tucidinostat   Click here for help

GtoPdb Ligand ID: 8305

Synonyms: chidamide | CS-055 | CS055 | HBI-8000
Approved drug
tucidinostat is an approved drug (China)
Compound class: Synthetic organic
Comment: Tucidinostat (chidamide) is an orally active inhibitor of histone deacetylase (HDAC) enzymes [4]. It has some subtype selectivity for HDAC isoenzymes 1, 2, 3 and 10. Note that we show this compound with no specified stereochemistry.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 97.11
Molecular weight 390.15
XLogP 2.47
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES O=C(C=Cc1cccnc1)NCc1ccc(cc1)C(=O)Nc1cc(F)ccc1N
Isomeric SMILES O=C(C=Cc1cccnc1)NCc1ccc(cc1)C(=O)Nc1cc(F)ccc1N
InChI InChI=1S/C22H19FN4O2/c23-18-8-9-19(24)20(12-18)27-22(29)17-6-3-16(4-7-17)14-26-21(28)10-5-15-2-1-11-25-13-15/h1-13H,14,24H2,(H,26,28)(H,27,29)
InChI Key WXHHICFWKXDFOW-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Chidamide was developed and tested in China, where it now has regulatory approval for the treatment of cancers. Preclinical studies have shown efficacy in various types of cancer, such as pancreatic cancer [5], colon cancer [4], hepatocellular carcinoma cells [6] and leukemias [2,7]. Phase 1 clinical trial results are reported in [1]. Results from a Phase 3 study using tucidinostat plus exemestane (an aromatase inhibitor) in patients with advanced, hormone receptor-positive, HER2 negative breast cancer were published in 2019 [3]. Progression-free survival was improved using this treatment combination compared to exemestane alone.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Chidamide is an inhibitor of histone deacetylase (HDAC) activity, which increases acetylation of histone H3. This leads to downstream activation of the PI3K/Akt and MAPK/Ras signaling pathways and ultimately results in cell cycle arrest and apoptosis [4].