Tmic
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Record Information
Version2.0
Creation Date2009-07-21 20:26:40 UTC
Update Date2014-12-24 20:25:51 UTC
Accession NumberT3D2760
Identification
Common NameTrimethadione
ClassSmall Molecule
DescriptionTrimethadione is only found in individuals that have used or taken this drug. It is an anticonvulsant effective in absence seizures, but generally reserved for refractory cases because of its toxicity. (From AMA Drug Evaluations Annual, 1994, p378) Trimethadione reduces T-type calcium currents in thalamic neurons, including thalamic relay neurons. It does so via the inhibition of voltage dependent T-type calcium channels. This raises the threshold for repetitive activity in the thalamus, and inhibits corticothalamic transmission. Thus, the abnormal thalamocortical rhythmicity, which is thought to underlie the 3-Hz spike-and-wave discharge seen on electroencephalogram(EEG) with absence seizures, is dampened.
Compound Type
  • Amide
  • Amine
  • Anticonvulsant
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Minoale
Tridione
Trimetadione
Trimethadion
Triméthadione
Trimethadionum
Trimethdione
Trimethinum
Troxidone
Chemical FormulaC6H9NO3
Average Molecular Mass143.141 g/mol
Monoisotopic Mass143.058 g/mol
CAS Registry Number127-48-0
IUPAC Nametrimethyl-1,3-oxazolidine-2,4-dione
Traditional Nametrimethadione
SMILESCN1C(=O)OC(C)(C)C1=O
InChI IdentifierInChI=1S/C6H9NO3/c1-6(2)4(8)7(3)5(9)10-6/h1-3H3
InChI KeyInChIKey=IRYJRGCIQBGHIV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oxazolidinediones. Oxazolidinediones are compounds containing an oxazolidine ring which bears two ketones.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassOxazolidines
Direct ParentOxazolidinediones
Alternative Parents
Substituents
  • Oxazolidinedione
  • Dicarboximide
  • Carbamic acid ester
  • Carbonic acid derivative
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point46°C
Boiling PointNot Available
Solubility5E+004 mg/L
LogP0
Predicted Properties
PropertyValueSource
Water Solubility212 g/LALOGPS
logP0.07ALOGPS
logP0.5ChemAxon
logS0.17ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.61 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.2 m³·mol⁻¹ChemAxon
Polarizability13.59 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-8900000000-43db0866b0f6797cbff6View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0006-1900000000-5560efcfc7260e1dcfefView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-8900000000-43db0866b0f6797cbff6View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0006-1900000000-5560efcfc7260e1dcfefView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9100000000-88bba4b2f392389bb2d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-cadbfe428b3321b1cc08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-5ed5d9dd884dba589024View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-d3d40f4617407850f4a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2900000000-0d39e71814a5ed15503fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-6900000000-690c1be64c11bb697283View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-79613f1372991c39908aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9200000000-46082deb9c636fb8f625View in MoNA
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityDione anticonvulsants reduce T-type calcium currents in thalamic neurons, including thalamic relay neurons. It does so via the inhibition of voltage dependent T-type calcium channels. This raises the threshold for repetitive activity in the thalamus, and inhibits corticothalamic transmission. Thus, the abnormal thalamocortical rhythmicity, which is thought to underlie the 3-Hz spike-and-wave discharge seen on electroencephalogram(EEG) with absence seizures, is dampened.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed in the control of absence (petit mal) seizures that are refractory to treatment with other medications.
Minimum Risk LevelNot Available
Health EffectsMay cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.
SymptomsSymptoms of overdose include clumsiness or unsteadiness, coma, dizziness (severe), drowsiness (severe), nausea (severe), and problems with vision.
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00347
HMDB IDHMDB14491
PubChem Compound ID5576
ChEMBL IDCHEMBL695
ChemSpider ID5374
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID131804
BioCyc IDNot Available
CTD IDNot Available
Stitch IDTrimethadione
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkTrimethadione
References
Synthesis ReferenceNot Available
MSDST3D2760.pdf
General References
  1. Drugs.com [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Scaffold protein binding
Specific Function:
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1G gives rise to T-type calcium currents. T-type calcium channels belong to the "low-voltage activated (LVA)" group and are strongly blocked by mibefradil. A particularity of this type of channel is an opening at quite negative potentials and a voltage-dependent inactivation. T-type channels serve pacemaking functions in both central neurons and cardiac nodal cells and support calcium signaling in secretory cells and vascular smooth muscle. They may also be involved in the modulation of firing patterns of neurons which is important for information processing as well as in cell growth processes.
Gene Name:
CACNA1G
Uniprot ID:
O43497
Molecular Weight:
262468.62 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. [17139284 ]
  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. [17016423 ]