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389-08-2 分子结构
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5,5-diphenylimidazolidine-2,4-dione

ChemBase编号:137
分子式:C15H12N2O2
平均质量:252.26798
单一同位素质量:252.08987763
SMILES和InChIs

SMILES:
O=C1NC(=O)NC1(c1ccccc1)c1ccccc1
Canonical SMILES:
O=C1NC(=O)NC1(c1ccccc1)c1ccccc1
InChI:
InChI=1S/C15H12N2O2/c18-13-15(17-14(19)16-13,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,16,17,18,19)
InChIKey:
CXOFVDLJLONNDW-UHFFFAOYSA-N

引用这个纪录

CBID:137 http://www.chembase.cn/molecule-137.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
5,5-diphenylimidazolidine-2,4-dione
IUPAC传统名
phenytoin
silantin
5,5-diphenylimidazolidine-2,4-dione
商标名
Aleviatin
Antisacer
Auranile
Causoin
Citrullamon
Citrulliamon
Comital
Comitoina
Convul
Danten
Dantinal
Dantoinal
Dantoinal klinos
Dantoine
Denyl
Di-Hydan
Di-Lan
Di-Phetine
Didan TDC 250
Difenilhidantoina
Difenin
Difetoin
Difhydan
Dihycon
Dilabid
Dilantin
Dilantin acid
Dilantin-125
Dilantine
Dillantin
Dintoin
Dintoina
Diphantoin
Diphedal
Diphedan
Diphenat
Diphenin
Diphenine
Diphentoin
Diphentyn
Diphenylan
Ditoinate
Ekko
Elepsindon
Enkelfel
Epamin
Epanutin
Epasmir 5
Epdantoin Simple
Epdantoine simple
Epelin
Epifenyl
Epihydan
Epilan
Epilan D
Epilan-D
Epilantin
Epinat
Epised
Eptal
Eptoin
Fenantoin
Fenidantoin s
Fentoin
Fenylepsin
Fenytoin Dak
Fenytoine
Gerot-epilan-D
Hidan
Hidantal
Hidantilo
Hidantina
Hidantina senosian
Hidantina vitoria
Hidantomin
Hindatal
Hydantal
Hydantin
Hydantoin
Hydantoinal
Hydantol
Ictalis simple
Idantoil
Idantoin
Iphenylhydantoin
Kessodanten
Labopal
Lehydan
Lepitoin
Lepsin
Mesantoin
Minetoin
Neos-Hidantoina
Neosidantoina
Novantoina
Novophenytoin
Om hidantoina simple
Om-Hydantoine
Oxylan
Phanantin
Phanatine
Phenatine
Phenatoine
Phenhydan
Phenhydanin
Phenitoin
Phentoin
Phentytoin
Phenytex
Phenytoin AWD
Phenytoin-Gerot
Prompt Phenytoin Sodium
Ritmenal
Saceril
Sanepil
Silantin
Sinergina
Sodanthon
Sodantoin
Sodanton
Solantin
Solantoin
Solantyl
Sylantoic
TOIN
Tacosal
Thilophenyl
Toin unicelles
Zentronal
Zentropil
别名
5,5-联苯基乙内酰脲
苯妥英
5,5-二苯基海因
5,5-联苯基乙内酰脲
5,5-二苯基海因
苯妥英
5,5-Dwufenylohydantoina
Difenilhidantoina [Spanish]
Diphenylhydantoine [French]
Diphenylan Sodium
Diphenylhydantoin
Diphenylhydatanoin
DPH
Fenitoina [INN-Spanish]
Phenytoin Sodium
Phenytoine
Phenytoine [INN-French]
Phenytoinum [INN-Latin]
5,5-diphenylhydantoin
Dihydantoin
Phenytoin
Di-Hydan; Dihycon; Dilabid; Diphedan
5,5-DIPHENYLHYDANTOIN
5,5-diphenylimidazolidine-2,4-dione
5,5-Diphenylhydantoin
5,5-Diphenyl-2,4-imidazolidinedione
Phenytoin
Aleviatin
Di-Hydan
Epanutin
Epsolin
Fenantoin
Fenitoin
Fenytoine
Pentran
Phenantoin
Phenhydan
Pyoredol
Zentropil
Phenytoin
CAS号
389-08-2
57-41-0
EC号
200-328-6
MDL号
MFCD00005264
Beilstein号
384532
默克索引号
147322
PubChem SID
46508847
160963600
24278370
PubChem CID
1775

