3-(carbamoyloxy)-2-phenylpropyl carbamate

• ChemBase编号: 825
• 分子式: C11H14N2O4
• 平均质量: 238.23986
• 单一同位素质量: 238.09535694
• SMILES: O(CC(c1ccccc1)COC(=O)N)C(=O)N
• Canonical SMILES: NC(=O)OCC(c1ccccc1)COC(=O)N
• InChI: InChI=1S/C11H14N2O4/c12-10(14)16-6-9(7-17-11(13)15)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,12,14)(H2,13,15)
• InChIKey: WKGXYQFOCVYPAC-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-(carbamoyloxy)-2-phenylpropyl carbamate
• IUPAC传统名: felbatol; felbamate
• 商标名: Felbamyl; Felbatol; Taloxa
• 别名: 2-Phenyl-1,3-propanedioldicarbamate; Carbamic Acid 2-Phenyltrimethylene Ester; ADD-03055; W-554; Felbamyl; Felbatol; Taloxa; 2-Phenyl-1,3-propanediol dicarbamate; Felbamate; Felbamate; 3-(carbamoyloxy)-2-phenylpropyl carbamate

登记号

• CAS号: 25451-15-4
• EC号: 247-001-4
• MDL号: MFCD00865296
• PubChem SID: 46506375; 160964288; 24277968
• PubChem CID: 3331
• CHEBI ID: 4995
• ATC码: N03AX10
• CHEMBL: 1094
• Chemspider ID: 3214
• DrugBank ID: DB00949
• KEGG ID: D00536
• 美国药典/FDA物质标识码: X72RBB02N8
• 维基百科标题: Felbamate
• Medline Plus: a606011

理论计算性质

JChem

• Acid pKa: 14.982562
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 0.67956793
• LogD (pH = 7.4): 0.67956793
• Log P: 0.67956793
• 摩尔折射率: 59.5868 cm^3
• 极化性: 23.403934 Å^3
• 极化表面积: 104.64 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.56
• LOG S: -2.51
• 溶解度: 7.42e-01 g/l

分子性质

理化性质

• 溶解度: alcohol: soluble; Dimethyl Sulfoxide; Dimethylformamide; Slightly soluble in water; Water
• 外观: White Powder
• 熔点: 148-150°C
• 疏水性(logP): 0.3; 0.497

安全信息

• 保存条件: -20°C Freezer
• RTECS编号: TZ1070000
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 作用靶点: Others
• 给药途径: Oral
• 生物利用度: > 90%
• 半衰期: 20-23 hours
• 代谢: Hepatic
• 法定药品分级: Unscheduled
• 妊娠期药物分类: C (USA)
• 相关基因信息: human ... GRIN2B(2904)

产品相关信息

• 纯度: 95%
• 成盐信息: Free Base

详细说明

DrugBank - DB00949

• Drug Groups: approved
• Description: Felbamate is an anticonvulsant drug used in the treatment of epilepsy. It is used to treat partial seizures (with and without generalization) in adults and partial and generalized seizures associated with Lennox-Gastaut syndrome in children. It has a weak inhibitory effect on GABA receptor binding sites.
• Indication: For use only in those patients who respond inadequately to alternative treatments and whose epilepsy is so severe that a substantial risk of aplastic anemia and/or liver failure is deemed acceptable in light of the benefits conferred by its use.
• Pharmacology: Felbamate is an antiepileptic indicated as monotherapy or as an adjunct to other anticonvulsants for the treatment of partial seizures resulting from epilepsy. Receptor-binding studies in vitro indicate that felbamate has weak inhibitory effects on GABA-receptor binding, benzodiazepine receptor binding, and is devoid of activity at the MK-801 receptor binding site of the NMDA receptor-ionophore complex. However, felbamate does interact as an antagonist at the strychnine-insensitive glycine recognition site of the NMDA receptor-ionophore complex.
• Toxicity: LD₅₀=5000 mg/kg (Orally in rats)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: >90%
• Half Life: 20-23 hours
• Protein Binding: 20-36%
• Distribution: * 756±82 mL/kg
• Clearance: * 26 +/- 3 mL/hr/kg [single 1200 mg dose]; * 30 +/- 8 mL/hr/kg [multiple daily doses of 3600 mg]
• References: Leppik IE, Dreifuss FE, Pledger GW, Graves NM, Santilli N, Drury I, Tsay JY, Jacobs MP, Bertram E, Cereghino JJ, et al.: Felbamate for partial seizures: results of a controlled clinical trial. Neurology. 1991 Nov;41(11):1785-9. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - F0778

Biochem/physiol Actions
Anticonvulsant agent that is an allosteric antagonist at the NR2B subunit of the NMDA glutamate receptor; also has γ-aminobutyric acid (GABAA) receptor agonist properties.

Toronto Research Chemicals - F231000

Antiepileptic, structurally similar to meprobamate.

参考文献

• Leppik IE, Dreifuss FE, Pledger GW, Graves NM, Santilli N, Drury I, Tsay JY, Jacobs MP, Bertram E, Cereghino JJ, et al.: Felbamate for partial seizures: results of a controlled clinical trial. Neurology. 1991 Nov;41(11):1785-9. Pubmed
• Swinyard, E.A., et al.: Epilepsia, 27, 27 (1986)
• Remmel, R.P., et al.: Ther. Drug Monit., 12, 90 (1986)
• Sofia, R.D., et al.: Epilepsy Res. Suppl., 3, 103 (1986)