5-ethyl-5-phenyl-1,3-diazinane-4,6-dione

• ChemBase编号: 673
• 分子式: C12H14N2O2
• 平均质量: 218.25176
• 单一同位素质量: 218.1055277
• SMILES: O=C1NCNC(=O)C1(CC)c1ccccc1
• Canonical SMILES: CCC1(C(=O)NCNC1=O)c1ccccc1
• InChI: InChI=1S/C12H14N2O2/c1-2-12(9-6-4-3-5-7-9)10(15)13-8-14-11(12)16/h3-7H,2,8H2,1H3,(H,13,15)(H,14,16)
• InChIKey: DQMZLTXERSFNPB-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-ethyl-5-phenyl-1,3-diazinane-4,6-dione
• IUPAC传统名: primidone
• 商标名: Apo-Primidone; Cyral; Desoxyphenobarbitone; Hexadiona; Hexamidine; Lepimidin; Lepsiral; Liskantin; Majsolin; Medi-Pets; Midone; Milepsin; Misodine; Misolyne; Mizodin; Mizolin; Myidone; Mylepsin; Mylepsinum; Mysedon; Mysoline; Neurosyn; Pms Primidone; Prilepsin; Primacione; Primaclone; Primacone; Primakton; Primidon; Primidone Methanol Solution; Primoline; Prysoline; Pyrimidone "Medi-Pets"; Pyrimidone Medi-Pets; Resimatil; Sertan
• 别名: 2-脱氧苯巴比妥; 5-乙基-5-苯基六氢嘧啶-4,6-二酮; 普里米酮; Primidone; Primidone; 2-Desoxyphenobarbital; primaclone; 5-Ethyl-5-phenylhexahydropyrimidine-4,6-dione; Mysoline; Neurosyn; Mylepsin; 5-Ethyldihydro-5-phenyl-4,6(1H,5H)-pyrimidinedione; Liskantin; Mylepsinum; Mysoline; Resimatil; Sertan

登记号

• CAS号: 125-33-7
• EC号: 204-737-0
• MDL号: MFCD00038662
• PubChem SID: 46507775; 160964136; 24277732
• PubChem CID: 4909
• ATC码: N03AA03
• CHEMBL: 856
• Chemspider ID: 4740
• DrugBank ID: DB00794
• KEGG ID: D00474
• 美国药典/FDA物质标识码: 13AFD7670Q
• 维基百科标题: Primidone

理论计算性质

JChem

• Acid pKa: 11.497226
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 1.1182984
• LogD (pH = 7.4): 1.1182681
• Log P: 1.1182989
• 摩尔折射率: 59.0376 cm^3
• 极化性: 23.068121 Å^3
• 极化表面积: 58.2 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: 0.62
• LOG S: -2.32
• 溶解度: 1.04e+00 g/l

分子性质

理化性质

• 溶解度: 500 mg/L; DMSO
• 外观: White Solid
• 熔点: 279 - 281°C; 281-282°C
• 自燃点: > 360°C
• 疏水性(logP): 1.6

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS编号: UV9100000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): III
• 澳大利亚Hazchem: 2X
• 危险公开号: 22-40; R:22
• 安全公开号: 22-36-45; S:36/37/39
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H302-H351
• GHS警示性声明: P281
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

药理学性质

• 给药途径: oral
• 生物利用度: ~100%
• 排泄: Renal
• 半衰期: Primidone: 5-18 hours,; Phenobarbital: 75-120 hours,; PEMA: 16 hours; Time to reach steady state:; Primidone: 2-3 days,; Phenobarbital&PEMA 1-4weeks
• 代谢: Hepatic
• 蛋白结合率: 25%
• 法定药品分级: POM (UK); Rx-only (US)
• 妊娠期药物分类: D (US)

产品相关信息

• 级别: analytical standard, for drug analysis
• 成盐信息: Free Base

详细说明

MP Biomedicals - 02151948

Shows activity as an anticonvulsant.

