Pracinostat

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
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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Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
UHistone deacetylase 1Not AvailableHumans
UHistone deacetylase 2Not AvailableHumans
UHistone deacetylase 3Not AvailableHumans
UHistone deacetylase 6Not AvailableHumans
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
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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.
DrugInteraction
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Pracinostat.
AdenosineThe risk or severity of QTc prolongation can be increased when Adenosine is combined with Pracinostat.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Pracinostat.
AlfuzosinThe risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Pracinostat.
AlimemazineThe risk or severity of QTc prolongation can be increased when Alimemazine is combined with Pracinostat.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Pracinostat hydrochlorideNot AvailableNot AvailableCHLPUMOYKYJFFH-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
PubChem Compound
49855250
PubChem Substance
347827719
ChemSpider
25027185
BindingDB
50353227
ChEBI
95071
ChEMBL
CHEMBL1851943
ZINC
ZINC000043152558
Wikipedia
Pracinostat

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentAcute Myeloid Leukemia1
2CompletedTreatmentAcute Myeloid Leukemia1
2CompletedTreatmentMetastatic Sarcoma1
2CompletedTreatmentMyelodysplastic Syndrome2
2CompletedTreatmentMyeloproliferative Disorders (MPD)2

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
PropertyValueSource
Water Solubility0.0306 mg/mLALOGPS
logP3.98ALOGPS
logP2.57Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.29Chemaxon
pKa (Strongest Basic)9.89Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area70.39 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity106.24 m3·mol-1Chemaxon
Polarizability42.85 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-0039000000-5c7422962667954f4e64
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0092000000-b8c2f9d3abea393d462a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-d452cd326eb323cd36c5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-0090000000-eae15e26fc446afc3f66
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00b9-1196000000-f1f32042c815c0e0379d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004j-1490000000-bee2ce9984ba7714acf6
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-214.3377081
predicted
DarkChem Lite v0.1.0
[M-H]-185.64342
predicted
DeepCCS 1.0 (2019)
[M+H]+215.2109081
predicted
DarkChem Lite v0.1.0
[M+H]+188.04022
predicted
DeepCCS 1.0 (2019)
[M+Na]+214.9893081
predicted
DarkChem Lite v0.1.0
[M+Na]+195.2014
predicted
DeepCCS 1.0 (2019)

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