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115-67-3 molecular structure
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5-ethyl-3,5-dimethyl-1,3-oxazolidine-2,4-dione

ChemBase ID: 499
Molecular Formular: C7H11NO3
Molecular Mass: 157.16714
Monoisotopic Mass: 157.07389322
SMILES and InChIs

SMILES:
O1C(CC)(C(=O)N(C1=O)C)C
Canonical SMILES:
CCC1(C)OC(=O)N(C1=O)C
InChI:
InChI=1S/C7H11NO3/c1-4-7(2)5(9)8(3)6(10)11-7/h4H2,1-3H3
InChIKey:
VQASKUSHBVDKGU-UHFFFAOYSA-N

Cite this record

CBID:499 http://www.chembase.cn/molecule-499.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-ethyl-3,5-dimethyl-1,3-oxazolidine-2,4-dione
IUPAC Traditional name
@paramethadione
Brand Name
Isoethadione
Paradione
Paradione (TN)
Parametadiona [INN-Spanish]
Parametadione
Parametadione [DCIT]
Paramethadione [BAN:INN]
Paramethadionum [INN-Latin]
Synonyms
Paramethadione
CAS Number
115-67-3
PubChem SID
160963962
46509173
PubChem CID
8280

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00617 external link
PubChem 8280 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 1.0266687  LogD (pH = 7.4) 1.0266687 
Log P 1.0266687  Molar Refractivity 37.7242 cm3
Polarizability 14.95568 Å3 Polar Surface Area 46.61 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 0.9  LOG S -0.07 
Solubility (Water) 1.35e+02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
8.4 mg/mL expand Show data source
Hydrophobicity(logP)
0.3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00617 external link
Item Information
Drug Groups approved
Description Paramethadione is an anticonvulsant in the oxazolidinedione class. It is associated with fetal trimethadione syndrome, which is also known as paramethadione syndrome.
Indication Used for the control of absence (petit mal) seizures that are refractory to treatment with other medications.
Pharmacology 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).
Toxicity Symptoms of overdose include clumsiness or unsteadiness, coma, severe dizziness, severe drowsiness, severe nausea, and problems with vision.
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic (mainly via cytochrome P450 isozyme 2C9), paramethadione is completely demethylated to 5-ethyl-5-methyl-2,4-oxazolidinedione, the active metabolite.
Absorption Rapid via the digestive tract.
Half Life 12 to 24 hours (however the half-life for the active metabolite is not known)
Protein Binding Not significant
References
Hoffman DJ, Chun AH: Paramethadione and metabolite serum levels in humans after a single oral paramethadione dose. J Pharm Sci. 1975 Oct;64(10):1702-3. [Pubmed]
Feldman GL, Weaver DD, Lovrien EW: The fetal trimethadione syndrome: report of an additional family and further delineation of this syndrome. Am J Dis Child. 1977 Dec;131(12):1389-92. [Pubmed]
External Links
Wikipedia
Drugs.com

REFERENCES

REFERENCES

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  • • Hoffman DJ, Chun AH: Paramethadione and metabolite serum levels in humans after a single oral paramethadione dose. J Pharm Sci. 1975 Oct;64(10):1702-3. Pubmed
  • • Feldman GL, Weaver DD, Lovrien EW: The fetal trimethadione syndrome: report of an additional family and further delineation of this syndrome. Am J Dis Child. 1977 Dec;131(12):1389-92. Pubmed
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PATENTS

PATENTS

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