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57-41-0 molecular structure
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5,5-diphenylimidazolidine-2,4-dione

ChemBase ID: 137
Molecular Formular: C15H12N2O2
Molecular Mass: 252.26798
Monoisotopic Mass: 252.08987763
SMILES and 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

Cite this record

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

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5,5-diphenylimidazolidine-2,4-dione
IUPAC Traditional name
phenytoin
silantin
5,5-diphenylimidazolidine-2,4-dione
Brand Name
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
Synonyms
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-diphenylimidazolidine-2,4-dione
5,5-Diphenylhydantoin
5,5-DIPHENYLHYDANTOIN
5,5-Diphenyl-2,4-imidazolidinedione
Phenytoin
Aleviatin
Di-Hydan
Epanutin
Epsolin
Fenantoin
Fenitoin
Fenytoine
Pentran
Phenantoin
Phenhydan
Pyoredol
Zentropil
Phenytoin
5,5-联苯基乙内酰脲
苯妥英
5,5-二苯基海因
苯妥英
5,5-联苯基乙内酰脲
5,5-二苯基海因
CAS Number
57-41-0
389-08-2
EC Number
200-328-6
MDL Number
MFCD00005264
Beilstein Number
384532
Merck Index
147322
PubChem SID
24278370
160963600
46508847
PubChem CID
1775

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 8.486641  H Acceptors
H Donor LogD (pH = 5.5) 2.1474779 
LogD (pH = 7.4) 2.1141331  Log P 2.1479204 
Molar Refractivity 70.1823 cm3 Polarizability 27.12261 Å3
Polar Surface Area 58.2 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.26  LOG S -3.55 
Solubility (Water) 7.11e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
32 mg/L expand Show data source
DMSO: soluble expand Show data source
Melting Point
293-295 °C(lit.) expand Show data source
293-298°C expand Show data source
294 - 297°C expand Show data source
Hydrophobicity(logP)
2.085 expand Show data source
2.2 expand Show data source
Storage Condition
-20°C expand Show data source
RTECS
MU1050000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
45-61-22 expand Show data source
45-61-22-43 expand Show data source
Safety Statements
53-20-24-37-45 expand Show data source
53-45 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H302-H350-H360 expand Show data source
H350-H360-H317-H303 expand Show data source
GHS Precautionary statements
P201-P308 + P313 expand Show data source
P261-P280-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
Storage Temperature
room temp expand Show data source
Gene Information
human ... CNR1(1268), CNR2(1269), CYP2C9(1559)rat ... Faah(29347), Scn1a(81574), Scnn1g(24768), Slc6a1(79212) expand Show data source
Mechanism of Action
Apparent motor cortex depressant expand Show data source
Apparent primary site of action is motor-cortex where spread of seizure activity is inhibited expand Show data source
May promote neuronal sodium-efflux so stabilizing threshold against hyperexcitability caused by events capable of reducing membrane sodium gradient expand Show data source
Reduces posttetanic potentiation at synapses preventing cortical seizure foci from detonating adjacent cortical areas expand Show data source
Reduces the maximal activity of brain-stem centers responsible for the tonic-phase of grand-mal seizures expand Show data source
Purity
≥99% expand Show data source
95% expand Show data source
98% expand Show data source
99% expand Show data source
Grade
certified reference material expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Packaging
pkg of 1 g expand Show data source
Application(s)
Anticonvulsant expand Show data source
Antiepileptic (veterinary product) expand Show data source
Pharmacopeia Traceability
traceable to PhEur P1290000 expand Show data source
traceable to USP 1535008 expand Show data source
Empirical Formula (Hill Notation)
C15H12N2O2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich Selleck Chemicals Selleck Chemicals
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
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 - 161926 external link
Biochem/physiol Actions
Reduces incidence of grand mal seizures; appears to stabilize excitable membranes perhaps through effects on Na+, K+, and Ca2+ channels.
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
Reduces incidence of grand mal seizures; appears to stabilize excitable membranes perhaps through effects on Na+, K+, and Ca2+ channels.
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]

REFERENCES

REFERENCES

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  • • 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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PATENTS

PATENTS

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INTERNET

INTERNET

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