161543
5-(4-羟基苯基)-5-苯基乙内酰脲
98%
别名:
4-Hydroxydiphenylhydantoin, p-Hydroxyphenytoin, NSC 156081
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经验公式（希尔记法）:
C15H12N2O3
化学文摘社编号:
分子量:
268.27
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
220-492-2
MDL number:
Assay:
98%
Form:
solid
InChI key
XEEDURHPFVXALT-UHFFFAOYSA-N
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)
SMILES string
Oc1ccc(cc1)C2(NC(=O)NC2=O)c3ccccc3
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
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
Used in studies investigating
Transport across the human placenta barrier
Effects on cellular glucose transport
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
存储类别
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
A Takahashi et al.
Japanese journal of pharmacology, 82(1), 82-84 (2000-06-30)
The effects of phenytoin and its major metabolite, 5-(4-hydroxyphenyl)-5-phenylhydantoin (HPPH), on bone resorption of neonatal mouse calvaria were examined in vitro. Both phenytoin and HPPH induced significant bone resorption as compared to the controls after 72 h in culture. This
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
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
T Yao et al.
Se pu = Chinese journal of chromatography, 15(4), 316-318 (1997-07-01)
A chiral RP-HPLC method was developed to assay the 5-(p-hydroxyphenyl)-5-Phenylhydantoin (p-HPPH) enantiomers, the major metabolite of antiepileptic drug phenytoin, in rat hepatic microsomes. A 50 mm FLC-C8 column was used as the analytical column, beta-cyclodextrin (beta-CD) as chiral mobile phase
Joo-Ho Park et al.
Biotechnology and bioengineering, 78(7), 779-793 (2002-05-10)
We developed a kinetic model that describes a heterogeneous reaction system for the production of D-p-hydroxyphenylglycine from D,L-p-hydroxyphenyl-hydantoin using D-hydantoinase of Bacillus stearothermophilus SD1 and N-carbamoylase of Agrobacterium tumefaciens NRRL B11291. As a biocatalyst, whole cells with separately or co-expressed
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