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1535008

USP

Phenytoin

United States Pharmacopeia (USP) Reference Standard

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
Beilstein:
384532
MDL number:
MFCD00005264
UNSPSC Code:
41116107
PubChem Substance ID:
329750826
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

phenytoin

manufacturer/tradename

USP

mp

293-295 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

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

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Phenytoin USP Reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Phenytoin Sodium
  • Phenytoin Chewable Tablets
  • Phenytoin Oral Suspension
  • Phenytoin Sodium Injection
  • Extended Phenytoin Sodium Capsules
  • Phenytoin Compounded Topical Gel
  • Fosphenytoin Sodium Injection

Biochem/physiol Actions

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

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

Sales restrictions may apply.

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Phenytoin Related Compound A, United States Pharmacopeia (USP) Reference Standard

1535507

Phenytoin sodium, United States Pharmacopeia (USP) Reference Standard

1535020

Phenytoin Related Compound B, United States Pharmacopeia (USP) Reference Standard

P1290000

Phenytoin, European Pharmacopoeia (EP) Reference Standard

P1300000

Phenytoin sodium, European Pharmacopoeia (EP) Reference Standard

Y0001167

Phenytoin for system suitability, European Pharmacopoeia (EP) Reference Standard

PHR1492

Phenytoin sodium, Pharmaceutical Secondary Standard; Certified Reference Material

PHR1574

Phenytoin Related Compound A, Pharmaceutical Secondary Standard; Certified Reference Material

PHR1692

Phenytoin Related Compound B, Pharmaceutical Secondary Standard; Certified Reference Material

BP1238

Phenytoin sodium, British Pharmacopoeia (BP) Reference Standard

PHR2246

1-Methyl-5,5-diphenylimidazolidine-2,4-dione, Pharmaceutical Secondary Standard; Certified Reference Material

PHR9055

Benzil, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

PHR2247

5-(4-Methylphenyl)hydantoin

PHR2553

Phenytoin Impurity F, Pharmaceutical Secondary Standard; Certified Reference Material

Pictograms

Health hazardExclamation mark
GHS08,GHS07

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

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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Deborah Pugin et al.
Critical care (London, England), 18(3), R103-R103 (2014-06-03)
Seizures refractory to third-line therapy are also labeled super-refractory status epilepticus (SRSE). These seizures are extremely difficult to control and associated with poor outcome. We aimed to characterize efficacy and side-effects of continuous infusions of pentobarbital (cIV-PTB) treating SRSE. We
H Kamp et al.
Bioanalysis, 4(18), 2291-2301 (2012-10-11)
BASF and Metanomics have built-up the database MetaMap(®)-Tox containing rat plasma metabolome data for more than 500 reference compounds. Phenytoin was administered to five Wistar rats of both sexes at dietary dose levels of 600 and 2400 ppm over 28
Anoop S V Shah et al.
Clinical toxicology (Philadelphia, Pa.), 48(8), 800-805 (2010-10-07)
Seizures are a common sequela of self-poisoning. However, their mechanism differs from seizures of other etiologies. Toxicological seizures result from alterations in the excitatory and inhibitory balance of otherwise normal neurons. In contrast, idiopathic or trauma related seizures usually start
Precision, bias, and clinical utility of the Sheiner-Tozer equation to guide phenytoin dosing in critically ill adults.
Jennifer Bolt et al.
Journal of clinical pharmacology, 53(4), 451-455 (2013-02-26)
Hannah Priyadarshini Gideon et al.
PLoS pathogens, 11(1), e1004603-e1004603 (2015-01-23)
Lung granulomas are the pathologic hallmark of tuberculosis (TB). T cells are a major cellular component of TB lung granulomas and are known to play an important role in containment of Mycobacterium tuberculosis (Mtb) infection. We used cynomolgus macaques, a
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