DrugBank - DB00794

• Drug Groups: approved
• Description: An antiepileptic agent related to the barbiturates; it is partly metabolized to phenobarbital in the body and owes some of its actions to this metabolite. Adverse effects are reported to be more frequent than with phenobarbital. (From Martindale, The Extra Pharmacopoeia, 30th ed, p309)
• Indication: For the treatment of epilepsy
• Pharmacology: Primidone is a barbiturate with anticonvulsant properties. Primidone, either alone or used concomitantly with other anticonvulsants, is indicated in the control of grand mal, psychomotor, and focal epileptic seizures. It may control grand mal seizures refractory to other anticonvulsant therapy. Primidone raises electro- or chemoshock seizure thresholds or alters seizure patterns in experimental animals. Primidone per se has anticonvulsant activity as do its two metabolites, phenobarbital and phenylethylmalonamide (PEMA). In addition to its anticonvulsant activity, Primidone potentiates that of phenobarbital in experimental animals.
• 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
• Absorption: 90 to 100%
• Half Life: 3-23 hours
• Protein Binding: 70%
• References: Murphy K, Delanty N: Primary Generalized Epilepsies. Curr Treat Options Neurol. 2000 Nov;2(6):527-542. [Pubmed] ; Kagitani-Shimono K, Imai K, Okamoto N, Ono J, Okada S: Unverricht-Lundborg disease with cystatin B gene abnormalities. Pediatr Neurol. 2002 Jan;26(1):55-60. [Pubmed] ; Brown GM, Stone GH, Rathbone MP: Primidone and rapid cycling affective disorders. Lancet. 1993 Oct 9;342(8876):925. [Pubmed] ; Schaffer LC, Schaffer CB, Caretto J: The use of primidone in the treatment of refractory bipolar disorder. Ann Clin Psychiatry. 1999 Jun;11(2):61-6. [Pubmed] ; Young MC, Hughes IA: Loss of therapeutic control in congenital adrenal hyperplasia due to interaction between dexamethasone and primidone. Acta Paediatr Scand. 1991 Jan;80(1):120-4. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1965

Research Area: Neurological Disease
Biological Activity:
Primidone(Mysoline) is an anticonvulsant of the pyrimidinedione class, the active metabolites of which, phenobarbital (major) and phenylethylmalonamide (PEMA) (minor), are also anticonvulsants. It is used mainly to treat complex partial, simple partials, generalized tonic-clonic seizures, myoclonic, akinetic seizures. [1]

Sigma Aldrich - P7295

Biochem/physiol Actions
抗惊厥药
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P7295.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - P734000

Anticonvulsant.

参考文献

• Murphy K, Delanty N: Primary Generalized Epilepsies. Curr Treat Options Neurol. 2000 Nov;2(6):527-542. Pubmed
• Kagitani-Shimono K, Imai K, Okamoto N, Ono J, Okada S: Unverricht-Lundborg disease with cystatin B gene abnormalities. Pediatr Neurol. 2002 Jan;26(1):55-60. Pubmed
• Brown GM, Stone GH, Rathbone MP: Primidone and rapid cycling affective disorders. Lancet. 1993 Oct 9;342(8876):925. Pubmed
• Schaffer LC, Schaffer CB, Caretto J: The use of primidone in the treatment of refractory bipolar disorder. Ann Clin Psychiatry. 1999 Jun;11(2):61-6. Pubmed
• Young MC, Hughes IA: Loss of therapeutic control in congenital adrenal hyperplasia due to interaction between dexamethasone and primidone. Acta Paediatr Scand. 1991 Jan;80(1):120-4. Pubmed
• http://en.wikipedia.org/wiki/Primidone
• Bogue, C., et al.: Br. J. Pharmacol., 8, 230 (1953)
• Daley, R.D., Anal. Profiles Drug Subs., 2, 409 (1953)