5-(hex-3-yn-2-yl)-1-methyl-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

• ChemBase编号: 357
• 分子式: C14H18N2O3
• 平均质量: 262.30432
• 单一同位素质量: 262.13174245
• SMILES: O=C1N(C(=O)NC(=O)C1(C(C)C#CCC)CC=C)C
• Canonical SMILES: CCC#CC(C1(CC=C)C(=O)NC(=O)N(C1=O)C)C
• InChI: InChI=1S/C14H18N2O3/c1-5-7-8-10(3)14(9-6-2)11(17)15-13(19)16(4)12(14)18/h6,10H,2,5,9H2,1,3-4H3,(H,15,17,19)
• InChIKey: NZXKDOXHBHYTKP-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-(hex-3-yn-2-yl)-1-methyl-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
• IUPAC传统名: methohexital sodium; methohexital
• 商标名: Brevital; Brevital sodium; Brietal
• 别名: Methodrexitone; Methohexitone; Methohexital; 1-Methyl-5-(1-methyl-2-pentyn-1-yl)-5-(2-propen-1-yl)-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbituric Acid; Brevital; Brietal; Compound 22451; Compound 25398; Enallynymall

登记号

• CAS号: 151-83-7
• PubChem SID: 46507954; 160963820
• PubChem CID: 9034
• CHEBI ID: 102216
• ATC码: N05CA15; N01AF01
• CHEMBL: 7413
• Chemspider ID: 8683
• DrugBank ID: DB00474
• KEGG ID: D04985
• 美国药典/FDA物质标识码: E5B8ND5IPE
• 维基百科标题: Methohexital

理论计算性质

JChem

• Acid pKa: 8.731305
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 2.2865314
• LogD (pH = 7.4): 2.2672198
• Log P: 2.2867832
• 摩尔折射率: 71.5071 cm^3
• 极化性: 26.970406 Å^3
• 极化表面积: 66.48 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.43
• LOG S: -3.7
• 溶解度: 5.24e-02 g/l

分子性质

理化性质

• 疏水性(logP): 1.8

药理学性质

• 给药途径: Intravenous, rectal
• 生物利用度: I.V. ~100%; Rectal ~17%
• 半衰期: 5.6 ± 2.7 minutes
• 代谢: Hepatic
• 法定药品分级: Schedule IV
• 妊娠期药物分类: B (USA)

详细说明

DrugBank - DB00474

• Drug Groups: approved
• Description: An intravenous anesthetic with a short duration of action that may be used for induction of anesthesia. [PubChem]
• Indication: Methohexital is indicated for use as an intravenous anaesthetic. It has also been commonly used to induce deep sedation.
• Pharmacology: Methohexital, a barbiturate, is used 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. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.
• Toxicity: The onset of toxicity following an overdose of intravenously administered methohexital will be within seconds of the infusion. If methohexital is administered rectally or is ingested, the onset of toxicity may be delayed. The manifestations of an ultrashort-acting barbiturate in overdose include central nervous system depression, respiratory depression, hypotension, loss of peripheral vascular resistance, and muscular hyperactivity ranging from twitching to convulsive-like movements. Other findings may include convulsions and allergic reactions. Following massive exposure to any barbiturate, pulmonary edema, circulatory collapse with loss of peripheral vascular tone, and cardiac arrest may occur.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolism occurs in the liver through demethylation and oxidation. Side-chain oxidation is the most important biotransformation involved in termination of biologic activity.
• Absorption: The absolute bioavailability following rectal administration of methohexital is 17%.
• Half Life: 5.6 ± 2.7 minutes
• Protein Binding: 73%
• Elimination: Excretion occurs via the kidneys through glomerular filtration.
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - M260650

Methohexital is a short-acting barbiturate used as a sedative. Methohexital is used an anesthetic for oral surgery and dentistry and is also used to induce anesthesia prior to electroconvulsive therapy (ECT). Methohexital is a Controlled Substance.

参考文献

• Avramov, M.N. et al.: Anesth. Analges., 81, 596 (1995)
• Hamid, S.K. et al.: Br. J. Anaesth., 77, 727 (1995)