vorinostat   

GtoPdb Ligand ID: 6852

Synonyms: MK-0683 | MK0683 | SAHA | suberoylanilide hydroxamic acid | Zolinza®
vorinostat is an approved drug (FDA (2006))
Compound class: Synthetic organic
Comment: Vorinostat inhibits Class I, II and IV histone deacetylases (our pages for HDACs are available using this link).
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: vorinostat

2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 78.43
Molecular weight 264.15
XLogP 1.85
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES ONC(=O)CCCCCCC(=O)Nc1ccccc1
Isomeric SMILES ONC(=O)CCCCCCC(=O)Nc1ccccc1
InChI InChI=1S/C14H20N2O3/c17-13(15-12-8-4-3-5-9-12)10-6-1-2-7-11-14(18)16-19/h3-5,8-9,19H,1-2,6-7,10-11H2,(H,15,17)(H,16,18)
InChI Key WAEXFXRVDQXREF-UHFFFAOYSA-N
Bioactivity Comments
This drug has the highest pKi value against HDAC1. Rank order of pKi is HDAC1>HDAC2=HDAC6>HDAC3>>HDAC8>>HDAC5 [1]. HDAC1 has been tagged as the drug's primary target for data retrieval purposes only and in no way infers that this is the only target of this drug.
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
histone deacetylase 1 Hs Inhibitor Inhibition 8.9 pKi - 1
pKi 8.9 (Ki 1.3x10-9 M) [1]
histone deacetylase 2 Hs Inhibitor Inhibition 8.8 pKi - 1
pKi 8.8 (Ki 1.6x10-9 M) [1]
histone deacetylase 6 Hs Inhibitor Inhibition 8.8 pKi - 1
pKi 8.8 (Ki 1.6x10-9 M) [1]
histone deacetylase 3 Hs Inhibitor Inhibition 8.3 pKi - 1
pKi 8.3 (Ki 5x10-9 M) [1]
histone deacetylase 11 Hs Inhibitor Inhibition 7.4 pKi - 2
pKi 7.4 (Ki 3.6x10-8 M) [2]
histone deacetylase 10 Hs Inhibitor Inhibition 7.3 pKi - 2
pKi 7.3 (Ki 5x10-8 M) [2]
histone deacetylase 9 Hs Inhibitor Inhibition 7.2 pKi - 2
pKi 7.2 (Ki 6.5x10-8 M) [2]
histone deacetylase 8 Hs Inhibitor Inhibition 6.3 – 6.7 pKi - 1-2
pKi 6.3 – 6.7 (Ki 4.8x10-7 – 2.05x10-7 M) [1-2]
histone deacetylase 5 Hs Inhibitor Inhibition 5.4 pKi - 1
pKi 5.4 (Ki 3.6x10-6 M) [1]
Ligand mentioned in the following text fields