CAS 57-41-0|CAS 389-08-2|Convul|5,5-联苯基乙内酰脲|Idantoin|Solantoin|Zentronal|Phenhydan|Tacosal|Phentoin|Minetoin|Fentoin|Fenylepsin|Neos-Hidantoina|Difenin|Dintoin|Sylantoic|Prompt Phenytoin Sodi...

General Information

Structure

Molecular Formula

C₁₅H₁₂N₂O₂

Molecular Mass

252.26798

Exact Mass

252.08987763

Charge

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

Calculated Properties

JChem

LogD (pH = 7.4)

2.11

LogD (pH = 5.5)

2.15

Log P

2.15

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

8.49

Polar Surface Area

58.20

Polarizability

25.48

Molar Refractivity

70.18

LOG S

-3.32

Data Source

Names and Identifiers

Brand Name

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

Synonyms

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 Traditional name

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

IUPAC name

5,5-diphenylimidazolidine-2,4-dione

API Name

Phenytoin

International Nonproprietary Name (INN)

phenytoinumphenytoinfenitoinaphenytoine

Names and Identifiers

Registration numbers

EC Number

Merck Index

CAS Number

Beilstein Number

MDL Number

PubChem SID

242783701609636004650884787350410

PubChem CID

1775

DrugBank ID

DB00252

UniProt Database

P11712O54912A6NGU5

CHEBI ID

CHEBI:8107CHEBI:100921

PubMed Citation Links

7602118710582512952753918624415744730152468361069882816303054

BRENDA Database

1.14.11.21.1.1.911.1.1.191.1.1.121.1.1.721.1.1.1691.1.1.211.1.99.271.1.1.91.1.1.21.1.1.1841.14.13.50

BKMS React Database

10887610387749993

Patent number

WO2012174723

BRENDA Ligand Database

ACToR Database

CompTox Database

SureChEMBL Database

IEDB Database

MetaboLights Database

MTBLS379MTBLS1115MTBLS2145

KEGG DRUG Database

LINCS Database

NMRShiftDB Database

BindingDB Database

Wikipedia Title

HMDB Database

Reaxys Registry

Reactom Database

ArrayExpress (Gene Expression Altlas)

E-TABM-1216

KEGG ID

C07443

CHEMBL

CHEMBL16

Drug Central Database

2,152

Registration numbers

Properties

Safety Information

-20°C

Download link

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Pharmacology Properties

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

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

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

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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
Reduces incidence of grand mal seizures; appears to stabilize excitable membranes perhaps through effects on Na+, K+, and Ca2+ channels.

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
Reduces incidence of grand mal seizures; appears to stabilize excitable membranes perhaps through effects on Na+, K+, and Ca2+ channels.

ChEBI

CHEBI:8107

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

Molecule Details

References

PubChem Literature

From Data Sources

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

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 398C, (ir)

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

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1446C, (nmr)

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

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

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

• 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)

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

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

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

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

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DKQ000; DNU000

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

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

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

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 352

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Brand Name

Synonyms

IUPAC Traditional name

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

IUPAC name

5,5-diphenylimidazolidine-2,4-dione

API Name

Phenytoin

International Nonproprietary Name (INN)

phenytoinumphenytoinfenitoinaphenytoine

Registration numbers

EC Number

Merck Index

CAS Number

Beilstein Number

MDL Number

PubChem SID

242783701609636004650884787350410

PubChem CID

1775

DrugBank ID

DB00252

UniProt Database

P11712O54912A6NGU5

CHEBI ID

CHEBI:8107CHEBI:100921

PubMed Citation Links

7602118710582512952753918624415744730152468361069882816303054

BRENDA Database

1.14.11.21.1.1.911.1.1.191.1.1.121.1.1.721.1.1.1691.1.1.211.1.99.271.1.1.91.1.1.21.1.1.1841.14.13.50

BKMS React Database

10887610387749993

Patent number

WO2012174723

BRENDA Ligand Database

ACToR Database

CompTox Database

SureChEMBL Database

IEDB Database

MetaboLights Database

MTBLS379MTBLS1115MTBLS2145

KEGG DRUG Database

LINCS Database

NMRShiftDB Database

BindingDB Database

Wikipedia Title

HMDB Database

Reaxys Registry

Reactom Database

ArrayExpress (Gene Expression Altlas)

E-TABM-1216

KEGG ID

C07443

CHEMBL

CHEMBL16

Drug Central Database

2,152

Molecule Details

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

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
Reduces incidence of grand mal seizures; appears to stabilize excitable membranes perhaps through effects on Na+, K+, and Ca2+ channels.

PHR1139

ChEBI

CHEBI:8107

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

References

PubChem Literature

From Data Sources

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

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 398C, (ir)

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

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1446C, (nmr)

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

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

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

• 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)

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

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

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

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

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DKQ000; DNU000

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

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

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

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 352

Bioactivity

PubChem BioAssay

Properties

Safety Information

-20°C

Download link

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Pharmacology Properties

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

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

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

Molecule

ID:137