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Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-10-17 11:10:02 UTC |
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Update Date | 2019-07-23 05:46:41 UTC |
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HMDB ID | HMDB0005037 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Sumatriptan |
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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. |
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Structure | |
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Synonyms | Value | Source |
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(3-[2-(dimethylamino)Ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide | ChEBI | 1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide | ChEBI | 3-(2-(dimethylamino)Ethyl)-N-methyl-1H-indole-5-methanesulfonamide | ChEBI | 3-[2-(dimethylamino)Ethyl]-N-methylindole-5-methanesulfonamide | ChEBI | Imigran | ChEBI | Imitrex | ChEBI | Sumatran | ChEBI | Sumatriptanum | ChEBI | Sumax | ChEBI | (3-[2-(dimethylamino)Ethyl]-1H-indol-5-yl)-N-methylmethanesulphonamide | Generator | 1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulphonamide | Generator | 3-(2-(dimethylamino)Ethyl)-N-methyl-1H-indole-5-methanesulphonamide | Generator | 3-[2-(dimethylamino)Ethyl]-N-methylindole-5-methanesulphonamide | Generator | Imigran recovery | HMDB | glaxo Wellcome brand OF sumatriptan | MeSH | Sumatriptan GSK brand | MeSH | GSK Brand OF sumatriptan | MeSH | Sumatriptan succinate | MeSH | Succinate, sumatriptan | MeSH |
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Chemical Formula | C14H21N3O2S |
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Average Molecular Weight | 295.4 |
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Monoisotopic Molecular Weight | 295.135447621 |
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IUPAC Name | 1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide |
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Traditional Name | sumatriptan |
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CAS Registry Number | 103628-46-2 |
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SMILES | CNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1 |
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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 |
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InChI Key | KQKPFRSPSRPDEB-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | This 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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Indoles and derivatives |
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Sub Class | Tryptamines and derivatives |
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Direct Parent | Tryptamines and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Biological location: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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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) |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0zfr-7390000000-5809ad2270f77ffcec79 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-03di-0190000000-c12ee3ac5f29c3420996 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0a4i-2910000000-8769dc29dcac8fede7d1 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0002-0390000000-cdddf05865e6d570c337 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0a4i-2910000000-8769dc29dcac8fede7d1 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000t-0090000000-42a6041e68fbb33f3c3c | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0uxr-1290000000-18f63d6714d369042ced | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a59-1910000000-b311f02f2295ff294573 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-3090000000-23dacc0baf4eac1e818a | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00mo-9280000000-45a6f0dbb82744e4f102 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-01r6-9120000000-ca48d4e064a2f6323651 | JSpectraViewer | MoNA | MS | Mass Spectrum (Electron Ionization) | splash10-0a4i-9400000000-93cc7dc7e521f98aa292 | JSpectraViewer | MoNA |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 0.000 uM | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities | Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00669 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB023604 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 5165 |
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KEGG Compound ID | C07319 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Sumatriptan |
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METLIN ID | 2612 |
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PubChem Compound | 5358 |
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PDB ID | Not Available |
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ChEBI ID | 10650 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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References |
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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 |
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Material Safety Data Sheet (MSDS) | Not Available |
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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 ]
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