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

• ChemBase ID: 1183
• Molecular Formular: C12H16N2O3
• Molecular Mass: 236.26704
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(cyclohex-1-en-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: hexobarbital
• Brand Name: Citopan; Evipan; Noctivane; Sombucaps; Sombulex; Somnalert; Evipal; Cyclopan; Cyclopal; Barbidorm
• Synonyms: Hexobarbital; Hexobarbitone; 5-(1-cyclohexen-1-yl)-1,5-dimethylbarbituric acid; Methexenyl; Methylhexabital; Hexobarbital; 伊维派; 环己巴比妥; 海索比妥

Database IDs

• CAS Number: 56-29-1
• EC Number: 200-264-9
• MDL Number: MFCD00057562
• PubChem SID: 160964645; 24895418
• PubChem CID: 3608
• CHEBI ID: 5706
• ATC CODE: N01AF02; N05CA16
• CHEMBL: 7728
• Chemspider ID: 3482
• DrugBank ID: DB01355
• KEGG ID: D01071
• Unique Ingredient Identifier: AL8Z8K3P6S
• Wikipedia Title: Hexobarbital

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.405108
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.2470881
• LogD (pH = 7.4): 1.2071804
• Log P: 1.2476219
• Molar Refractivity: 61.9474 cm^3
• Polarizability: 23.677336 Å^3
• Polar Surface Area: 66.48 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.8
• LOG S: -2.19
• Solubility (Water): 1.51e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.98 [SANGSTER (1994)]

Safety Information

• RTECS: CQ2625000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Drug Control: USDEA Schedule III; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Protein Bound: 25%

Product Information

• Grade: analytical standard, for drug analysis

DETAILS

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

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