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 8.486641  质子受体
质子供体 LogD (pH = 5.5) 2.1474779 
LogD (pH = 7.4) 2.1141331  Log P 2.1479204 
摩尔折射率 70.1823 cm3 极化性 27.12261 Å3
极化表面积 58.2 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 2.26  LOG S -3.55 
溶解度 7.11e-02 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
32 mg/L expand 查看数据来源
DMSO: soluble expand 查看数据来源
熔点
293-295 °C(lit.) expand 查看数据来源
293-298°C expand 查看数据来源
294 - 297°C expand 查看数据来源
疏水性(logP)
2.085 expand 查看数据来源
2.2 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
RTECS编号
MU1050000 expand 查看数据来源
欧盟危险性物质标志
有毒(Toxic) 有毒(Toxic) (T) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
45-61-22 expand 查看数据来源
45-61-22-43 expand 查看数据来源
安全公开号
53-20-24-37-45 expand 查看数据来源
53-45 expand 查看数据来源
TSCA收录
expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS08 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H302-H350-H360 expand 查看数据来源
H350-H360-H317-H303 expand 查看数据来源
GHS警示性声明
P201-P308 + P313 expand 查看数据来源
P261-P280-P302+P352-P321-P405-P501A expand 查看数据来源
个人保护装置
Eyeshields, Gloves, type P2 (EN 143) respirator cartridges expand 查看数据来源
保存温度
room temp expand 查看数据来源
相关基因信息
human ... CNR1(1268), CNR2(1269), CYP2C9(1559)rat ... Faah(29347), Scn1a(81574), Scnn1g(24768), Slc6a1(79212) expand 查看数据来源
生物活性机理
Apparent motor cortex depressant expand 查看数据来源
Apparent primary site of action is motor-cortex where spread of seizure activity is inhibited expand 查看数据来源
May promote neuronal sodium-efflux so stabilizing threshold against hyperexcitability caused by events capable of reducing membrane sodium gradient expand 查看数据来源
Reduces posttetanic potentiation at synapses preventing cortical seizure foci from detonating adjacent cortical areas expand 查看数据来源
Reduces the maximal activity of brain-stem centers responsible for the tonic-phase of grand-mal seizures expand 查看数据来源
纯度
≥99% expand 查看数据来源
95% expand 查看数据来源
98% expand 查看数据来源
99% expand 查看数据来源
级别
certified reference material expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
包装
pkg of 1 g expand 查看数据来源
应用领域
Anticonvulsant expand 查看数据来源
Antiepileptic (veterinary product) expand 查看数据来源
Pharmacopeia Traceability
traceable to PhEur P1290000 expand 查看数据来源
traceable to USP 1535008 expand 查看数据来源
Empirical Formula (Hill Notation)
C15H12N2O2 expand 查看数据来源

