acetohexamide   Click here for help

GtoPdb Ligand ID: 6793

Synonyms: Dymelor®
Approved drug
acetohexamide is an approved drug (FDA (1964))
Compound class: Synthetic organic
Comment: A sulfonylurea family drug.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 100.72
Molecular weight 324.11
XLogP 2.96
No. Lipinski's rules broken 0
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Canonical SMILES O=C(NS(=O)(=O)c1ccc(cc1)C(=O)C)NC1CCCCC1
Isomeric SMILES O=C(NS(=O)(=O)c1ccc(cc1)C(=O)C)NC1CCCCC1
InChI InChI=1S/C15H20N2O4S/c1-11(18)12-7-9-14(10-8-12)22(20,21)17-15(19)16-13-5-3-2-4-6-13/h7-10,13H,2-6H2,1H3,(H2,16,17,19)
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Summary of Clinical Use Click here for help
Used in the management of diabetes mellitus type 2
Mechanism Of Action and Pharmacodynamic Effects Click here for help
A sulfonylurea hypoglycemic agent hepatically metabolized to 1-hydrohexamide. Lowers blood sugar by stimulating the pancreatic β cells to secrete insulin and use it efficiently.
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) [3]. SUR2 (ABCC9) has also been identified [1]. 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 [2]. Co-expression of Kir6.2 with SUR1, reconstitutes the ATP-dependent K+ conductivity inhibited by the sulfonyureas [1].