5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione

• ChemBase编号: 1045
• 分子式: C12H12N2O3
• 平均质量: 232.23528
• 单一同位素质量: 232.08479225
• SMILES: O=C1NC(=O)NC(=O)C1(CC)c1ccccc1
• Canonical SMILES: CCC1(C(=O)NC(=O)NC1=O)c1ccccc1
• InChI: InChI=1S/C12H12N2O3/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16/h3-7H,2H2,1H3,(H2,13,14,15,16,17)
• InChIKey: DDBREPKUVSBGFI-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione
• IUPAC传统名: phenobarbital
• 商标名: Adonal; Aephenal; Agrypnal; Amylofene; Aphenylbarbit; Aphenyletten; Barbenyl; Barbinal; Barbiphen; Barbiphenyl; Barbipil; Barbita; Barbivis; Barbonal; Barbophen; Bardorm; Bartol; Bialminal; Blu-Phen; Cabronal; Calmetten; Calminal; Cardenal; Chinoin; Codibarbita; Coronaletta; Cratecil; Damoral; Dezibarbitur; Dormina; Dormiral; Dormital; Doscalun; Duneryl; Ensobarb; Ensodorm; Epanal; Epidorm; Epilol; Episedal; Epsylone; Eskabarb; Etilfen; Euneryl; Fenbital; Fenemal; Fenosed; Fenylettae; Gardenal; Gardepanyl; Glysoletten; Haplopan; Haplos; Helional; Hennoletten; Henotal; Hypnaletten; Hypnette; Hypno-Tablinetten; Hypnogen; Hypnolone; Hypnoltol; Hysteps; Lefebar; Leonal; Lephebar; Lepinal; Lepinaletten; Linasen; Liquital; Lixophen; Lubergal; Lubrokal; Lumen; Lumesettes; Lumesyn; Luminal; Lumofridetten; Luphenil; Luramin; Molinal; Neurobarb; Nirvonal; Noptil; Nova-Pheno; Nunol; Parkotal; Pharmetten; Phen-Bar; Phenaemal; Phenemal; Phenemalum; Phenobal; Phenobarbyl; Phenoluric; Phenolurio; Phenomet; Phenonyl; Phenoturic; Phenyletten; Phenyral; Phob; Polcominal; Promptonal; Seda-Tablinen; Sedabar; Sedicat; Sedizorin; Sedlyn; Sedofen; Sedonal; Sedonettes; Sevenal; Sinoratox; Solfoton; Solfoton Talpheno; Solu-Barb; Sombutol; Somnolens; Somnoletten; Somnosan; Somonal; Spasepilin; Starifen; Starilettae; Stental; Stental Extentabs; Talpheno; Teolaxin; Teoloxin; Thenobarbital; Theoloxin; Triabarb; Tridezibarbitur; Triphenatol; Versomnal; Zadoletten; Zadonal
• 别名: Phenobarbitol; Phenobarbituric Acid; Phenylethylbarbiturate; Phenylethylbarbituric Acid; Phenylethylmalonylurea; Fenobarbital; Phenobarbitone; Phenobarbital; 5-Ethyl-5-phenylbarbituric acid solution; Phenobarbital solution; 5-Ethyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione; Agrypnal; Barbiphenyl; Barbipil; Gardenal; 5-Ethyl-5-phenyl-2,4,6-pyrimidinetrione; 5-Ethyl-5-phenylbarbituric acid; Luminal; Phenobarbital

登记号

• CAS号: 50-06-6
• EC号: 200-007-0
• MDL号: MFCD00066494
• Beilstein号: 233363
• PubChem SID: 24898226; 160964508; 46505776
• PubChem CID: 4763

理论计算性质

JChem

• Acid pKa: 8.136713
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 1.4053402
• LogD (pH = 7.4): 1.3341205
• Log P: 1.4063301
• 摩尔折射率: 59.7463 cm^3
• 极化性: 23.17525 Å^3
• 极化表面积: 75.27 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.4
• LOG S: -2.93
• 溶解度: 2.76e-01 g/l

分子性质

理化性质

• 溶解度: 1.11 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; Alcohol; Chloroform; Water
• 外观: White Solid
• 熔点: 174-178 °C; 174-1780C
• 闪点: 11 °C; 51.8 °F
• 疏水性(logP): 1.47 [HANSCH,C ET AL. (1995)]

