sumatriptan   Click here for help

GtoPdb Ligand ID: 54

Synonyms: GR-43175C | Imigran® | Tosymra® (nasal spray)
Approved drug
sumatriptan is an approved drug (FDA (1992))
Compound class: Synthetic organic
Comment: Sumatriptan is a selective serotonin 5-HT1B/ID receptor agonist.
Marketed formulations contain sumatriptan succinate (PubChem CID 59772).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 73.58
Molecular weight 295.14
XLogP 0.88
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CNS(=O)(=O)Cc1ccc2c(c1)c(CCN(C)C)c[nH]2
Isomeric SMILES CNS(=O)(=O)Cc1ccc2c(c1)c(CCN(C)C)c[nH]2
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
InChI Key KQKPFRSPSRPDEB-UHFFFAOYSA-N
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT1D receptor Primary target of this compound Hs Agonist Full agonist 8.0 – 8.7 pKi - 8,11,15-16,23
pKi 8.0 – 8.7 (Ki 1x10-8 – 1.99x10-9 M) [8,11,15-16,23]
5-HT1F receptor Hs Agonist Full agonist 7.2 – 7.9 pKi - 1-2,16,22
pKi 7.2 – 7.9 [1-2,16,22]
5-HT1B receptor Primary target of this compound Hs Agonist Partial agonist 6.5 – 8.1 pKi - 7,11,15-18,23
pKi 6.5 – 8.1 (Ki 3.16x10-7 – 7.94x10-9 M) [7,11,15-18,23]
5-HT7 receptor Rn Antagonist Antagonist 6.2 – 6.6 pKi - 20-21
pKi 6.2 – 6.6 [20-21]
5-HT1A receptor Hs Agonist Full agonist 6.0 pKi - 16
pKi 6.0 [16]
5-HT7 receptor Hs Antagonist Antagonist 5.7 – 6.0 pKi - 4,9
pKi 5.7 – 6.0 [4,9]
5-ht1e receptor Hs Agonist Full agonist 5.6 – 5.8 pKi - 2-3,14,16,18
pKi 5.6 – 5.8 [2-3,14,16,18]
5-HT6 receptor Hs Antagonist Antagonist 5.6 pKi - 10
pKi 5.6 [10]
5-HT5A receptor Hs Agonist Full agonist 5.3 pKi - 6,19
pKi 5.3 [6,19]
5-HT6 receptor Rn Antagonist Antagonist 5.2 pKi - 5
pKi 5.2 [5]
5-HT5A receptor Mm Agonist Full agonist 4.8 pKi - 6,13
pKi 4.8 [6,13]
5-HT1F receptor Hs Agonist Full agonist 7.2 pIC50 - 12
pIC50 7.2 [12]