| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- Imigran
- Imigran Recovery
- Imitrex
- 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 |
|
| 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 |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
Not Available
|
| Biofluid Locations |
Not Available
|
| Tissue Location |
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank 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  |
| KEGG Compound ID |
C07319 |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Sumatriptan |
| NuGOwiki Link |
HMDB05037 |
| Metagene Link |
HMDB05037 |
| METLIN ID |
2612 |
| PubChem Compound |
5358 |
| PDB ID |
Not Available |
| ChEBI ID |
10650 |
| 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 |
- 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
- 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
|
