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.
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2D Structure
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Physico-chemical Properties
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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
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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
1. Wängler B, Beck C, Shiue CY, Schneider S, Schwanstecher C, Schwanstecher M, Feilen PJ, Alavi A, Rösch F, Schirrmacher R. (2004)
Synthesis and in vitro evaluation of (S)-2-([11C]methoxy)-4-[3-methyl-1-(2-piperidine-1-yl-phenyl)-butyl-carbamoyl]-benzoic acid ([11C]methoxy-repaglinide): a potential beta-cell imaging agent.
Bioorg Med Chem Lett, 14 (20): 5205-9. [PMID:15380228]