Phenytoin sodium

Base Information

• Chemical Name: Phenytoin sodium
• CAS No.: 630-93-3
• Deprecated CAS: 1421-15-4,143-75-9,8017-52-5,143-75-9,8017-52-5
• Molecular Formula: C₁₅H₁₁N₂O₂*Na
• Molecular Weight: 274.254
• Hs Code.: 29332100
• European Community (EC) Number: 211-148-2
• UNII: 4182431BJH
• DSSTox Substance ID: DTXSID2023775
• Wikidata: Q27258415
• NCI Thesaurus Code: C48011
• RXCUI: 71227
• Mol file: 630-93-3.mol

Synonyms:5,5-Diphenylhydantoin;5,5-diphenylimidazolidine-2,4-dione;Antisacer;Difenin;Dihydan;Dilantin;Diphenylhydantoin;Diphenylhydantoinate, Sodium;Epamin;Epanutin;Fenitoin;Hydantol;Phenhydan;Phenytoin;Phenytoin Sodium;Sodium Diphenylhydantoinate

Chemical Property of Phenytoin sodium

Chemical Property:

• Appearance/Colour: White powder.
• Melting Point: 290-299oC
• Boiling Point: 428.2 °C at 760 mmHg
• Flash Point: 212.8 °C
• PSA: 49.41000
• LogP: 2.21300
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: aqueous base: soluble
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 274.07182188
• Heavy Atom Count: 20
• Complexity: 356

Purity/Quality:

99% ^*data from raw suppliers

5,5-DiphenylHydantoinSodium ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-43-62-63
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2(C(=O)[N-]C(=O)N2)C3=CC=CC=C3.[Na+]
• Recent ClinicalTrials: A Study to Assess the Effect of Itraconazole, Phenytoin and Gemfibrozil on the Drug Levels of BMS-986166 in Healthy Participants
• Recent EU Clinical Trials: Emergency Treatment with Levetiracetam or Phenytoin in Status Epilepticus in Children (EcLiPSE) – an open label randomised controlled trial
• Uses: antibacterial Antiepileptic 5,5-Diphenylhydantoin sodium salt has been used:in the cream preparation for treating burn woundsin seizure behavior testing as an anticonvulsant in Drosophilain in vivo embryo toxicity test in mouse embryonic stem cells
• Clinical Use: Phenytoin sodium’s cardiovascular effects were uncoveredduring observation of toxic manifestations of the drugin patients being treated for seizure disorders. Phenytoinsodium was found to cause bradycardia, prolong the PRinterval, and produce T-wave abnormalities on electrocardiograms.It is a class IB antiarrhythmic agent. Today,phenytoin sodium’s greatest clinical use as an antiarrhythmicdrug is in the treatment of digitalis-induced arrhythmias.34 Its action is similar to that of lidocaine. It depressesventricular automaticity produced by digitalis, without adverseintraventricular conduction. Because it also reversesthe prolongation of AV conduction by digitalis, phenytoinsodium is useful in supraventricular tachycardias caused bydigitalis intoxication.

Technology Process of Phenytoin sodium

There total 2 articles about Phenytoin sodium which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

phenythoin (57-41-0) → sodium phenytoin (630-93-3,64915-84-0)

Guidance literature:

With sodium hydroxide; In ethanol; at 42 ℃; for 0.25h; Temperature;

Reference yield:

2-hydroxy-2-phenylacetophenone (119-53-9,579-44-2) → sodium phenytoin (630-93-3,64915-84-0)

Guidance literature:

Multi-step reaction with 3 steps

1: iron(III) chloride hexahydrate; acetic acid / water / 1 h / Reflux

2: potassium hydroxide; dmap / water; butan-1-ol / 0.67 h / 119 °C

3: sodium hydroxide / ethanol / 0.25 h / 42 °C

With dmap; iron(III) chloride hexahydrate; acetic acid; potassium hydroxide; sodium hydroxide; In ethanol; water; butan-1-ol;

Reference yield: 71.0%

diethylene glycol ditosylate (7460-82-4) + sodium phenytoin (630-93-3,64915-84-0) → 2-[2-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)ethoxy]ethyl-4-methylbenzenesulphonate (1418003-55-0)

Guidance literature:

In N,N-dimethyl-formamide; at 60 - 80 ℃; for 4h;

DOI:10.1007/s12272-012-1207-3

upstream raw materials:

phenythoin

2-hydroxy-2-phenylacetophenone

Downstream raw materials:

1,3-bis-(2-hydroxy-3-morpholin-4-yl-propyl)-5,5-diphenyl-imidazolidine-2,4-dione

3-(2-hydroxy-3-morpholin-4-yl-propyl)-5,5-diphenyl-imidazolidine-2,4-dione

5,5-diphenyl-3-[2-(1,1,3-trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-ethyl]-imidazolidine-2,4-dione

3-benzyloxymethyl-5,5-diphenylhydantoin

Refernces

• 1、 -. "Synthetic method of phenytoin sodium". Paragraph 0025; 0034; 0038; 0039; 0042; 0046; 0050. . Retrieved 2019/03/28.