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Merck

PHR1139

Phenytoin

Pharmaceutical Secondary Standard; Certified Reference Material

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C15H12N2O2
CAS Number:
57-41-0
Molecular Weight:
252.27
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329823159
EC Number:
200-328-6
Beilstein/REAXYS Number:
384532
MDL number:
MFCD00005264

Key Documents

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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

SMILES string

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

grade

certified reference material, pharmaceutical secondary standard

agency

traceable to Ph. Eur. P1290000, traceable to USP 1535008

API family

phenytoin

CofA

current certificate can be downloaded

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

mp

293-295 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-30°C

Quality Level

300

Gene Information

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

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Analysis Note

These secondary standards offer multi-traceability to the USP and EP (PhEur) primary standards, where they are available.

Application

Phenytoin may be used as a pharmaceutical reference standard in the determination of the analyte in pharmaceutical formulations and combined dosage forms by electrochemical, spectrophotometric, and chromatographic techniques.
These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Biochem/physiol Actions

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

General description

Phenytoin is a well-known aromatic anticonvulsant which undergoes metabolism in the hepatic microsomal system. It finds its application as the most effective treatment available for seizure disorders. It belongs to the class of phenyl hydantoins compounds. It can hinder the unnecessary activity of the brain during seizures by bringing stability to the sodium channels, causing decreased electrical conductivity among brain cells.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.
This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.
To see an example of a Certificate of Analysis for this material enter LRAB7779 in the slot below. This is an example certificate only and may not be the lot that you receive.
Values of analytes vary lot to lot.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk

WGK 3

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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Familial occurrence of hypersensitivity to phenytoin
Gennis MA, et al.
The American Journal of Medicine, 91(6), 631-634 (1991)
Phenytoin: pharmacokinetics and bioavailability
Gugler R, et al.
Clinical Pharmacology and Therapeutics, 19(2), 135-142 (1976)
Development and validation of a stability-indicating isocratic reverse phase-liquid chromatography assay for determination of phenytoin in bulk and pharmaceutical formulations
Yong TS and Gan SN
International Journal of Pharmacy and Pharmaceutical Sciences, 38(3), 420-427 (2015)
Cimetidine interaction with phenytoin.
Hetzel DJ, et al.
British Medical Journal, 282(6275), 1512-1512 (1981)
A poly (vinylchloride) membrane electrode for determination of phenytoin in pharmaceutical formulations
Cosofret,VV and Buck RP
Journal of Pharmaceutical and Biomedical Analysis, 4(1), 45-51 (1986)
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