citarinostat   Click here for help

GtoPdb Ligand ID: 9426

Synonyms: ACY-241 | Compound (I) [WO2016200919] [2] | HDAC-IN-2
PDB Ligand
Compound class: Synthetic organic
Comment: Citarinostat (ACY-241) is a next-generation HDAC6 inhibitor, that is under investigation for potential antineoplastic activity [1]. Note that it exhibits only ~10-fold enzymic selectivity against the class I isoform, HDAC1.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 13
Topological polar surface area 107.45
Molecular weight 467.17
XLogP 4.36
No. Lipinski's rules broken 1
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Canonical SMILES ONC(=O)CCCCCCNC(=O)c1cnc(nc1)N(c1ccccc1Cl)c1ccccc1
Isomeric SMILES ONC(=O)CCCCCCNC(=O)c1cnc(nc1)N(c1ccccc1Cl)c1ccccc1
InChI InChI=1S/C24H26ClN5O3/c25-20-12-7-8-13-21(20)30(19-10-4-3-5-11-19)24-27-16-18(17-28-24)23(32)26-15-9-2-1-6-14-22(31)29-33/h3-5,7-8,10-13,16-17,33H,1-2,6,9,14-15H2,(H,26,32)(H,29,31)
Bioactivity Comments
In vitro combination treatment of MiaPaCa-2 pancreatic cancer, TOV-21G ovarian cancer, and T47D breast cancer cells (with the tubulin inhibitor paclitaxel) more efficiently reduces proliferation and enhances apoptosis than single agent exposure [1]. In vivo, ACY-421 + paclitaxel inhibits tumor xenograft growth.
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
histone deacetylase 6 Primary target of this compound Hs Inhibitor Inhibition 8.6 pIC50 - 1
pIC50 8.6 (IC50 2.6x10-9 M) [1]
histone deacetylase 1 Hs Inhibitor Inhibition 7.5 pIC50 - 1
pIC50 7.5 (IC50 3.5x10-8 M) [1]
histone deacetylase 2 Hs Inhibitor Inhibition 7.3 pIC50 - 1
pIC50 7.3 (IC50 4.5x10-8 M) [1]
histone deacetylase 3 Hs Inhibitor Inhibition 7.3 pIC50 - 1
pIC50 7.3 (IC50 4.6x10-8 M) [1]
histone deacetylase 8 Hs Inhibitor Inhibition 6.9 pIC50 - 1
pIC50 6.9 (IC50 1.37x10-7 M) [1]