5-ethyl-3,5-dimethyl-1,3-oxazolidine-2,4-dione

• ChemBase编号: 499
• 分子式: C7H11NO3
• 平均质量: 157.16714
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 5-ethyl-3,5-dimethyl-1,3-oxazolidine-2,4-dione
• IUPAC传统名: @paramethadione
• 商标名: Isoethadione; Paradione; Paradione (TN); Parametadiona [INN-Spanish]; Parametadione; Parametadione [DCIT]; Paramethadione [BAN:INN]; Paramethadionum [INN-Latin]
• 别名: Paramethadione

登记号

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

理论计算性质

JChem

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 1.0266687
• LogD (pH = 7.4): 1.0266687
• Log P: 1.0266687
• 摩尔折射率: 37.7242 cm^3
• 极化性: 14.95568 Å^3
• 极化表面积: 46.61 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.9
• LOG S: -0.07
• 溶解度: 1.35e+02 g/l

分子性质

理化性质

• 溶解度: 8.4 mg/mL
• 疏水性(logP): 0.3

详细说明

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

参考文献

• 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