630-93-3

Basic information

• Product Name: Phenytoin sodium
• Synonyms: solantoin;solantyl;solublephenytoin;tacosal;5,5-Diphenylhydatoin sodium salt;5,5-Diphenyl-2,4;PHENYTOINUM NATRICUM;2,4-Imidazolidinedione, 5,5-diphenyl-, monosodium salt
• CAS NO: 630-93-3
• Molecular Formula: C₁₅H₁₁N₂O₂*Na
• Molecular Weight: 274.25
• EINECS: 211-148-2
• Product Categories: Classes of Metal Compounds;Na (Sodium) Compounds (excluding simple sodium salts);Typical Metal Compounds;Sodium channel;API intermediate;RONDOMYCIN
• Mol File: 630-93-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 428.2 °C at 760 mmHg
• Flash Point: 212.8 °C
• Appearance: White to almost white/Crystalline Powder
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: aqueous base: soluble
• Merck: 14,7322
• CAS DataBase Reference: Phenytoin sodium(CAS DataBase Reference)
• NIST Chemistry Reference: Phenytoin sodium(630-93-3)
• EPA Substance Registry System: Phenytoin sodium(630-93-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43-62-63
• Safety Statements: 22-36/37/39-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: MU1400000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 630-93-3(Hazardous Substances Data)

Usage

Description

Phenytoin sodium, also known as 5,5-diphenylhydantoin sodium salt, is an anticonvulsant and antiepileptic medication with a long history of use in treating various types of seizures. It functions by stabilizing the inactive state of voltage-gated sodium channels, thereby reducing the spread of seizure activity in the brain. Its chemical structure and properties make it a versatile compound with applications in both medical and non-medical fields.

Uses

Used in Pharmaceutical Industry:
Phenytoin sodium is used as an antiepileptic drug for the treatment of various types of seizures, including generalized tonic-clonic seizures, partial seizures, and status epilepticus. Its ability to stabilize the inactive state of voltage-gated sodium channels helps prevent the spread of seizure activity in the brain.
Used in Antibacterial Applications:
Phenytoin sodium has been found to possess antibacterial properties, making it useful in the development of new antimicrobial agents. Its ability to inhibit bacterial growth can be utilized in the formulation of antibiotics and other antimicrobial products.
Used in Cosmetics Industry:
In the cosmetics industry, Phenytoin sodium is used in the preparation of creams for treating burn wounds. Its anti-inflammatory and wound-healing properties make it an effective component in formulations designed to promote skin regeneration and reduce the risk of infection.
Used in Neuroscientific Research:
Phenytoin sodium is used as an anticonvulsant in seizure behavior testing with model organisms such as Drosophila. This allows researchers to study the effects of various compounds on seizure susceptibility and develop new treatments for epilepsy.
Used in Toxicological Studies:
Phenytoin sodium has been employed in in vivo embryo toxicity tests in mouse embryonic stem cells. This helps researchers evaluate the potential teratogenic effects of various compounds and understand the mechanisms underlying their toxicity.

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.

Safety Profile

Confirmed carcinogen. Experimental teratogen. Other experimental reproductive effects. Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Human systemic effects by ingestion: anorexia, respiratory depression, nausea or vomiting, hemorrhage, dermatitis, and endocrine effects. Mutation data reported. An anticonvulsant and cardiac depressant used for the treatment of grand mal and psychomotor seizures. When heated to decomposition it emits very toxic fumes of NOx and Na2O.

InChI:InChI=1/C15H12N2O2.Na/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);

Upstream product

• 57-41-0 phenythoin 
• 119-53-9 2-hydroxy-2-phenylacetophenone 

Downstream Products

• 27512-05-6 3-benzyloxymethyl-5,5-diphenylhydantoin 
• 27512-00-1 3-methoxymethyl-5,5-diphenylhydantoin 
• 1053-09-4 3-benzoyl-5,5-diphenylhydantoin 
• 28997-32-2 3-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl]-5,5-diphenyl-imidazolidine-2,4-dione 
• 1418003-58-3 3-{2-[2-(morpholin-4-yl)ethoxy]ethyl}-5,5-diphenylimidazolidine-2,4-dione 
• 1418003-56-1 2-{2-[2-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)ethoxy]ethoxy}ethyl-4-methylbenzenesulphonate 
• 1418003-55-0 2-[2-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)ethoxy]ethyl-4-methylbenzenesulphonate 
• 1418003-61-8 3-{2-[2-(4-(4-chlorophenyl)piperazin-1-yl)ethoxy]ethyl}-5,5-diphenylimidazolidine-2,4-dione 
• 1418003-60-7 3-{2-[2-(4-phenylpiperazin-1-yl)ethoxy]ethyl}-5,5-diphenylimidazolidine-2,4-dione 
• 1418003-59-4 3-{2-[2-(piperidin-1-yl)ethoxy]ethyl}-5,5-diphenylimidazolidine-2,4-dione 
• 1418003-57-2 3-{2-[2-(benzylamino)ethoxy]ethyl}-5,5-diphenylimidazolidine-2,4-dione 
• 1418003-66-3 N-{2-[2-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)ethoxy]ethyl}aminoguanidine 
• 1418003-69-6 N,N-(butane-1,4-diyl)bis[2-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)acetamide] 
• 1418003-68-5 N,N-(propane-1,3-diyl)bis[2-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)acetamide] 

Relevant articles and documents

Method for preparing phenytoin sodium

The invention relates to the field of biological medicines, and discloses a method for preparing phenytoin sodium. The method is characterized by comprising the following steps: (1) carrying out an oxidation reaction on benzoin in a first solvent to obtain diphenyl ethanedione, wherein the first solvent is a mixed solution of an alcohol and water, and the alcohol is at least one selected from C1-C3 monohydric alcohols; (2) carrying out a rearrangement reaction on diphenyl ethanedione to obtain phenytoin; and (3) carrying out salt forming reaction on the phenytoin in water, and performing purifying to obtain the phenytoin sodium. According to the method provided by the invention, few solvent systems are introduced, acetic acid is prevented from being used, subsequent treatment is relativelysimple, and the prepared phenytoin sodium is relatively high in yield and purity and is convenient to large-scale production.

AN IMPROVED PROCESS FOR THE PREPARATION OF PHENYTOIN SODIUM

The present invention relates to an improved process for the preparation of Phenytoin Sodium of formula (I) by reacting Phenytoin with aqueous solution of Sodium hydroxide in presence of aqueous Sodium chloride.