Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Trichostatin A
- DrugBank Accession Number
- DB04297
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Trichostatin A (DB04297)
- Weight
- Average: 302.3682
Monoisotopic: 302.16304258 - Chemical Formula
- C17H22N2O3
- Synonyms
- TSA
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UHistone deacetylase 7 Not Available Humans UHistone deacetylase 8 Not Available Humans UAcetoin utilization protein Not Available Aquifex aeolicus (strain VF5) UCaspase-8 activatorHumans UProstaglandin E2 Receptors regulatorHumans UTumor necrosis factor downregulatorHumans - 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 outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!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 softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Trichostatin A is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Trichostatin A is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Trichostatin A is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Trichostatin A is combined with Benzyl alcohol. Bupivacaine The 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
- External Links
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data1 Unknown Status Treatment Relapsed or Refractory Hematologic Malignancies 1 somestatus stop reason just information to hide
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 0.0425 mg/mL ALOGPS logP 2.36 ALOGPS logP 2.41 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 9.57 Chemaxon pKa (Strongest Basic) 3.36 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 69.64 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 90.24 m3·mol-1 Chemaxon Polarizability 34.06 Å3 Chemaxon Number of Rings 1 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
Property Value Probability Human Intestinal Absorption + 0.9575 Blood Brain Barrier + 0.7176 Caco-2 permeable - 0.5105 P-glycoprotein substrate Non-substrate 0.6224 P-glycoprotein inhibitor I Non-inhibitor 0.6538 P-glycoprotein inhibitor II Non-inhibitor 0.5915 Renal organic cation transporter Non-inhibitor 0.9379 CYP450 2C9 substrate Non-substrate 0.8562 CYP450 2D6 substrate Non-substrate 0.8119 CYP450 3A4 substrate Substrate 0.5678 CYP450 1A2 substrate Non-inhibitor 0.6158 CYP450 2C9 inhibitor Non-inhibitor 0.6977 CYP450 2D6 inhibitor Non-inhibitor 0.8863 CYP450 2C19 inhibitor Non-inhibitor 0.7953 CYP450 3A4 inhibitor Non-inhibitor 0.7435 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8711 Ames test AMES toxic 0.6244 Carcinogenicity Carcinogens 0.6893 Biodegradation Not ready biodegradable 0.9746 Rat acute toxicity 2.2849 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9802 hERG inhibition (predictor II) Non-inhibitor 0.8463
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0002-0930000000-a5fe2eb618c66c9c45b3 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0072-0891000000-0ee7b933ce8a3c87bbbe Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-4269000000-dd7838cd330cab2418f9 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0900000000-eee69ce6e53ed7521734 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-052g-9760000000-648a1b69daa2528f6aed Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-007k-3920000000-d120b5d234465c46f7c8 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00kg-9430000000-aa08642255a1bdc4b74d Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 201.278747 predictedDarkChem Lite v0.1.0 [M-H]- 201.433147 predictedDarkChem Lite v0.1.0 [M-H]- 174.9901 predictedDeepCCS 1.0 (2019) [M+H]+ 201.250747 predictedDarkChem Lite v0.1.0 [M+H]+ 201.606447 predictedDarkChem Lite v0.1.0 [M+H]+ 177.38567 predictedDeepCCS 1.0 (2019) [M+Na]+ 201.671747 predictedDarkChem Lite v0.1.0 [M+Na]+ 201.565347 predictedDarkChem Lite v0.1.0 [M+Na]+ 183.2982 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4) (By similarity). Histone deacetylation gives a tag for epigenetic repression and plays an important role in transcriptional regulation, cell cycle progression and developmental events (By similarity). Histone deacetylases act via the formation of large multiprotein complexes (By similarity). Involved in muscle maturation by repressing transcription of myocyte enhancer factors such as MEF2A, MEF2B and MEF2C (By similarity). During muscle differentiation, it shuttles into the cytoplasm, allowing the expression of myocyte enhancer factors (By similarity). May be involved in Epstein-Barr virus (EBV) latency, possibly by repressing the viral BZLF1 gene (PubMed:12239305). Positively regulates the transcriptional repressor activity of FOXP3 (PubMed:17360565). Serves as a corepressor of RARA, causing its deacetylation and inhibition of RARE DNA element binding (PubMed:28167758). In association with RARA, plays a role in the repression of microRNA-10a and thereby in the inflammatory response (PubMed:28167758). Also acetylates non-histone proteins, such as ALKBH5 (PubMed:37369679)
- Specific Function
- 14-3-3 protein binding
- Gene Name
- HDAC7
- Uniprot ID
- Q8WUI4
- Uniprot Name
- Histone deacetylase 7
- Molecular Weight
- 102926.225 Da
References
