Record Information
Version3.6
Creation Date2006-10-17 11:10:02 UTC
Update Date2013-03-26 20:52:33 UTC
HMDB IDHMDB05037
Secondary Accession NumbersNone
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
Thumb
Synonyms
  1. Imigran
  2. Imigran Recovery
  3. Imitrex
  4. Sumatriptan
Chemical FormulaC14H21N3O2S
Average Molecular Weight295.4
Monoisotopic Molecular Weight295.135447621
IUPAC Name1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide
Traditional IUPAC 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
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassIndoles
Sub ClassTryptamines and Derivatives
Other Descriptors
  • Indoles
  • sulfonamide(ChEBI)
  • tryptamines(ChEBI)
Substituents
  • Pyrrole
  • Sulfonamide
  • Sulfonyl
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct ParentTryptamines and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 area65.2ChemAxon
rotatable bond count5ChemAxon
refractivity82.08ChemAxon
polarizability32.23ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue Location
  • Brain
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023604
KNApSAcK IDNot Available
Chemspider ID5165
KEGG Compound IDC07319
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSumatriptan
NuGOwiki LinkHMDB05037
Metagene LinkHMDB05037
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

Gene Name:
MAOA
Uniprot ID:
P21397
Gene Name:
MAPK1
Uniprot ID:
P28482
Gene Name:
MAPK3
Uniprot ID:
P27361
Gene Name:
BRSK1
Uniprot ID:
Q8TDC3
Gene Name:
HTR2B
Uniprot ID:
P41595
Gene Name:
HTR1B
Uniprot ID:
P28222
Gene Name:
HTR1F
Uniprot ID:
P30939
Gene Name:
HTR1D
Uniprot ID:
P28221