NAV

Trichostatin A

Identification

Generic Name
Trichostatin A
DrugBank Accession Number
DB04297
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 302.3682
Monoisotopic: 302.16304258
Chemical Formula
C17H22N2O3
Synonyms
  • TSA
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHistone deacetylase 7Not AvailableHumans
UHistone deacetylase 8Not AvailableHumans
UAcetoin utilization proteinNot AvailableAquifex aeolicus (strain VF5)
UCaspase-8
activator
Humans
UProstaglandin E2 Receptors
regulator
Humans
UTumor necrosis factor
downregulator
Humans
Absorption

Not Available

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 outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
Integrate drug-drug
interactions in your software
AmbroxolThe risk or severity of methemoglobinemia can be increased when Trichostatin A is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Trichostatin A is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Trichostatin A is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Trichostatin A is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Trichostatin A is combined with Bupivacaine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Alkyl-phenylketones
Alternative Parents
Phenylpropanes / Dialkylarylamines / Benzoyl derivatives / Aryl alkyl ketones / Aniline and substituted anilines / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Alkyl-phenylketone / Amine / Aniline or substituted anilines / Aromatic homomonocyclic compound / Aryl alkyl ketone / Benzenoid / Benzoyl / Dialkylarylamine / Hydrocarbon derivative / Monocyclic benzene moiety
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
hydroxamic acid, trichostatin (CHEBI:46024) / Linear polyketides (LMPK01000055)
Affected organisms
Not Available

Chemical Identifiers

UNII
3X2S926L3Z
CAS number
58880-19-6
InChI Key
RTKIYFITIVXBLE-QEQCGCAPSA-N
InChI
InChI=1S/C17H22N2O3/c1-12(5-10-16(20)18-22)11-13(2)17(21)14-6-8-15(9-7-14)19(3)4/h5-11,13,22H,1-4H3,(H,18,20)/b10-5+,12-11+/t13-/m1/s1
IUPAC Name
(2E,4E,6R)-7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide
SMILES
C[C@H](\C=C(/C)\C=C\C(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C

References

General References
Not Available
PubChem Compound
444732
PubChem Substance
46506659
ChemSpider
392575
BindingDB
50005711
ChEBI
46024
ChEMBL
CHEMBL99
ZINC
ZINC000100014731
PDBe Ligand
TSN
Wikipedia
Trichostatin_A
PDB Entries
1c3r / 1t64 / 3c10 / 4qa3 / 5d1b / 5edu / 5eef / 5eek / 5g0g / 5wgi …
show 4 more

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
1Unknown StatusTreatmentRelapsed or Refractory Hematologic Malignancies1