安全信息

• 保存条件: Controlled Substance, -20°C Freezer
• RTECS编号: CQ6825000
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 有毒(Toxic) (T)
• 联合国危险货物编号: 1230; 2811
• 德国WGK号: 1; 3
• 联合国危险货物等级: 3; 6.1
• 联合国危险货物包装类别(PG): 2; 3
• 危险公开号: 11-23/24/25-39/23/24/25; 61-25-40-43
• 安全公开号: 16-36/37-45; 53-36/37-45
• GHS危险品标识: GHS02; GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H225-H301-H311-H331-H370; H301-H317-H351-H360D
• GHS警示性声明: P201-P280-P301 + P310-P308 + P313; P210-P260-P280-P301 + P310-P311
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1230 3/PG 2; UN 2811 6.1/PG 3
• 毒品管制信息: Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschlandregulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule IV; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule IV; regulated under CDSA - not available from Sigma-Aldrich Canada
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥99.0% (T)
• 浓度: 1.0 mg/mL±5% in methanol
• 级别: drug standard; purum
• Empirical Formula (Hill Notation): C12H12N2O3

详细说明

DrugBank - DB01174

• Drug Groups: approved
• Description: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It promotes binding to inhibitory gamma-aminobutyric acid subtype receptors, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations. [PubChem]
• Indication: For the treatment of all types of seizures except absence seizures.
• Pharmacology: Phenobarbital, the longest-acting barbiturate, is used for its anticonvulsant and sedative-hypnotic properties in the management of all seizure disorders except absence (petit mal).
• Toxicity: CNS and respiratory depression which may progress to Cheyne-Stokes respiration, areflexia, constriction of the pupils to a slight degree (though in severe poisoning they may wshow paralytic dilation), oliguria, tachycardia, hypotension, lowered body temperature, and coma. Typical shock syndrome (apnea, circulatory collapse, respiratory arrest, and death) may occur.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic (mostly via CYP2C19).
• Absorption: Absorbed in varying degrees following oral, rectal or parenteral administration. The salts are more rapidly absorbed than are the acids. The rate of absorption is increased if the sodium salt is ingested as a dilute solution or taken on an empty stomach.
• Half Life: 53 to 118 hours (mean 79 hours)
• Protein Binding: 20 to 45%
• References: Kwan P, Brodie MJ: Phenobarbital for the treatment of epilepsy in the 21st century: a critical review. Epilepsia. 2004 Sep;45(9):1141-9. [Pubmed] ; Taylor S, Tudur Smith C, Williamson PR, Marson AG: Phenobarbitone versus phenytoin monotherapy for partial onset seizures and generalized onset tonic-clonic seizures. Cochrane Database Syst Rev. 2001;(4):CD002217. [Pubmed] ; Tudur Smith C, Marson AG, Williamson PR: Carbamazepine versus phenobarbitone monotherapy for epilepsy. Cochrane Database Syst Rev. 2003;(1):CD001904. [Pubmed] ; Kalviainen R, Eriksson K, Parviainen I: Refractory generalised convulsive status epilepticus : a guide to treatment. CNS Drugs. 2005;19(9):759-68. [Pubmed] ; Booth D, Evans DJ: Anticonvulsants for neonates with seizures. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004218. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - P1636

Biochem/physiol Actions
Anesthetic; sedative; hypnotic; anticonvulsant

Sigma Aldrich - 04710

Biochem/physiol Actions
Anesthetic; sedative; hypnotic; anticonvulsant
Other Notes
Sales restrictions may apply

Toronto Research Chemicals - P316760

This is a controlled substance (depressant). Anticonvulsant; sedative; hypnotic.

参考文献

• Kwan P, Brodie MJ: Phenobarbital for the treatment of epilepsy in the 21st century: a critical review. Epilepsia. 2004 Sep;45(9):1141-9. Pubmed
• Taylor S, Tudur Smith C, Williamson PR, Marson AG: Phenobarbitone versus phenytoin monotherapy for partial onset seizures and generalized onset tonic-clonic seizures. Cochrane Database Syst Rev. 2001;(4):CD002217. Pubmed
• Tudur Smith C, Marson AG, Williamson PR: Carbamazepine versus phenobarbitone monotherapy for epilepsy. Cochrane Database Syst Rev. 2003;(1):CD001904. Pubmed
• Kalviainen R, Eriksson K, Parviainen I: Refractory generalised convulsive status epilepticus : a guide to treatment. CNS Drugs. 2005;19(9):759-68. Pubmed
• Booth D, Evans DJ: Anticonvulsants for neonates with seizures. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004218. Pubmed
• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)
• Chao, M.K.C., et al.: Anal. Profiles Drug Subs., 7, 359 (1971)