Basic information
- CAS
115-67-3- Standard SMILES
CCC1(C)OC(=O)N(C)C1=O- InChIKey
VQASKUSHBVDKGU-UHFFFAOYSA-N- Molecular formula
- C7H11NO3
- Average molar mass
- 157.17 g/mol
- Monoisotopic mass
- 157.07389321
Overview
Paramethadione can cause developmental toxicity according to state or federal government labeling requirements.
Names & identifiers
- Preferred name
- Paramethadione
- IUPAC
- 5-ethyl-3,5-dimethyl-1,3-oxazolidine-2,4-dione
- English name
- PARAMETHADIONE (500 MG)
- Molecular formula
- C7H11NO3
- Molecular weight
- 157.17
Names & synonyms
PARAMETHADIONEParametadione115-67-3ParadioneIsoethadione5-Ethyl-3,5-dimethyl-1,3-oxazolidine-2,4-dioneParamethadionumParametadiona2,4-Oxazolidinedione, 5-ethyl-3,5-dimethyl-3,5-Dimethyl-5-ethyloxazolidine-2,4-dione5-Ethyl-3,5-dimethyl-2,4-oxazolidinedioneA 348
Show more names
a348HSDB 3245BRN 0127715IsethadionumParamethodione
NSC-760129Z615FRW64NDTXSID80234205-ethyl-3,5-dimethyloxazolinedioneRefChem:58021DTXCID703420N03AC01204-098-8
Database identifiers
- CAS
115-67-3- PubChem CID
- 8280
- DTXSID
DTXSID8023420- ChEMBL
CHEMBL1100- ChEBI
CHEBI:7921- UNII
- Z615FRW64N
- EC Number
- 204-098-8
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 46.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 214
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antiepileptics
pHABOUT 6 (1 IN 40 SOLN)
LogP0.3
OdorFRUITY, ESTERLIKE ODOR
Density1.118-1.1240 @ 25 °C/4 DEG
Color/Form
CLEAR, COLORLESS LIQUID
Liquid
Solubility
SLIGHTLY SOL IN WATER; FREELY SOL IN ALCOHOL, BENZENE, CHLOROFORM, ETHER
1.35e+02 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Boiling Point
101 to 102 °C at 11.3 mm Hg
101.5 °C
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
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
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Regulatory InformationHazard Traits - Developmental Toxicity
FDA Requirements
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
Special Reports
Graca LM, Machado MH; Acta Med Port 8 (7-8): 441-9 (1995). Teratogenic effects of exogenous agents.
Brent RL, Beckman DA; Clin Obstet Gynecol 37 (3): 646-70 (1994). The contribution of environmental teratogens to embryonic and fetal loss.
Stevenson RE; Human Malformations and Related Anomalies (Oxford Monographs on Medical Genetics 27: 137-68 (1993). The environmental basis of human anomalies.
Schardein JL; Chemically Induced Birth Defects 2: 157-207 (1993). /A review of the/ anticonvulsants.
For more Special Reports (Complete) data for PARAMETHADIONE (7 total), please visit the HSDB record page.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety & protection
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Protein BindingNot significant
Pharmacodynamics
Paramethadione is an oxazolidinedione anticonvulsant similar to trimethadione that acts on the central nervous system (CNS) to reduce the number of absence seizures (often seen in epileptics). Absence seizures involve an interruption to consciousness where the person experiencing the seizure seems to become vacant and unresponsive for a short period of time (usually up to 30 seconds). Paramethadione acts on thalamic neurons in the thalamic reticular nucleus (which studies have shown to be associated with absence seizures, von Krosigk et al., 1993).
Mechanism of Action
Dione anticonvulsants such as paramethadione reduce T-type calcium currents in thalamic neurons (including thalamic relay neurons). This inhibits corticothalamic transmission and raises the threshold for repetitive activity in the thalamus. This results in a dampening of the abnormal thalamocortical rhythmicity proposed to underlie the 3-Hz spike-and-wave discharge seen on electroencephalogram (EEG) during absence seizures.
Dione anticonvulsants reduce T-type calcium currents in thalamic neurons, including thalamic relay neurons. 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. The maximal seizure pattern in patients undergoing electroconvulsive therapy is not modified. /Dione anticonvulsants/
Biological Half-Life
12 to 24 hours (however the half-life for the active metabolite is not known)
Paramethadion - 12 to 24 hours; active metabolite - unknown.
Metabolism/Metabolites
Primarily hepatic (mainly via cytochrome P450 isozyme 2C9), paramethadione is completely demethylated to 5-ethyl-5-methyl-2,4-oxazolidinedione, the active metabolite.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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