GtoPdb Ligand ID: 6841

Synonyms: (-)-repaglinide | AGEE-623ZW | Prandin®
repaglinide is an approved drug (FDA (1997), EMA (1998))
Compound class: Synthetic organic
Comment: A sulfonylurea receptor 1, Kir6.2 blocker, belonging to the metiglinides drug family.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 78.87
Molecular weight 452.27
XLogP 6.06
No. Lipinski's rules broken 1
Canonical SMILES CCOc1cc(ccc1C(=O)O)CC(=O)NC(c1ccccc1N1CCCCC1)CC(C)C
Isomeric SMILES CCOc1cc(ccc1C(=O)O)CC(=O)N[C@H](c1ccccc1N1CCCCC1)CC(C)C
InChI InChI=1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1
No information available.
Summary of Clinical Use
Used to treat diabetes mellitus type 2, often as adjunct to diet and exercise, to improve glycemic control
Mechanism Of Action and Pharmacodynamic Effects
A meglitinide class drug, a short-acting insulin secretagogue. Action is dependent on the presence functioning β cells and glucose. Repaglinide increases insulin release by inhibiting ATP-sensitive potassium channels in a glucose-dependent manner.
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