CAS 57-41-0|CAS 389-08-2|Dintoin|Auranile|5,5-联苯基乙内酰脲|Neos-Hidantoina|Tacosal|Fentoin|Fenylepsin|Hidantilo|Idantoin|silantin|Sylantoic|Prompt Phenytoin Sodium|Minetoin|Convul|Difenin|Zentrona...

基本信息

化学结构

分子式

C₁₅H₁₂N₂O₂

分子量

252.26798

精确质量

252.08987763

电荷

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

Canonic Smiles

O=C1NC(=O)NC1(c1ccccc1)c1ccccc1

Isomeric Smiles

O=C1NC(=O)NC1(c1ccccc1)c1ccccc1

计算属性

JChem

LogD (pH = 7.4)

2.11

LogD (pH = 5.5)

2.15

Log P

2.15

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

8.49

极化表面积

58.20

极化性

25.48

摩尔折射率

70.18

LOG S

-3.32

数据来源

名称和标识

商标名

DintoinAuranileNeos-HidantoinaTacosalFentoinFenylepsinHidantiloIdantoinSylantoicPrompt Phenytoin SodiumMinetoinConvulDifeninZentronalEpifenylPhenhydanSolantoinPhentoinSodantonEpelinOm-HydantoineEptalEpaminDiphedanDiphenylanDilabidEpdantoine simplePhenytexOm hidantoina simpleIctalis simpleDiphentynDi-HydanDifetoinDenylMesantoinHidantalZentropilAleviatinPhanatineHydantoinEpilantinFenidantoin sEpanutinHindatalDi-PhetineElepsindonDiphenatHidantominHydantoinalEpilan-DDiphantoinDantoineDilantineDifhydanDilantinRitmenalNovantoinaHydantinDitoinateEpinatEpilanDantenPhenitoinPhenatineKessodantenEkkoSilantinOxylanHidantina vitoriaLepitoinCitrullamonPhenatoineComitoinaToin unicellesPhenytoin AWDFenytoineLabopalCitrulliamonIphenylhydantoinSodantoinPhanantinDipheninFenytoin DakPhenhydaninDantoinal klinosPhentytoinDantoinalCausoinHidantinaLehydanDi-LanSacerilSolantinEpdantoin SimpleHydantalSodanthonTOINHydantolSolantylEpisedDiphedalLepsinDintoinaDillantinThilophenylSanepilGerot-epilan-DEpilan DEpasmir 5SinerginaEpihydanNovophenytoinDantinalEnkelfelDilantin-125IdantoilDidan TDC 250ComitalNeosidantoinaDifenilhidantoinaPhenytoin-GerotAntisacerHidanHidantina senosianDiphentoinFenantoinDiphenineDilantin acidEptoinDihycon

别名

5,5-联苯基乙内酰脲Phenytoin SodiumPhenytoinePhenytoin5,5-diphenylhydantoinPhenytoinum [INN-Latin]Diphenylan Sodium苯妥英DihydantoinDPHPhenytoine [INN-French]5,5-二苯基海因5,5-DiphenylhydantoinDiphenylhydantoinDiphenylhydantoine [French]Diphenylhydatanoin5,5-DwufenylohydantoinaDifenilhidantoina [Spanish]Fenitoina [INN-Spanish]Di-Hydan; Dihycon; Dilabid; Diphedan5,5-diphenylimidazolidine-2,4-dionePhenytoin5,5-Diphenyl-2,4-imidazolidinedione5,5-二苯基海因Phenytoin苯妥英5,5-DIPHENYLHYDANTOINDi-HydanPhenantoinAleviatinEpanutinPhenhydanPyoredolFenitoinFenantoinZentropilPentranFenytoineEpsolin5,5-联苯基乙内酰脲DILANTIN5,5-diphenyltetrahydro-1H-2,4-imidazoledionephenytoin5,5-diphenylimidazolidine-2,4-dione5,5-Diphenyl-imidazolidine-2,4-dionePHENTYTOIN

IUPAC传统名

silantin phenytoin 5,5-diphenylimidazolidine-2,4-dione

IUPAC标准名

5,5-diphenylimidazolidine-2,4-dione

API名称

Phenytoin

国际非专利药品(INN)

phenytoinumphenytoinfenitoinaphenytoine

名称和标识

数据登录号

默克索引号

EC号

CAS号

Beilstein号

MDL号

PubChem SID

242783701609636004650884787350410

PubChem CID

1775

DrugBank ID

DB00252

KEGG DRUG Database

D00512

BRENDA数据库

1.1.1.191.1.1.121.14.11.21.1.1.721.1.1.1691.1.1.911.1.99.271.14.13.501.1.1.1841.1.1.21.1.1.91.1.1.21

