repaglinide   Click here for help

GtoPdb Ligand ID: 6841

Synonyms: (-)-repaglinide | AGEE-623ZW | Prandin®
Approved drug PDB Ligand
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.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: repaglinide

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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 Click here for help
Used to treat diabetes mellitus type 2, often as adjunct to diet and exercise, to improve glycemic control
Mechanism Of Action and Pharmacodynamic Effects Click here for help
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.
External links Click here for help