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Merck

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:
630-93-3
Molecular Weight:
274.25
NACRES:
NA.77
PubChem Substance ID:
24277707
UNSPSC Code:
12352200
EC Number:
211-148-2
MDL number:
MFCD00069674
Assay:
≥99%
Form:
powder
Quality level:
200

Key Documents

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InChI key

FJPYVLNWWICYDW-UHFFFAOYSA-M

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

SMILES string

[Na]N1C(=O)NC(C1=O)(c2ccccc2)c3ccccc3

assay

≥99%

form

powder

solubility

aqueous base: soluble

Quality Level

200

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)

Related Categories

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.

pictograms

Health hazardExclamation mark
GHS08,GHS07

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

D4505-VAR: + D4505-BULK: + D4505-25G: + D4505-100G: + D4505-500G: + D4505-1KG:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD9297
BCCD8766
BCCD3769
BCCD0776
BCCB8245

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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)
An RNAi-mediated screen identifies novel targets for next-generation antiepileptic drugs based on increased expression of the homeostatic regulator pumilio
Lin WH, et al.
Journal of Neurogenetics, 32(2), 106-117 (2018)
Diphenylhydantoin promotes proliferation in the subventricular zone and dentate gyrus
Galvez-Contreras AY, et al.
American journal of neuroscience, 3(1), 1-1 (2012)
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)
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
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