PubMed文献链接

7105825918624412952753760211810698828152468361574473016303054

CompTox数据库

DTXSID8020541

BRENDA Ligand数据库

10887649993103877

CHEBI ID

CHEBI:8107CHEBI:100921

LINCS数据库

LSM-5663

ACToR数据库

125-59-757-41-0

MetaboLights数据库

MTBLS379MTBLS1115MTBLS2145

BKMS React数据库

SureChEMBL数据库

IEDB Database

UniProt数据库

专利号

Reaxys Registry

CHEMBL

Reactom Database

KEGG ID

Drug Central Database

BindingDB数据库

维基百科标题

NMRShiftDB数据库

ArrayExpress (Gene Expression Altlas)

E-TABM-1216

HMDB数据库

HMDB0014397

数据登录号

化合物性质

药理学性质

相关基因信息

human ... CNR1(1268), CNR2(1269), CYP2C9(1559)rat ... Faah(29347), Scn1a(81574), Scnn1g(24768), Slc6a1(79212)

生物活性机理

Reduces posttetanic potentiation at synapses preventing cortical seizure foci from detonating adjacent cortical areas

May promote neuronal sodium-efflux so stabilizing threshold against hyperexcitability caused by events capable of reducing membrane sodium gradient

Apparent motor cortex depressant

Apparent primary site of action is motor-cortex where spread of seizure activity is inhibited

Reduces the maximal activity of brain-stem centers responsible for the tonic-phase of grand-mal seizures

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

DrugBank

DB00252

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]

Selleck Chemicals

S2525

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]

MP Biomedicals

05213294

MP Biomedicals Rare Chemical collection

Sigma Aldrich

D4007

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。

161926

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。

PHR1139

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。

ChEBI

CHEBI:8107

A imidazolidine-2,4-dione that consists of hydantoin bearing two phenyl substituents at position 5.

描述信息

参考文献

PubChem文献

数据源提供

• Shah AS et al. Clin Toxicol (Phila). 2010 Oct;48

• 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)

• Goenechea, S., Mikrochim. Acta, 1972, 276, (ir)

• Long, R.C. et al., J. Magn. Reson., 1974, 16, 228, (nmr)

• 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

• Camerman, A. et al., Acta Cryst. B, 1971, 27, 2205, (cryst struct)

• Simig, G. et al., Tetrahedron, 1975, 31, 1195, (synth)

• Woodbury, D.M., Adv. Neurol., 1980, 27, 447, (rev)

• Jones, G.L. et al., Handb. Exp. Pharmacol., 1985, 74, 351, (rev, pharmacol)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 4403, (synonyms)

• Ruecker, G. et al., Arch. Pharm. (Weinheim, Ger.), 1971, 304, 883, (ms)

• Philip, J. et al., Anal. Profiles Drug Subst., 1984, 13, 417, (rev)

• Gillis, R.A. et al., J. Pharmacol. Exp. Ther., 1971, 179, 599, (pharmacol)

• IARC Monog., 1977, 13, 201; Suppl. 7, 319; Suppl. 6, 463, (rev, tox)

• Antiepileptic Drugs, (Eds., Levy, R.H. et al), 4th edn., Raven Press, 1995, 301, (rev)

• Glazko, A.J., Ther. Drug Monit., 1986, 8, 490, (rev)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

商标名

别名

IUPAC传统名

silantin phenytoin 5,5-diphenylimidazolidine-2,4-dione

IUPAC标准名

5,5-diphenylimidazolidine-2,4-dione

API名称

Phenytoin

国际非专利药品(INN)

phenytoinumphenytoinfenitoinaphenytoine

数据登录号

默克索引号

EC号

CAS号

Beilstein号

MDL号

PubChem SID

242783701609636004650884787350410

PubChem CID

1775

DrugBank ID

DB00252

KEGG DRUG Database

D00512

BRENDA数据库

1.1.1.191.1.1.121.14.11.21.1.1.721.1.1.1691.1.1.911.1.99.271.14.13.501.1.1.1841.1.1.21.1.1.91.1.1.21

PubMed文献链接

7105825918624412952753760211810698828152468361574473016303054

CompTox数据库

DTXSID8020541

BRENDA Ligand数据库

10887649993103877

CHEBI ID

CHEBI:8107CHEBI:100921

LINCS数据库

LSM-5663

ACToR数据库

125-59-757-41-0

MetaboLights数据库

MTBLS379MTBLS1115MTBLS2145

BKMS React数据库

SureChEMBL数据库

IEDB Database

UniProt数据库

专利号

Reaxys Registry

CHEMBL

Reactom Database

KEGG ID

Drug Central Database

BindingDB数据库

维基百科标题

NMRShiftDB数据库

ArrayExpress (Gene Expression Altlas)

E-TABM-1216

HMDB数据库

HMDB0014397

描述信息

DrugBank

DB00252

Drug Groups

approved

Description

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

Toxicity

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

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S2525