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161543

5-(4-Hydroxyphenyl)-5-phenylhydantoin

Name: 5-(4-Hydroxyphenyl)-5-phenylhydantoin
Brand: ALDRICH

98%

Synonym(s):

4-Hydroxydiphenylhydantoin, p-Hydroxyphenytoin, NSC 156081

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₁₂N₂O₃

CAS Number:

2784-27-2

Molecular Weight:

268.27

NACRES:

NA.22

PubChem Substance ID:

24849940

UNSPSC Code:

12352100

EC Number:

220-492-2

MDL number:

MFCD00005262

Assay:

98%

Form:

solid

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Properties

assay

98%

form

solid

mp

>300 °C (lit.)

solubility

soluble 50 mg/mL, clear, colorless to faintly yellow (DMF:MeOH(2:1))

functional group

phenyl

SMILES string

Oc1ccc(cc1)C2(NC(=O)NC2=O)c3ccccc3

InChI

1S/C15H12N2O3/c18-12-8-6-11(7-9-12)15(10-4-2-1-3-5-10)13(19)16-14(20)17-15/h1-9,18H,(H2,16,17,19,20)

InChI key

XEEDURHPFVXALT-UHFFFAOYSA-N

Description

General description

5-(4-Hydroxyphenyl)-5-phenylhydantoin is the major metabolite of phenytoin.

Application

5-(4-Hydroxyphenyl)-5-phenylhydantoin was used in enantiomeric separation of chiral pharmaceuticals using a teicoplanin chiral stationary phase by aqueous and non-aqueous packed capillary electrochromatography. It was used as internal standard in determination of phenylbutazone and its metabolite oxyphenbutazone in human plasma by GLC.

Reactant for activation of hydroxylated metabolites of carbamazepine and phenytoin

Used in studies investigating
Transport across the human placenta barrier
Effects on cellular glucose transport

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

8214KL

3702HE

00213DG

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Phenytoin overview--metabolite interference in some immunoassays could be clinically important.

William L Roberts et al.

Archives of pathology & laboratory medicine, 128(7), 734-734 (2004-07-02)

Involvement of multiple UDP-glucuronosyltransferase 1A isoforms in glucuronidation of 5-(4'-hydroxyphenyl)-5-phenylhydantoin in human liver microsomes.

Miki Nakajima et al.

Drug metabolism and disposition: the biological fate of chemicals, 30(11), 1250-1256 (2002-10-19)

In humans, orally administered phenytoin, 5,5-diphenylhydantoin, is mainly excreted as 5-(4'-hydroxyphenyl)-5-phenylhydantoin (4'-HPPH) O-glucuronide. Phenytoin is oxidized to 4'-HPPH by CYP2C9 and to a minor extent by CYP2C19, and then 4'-HPPH is metabolized to 4'-HPPH O-glucuronide by UDP-glucuronosyltransferase (UGT). In the

CYP2C9 inhibition: impact of probe selection and pharmacogenetics on in vitro inhibition profiles.

Vikas Kumar et al.

Drug metabolism and disposition: the biological fate of chemicals, 34(12), 1966-1975 (2006-09-12)

Drug-drug interactions may cause serious adverse events in the clinical setting, and the cytochromes P450 are the enzyme system most often implicated in these interactions. Cytochrome P450 2C is the second most abundant subfamily of cytochrome P450 enzymes and is

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Global Trade Item Number

SKU	GTIN
161543-1G	04061826704974