quisinostat   Click here for help

GtoPdb Ligand ID: 7503

Synonyms: JNJ-26481585
PDB Ligand Antimalarial Ligand
Compound class: Synthetic organic
Comment: Quisinostat is an HDAC inhibitor. The compound has highest potency for HDAC1 and modest potency with HDACs 2, 4, 10, and 11. Quisinostat exhibits >30-fold selectivity against HDACs 3, 5, 8, and 9, with lowest potency for HDACs 6 and 7 [1].

The compound also has antimalarial activity [2]. The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 95.31
Molecular weight 394.21
XLogP 2.23
No. Lipinski's rules broken 0
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Canonical SMILES ONC(=O)c1cnc(nc1)N1CCC(CC1)CNCc1cn(c2c1cccc2)C
Isomeric SMILES ONC(=O)c1cnc(nc1)N1CCC(CC1)CNCc1cn(c2c1cccc2)C
InChI InChI=1S/C21H26N6O2/c1-26-14-17(18-4-2-3-5-19(18)26)11-22-10-15-6-8-27(9-7-15)21-23-12-16(13-24-21)20(28)25-29/h2-5,12-15,22,29H,6-11H2,1H3,(H,25,28)
1. Arts J, King P, Mariën A, Floren W, Beliën A, Janssen L, Pilatte I, Roux B, Decrane L, Gilissen R et al.. (2009)
JNJ-26481585, a novel "second-generation" oral histone deacetylase inhibitor, shows broad-spectrum preclinical antitumoral activity.
Clin Cancer Res, 15 (22): 6841-51. [PMID:19861438]
2. Huang Z, Li R, Tang T, Ling D, Wang M, Xu D, Sun M, Zheng L, Zhu F, Min H et al.. (2020)
A novel multistage antiplasmodial inhibitor targeting Plasmodium falciparum histone deacetylase 1.
Cell Discov, 6 (1): 93. [PMID:33311461]
3. Stühmer T, Arts J, Chatterjee M, Borawski J, Wolff A, King P, Einsele H, Leo E, Bargou RC. (2010)
Preclinical anti-myeloma activity of the novel HDAC-inhibitor JNJ-26481585.
Br J Haematol, 149 (4): 529-36. [PMID:20331455]
4. Tong WG, Wei Y, Stevenson W, Kuang SQ, Fang Z, Zhang M, Arts J, Garcia-Manero G. (2010)
Preclinical antileukemia activity of JNJ-26481585, a potent second-generation histone deacetylase inhibitor.
Leuk Res, 34 (2): 221-8. [PMID:19682743]
5. Wang M, Tang T, Li R, Huang Z, Ling D, Zheng L, Ding Y, Liu T, Xu W, Zhu F et al.. (2022)
Drug Repurposing of Quisinostat to Discover Novel Plasmodium falciparum HDAC1 Inhibitors with Enhanced Triple-Stage Antimalarial Activity and Improved Safety.
J Med Chem, 65 (5): 4156-4181. [PMID:35175762]