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D4505

5,5-Diphenylhydantoin sodium salt

≥99%

Synonym(s):

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

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About This Item

Linear Formula:
C15H11N2O2Na
CAS Number:
Molecular Weight:
274.25
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
211-148-2
MDL number:
Assay:
≥99%
Form:
powder
Quality level:
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Quality Level

assay

≥99%

form

powder

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

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.
Reduces incidence of grand mal seizures; appears to stabilize excitable membranes.

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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1 of 1

This Item
D40071535507SML0117
form

powder

form

powder

form

-

form

powder

assay

≥99%

assay

≥98%

assay

-

assay

≥98% (HPLC)

Quality Level

200

Quality Level

100

Quality Level

-

Quality Level

100

solubility

aqueous base: soluble

solubility

DMSO: soluble

solubility

-

solubility

H2O: ≥15 mg/mL

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)

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)

Gene Information

human ... SCN10A(6336), SCN11A(11280), SCN1A(6323), SCN2A(6326), SCN3A(6328), SCN4A(6329), SCN5A(6331), SCN7A(6332), SCN8A(6334), SCN9A(6335)

Gene Information

-


pictograms

Health hazardExclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges



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Activation of c-Jun and suppression of phospho-p44/42 were involved in diphenylhydantoin-induced apoptosis of cultured rat cerebellar granule neurons
Zhao LZ, et al.
Acta Pharmacologica Sinica, 24(6), 539-548 (2003)
Ravi Goyal et al.
PloS one, 10(6), e0130739-e0130739 (2015-06-26)
Long-term hypoxia (LTH) is an important stressor related to health and disease during development. At different time points from fetus to adult, we are exposed to hypoxic stress because of placental insufficiency, high-altitude residence, smoking, chronic anemia, pulmonary, and heart
Expression of biomarker genes of differentiation in D3 mouse embryonic stem cells after exposure to different embryotoxicant and non-embryotoxicant model chemicals
Romero AC, et al.
Data in Brief, 5(2), 354-354 (2015)



Global Trade Item Number

SKUGTIN
D4505-25G04061833564479
D4505-100G04061833564462

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