Basic information
- CAS
127-48-0- Standard SMILES
CN1C(=O)OC(C)(C)C1=O- InChIKey
IRYJRGCIQBGHIV-UHFFFAOYSA-N- Molecular formula
- C6H9NO3
- Average molar mass
- 143.14 g/mol
- Monoisotopic mass
- 143.05824315
Overview
Trimethadione can cause developmental toxicity according to state or federal government labeling requirements.
Names & identifiers
- Preferred name
- Trimethadione
- IUPAC
- 3,5,5-trimethyl-1,3-oxazolidine-2,4-dione
- English name
- 3,5,5-Trimethyloxazolidine-2,4-dione
- Molecular formula
- C6H9NO3
- Molecular weight
- 143.14
Names & synonyms
trimethadione127-48-0TridioneTroxidoneTrimethadionAbsentolEpidioneTrimetadioneMinoaleviatinPtimalConvenixaPetimalin
Show more names
a2297A 2297PitmalEpidoneEtydionPetidon
AbsetilEpixalPetilepEdionTridone3,5,5-Trimethyl-1,3-oxazolidine-2,4-dioneTrimetadionaTrimethadionum
Database identifiers
- CAS
127-48-0- PubChem CID
- 5576
- DTXSID
DTXSID9021396- ChEMBL
CHEMBL695- ChEBI
CHEBI:9727- UNII
- R7GV3H6FQ4
- EC Number
- 204-845-8
- Nikkaji
- J2.519D
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 46.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 197
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antiepileptics
SpringerMaterials PropertiesCrystal structure
LogP-0.37
Solubility
2.12e+02 g/L
<0.3 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point46 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 45 · 45-46°C
- Boiling point
- 78 · 78-80°C 5mm
- Density
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H312 (87%): Harmful in contact with skin [Warning Acute toxicity, dermal]
P203, P261, P271, P280, P302+P352, P304+P340, P317, P318, P321, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Hazard Traits - Developmental Toxicity
2,4-Oxazolidinedione, 3,5,5-trimethyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (87%)
Toxicology
Health EffectsMay cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.
Toxicity Summary
Dione 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.
Signs and SymptomsSymptoms of overdose include clumsiness or unsteadiness, coma, dizziness (severe), drowsiness (severe), nausea (severe), and problems with vision.
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Protein Binding90%
Pharmacodynamics
Paramethadione and trimethadione are anticonvulsants indicated in the control of absence (petit mal) seizures that are refractory to treatment with other medications. Dione anticonvulsants are used in the treatment of epilepsy. They act on the central nervous system (CNS) to reduce the number of seizures.
Mechanism of Action
Dione 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.
Metabolism/MetabolitesTrimethadione has known human metabolites that include Dimethadione.
FDA Pharmacological Classification
R7GV3H6FQ4
TRIMETHADIONE
Established Pharmacologic Class [EPC] - Anti-epileptic Agent
Physiologic Effects [PE] - Decreased Central Nervous System Disorganized Electrical Activity
Trimethadione is an Anti-epileptic Agent. The physiologic effect of trimethadione is by means of Decreased Central Nervous System Disorganized Electrical Activity.
MeSH Pharmacological ClassificationDrugs used to prevent SEIZURES or reduce their severity.
Cellular LocationsMembrane
Uses & manufacturing
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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