Polarizability 32.23 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location
  • Brain
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023604
KNApSAcK ID Not Available
Chemspider ID 5165 Link_out
KEGG Compound ID C07319 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Sumatriptan Link_out
NuGOwiki Link HMDB05037 Link_out
Metagene Link HMDB05037 Link_out
METLIN ID 2612 Link_out
PubChem Compound 5358 Link_out
PDB ID Not Available
ChEBI ID 10650 Link_out
References
Synthesis Reference Torner 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 Link_out
  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 Link_out

Enzymes
Name: Amine oxidase [flavin-containing] A
Reactions: Not Available
Gene Name: MAOA
Uniprot ID: P21397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Mitogen-activated protein kinase 1
Reactions: Not Available
Gene Name: MAPK1
Uniprot ID: P28482 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Mitogen-activated protein kinase 3
Reactions: Not Available
Gene Name: MAPK3
Uniprot ID: P27361 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Inhibitor of nuclear factor kappa-B kinase subunit beta
Reactions: Not Available
Gene Name: IKBKB
Uniprot ID: O14920 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: RAC-alpha serine/threonine-protein kinase
Reactions: Not Available
Gene Name: AKT1
Uniprot ID: P31749 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: BR serine/threonine-protein kinase 1
Reactions: Not Available
Gene Name: BRSK1
Uniprot ID: Q8TDC3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 2B
Reactions: Not Available
Gene Name: HTR2B
Uniprot ID: P41595 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 1B
Reactions: Not Available
Gene Name: HTR1B
Uniprot ID: P28222 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 1F
Reactions: Not Available
Gene Name: HTR1F
Uniprot ID: P30939 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-hydroxytryptamine receptor 1D
Reactions: Not Available
Gene Name: HTR1D
Uniprot ID: P28221 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA