Thenoyltrifluoroacetone

Identification

Generic Name
Thenoyltrifluoroacetone
DrugBank Accession Number
DB04795
Background

Thenoyltrifluoroacetone is a chelating agent and inhibitor of cellular respiration.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 222.184
Monoisotopic: 221.996234709
Chemical Formula
C8H5F3O2S
Synonyms
  • 1-Thenoyl-3,3,3-trifluoroacetone
  • 1,1,1-Trifluoro-3-(2-thenoyl)acetone
  • 2-Thenoyltrifluoroacetone
  • alpha-Thenoyltrifluoroacetone
  • Perfluoroacetyl(2-thenoyl)methane

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Studies indicate that thenoyltrifluoroacetone is a potent inhibitor of carboxylesterase activity, in addition to its ability to inhibit mitochondrial complex II activity.

Mechanism of action
TargetActionsOrganism
ULiver carboxylesterase 1Not AvailableHumans
USuccinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrialNot AvailableHumans
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
Medicalerrors
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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
Technetium Tc-99m oxidronateThenoyltrifluoroacetone may decrease effectiveness of Technetium Tc-99m oxidronate as a diagnostic agent.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Aryl alkyl ketones
Alternative Parents
Beta-diketones / Thiophenes / Heteroaromatic compounds / Alpha-haloketones / Organofluorides / Organic oxides / Hydrocarbon derivatives / Alkyl fluorides
Substituents
1,3-dicarbonyl compound / 1,3-diketone / Alkyl fluoride / Alkyl halide / Alpha-haloketone / Aromatic heteromonocyclic compound / Aryl alkyl ketone / Heteroaromatic compound / Hydrocarbon derivative / Organic oxide
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
MYQ9MNW7NI
CAS number
326-91-0
InChI Key
TXBBUSUXYMIVOS-UHFFFAOYSA-N
InChI
InChI=1S/C8H5F3O2S/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2
IUPAC Name
4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione
SMILES
FC(F)(F)C(=O)CC(=O)C1=CC=CS1

References

General References
  1. Zhang JG, Fariss MW: Thenoyltrifluoroacetone, a potent inhibitor of carboxylesterase activity. Biochem Pharmacol. 2002 Feb 15;63(4):751-4. [Article]
PubChem Compound
5601
PubChem Substance
46504456
ChemSpider
5399
ChEMBL
CHEMBL1236433
ZINC
ZINC000100004957
PDBe Ligand
TTF
Wikipedia
Thenoyltrifluoroacetone
PDB Entries
1zp0 / 6myp

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)42 °CPhysProp
boiling point (°C)96-98 °C at 8.00E+00 mm HgPhysProp
logP1.46HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0752 mg/mLALOGPS
logP2.37ALOGPS
logP2.8ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)7.17ChemAxon
pKa (Strongest Basic)-8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity44.26 m3·mol-1ChemAxon
Polarizability16.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9964
Caco-2 permeable+0.537
P-glycoprotein substrateNon-substrate0.8104
P-glycoprotein inhibitor INon-inhibitor0.7748
P-glycoprotein inhibitor IINon-inhibitor0.783
Renal organic cation transporterNon-inhibitor0.8788
CYP450 2C9 substrateNon-substrate0.8094
CYP450 2D6 substrateNon-substrate0.8448
CYP450 3A4 substrateNon-substrate0.7506
CYP450 1A2 substrateNon-inhibitor0.6133
CYP450 2C9 inhibitorInhibitor0.582
CYP450 2D6 inhibitorNon-inhibitor0.7097
CYP450 2C19 inhibitorInhibitor0.7893
CYP450 3A4 inhibitorNon-inhibitor0.7544
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5302
Ames testNon AMES toxic0.5586
CarcinogenicityNon-carcinogens0.6418
BiodegradationNot ready biodegradable0.8573
Rat acute toxicity2.7650 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9736
hERG inhibition (predictor II)Non-inhibitor0.9203
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.36 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da
References
  1. Zhang JG, Fariss MW: Thenoyltrifluoroacetone, a potent inhibitor of carboxylesterase activity. Biochem Pharmacol. 2002 Feb 15;63(4):751-4. [Article]
  2. 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
Succinate dehydrogenase activity
Specific Function
Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate ...
Gene Name
SDHA
Uniprot ID
P31040
Uniprot Name
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial
Molecular Weight
72690.975 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]

Drug created on September 11, 2007 17:49 / Updated on June 12, 2020 16:52