glibenclamide   Click here for help

GtoPdb Ligand ID: 2414

Synonyms: Amglidia® | Diabeta® | glyburide | Glynase®
Approved drug PDB Ligand Immunopharmacology Ligand
glibenclamide is an approved drug (FDA (as glyburide, 1984), EMA (2018))
Compound class: Synthetic organic
Comment: A sulfonylurea family drug inhibiting sulfonylurea receptor 1 (ABCC8)/Kir6.2 (KCNJ11). Glibenclamide induced blockade of SUR1-TRPM4 channels reduces inflammatory markers and improves clinical symptoms in mouse experimental autoimmune encephalomyelitis (EAE), and may be of relevance in multiple sclerosis as SUR1-TRPM4-expressing lesions from MS provide a potentially disease modiifying target [12].
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View more information in the IUPHAR Pharmacology Education Project: glibenclamide

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 121.98
Molecular weight 493.14
XLogP 4.89
No. Lipinski's rules broken 0
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Canonical SMILES COc1ccc(cc1C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)NC1CCCCC1)Cl
Isomeric SMILES COc1ccc(cc1C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)NC1CCCCC1)Cl
InChI InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)
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Summary of Clinical Use Click here for help
Glibenclamide is an oral antihyperglycemic agent used to treat adult patients with non-insulin-dependent diabetes mellitus (NIDDM) and who respond inadequately to dietary measures alone. The 2018 EMA approval covers use of glibenclamide Amglidia® (a liquid suspension) to treat newborns and children with neonatal diabetes.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The sulfonyurea drugs appear to bind sulfonylurea receptors and it has been shown experimentally that tritiated glibenclamide can be used to pull out a 140 kDa protein identified as SUR1 (now known as ABCC8) [37]. SUR2 (ABCC9) has also been identified [20]. However, this is not the full mechanism of action and the functional channel has been characterised as a hetero-octamer formed by four SUR and four Kir6.2 subunits, with the Kir6.2 subunits forming the core ion pore and the SUR subunits providing the regulatory properties [33]. Co-expression of Kir6.2 with SUR1, reconstitutes the ATP-dependent K+ conductivity inhibited by the sulfonyureas [20].
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