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D4505 Sigma-Aldrich

5,5-Diphenylhydantoin sodium salt

≥99%

Synonym: 5,5-Diphenyl-2,4-imidazolidinedione, Phenytoin

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Properties

Related Categories Anticonvulsants, Application Index, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents,
Quality Level   200
assay   ≥99%
solubility   aqueous base: soluble
SMILES string   [Na]N1C(=O)NC(C1=O)(c2ccccc2)c3ccccc3
InChI   1S/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);/q;+1/p-1
InChI key   FJPYVLNWWICYDW-UHFFFAOYSA-M
Gene Information   human ... CNR1(1268), CNR2(1269), CYP2C9(1559), SCN10A(6336), SCN11A(11280), SCN1A(6323), SCN2A(6326), SCN3A(6328), SCN4A(6329), SCN5A(6331), SCN7A(6332), SCN8A(6334), SCN9A(6335)
rat ... Faah(29347), Scn1a(81574), Scnn1g(24768), Slc6a1(79212)

Description

General description

5,5-Diphenylhydantoin sodium salt is a derivative of phenytoin. 5,5-Diphenylhydantoin is used for treating epilepsy and has antiepileptic activity. It functions by blocking the sodium channels and modulates excitation of neurons. However, the side effects include hypertrichosis and overgrowth of gum tissue around the teeth. It promotes proliferation of the neural stem cells by modulating growth factors. Diphenylhydantoin is toxic and induces apoptosis in cultured cerebellar granule neurons.

Application

5,5-Diphenylhydantoin sodium salt has been used:
• in the cream preparation for treating burn wounds
• in seizure behavior testing as an anticonvulsant in Drosophila
• in in vivo embryo toxicity test in mouse embryonic stem cells

Biochem/physiol Actions

Reduces incidence of grand mal seizures; appears to stabilize excitable membranes perhaps through effects on Na+, K+, and Ca2+ channels.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
WGK 3
RTECS 
MU1400000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Discover Bioactive Small Molecules for ADME/Tox

A significant number of drugs that fail in clinical trials have been associated with safety issues, including unexpected drug-drug interactions (DDI) or lack of efficacy due to poor pharmacokinetics....
Keywords: Absorption, Bioactive small molecules, Clinical, Metabolism

Peer-Reviewed Papers
15

References

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