Marvin  01180817162D          

 20 21  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991    0.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4990   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5609   -1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2638   -3.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8158   -2.4082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227   -2.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7539   -1.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4124    0.0000 S   0  0  3  0  0  0  0  0  0  0  0  0
   -2.5558    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  8  1  0  0  0  0
  4  2  1  0  0  0  0
  3  4  2  0  0  0  0
  9  4  1  0  0  0  0
  5  1  1  0  0  0  0
  3  6  1  0  0  0  0
  6  5  2  0  0  0  0
  6 10  1  0  0  0  0
  9  7  2  0  0  0  0
  8  7  1  0  0  0  0
  9 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 11  1  0  0  0  0
 11 12  1  0  0  0  0
 17 13  1  0  0  0  0
 13 15  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  2  0  0  0  0
M  END
> <ID>
CHEBI:10650

> <NAME>
sumatriptan

> <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.

> <STAR>
3

> <SYNONYM>
Sumax; Sumatran; 3-[2-(dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide; 3-(2-(dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide; 1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide; (3-[2-(dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide

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

> <INN>
sumatriptanum; sumatriptan; sumatriptan; sumatriptan

> <BRAND_NAME>
Imitrex; Imigran

> <FORMULA>
C14H21N3O2S

> <MASS>
295.40000

> <MONOISOTOPIC_MASS>
295.13545

> <CHARGE>
0

> <SMILES>
CNS(=O)(=O)Cc1ccc2[nH]cc(CCN(C)C)c2c1

> <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

> <BEILSTEIN_REGISTRY_NUMBER>
5346011

> <CAS_REGISTRY_NUMBER>
103628-46-2

> <REAXYS_REGISTRY_NUMBER>
5346011

> <CHEMIDPLUS>
103628-46-2

> <DRUGBANK_ACCESSION>
DB00669

> <KEGG_COMPOUND_ACCESSION>
C07319

> <KEGG_DRUG_ACCESSION>
D00451

> <LINCS_ACCESSION>
LSM-5618

> <NIST_CHEMISTRY_WEBBOOK>
103628-46-2

> <WIKIPEDIA_ACCESSION>
Sumatriptan

> <PUBMED_CITATION>
11045888; 11401410; 12172708; 12856385; 12917936; 15652399; 16120224; 16142613; 17557349; 18442019; 19619527; 19825906; 22106962; 22150557; 22272067; 22302025; 22336849; 22336867; 22336868; 22435741

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