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).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: sumatriptan

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1992))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide
International Nonproprietary Names Click here for help
INN number INN
6125 sumatriptan
Synonyms Click here for help
GR-43175C | Imigran® | Tosymra® (nasal spray)
Database Links Click here for help
Specialist databases
GPCRdb Ligand sumatriptan
Other databases
CAS Registry No. 103628-46-2
ChEBI CHEBI:10650
ChEMBL Ligand CHEMBL128
DrugBank Ligand DB00669
DrugCentral Ligand 2543
GtoPdb PubChem SID 135651095
PubChem CID 5358
Search Google for chemical match using the InChIKey KQKPFRSPSRPDEB-UHFFFAOYSA-N
Search Google for chemicals with the same backbone KQKPFRSPSRPDEB
Search PubMed clinical trials sumatriptan
Search PubMed titles sumatriptan
Search PubMed titles/abstracts sumatriptan
UniChem Compound Search for chemical match using the InChIKey KQKPFRSPSRPDEB-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey KQKPFRSPSRPDEB-UHFFFAOYSA-N
Wikipedia Sumatriptan