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D4007

Sigma-Aldrich

5,5-Diphenylhydantoin

≥98%

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Synonym(s):
5,5-Diphenyl-2,4-imidazolidinedione, Phenytoin
Empirical Formula (Hill Notation):
C15H12N2O2
CAS Number:
57-41-0
Molecular Weight:
252.27
Beilstein:
384532
EC Number:
200-328-6
MDL number:
MFCD00005264
PubChem Substance ID:
24278370
NACRES:
NA.77

Quality Level

100

Assay

≥98%

form

powder

mp

293-295 °C (lit.)

solubility

DMSO: soluble

SMILES string

O=C1NC(=O)C(N1)(c2ccccc2)c3ccccc3

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)

InChI key

CXOFVDLJLONNDW-UHFFFAOYSA-N

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)

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General description

5,5-Diphenylhydantoin is an anticonvulsant, which is used to treat tonic-clonic seizures, complex partial seizures and neurosurgical related seizures. It induces osteoblast proliferation and differentiation. 5,5-Diphenylhydantoin used to treat epilepsy. It reduces the hyperexcitability of tissues and may be associated with cerebellar atrophy.

Application

5,5-Diphenylhydantoin has been used for phenytoin treatment. It has also been used to slow down or prevent mesoendoderm cell migration.

Biochem/physiol Actions

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

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Danger

Hazard Statements

H302 - H351 - H360FD

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Repr. 1B

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Xing J, et al.
Scientific Reports, 7(1), 8491-8491 (2017)
Advanced Therapy in Epilepsy (2009)
Phenytoin activates SMAD3 phosphorylation and periostin expression in drug-induced gingival enlargement
Kim SS, et al.
Histology and Histopathology, 33(12), 1287-1298 (2018)
Giulio G Muccioli et al.
Journal of medicinal chemistry, 49(1), 417-425 (2006-01-06)
The demonstration of the essential role of fatty acid amide hydrolase (FAAH) in hydrolyzing endogenous bioactive fatty acid derivatives has launched the quest for the discovery of inhibitors for this enzyme. Along this line, a set of 58 imidazolidine-2,4-dione and
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