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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 115-67-3
• PubChem SID: 160963962; 46509173
• PubChem CID: 8280

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.0266687
• LogD (pH = 7.4): 1.0266687
• Log P: 1.0266687
• Molar Refractivity: 37.7242 cm^3
• Polarizability: 14.95568 Å^3
• Polar Surface Area: 46.61 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.9
• LOG S: -0.07
• Solubility (Water): 1.35e+02 g/l

PROPERTIES

Physical Property

• Solubility: 8.4 mg/mL
• Hydrophobicity(logP): 0.3

DETAILS

DrugBank - DB00617

• 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

• 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