sumatriptan (CHEBI:10650)

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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-HT_1D 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

Average Mass

295.40000

Monoisotopic Mass

295.13545

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.

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 base of sumatriptan(1+) (CHEBI:64364)

Incoming	sumatriptan(1+) (CHEBI:64364) is conjugate acid of sumatriptan (CHEBI:10650)

IUPAC Name

1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide

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

Last Modified

22 February 2017