glibenclamide   

GtoPdb Ligand ID: 2414

Synonyms: Amglidia® | Diabeta® | glyburide | Glynase®
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 [8].
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2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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)
InChI Key ZNNLBTZKUZBEKO-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (as glyburide, 1984), EMA (2018))
IUPAC Name
5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide
International Nonproprietary Names
INN number INN
2386 glibenclamide
Synonyms
Amglidia® | Diabeta® | glyburide | Glynase®
Database Links
BindingDB Ligand 50012957
CAS Registry No. 10238-21-8
ChEBI CHEBI:5441
ChEMBL Ligand CHEMBL472
DrugBank Ligand DB01016
DrugCentral Ligand 1314
GtoPdb PubChem SID 135650306
PubChem CID 3488
RCSB PDB Ligand GBM
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Search UniChem for chemical match using the InChIKey ZNNLBTZKUZBEKO-UHFFFAOYSA-N
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Wikipedia Glibenclamide

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Tocris
Glibenclamide
Cat. No. 0911