tacedinaline   

GtoPdb Ligand ID: 8367

Synonyms: CI-994 | CI994
Compound class: Synthetic organic
Comment: Tacedinaline inhibits the histone deacetylase enzyme HDAC1 [6], and is reported to have antitumour activity in preclinical studies [2,4-5].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 84.22
Molecular weight 269.12
XLogP 1.43
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC(=O)Nc1ccc(cc1)C(=O)Nc1ccccc1N
Isomeric SMILES CC(=O)Nc1ccc(cc1)C(=O)Nc1ccccc1N
InChI InChI=1S/C15H15N3O2/c1-10(19)17-12-8-6-11(7-9-12)15(20)18-14-5-3-2-4-13(14)16/h2-9H,16H2,1H3,(H,17,19)(H,18,20)
InChI Key VAZAPHZUAVEOMC-UHFFFAOYSA-N
No information available.
Summary of Clinical Use
Tacedinaline reached Phase 3 clinical trial as a potential treatment for advanced non-small cell lung cancer (NSCLC) and Phase 2 for multiple myeloma (MM) and advanced pancreatic cancer. Development appears to have been terminated.
Mechanism Of Action and Pharmacodynamic Effects
The HDAC inhibitor vorinostat was the first compound designed to inhibit HDACs to be approved for clinical use. HDAC inhibition increases acetylation of histone H3 and leads to downstream activation of the PI3K/Akt and MAPK/Ras signaling pathways and ultimately results in cell cycle arrest and apoptosis [3]. HDAC inhibitors are predicted to have application across a wide range of haematological and solid tumor types.