21616-46-6

Basic information

• Product Name: 3-(hydroxymethyl)phenytoin
• Synonyms: 3-(hydroxymethyl)phenytoin
• CAS NO: 21616-46-6
• Molecular Formula: C₁₆H₁₄N₂O₃
• Molecular Weight: 282.29396
• Mol File: 21616-46-6.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 424.91°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.1658 (rough estimate)
• Refractive Index: 1.6240 (estimate)
• Water Solubility: 0.14g/L(22 oC)
• CAS DataBase Reference: 3-(hydroxymethyl)phenytoin(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(hydroxymethyl)phenytoin(21616-46-6)
• EPA Substance Registry System: 3-(hydroxymethyl)phenytoin(21616-46-6)

Safety Data

• Hazardous Substances Data: 21616-46-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H14N2O3/c19-11-18-14(20)16(17-15(18)21,12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,19H,11H2,(H,17,21)

Upstream product

• 50-00-0 formaldehyd 
• 57-41-0 phenythoin 
• 584-08-7 potassium carbonate 

Downstream Products

• 33588-93-1 3-bromomethyl-5,5-diphenyl-imidazolidine-2,4-dione 
• 71919-17-0 4-((2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methoxy)-4-oxobutanoic acid 
• 71919-16-9 5-((2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methoxy)-5-oxopentanoic acid 
• 123360-25-8 <(2,4-dioxo-5,5-diphenyl-3-imidazolidinyl)methyl>-6-methylpyridine-3-carboxylate 
• 85901-32-2 Propionic acid 2,5-dioxo-4,4-diphenyl-imidazolidin-1-ylmethyl ester 
• 27506-79-2 (2,5-dioxo-4,4-diphenylimidazolidin-1-yl)methyl acetate 
• 85901-34-4 3-pentanoyloxymethyl 5,5-diphenylhydantoin 
• 93360-04-4 3-(hydroxymethyl)-5,5-diphenylhydantoin p-nitrophenyl carbonate 
• 85901-33-3 Butyric acid 2,5-dioxo-4,4-diphenyl-imidazolidin-1-ylmethyl ester 
• 123337-31-5 <(2,4-dioxo-5,5-diphenyl-3-imidazolidinyl)methyl>-3-bromopropionate 
• 85901-37-7 Heptanoic acid 2,5-dioxo-4,4-diphenyl-imidazolidin-1-ylmethyl ester 
• 85901-38-8 3-octanoyloxymethyl 5,5-diphenylhydantoin 
• 123337-30-4 <(2,4-dioxo-5,5-diphenyl-3-imidazolidinyl)methyl>bromoacetate 
• 85901-39-9 Nonanoic acid 2,5-dioxo-4,4-diphenyl-imidazolidin-1-ylmethyl ester 

Relevant articles and documents

Identification, synthesis, characterization and quality control strategy of new process-related impurities in fosphenytoin sodium

Fosphenytoin sodium is a water dissolvable phenytoin prodrug that is directed intravenously to convey phenytoin, conceivably more securely than intravenous phenytoin. It is most ordinarily utilized in the intense treatment of convulsive status epileptics. The examination of the procedure-related contaminants will not help exclusively to advance the process parameters yet additionally to create sensible analytical methods and set the quality standard for a quality control system in pharmaceutical manufacturing. During the production of fosphenytoin sodium, all the process-related impurities are controlled in every stage and three degradation impurities are managed in the final API as per USP monograph. Besides, five unknown and one known contaminants were detected by HPLC method. All these impurities were identified, synthesized, isolated and characterized by IR, 1D-NMR (1H, 13C, DEPT) and HRMS spectral techniques. The mechanism of the formed impurities is examined for the first time. Quality control procedures to manage these impurities were developed to acquire the mass medication of ICH grade quality.

Design, synthesis and biological evaluation of water-soluble phenytoin prodrugs considering the substrate recognition ability of human carboxylesterase 1

Human carboxylesterase 1 (hCES1) is a hydrolase that is mainly expressed in the liver and lung and plays the most important role in the metabolic activation of ester–type prodrugs. In this study, design, synthesis and evaluation of water–soluble phenytoin prodrugs were performed with consideration of the substrate recognition ability of hCES1. The phenytoin prodrugs were synthesized in two steps without column chromatography. It was confirmed that all prodrugs are efficiently converted to phenytoin in a human liver microsome (HLM) solution (up to 54.6 nmol/mg protein/min). Although some of the prodrugs were degraded in strongly basic solution, the solubility of all prodrugs was greater than that of phenytoin in buffer solutions at pH 7.4 and 8.3. Among the synthesized phenytoin prodrugs, the 3,3-dimethylglutarate prodrug was superior in terms of solubility and stability, and it showed solubility of 10 mg/mL or more (phenytoin: 0.1 mg/mL) in a solution of pH 8.3. It was also found that the 3,3-dimethylglutarate prodrug was selectively activated by hCES1 but not hCES2 or arylacetamidodeacetylase.

Organic amine salt of fosphenytoin stability and its preparation and use

The invention relates to a stable organic amine salt of fosphenytoin and the preparation method and use thereof, the related organic amine salt of fosphenytoin having a structure of the general formula as shown in general formula (I), and the use comprisi