5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione

• ChemBase编号: 1183
• 分子式: C12H16N2O3
• 平均质量: 236.26704
• 单一同位素质量: 236.11609238
• SMILES: O=C1N(C(=O)NC(=O)C1(C1=CCCCC1)C)C
• Canonical SMILES: O=C1NC(=O)C(C(=O)N1C)(C)C1=CCCCC1
• InChI: InChI=1S/C12H16N2O3/c1-12(8-6-4-3-5-7-8)9(15)13-11(17)14(2)10(12)16/h6H,3-5,7H2,1-2H3,(H,13,15,17)
• InChIKey: UYXAWHWODHRRMR-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione
• IUPAC传统名: hexobarbital
• 商标名: Citopan; Evipan; Noctivane; Sombucaps; Sombulex; Somnalert; Evipal; Cyclopan; Cyclopal; Barbidorm
• 别名: 伊维派; 环己巴比妥; 海索比妥; Hexobarbital; Hexobarbitone; 5-(1-cyclohexen-1-yl)-1,5-dimethylbarbituric acid; Methexenyl; Methylhexabital; Hexobarbital

登记号

• CAS号: 56-29-1
• EC号: 200-264-9
• MDL号: MFCD00057562
• PubChem SID: 160964645; 24895418
• PubChem CID: 3608
• CHEBI ID: 5706
• ATC码: N01AF02; N05CA16
• CHEMBL: 7728
• Chemspider ID: 3482
• DrugBank ID: DB01355
• KEGG ID: D01071
• 美国药典/FDA物质标识码: AL8Z8K3P6S
• 维基百科标题: Hexobarbital

理论计算性质

JChem

• Acid pKa: 8.405108
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 1.2470881
• LogD (pH = 7.4): 1.2071804
• Log P: 1.2476219
• 摩尔折射率: 61.9474 cm^3
• 极化性: 23.677336 Å^3
• 极化表面积: 66.48 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: 1.8
• LOG S: -2.19
• 溶解度: 1.51e+00 g/l

分子性质

理化性质

• 疏水性(logP): 1.98 [SANGSTER (1994)]

安全信息

• RTECS编号: CQ2625000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• 安全公开号: 36/37/39
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• 毒品管制信息: USDEA Schedule III; regulated under CDSA - not available from Sigma-Aldrich Canada

药理学性质

• 蛋白结合率: 25%

产品相关信息

• 级别: analytical standard, for drug analysis

详细说明

DrugBank - DB01355

• Drug Groups: approved
• Description: A barbiturate that is effective as a hypnotic and sedative. [PubChem]
• Indication: For the induction of anesthesia prior to the use of other general anesthetic agents and for induction of anesthesia for short surgical, diagnostic, or therapeutic procedures associated with minimal painful stimuli.
• Pharmacology: Hexobarbital is a barbiturate derivative having hypnotic and sedative effects. It was used in the 1940s-1950s as an agent for inducing anesthesia for surgery and has a relatively fast onset of effects and short duration of action. However it can be difficult to control the depth of anesthesia with hexobarbital which makes it quite dangerous, and it has now been replaced by safer drugs in human medicine, usually thiopental would be the barbiturate of choice for this application these days.
• Toxicity: Symptoms of an overdose typically include sluggishness, incoordination, difficulty in thinking, slowness of speech, faulty judgment, drowsiness or coma, shallow breathing, staggering, and in severe cases coma and death.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Protein Binding: 25%
• References: Takenoshita R, Toki S: [New aspects of hexobarbital metabolism: stereoselective metabolism, new metabolic pathway via GSH conjugation, and 3-hydroxyhexobarbital dehydrogenases] Yakugaku Zasshi. 2004 Dec;124(12):857-71. [Pubmed] ; Wahlstrom G: A study of the duration of acute tolerance induced with hexobarbital in male rats. Pharmacol Biochem Behav. 1998 Apr;59(4):945-8. [Pubmed] ; Korkmaz S, Ljungblad E, Wahlstrom G: Interaction between flumazenil and the anesthetic effects of hexobarbital in the rat. Brain Res. 1995 Apr 10;676(2):371-7. [Pubmed] ; Dall V, Orntoft U, Schmidt A, Nordholm L: Interaction of the competitive AMPA receptor antagonist NBQX with hexobarbital. Pharmacol Biochem Behav. 1993 Sep;46(1):73-6. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - H1005

Biochem/physiol Actions
静脉内麻醉药

参考文献

• Takenoshita R, Toki S: [New aspects of hexobarbital metabolism: stereoselective metabolism, new metabolic pathway via GSH conjugation, and 3-hydroxyhexobarbital dehydrogenases] Yakugaku Zasshi. 2004 Dec;124(12):857-71. Pubmed
• Wahlstrom G: A study of the duration of acute tolerance induced with hexobarbital in male rats. Pharmacol Biochem Behav. 1998 Apr;59(4):945-8. Pubmed
• Korkmaz S, Ljungblad E, Wahlstrom G: Interaction between flumazenil and the anesthetic effects of hexobarbital in the rat. Brain Res. 1995 Apr 10;676(2):371-7. Pubmed
• Dall V, Orntoft U, Schmidt A, Nordholm L: Interaction of the competitive AMPA receptor antagonist NBQX with hexobarbital. Pharmacol Biochem Behav. 1993 Sep;46(1):73-6. Pubmed