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Key Documents

D4505

Sigma-Aldrich

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
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

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

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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.

Pictograms

Health hazardExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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
Comparison of efficacy of topical phenytoin with hypericin in second-degree burn wound healing: an experimental study in rats
Sayar H, et al.
Medical Science Monitor Basic Research, 20(6), 36-36 (2014)
Phenytoin: a step by step insight into its multiple mechanisms of action?80 years of mechanistic studies in neuropharmacology
HJM Keppel
Journal of Neurology, 264(9), 2043-2047 (2017)

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