5-(butan-2-yl)-5-ethyl-1,3-diazinane-2,4,6-trione

• ChemBase编号: 122
• 分子式: C10H16N2O3
• 平均质量: 212.24564
• 单一同位素质量: 212.11609238
• SMILES: O=C1NC(=O)NC(=O)C1(C(CC)C)CC
• Canonical SMILES: CCC(C1(CC)C(=O)NC(=O)NC1=O)C
• InChI: InChI=1S/C10H16N2O3/c1-4-6(3)10(5-2)7(13)11-9(15)12-8(10)14/h6H,4-5H2,1-3H3,(H2,11,12,13,14,15)
• InChIKey: ZRIHAIZYIMGOAB-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-(butan-2-yl)-5-ethyl-1,3-diazinane-2,4,6-trione
• IUPAC传统名: butabarbital
• 商标名: Butabarb; Butalan; Butatab; Butatal; Buticaps; Butisol; Butisol Sodium; Medarsed; Nilox; Sarisol; Sarisol No. 1; Unicelles
• 别名: 5-sec-Butyl-5-ethylbarbituric Acid; Butabarb; Butatab; Butatal; Medarsed; NSC 27517; Nilox; Unicelles; sec-Butobarbitone; 5-Ethyl-5-(1-methylpropyl)-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-sec-Butyl-5-ethyl-Barbituric Acid; Butabarbital Sodium; Butabarbitone; Secbubarbital; Secbutobarbitone; Secbutobarbital; Secbutabarbital; Sodium Butabarbital; Butrate; Butabarbital; Butabarbital; Butisol

登记号

• CAS号: 125-40-6
• PubChem SID: 46505051; 160963585
• PubChem CID: 2479
• CHEBI ID: 3228
• CHEMBL: 449
• Chemspider ID: 2385
• DrugBank ID: DB00237
• KEGG ID: D03180
• 美国药典/FDA物质标识码: P0078O25A9
• 维基百科标题: Butabarbital
• Medline Plus: a682417

理论计算性质

JChem

• Acid pKa: 8.482024
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 1.4482353
• LogD (pH = 7.4): 1.4145478
• Log P: 1.4486825
• 摩尔折射率: 53.4019 cm^3
• 极化性: 20.98239 Å^3
• 极化表面积: 75.27 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.7
• LOG S: -2.18
• 溶解度: 1.39e+00 g/l

分子性质

理化性质

• 溶解度: 1360 mg/L
• 疏水性(logP): 1.5

药理学性质

• 半衰期: 100 hours
• 法定药品分级: Schedule III (Canada); Schedule III (US)

详细说明

DrugBank - DB00237

• Drug Groups: illicit; approved
• Description: Butabarbital (trade name Butisol) is a prescription barbiturate sleep aid. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its short duration of action gives butabarbital a high abuse potential, comparable to secobarbital. [Wikipedia]
• Indication: For short-term treatment of insomnia and anxiety disorders
• Pharmacology: Butabarbital, a barbiturate, is used for the treatment of short term insomnia. It belongs to a group of medicines called central nervous system (CNS) depressants that induce drowsiness and relieve tension or nervousness. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.
• Toxicity: Signs of overdose include confusion (severe), decrease in or loss of reflexes, drowsiness (severe), fever, irritability (continuing), low body temperature, poor judgment, shortness of breath or slow or troubled breathing, slow heartbeat, slurred speech, staggering, trouble in sleeping, unusual movements of the eyes, weakness (severe).
• Affected Organisms: Humans and other mammals
• Elimination: Barbiturates are metabolized primarily by the hepatic microsomal enzyme system, and most metabolic products are excreted in the urine.
• External Links: Wikipedia; Drugs.com

Toronto Research Chemicals - B689920

Controlled substance (depressant). Sedative, hypnotic.

参考文献

• Heller, D., et al.: J. Agric. Food Chem., 49, 4597 (2001)
• Ramirez, A., et al.: Anal. Chem., 79, 3155 (2001)