详细说明

详细说明

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich DrugBank DrugBank MP Biomedicals MP Biomedicals
Selleck Chemicals -  S2525 external link
Research Area: Neurological Disease
Biological Activity:
Phenytoin (Lepitoin; NSC 8722; Phenytek; Phenytoine; Sodanton; Zentropi) is an inactive voltage-gated sodium channel stabilizer. Phenytoin (Lepitoin; NSC 8722; Phenytek; Phenytoine; Sodanton; Zentropi) blocks voltage-dependent sodium channels to inhibit propagation from active electrical foci, an effect more useful for nontoxicological seizures. Phenytoin (Lepitoin; NSC 8722; Phenytek; Phenytoine; Sodanton; Zentropi) acts to suppress the abnormal brain activity seen in seizure by reducing electrical conductance among brain cells. Aside from seizures, Phenytoin sodium (Lepitoin; NSC 8722; Phenytek; Phenytoine; Sodanton; Zentropi) is an option in the treatment of trigeminal neuralgia in the event that carbamazepine or other 1st line treatment is deemed inappropriate. [1][2]
Sigma Aldrich -  D4007 external link
包装
5, 100 g in poly bottle
Biochem/physiol Actions
减少癫痫大发作的发生率;可能通过 Na+、K+ 和 Ca2+ 通道的影响而稳定可兴奋膜。
Sigma Aldrich -  PHR1139 external link
General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.
Biochem/physiol Actions
减少癫痫大发作的发生率;可能通过 Na+、K+ 和 Ca2+ 通道的影响而稳定可兴奋膜。
Sigma Aldrich -  161926 external link
Biochem/physiol Actions
减少癫痫大发作的发生率;可能通过 Na+、K+ 和 Ca2+ 通道的影响而稳定可兴奋膜。
DrugBank -  DB00252 external link
Item Information
Drug Groups approved
Description An anticonvulsant that is used in a wide variety of seizures. It is also an anti-arrhythmic and a muscle relaxant. The mechanism of therapeutic action is not clear, although several cellular actions have been described including effects on ion channels, active transport, and general membrane stabilization. The mechanism of its muscle relaxant effect appears to involve a reduction in the sensitivity of muscle spindles to stretch. Phenytoin has been proposed for several other therapeutic uses, but its use has been limited by its many adverse effects and interactions with other drugs. [PubChem]
Indication For the control of generalized tonic-clonic (grand mal) and complex partial (psychomotor, temporal lobe) seizures and prevention and treatment of seizures occurring during or following neurosurgery.
Pharmacology Phenytoin is an antiepileptic drug which can be useful in the treatment of epilepsy. The primary site of action appears to be the motor cortex where spread of seizure activity is inhibited. Phenytoin reduces the maximal activity of brain stem centers responsible for the tonic phase of tonic-clonic (grand mal) seizures. Phenytoin acts to dampen the unwanted, runaway brain activity seen in seizure by reducing electrical conductance among brain cells. It lacks the sedation effects associated with phenobarbital. There are some indications that phenytoin has other effects, including anxiety control and mood stabilization, although it has never been approved for those purposes by the FDA. Phenytoin is primarily metabolized by CYP2C9.
Toxicity Oral, mouse: LD50 = 150 mg/kg; Oral, rat: LD50 = 1635 mg/kg. Symptoms of overdose include coma, difficulty in pronouncing words correctly, involuntary eye movement, lack of muscle coordination, low blood pressure, nausea, sluggishness, slurred speech, tremors, and vomiting.
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic
Absorption Bioavailability 70-100% oral, 24.4% for rectal and intravenous administration. Rapid rate of absorption with peak blood concentration expected in 1½ to 3 hours.
Half Life 22 hours (range of 7 to 42 hours)
Protein Binding Highly protein bound, 90%
Elimination Most of the drug is excreted in the bile as inactive metabolites which are then reabsorbed from the intestinal tract and excreted in the urine. Urinary excretion of phenytoin and its metabolites occurs partly with glomerular filtration but, more importantly, by tubular secretion.
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
MP Biomedicals -  05213294 external link
MP Biomedicals Rare Chemical collection

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 398C, (ir)
  • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1446C, (nmr)
  • Camerman, A. et al., Acta Cryst. B, 1971, 27, 2205, (cryst struct)
  • Ruecker, G. et al., Arch. Pharm. (Weinheim, Ger.), 1971, 304, 883, (ms)
  • Gillis, R.A. et al., J. Pharmacol. Exp. Ther., 1971, 179, 599, (pharmacol)
  • Goenechea, S., Mikrochim. Acta, 1972, 276, (ir)
  • Long, R.C. et al., J. Magn. Reson., 1974, 16, 228, (nmr)
  • Simig, G. et al., Tetrahedron, 1975, 31, 1195, (synth)
  • IARC Monog., 1977, 13, 201; Suppl. 7, 319; Suppl. 6, 463, (rev, tox)
  • Woodbury, D.M., Adv. Neurol., 1980, 27, 447, (rev)
  • Philip, J. et al., Anal. Profiles Drug Subst., 1984, 13, 417, (rev)
  • Jones, G.L. et al., Handb. Exp. Pharmacol., 1985, 74, 351, (rev, pharmacol)
  • Glazko, A.J., Ther. Drug Monit., 1986, 8, 490, (rev)
  • Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 4403, (synonyms)
  • Antiepileptic Drugs, (Eds., Levy, R.H. et al), 4th edn., Raven Press, 1995, 301, (rev)
  • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 352
  • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DKQ000; DNU000
  • Shah AS et al. Clin Toxicol (Phila). 2010 Oct;48
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专利

专利

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