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 Solubility0.0425 mg/mLALOGPS
logP2.36ALOGPS
logP2.41Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.57Chemaxon
pKa (Strongest Basic)3.36Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area69.64 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity90.24 m3·mol-1Chemaxon
Polarizability34.06 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9575
Blood Brain Barrier+0.7176
Caco-2 permeable-0.5105
P-glycoprotein substrateNon-substrate0.6224
P-glycoprotein inhibitor INon-inhibitor0.6538
P-glycoprotein inhibitor IINon-inhibitor0.5915
Renal organic cation transporterNon-inhibitor0.9379
CYP450 2C9 substrateNon-substrate0.8562
CYP450 2D6 substrateNon-substrate0.8119
CYP450 3A4 substrateSubstrate0.5678
CYP450 1A2 substrateNon-inhibitor0.6158
CYP450 2C9 inhibitorNon-inhibitor0.6977
CYP450 2D6 inhibitorNon-inhibitor0.8863
CYP450 2C19 inhibitorNon-inhibitor0.7953
CYP450 3A4 inhibitorNon-inhibitor0.7435
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8711
Ames testAMES toxic0.6244
CarcinogenicityCarcinogens 0.6893
BiodegradationNot ready biodegradable0.9746
Rat acute toxicity2.2849 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9802
hERG inhibition (predictor II)Non-inhibitor0.8463
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0002-0930000000-a5fe2eb618c66c9c45b3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0072-0891000000-0ee7b933ce8a3c87bbbe
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-4269000000-dd7838cd330cab2418f9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-eee69ce6e53ed7521734
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052g-9760000000-648a1b69daa2528f6aed
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-007k-3920000000-d120b5d234465c46f7c8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kg-9430000000-aa08642255a1bdc4b74d
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]-201.278747
predicted
DarkChem Lite v0.1.0
[M-H]-201.433147
predicted
DarkChem Lite v0.1.0
[M-H]-174.9901
predicted
DeepCCS 1.0 (2019)
[M+H]+201.250747
predicted
DarkChem Lite v0.1.0
[M+H]+201.606447
predicted
DarkChem Lite v0.1.0
[M+H]+177.38567
predicted
DeepCCS 1.0 (2019)
[M+Na]+201.671747
predicted
DarkChem Lite v0.1.0
[M+Na]+201.565347
predicted
DarkChem Lite v0.1.0
[M+Na]+183.2982
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Histone deacetylase 7
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription corepressor activity
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
HDAC7
Uniprot ID
Q8WUI4
Uniprot Name
Histone deacetylase 7
Molecular Weight
102926.225 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details2. Histone deacetylase 8
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
HDAC8
Uniprot ID
Q9BY41
Uniprot Name
Histone deacetylase 8
Molecular Weight
41757.29 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details3. Acetoin utilization protein
Kind
Protein
Organism
Aquifex aeolicus (strain VF5)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Not Available
Gene Name
acuC1
Uniprot ID
O67135
Uniprot Name
Acetoin utilization protein
Molecular Weight
42662.46 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details4. Caspase-8
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Ubiquitin protein ligase binding
Specific Function
Most upstream protease of the activation cascade of caspases responsible for the TNFRSF6/FAS mediated and TNFRSF1A induced cell death. Binding to the adapter molecule FADD recruits it to either rec...
Gene Name
CASP8
Uniprot ID
Q14790
Uniprot Name
Caspase-8
Molecular Weight
55390.53 Da
References
  1. Komata T, Kanzawa T, Nashimoto T, Aoki H, Endo S, Kon T, Takahashi H, Kondo S, Tanaka R: Histone deacetylase inhibitors, N-butyric acid and trichostatin A, induce caspase-8- but not caspase-9-dependent apoptosis in human malignant glioma cells. Int J Oncol. 2005 May;26(5):1345-52. doi: 10.3892/ijo.26.5.1345. [Article]
Details5. Prostaglandin E2 Receptors (Protein Group)
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Regulator
General Function
Prostaglandin e receptor activity
Specific Function
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(q) proteins which activate a phosphatidylinositol-calcium second messenger system. May play a role as an importa...
Components:
NameUniProt ID
Prostaglandin E2 receptor EP1 subtypeP34995
Prostaglandin E2 receptor EP2 subtypeP43116
Prostaglandin E2 receptor EP3 subtypeP43115
Prostaglandin E2 receptor EP4 subtypeP35408
References
  1. Usami M, Kishimoto K, Ohata A, Miyoshi M, Aoyama M, Fueda Y, Kotani J: Butyrate and trichostatin A attenuate nuclear factor kappaB activation and tumor necrosis factor alpha secretion and increase prostaglandin E2 secretion in human peripheral blood mononuclear cells. Nutr Res. 2008 May;28(5):321-8. doi: 10.1016/j.nutres.2008.02.012. [Article]
Details6. Tumor necrosis factor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Downregulator
General Function
Tumor necrosis factor receptor binding
Specific Function
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct ac...
Gene Name
TNF
Uniprot ID
P01375
Uniprot Name
Tumor necrosis factor
Molecular Weight
25644.15 Da
References
  1. Usami M, Kishimoto K, Ohata A, Miyoshi M, Aoyama M, Fueda Y, Kotani J: Butyrate and trichostatin A attenuate nuclear factor kappaB activation and tumor necrosis factor alpha secretion and increase prostaglandin E2 secretion in human peripheral blood mononuclear cells. Nutr Res. 2008 May;28(5):321-8. doi: 10.1016/j.nutres.2008.02.012. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 28, 2022 04:34