refametinib   Click here for help

GtoPdb Ligand ID: 7942

Synonyms: BAY-869766 | RDEA119
PDB Ligand
Compound class: Synthetic organic
Comment: Refametinib (BAY-869766) is a potent and selective, allosteric inhibitor of MEK1/2 with potential antineoplastic activity [1]. This compound is available via AstraZeneca's openinnovation toolbox resource, which indicates that refametinib is associated with a risk of fetal toxicity.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 9
Topological polar surface area 116.27
Molecular weight 572.01
XLogP 3.2
No. Lipinski's rules broken 0
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Canonical SMILES OCC(CC1(CC1)S(=O)(=O)Nc1c(OC)cc(c(c1Nc1ccc(cc1F)I)F)F)O
Isomeric SMILES OC[C@H](CC1(CC1)S(=O)(=O)Nc1c(OC)cc(c(c1Nc1ccc(cc1F)I)F)F)O
InChI InChI=1S/C19H20F3IN2O5S/c1-30-15-7-13(21)16(22)18(24-14-3-2-10(23)6-12(14)20)17(15)25-31(28,29)19(4-5-19)8-11(27)9-26/h2-3,6-7,11,24-27H,4-5,8-9H2,1H3/t11-/m0/s1
1. Iverson C, Larson G, Lai C, Yeh LT, Dadson C, Weingarten P, Appleby T, Vo T, Maderna A, Vernier JM et al.. (2009)
RDEA119/BAY 869766: a potent, selective, allosteric inhibitor of MEK1/2 for the treatment of cancer.
Cancer Res, 69 (17): 6839-47. [PMID:19706763]
2. Weekes CD, Von Hoff DD, Adjei AA, Leffingwell DP, Eckhardt SG, Gore L, Lewis KD, Weiss GJ, Ramanathan RK, Dy GK et al.. (2013)
Multicenter phase I trial of the mitogen-activated protein kinase 1/2 inhibitor BAY 86-9766 in patients with advanced cancer.
Clin Cancer Res, 19 (5): 1232-43. [PMID:23434733]