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Merck

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:
Molecular Weight:
252.27
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
384532
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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)

SMILES string

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

InChI key

CXOFVDLJLONNDW-UHFFFAOYSA-N

grade

pharmaceutical primary standard

API family

phenytoin

manufacturer/tradename

USP

mp

293-295 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

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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.  ​

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

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

Disclaimer

Sales restrictions may apply.

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.

pictograms

Health hazardExclamation mark

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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

flash_point_f

Not applicable

flash_point_c

Not applicable


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Certificates of Analysis (COA)

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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
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)
P J Smith et al.
Endocrine reviews, 5(4), 514-524 (1984-01-01)
The studies described above indicate the likelihood of a significant effect of DPH on cellular functions that are regulated by T3 at concentrations of DPH that occur during treatment of patients with Dilantin. Thus, it is possible that sensitive measures
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

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