CHEBI:10650 - sumatriptan

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ChEBI Name sumatriptan
ChEBI ID CHEBI:10650
Definition A sulfonamide that consists of N,N-dimethyltryptamine bearing an additional (N-methylsulfamoyl)methyl substituent at position 5. Selective agonist for a vascular 5-HT1 receptor subtype (probably a member of the 5-HT1D family). Used (in the form of its succinate salt) for the acute treatment of migraine with or without aura in adults.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C14H21N3O2S
Net Charge 0
Average Mass 295.40000
Monoisotopic Mass 295.135
InChI 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
InChIKey KQKPFRSPSRPDEB-UHFFFAOYSA-N
SMILES CNS(=O)(=O)Cc1ccc2[nH]cc(CCN(C)C)c2c1
Roles Classification
Biological Role(s): serotonergic agonist
An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
Application(s): vasoconstrictor agent
Drug used to cause constriction of the blood vessels.
serotonergic agonist
An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
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ChEBI Ontology
Outgoing sumatriptan (CHEBI:10650) has functional parent N,N-dimethyltryptamine (CHEBI:28969)
sumatriptan (CHEBI:10650) has role serotonergic agonist (CHEBI:35941)
sumatriptan (CHEBI:10650) has role vasoconstrictor agent (CHEBI:50514)
sumatriptan (CHEBI:10650) is a sulfonamide (CHEBI:35358)
sumatriptan (CHEBI:10650) is a tryptamines (CHEBI:27162)
sumatriptan (CHEBI:10650) is conjugate acid of sumatriptan(1+) (CHEBI:64364)
Incoming sumatriptan(1+) (CHEBI:64364) is conjugate base of sumatriptan (CHEBI:10650)
IUPAC Name
1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide
INNs Sources
sumatriptán ChEBI
sumatriptan ChEBI
sumatriptan KEGG DRUG
sumatriptanum ChEBI
Synonyms Sources
(3-[2-(dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide NIST Chemistry WebBook
1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide IUPHAR
3-(2-(dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide ChemIDplus
3-[2-(dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide NIST Chemistry WebBook
Sumatran DrugBank
Sumax DrugBank
Brand Names Sources
Imigran KEGG DRUG
Imitrex KEGG DRUG
Database Links Databases
2543 DrugCentral
C07319 KEGG COMPOUND
D00451 KEGG DRUG
DB00669 DrugBank
HMDB0005037 HMDB
LSM-5618 LINCS
Sumatriptan Wikipedia
View more database links
Registry Numbers Types Sources
103628-46-2 CAS Registry Number NIST Chemistry WebBook
103628-46-2 CAS Registry Number ChemIDplus
5346011 Beilstein Registry Number Beilstein
5346011 Reaxys Registry Number Reaxys
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Last Modified
22 February 2017