Trimethadione (CHEM002179)

Record Information
Version1.0
Creation Date2009-07-21 20:26:40 UTC
Update Date2026-05-14 16:36:07 UTC
Accession NumberCHEM002179
Identification
Common NameTrimethadione
ClassSmall Molecule
Description
Trimethadione 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Anticonvulsant
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
TridioneKegg
TrimetadioneHMDB
TrimethadionHMDB
TrimethdioneHMDB
Abbott brand OF trimethadioneHMDB
TrimetinHMDB
TroxidoneHMDB
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 KeyIRYJRGCIQBGHIV-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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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
Concentrations
Not Available
External Links
DrugBank IDDB00347
HMDB IDHMDB0014491
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTrimethadione
Chemspider ID5374
ChEBI ID131804
PubChem Compound ID5576
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References