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Histone deacetylase that catalyzes the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4) (PubMed:10748112, PubMed:10922473, PubMed:10926844, PubMed:14701748, PubMed:28497810). Histone deacetylation gives a tag for epigenetic repression and plays an important role in transcriptional regulation, cell cycle progression and developmental events (PubMed:10748112, PubMed:10922473, PubMed:10926844, PubMed:14701748). Histone deacetylases act via the formation of large multiprotein complexes (PubMed:10748112, PubMed:10922473, PubMed:10926844, PubMed:14701748). Also involved in the deacetylation of cohesin complex protein SMC3 regulating release of cohesin complexes from chromatin (PubMed:22885700). May play a role in smooth muscle cell contractility (PubMed:15772115). In addition to protein deacetylase activity, also has protein-lysine deacylase activity: acts as a protein decrotonylase by mediating decrotonylation ((2E)-butenoyl) of histones (PubMed:28497810)
- Specific Function
- Dna-binding transcription factor binding
- Gene Name
- HDAC8
- Uniprot ID
- Q9BY41
- Uniprot Name
- Histone deacetylase 8
- Molecular Weight
- 41757.29 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- 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
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Activator
- General Function
- Thiol protease that plays a key role in programmed cell death by acting as a molecular switch for apoptosis, necroptosis and pyroptosis, and is required to prevent tissue damage during embryonic development and adulthood (PubMed:23516580, PubMed:35338844, PubMed:35446120, PubMed:8681376, PubMed:8681377, PubMed:8962078, PubMed:9006941, PubMed:9184224). Initiator protease that induces extrinsic apoptosis by mediating cleavage and activation of effector caspases responsible for FAS/CD95-mediated and TNFRSF1A-induced cell death (PubMed:23516580, PubMed:35338844, PubMed:35446120, PubMed:8681376, PubMed:8681377, PubMed:8962078, PubMed:9006941, PubMed:9184224). Cleaves and activates effector caspases CASP3, CASP4, CASP6, CASP7, CASP9 and CASP10 (PubMed:16916640, PubMed:8962078, PubMed:9006941). Binding to the adapter molecule FADD recruits it to either receptor FAS/TNFRSF6 or TNFRSF1A (PubMed:8681376, PubMed:8681377). The resulting aggregate called the death-inducing signaling complex (DISC) performs CASP8 proteolytic activation (PubMed:9184224). The active dimeric enzyme is then liberated from the DISC and free to activate downstream apoptotic proteases (PubMed:9184224). Proteolytic fragments of the N-terminal propeptide (termed CAP3, CAP5 and CAP6) are likely retained in the DISC (PubMed:9184224). In addition to extrinsic apoptosis, also acts as a negative regulator of necroptosis: acts by cleaving RIPK1 at 'Asp-324', which is crucial to inhibit RIPK1 kinase activity, limiting TNF-induced apoptosis, necroptosis and inflammatory response (PubMed:31827280, PubMed:31827281). Also able to initiate pyroptosis by mediating cleavage and activation of gasdermin-C and -D (GSDMC and GSDMD, respectively): gasdermin cleavage promotes release of the N-terminal moiety that binds to membranes and forms pores, triggering pyroptosis (PubMed:32929201, PubMed:34012073). Initiates pyroptosis following inactivation of MAP3K7/TAK1 (By similarity). Also acts as a regulator of innate immunity by mediating cleavage and inactivation of N4BP1 downstream of TLR3 or TLR4, thereby promoting cytokine production (By similarity). May participate in the Granzyme B (GZMB) cell death pathways (PubMed:8755496). Cleaves PARP1 and PARP2 (PubMed:8681376). Independent of its protease activity, promotes cell migration following phosphorylation at Tyr-380 (PubMed:18216014, PubMed:27109099)
- Specific Function
- Cysteine-type endopeptidase activity
- Gene Name
- CASP8
- Uniprot ID
- Q14790
- Uniprot Name
- Caspase-8
- Molecular Weight
- 55390.53 Da
References
- 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]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Regulator
- General 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 important modulator of renal function. Implicated the smooth muscle contractile response to PGE2 in various tissues
- Specific Function
- D1 dopamine receptor binding
Components:
| Name | UniProt ID |
|---|---|
| Prostaglandin E2 receptor EP1 subtype | P34995 |
| Prostaglandin E2 receptor EP2 subtype | P43116 |
| Prostaglandin E2 receptor EP3 subtype | P43115 |
| Prostaglandin E2 receptor EP4 subtype | P35408 |
References
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Downregulator
- General 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 action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation. Impairs regulatory T-cells (Treg) function in individuals with rheumatoid arthritis via FOXP3 dephosphorylation. Up-regulates the expression of protein phosphatase 1 (PP1), which dephosphorylates the key 'Ser-418' residue of FOXP3, thereby inactivating FOXP3 and rendering Treg cells functionally defective (PubMed:23396208). Key mediator of cell death in the anticancer action of BCG-stimulated neutrophils in combination with DIABLO/SMAC mimetic in the RT4v6 bladder cancer cell line (PubMed:16829952, PubMed:22517918, PubMed:23396208). Induces insulin resistance in adipocytes via inhibition of insulin-induced IRS1 tyrosine phosphorylation and insulin-induced glucose uptake. Induces GKAP42 protein degradation in adipocytes which is partially responsible for TNF-induced insulin resistance (By similarity). Plays a role in angiogenesis by inducing VEGF production synergistically with IL1B and IL6 (PubMed:12794819). Promotes osteoclastogenesis and therefore mediates bone resorption (By similarity)
- Specific Function
- Cytokine activity
- Gene Name
- TNF
- Uniprot ID
- P01375
- Uniprot Name
- Tumor necrosis factor
- Molecular Weight
- 25644.15 Da
References
- 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