Identification
- Generic Name
- Pracinostat
- DrugBank Accession Number
- DB05223
- Background
Pracinostat is a novel HDAC inhibitor with improved in vivo properties compared to other HDAC inhibitors currently in clinical trials, allowing oral dosing. Data demonstrate that Pracinostat is a potent and effective anti-tumor drug with potential as an oral therapy for a variety of human hematological and solid tumors.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Pracinostat (DB05223)
- Weight
- Average: 358.486
Monoisotopic: 358.236876222 - Chemical Formula
- C20H30N4O2
- Synonyms
- Pracinostat
- Pracinostatum
- External IDs
- SB 939
- SB-939
- SB939
Pharmacology
- Indication
For the treatment of various forms of cancer.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
SB939 is a novel compound with superior pharmaceutical, metabolic and pharmacokinetic properties. SB939 has demonstrated excellent in vivo anti-tumour activity in various animal models with dose proportional pharmacodynamic effects. The pharmacokinetics and pharmacodynamic attributes of SB939 explain and differentiate it as the best in class HDAC inhibitor.
- Mechanism of action
Inhibition of HDAC activity allows for the accumulation of acetyl groups on the histone lysine residues resulting in an open chromatin structure and transcriptional activation. In vitro, SB939 causes the accumulation of acetylated histones and induces cell cycle arrest and/or apoptosis of some transformed cells. The mechanism of the antineoplastic effect of SB939 has not been fully characterized.
Target Actions Organism UHistone deacetylase 1 Not Available Humans UHistone deacetylase 2 Not Available Humans UHistone deacetylase 3 Not Available Humans UHistone deacetylase 6 Not Available Humans - Absorption
Oral bioavailability in mice is 34%.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Pracinostat. Adenosine The risk or severity of QTc prolongation can be increased when Adenosine is combined with Pracinostat. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Pracinostat. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Pracinostat. Alimemazine The risk or severity of QTc prolongation can be increased when Alimemazine is combined with Pracinostat. Amantadine The risk or severity of QTc prolongation can be increased when Amantadine is combined with Pracinostat. Ambroxol The risk or severity of methemoglobinemia can be increased when Pracinostat is combined with Ambroxol. Amifampridine The risk or severity of QTc prolongation can be increased when Pracinostat is combined with Amifampridine. Amiodarone The risk or severity of QTc prolongation can be increased when Pracinostat is combined with Amiodarone. Amisulpride The risk or severity of QTc prolongation can be increased when Pracinostat is combined with Amisulpride. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Pracinostat hydrochloride Not Available Not Available CHLPUMOYKYJFFH-PFNYCKIMSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Cinnamic acids and derivatives
- Sub Class
- Not Available
- Direct Parent
- Cinnamic acids and derivatives
- Alternative Parents
- Benzimidazoles / Styrenes / N-substituted imidazoles / Heteroaromatic compounds / Trialkylamines / Hydroxamic acids / Amino acids and derivatives / Azacyclic compounds / Organic oxides / Hydrocarbon derivatives show 1 more
- Substituents
- Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzimidazole / Carbonyl group / Carboxylic acid derivative / Cinnamic acid or derivatives show 14 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- GPO2JN4UON
- CAS number
- 929016-96-6
- InChI Key
- JHDKZFFAIZKUCU-ZRDIBKRKSA-N
- InChI
- InChI=1S/C20H30N4O2/c1-4-7-8-19-21-17-15-16(10-12-20(25)22-26)9-11-18(17)24(19)14-13-23(5-2)6-3/h9-12,15,26H,4-8,13-14H2,1-3H3,(H,22,25)/b12-10+
- IUPAC Name
- (2E)-3-{2-butyl-1-[2-(diethylamino)ethyl]-1H-1,3-benzodiazol-5-yl}-N-hydroxyprop-2-enamide
- SMILES
- CCCCC1=NC2=C(C=CC(\C=C\C(=O)NO)=C2)N1CCN(CC)CC
References
- General References
- Not Available
- External Links
- PubChem Compound
- 49855250
- PubChem Substance
- 347827719
- ChemSpider
- 25027185
- BindingDB
- 50353227
- ChEBI
- 95071
- ChEMBL
- CHEMBL1851943
- ZINC
- ZINC000043152558
- Wikipedia
- Pracinostat
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Terminated Treatment Acute Myeloid Leukemia 1 2 Completed Treatment Acute Myeloid Leukemia 1 2 Completed Treatment Metastatic Sarcoma 1 2 Completed Treatment Myelodysplastic Syndrome 2 2 Completed Treatment Myeloproliferative Disorders (MPD) 2 2 Completed Treatment Prostate Cancer 1 2 Terminated Treatment Myelodysplastic Syndrome 1 1 Completed Other Healthy Subjects (HS) 1 1 Completed Other Healthy Subjects (HS) / Non-Smokers 1 1 Completed Treatment Hematological Malignancy / Myelodysplastic Syndrome / Solid Tumors 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0306 mg/mL ALOGPS logP 3.98 ALOGPS logP 2.57 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) 9.29 Chemaxon pKa (Strongest Basic) 9.89 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 70.39 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 106.24 m3·mol-1 Chemaxon Polarizability 42.85 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcription regulatory region sequence-specific dna binding
- Specific Function
- Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
- Gene Name
- HDAC1
- Uniprot ID
- Q13547
- Uniprot Name
- Histone deacetylase 1
- Molecular Weight
- 55102.615 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcription factor binding
- Specific Function
- Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
- Gene Name
- HDAC2
- Uniprot ID
- Q92769
- Uniprot Name
- Histone deacetylase 2
- Molecular Weight
- 55363.855 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcription factor binding
- Specific Function
- Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4), and some other non-histone substrates. Histone deacetylation gives a tag for ...
- Gene Name
- HDAC3
- Uniprot ID
- O15379
- Uniprot Name
- Histone deacetylase 3
- Molecular Weight
- 48847.385 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
- Gene Name
- HDAC6
- Uniprot ID
- Q9UBN7
- Uniprot Name
- Histone deacetylase 6
- Molecular Weight
- 131418.19 Da
Drug created at October 21, 2007 22:24 / Updated at January 14, 2023 19:03