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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关于此项目
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:
产品名称
5-(4-羟基苯基)-5-苯基乙内酰脲, 98%
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
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
General description
5-(4-Hydroxyphenyl)-5-phenylhydantoin is the major metabolite of phenytoin.
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
F Jabbaribar et al.
Journal of chromatographic science, 47(10), 877-880 (2009-11-26)
Determination of phenytoin in biological fluids is necessary due to its non-linear pharmacokinetics and narrow therapeutic index. A simple and rapid micellar electrokinetic chromatographic method was developed for simultaneous determination of phenytoin and its main metabolite, 5-(4-hydroxyphenyl)-5-phenylhydantoin, in human serum.
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
Upendra A Argikar et al.
Epilepsy research, 71(1), 54-63 (2006-07-04)
Phenytoin (PHT) is primarily metabolized to 5-(4'-hydroxyphenyl)-5-phenylhydantoin (p-HPPH), accounting for 67-88% of an administered dose in humans. p-HPPH is formed by the cytochrome (CYP) 450 enzymes CYP2C9 and CYP2C19, then glucuronidated and excreted into the urine. CYP2C9 catalyses the prochiral
GLC determination of plasma concentration of phenylbutazone and its metabolite oxyphenbutazone.
K K Midha et al.
Journal of pharmaceutical sciences, 63(8), 1234-1239 (1974-08-01)
F Kamali et al.
Journal of clinical periodontology, 26(12), 802-805 (1999-12-22)
The potential effect of co-medication with phenobarbitone, primidone and carbamazepine on plasma and saliva concentrations of 5-(4-hydroxyphenyl)-5-phenylhydantoin (4-HPPH), the major metabolite of phenytoin in man and on the incidence of phenytoin-induced gingival overgrowth was investigated in a group of 36
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