5,5-diphenylimidazolidine-2,4-dione

• ChemBase ID: 137
• Molecular Formular: C15H12N2O2
• Molecular Mass: 252.26798
• Monoisotopic Mass: 252.08987763
• 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

NAMES AND DATABASE IDS

Names

• 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: Di-Hydan; Dihycon; Dilabid; Diphedan; Phenytoin; 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; 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; 5,5-联苯基乙内酰脲; 5,5-二苯基海因; 苯妥英; 5,5-联苯基乙内酰脲; 苯妥英; 5,5-二苯基海因

Database IDs

• 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; 46508847; 160963600
• PubChem CID: 1775

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.486641
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.1474779
• LogD (pH = 7.4): 2.1141331
• Log P: 2.1479204
• Molar Refractivity: 70.1823 cm^3
• Polarizability: 27.12261 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.26
• LOG S: -3.55
• Solubility (Water): 7.11e-02 g/l

PROPERTIES

Physical Property

• Solubility: 32 mg/L; DMSO: soluble
• Melting Point: 293-295 °C(lit.); 293-298°C; 294 - 297°C
• Hydrophobicity(logP): 2.085; 2.2

Safety Information

• Storage Condition: -20°C
• RTECS: MU1050000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-61-22; 45-61-22-43
• Safety Statements: 53-20-24-37-45; 53-45
• TSCA Listed: 否
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H350-H360; H350-H360-H317-H303
• GHS Precautionary statements: P201-P308 + P313; P261-P280-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: room temp

Pharmacology Properties

• Gene Information: human ... CNR1(1268), CNR2(1269), CYP2C9(1559)rat ... Faah(29347), Scn1a(81574), Scnn1g(24768), Slc6a1(79212)
• Mechanism of Action: Apparent motor cortex depressant; Apparent primary site of action is motor-cortex where spread of seizure activity is inhibited; May promote neuronal sodium-efflux so stabilizing threshold against hyperexcitability caused by events capable of reducing membrane sodium gradient; Reduces posttetanic potentiation at synapses preventing cortical seizure foci from detonating adjacent cortical areas; Reduces the maximal activity of brain-stem centers responsible for the tonic-phase of grand-mal seizures

Product Information

• Purity: ≥99%; 95%; 98%; 99%
• Grade: certified reference material
• Salt Data: Free Base
• Packaging: pkg of 1 g
• Application(s): Anticonvulsant; Antiepileptic (veterinary product)
• Pharmacopeia Traceability: traceable to PhEur P1290000; traceable to USP 1535008
• Empirical Formula (Hill Notation): C15H12N2O2

DETAILS

MP Biomedicals - 05213294

MP Biomedicals Rare Chemical collection

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]

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。

Sigma Aldrich - 161926

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

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.

REFERENCES

• 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)
• 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