5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione

• ChemBase编号: 414
• 分子式: C12H14N2O2
• 平均质量: 218.25176
• 单一同位素质量: 218.1055277
• SMILES: O=C1N(C(=O)NC1(CC)c1ccccc1)C
• Canonical SMILES: CCC1(NC(=O)N(C1=O)C)c1ccccc1
• InChI: InChI=1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16)
• InChIKey: GMHKMTDVRCWUDX-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
• IUPAC传统名: @mephenytoin; mephenytoin
• 商标名: Epiazin; Gerot-Epilan; Insulton; Mesdontoin; Mesontoin; Methoin; Metydan; Phenantoin; Sacerno; Sedantional; Sedantoin; Sedantoinal; Triantoin
• 别名: Mephentoin; Methyl Hydantoin; Methylphenetoin; Mephenytoin; (±)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione; (±)-5-Ethyl-3-methyl-5-phenylhydantoin; (±)-Mephenytoin

登记号

• CAS号: 50-12-4
• EC号: 200-012-8
• MDL号: MFCD00022407
• PubChem SID: 160963877; 46508677
• PubChem CID: 4060
• ATC码: N03AB04
• CHEMBL: 861
• Chemspider ID: 3920
• DrugBank ID: DB00532
• KEGG ID: D00375
• 美国药典/FDA物质标识码: R420KW629U
• 维基百科标题: Mephenytoin
• Medline Plus: a611020

理论计算性质

JChem

• Acid pKa: 11.179447
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 1.6651723
• LogD (pH = 7.4): 1.665102
• Log P: 1.6651733
• 摩尔折射率: 59.538 cm^3
• 极化性: 23.067186 Å^3
• 极化表面积: 49.41 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.64
• LOG S: -2.35
• 溶解度: 9.70e-01 g/l

分子性质

理化性质

• 溶解度: 1270 mg/L
• 外观: off-white
• 熔点: 115-118 °C; 135-137 °C
• 疏水性(logP): 1.3

安全信息

• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 2
• 危险公开号: 22-36/37/38
• 安全公开号: 26
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 给药途径: Oral
• 半衰期: 7 hours
• 妊娠期药物分类: C (US)

产品相关信息

• Empirical Formula (Hill Notation): C12H14N2O2

详细说明

DrugBank - DB00532

• Drug Groups: approved
• Description: Mephenytoin is a hydantoin-derivative anticonvulsant used to control various partial seizures. It is generally reserved for treatment of individuals refractory to less toxic agents. Mephenytoin and oxazolidinedione derivatives are associated with higher incidences of blood dyscrasias compared to other anticonvulsants. As such, these agents should not be used concurrently.
• Indication: For the treatment of refractory partial epilepsy.
• Pharmacology: Mephenytoin is an antiepileptic drug which can be useful in the treatment of epilepsy. The primary site of action appears to be the motor cortex where spread of seizure activity is inhibited. Possibly by promoting sodium efflux from neurons, mephenytoin tends to stabilize the threshold against hyperexcitability caused by excessive stimulation or environmental changes capable of reducing membrane sodium gradient. This includes the reduction of posttetanic potentiation at synapses. Loss of posttetanic potentiation prevents cortical seizure foci from detonating adjacent cortical areas. Mephenytoin reduces the maximal activity of brain stem centers responsible for the tonic phase of tonic-clonic (grand mal) seizures.
• Affected Organisms: Humans and other mammals
• Half Life: Approximately 7 hours
• Distribution: * 1.4 L/kg
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - UC177

Biochem/physiol Actions
CYP2B6 and CYP2C19 substrate; anticonvulsive, antiepileptic.