bumetanide   Click here for help

GtoPdb Ligand ID: 4837

Synonyms: Bumex® | Burinex® | PF 1593 | Ro 10-6338
Approved drug PDB Ligand
bumetanide is an approved drug (FDA (1983))
Compound class: Synthetic organic
Comment: Bumetanide is a loop diuretic drug. It inhibits NKCC1 (SLC12A2) tranporters in the brain and kidney-specific NKCC2 (SLC12A1) transporters in the thick ascending limb of Henle's loop. The latter action modulates water and electrolyte homeostasis and is reponsible for the drug's diuretic effects.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: bumetanide

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 127.1
Molecular weight 364.11
XLogP 2.57
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CCCCNc1cc(cc(c1Oc1ccccc1)S(=O)(=O)N)C(=O)O
Isomeric SMILES CCCCNc1cc(cc(c1Oc1ccccc1)S(=O)(=O)N)C(=O)O
InChI InChI=1S/C17H20N2O5S/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23)
InChI Key MAEIEVLCKWDQJH-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1983))
IUPAC Name Click here for help
3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid
International Nonproprietary Names Click here for help
INN number INN
2943 bumetanide
Synonyms Click here for help
Bumex® | Burinex® | PF 1593 | Ro 10-6338
Database Links Click here for help
Specialist databases
GPCRdb Ligand bumetanide
Other databases
CAS Registry No. 28395-03-1 (source: Scifinder)
ChEBI CHEBI:3213
ChEMBL Ligand CHEMBL1072
DrugBank Ligand DB00887
DrugCentral Ligand 427
GtoPdb PubChem SID 178101539
PubChem CID 2471
RCSB PDB Ligand 82U
Search Google for chemical match using the InChIKey MAEIEVLCKWDQJH-UHFFFAOYSA-N
Search Google for chemicals with the same backbone MAEIEVLCKWDQJH
Search PubMed clinical trials bumetanide
Search PubMed titles bumetanide
Search PubMed titles/abstracts bumetanide
UniChem Compound Search for chemical match using the InChIKey MAEIEVLCKWDQJH-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey MAEIEVLCKWDQJH-UHFFFAOYSA-N
Wikipedia Bumetanide

Product suppliers

View disclaimer

Tocris
Bumetanide (links to external site)
Cat. No. 3108