UC180
(S)-(+)-Nirvanol
Synonym(s):
(S)-(+)-5-Ethyl-5-phenyl-2,4-imidazolidinedione, (S)-(+)-5-Ethyl-5-phenylhydantoin
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About This Item
Empirical Formula (Hill Notation):
C11H12N2O2
CAS Number:
Molecular Weight:
204.23
MDL number:
UNSPSC Code:
12161501
PubChem Substance ID:
NACRES:
NA.77
form
solid
Quality Level
color
off-white
solubility
DMF: soluble
storage temp.
2-8°C
SMILES string
CC[C@]1(NC(=O)NC1=O)c2ccccc2
InChI
1S/C11H12N2O2/c1-2-11(8-6-4-3-5-7-8)9(14)12-10(15)13-11/h3-7H,2H2,1H3,(H2,12,13,14,15)/t11-/m0/s1
InChI key
UDTWZFJEMMUFLC-NSHDSACASA-N
Related Categories
Biochem/physiol Actions
5-ethyl-5-phenylhydantoin (EPH) is a long-acting sedative. It is implicated to favor hepatocellular and thyroid follicular cell tumor progression.
CYP2B6 metabolite of (R)-(-)-mephenytoin; anticonvulsant; hypnotic.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Preparation Note
Nirvanol is soluble in DMF.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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J W Ko et al.
Drug metabolism and disposition: the biological fate of chemicals, 26(8), 775-778 (1998-08-11)
We tested the ability of human liver microsomes (HLMs) and recombinant human cytochrome P450 (CYP or P450) isoforms to catalyze the N-demethylation of nirvanol-free (S)-mephenytoin [(S)-MP] in vitro. In mixed HLMs, the kinetics of (S)-MP N-demethylation suggested two contributing activities.
R W Nims et al.
Journal of biochemical toxicology, 9(5), 269-278 (1994-10-01)
The abilities of structural congeners of phenobarbital to induce immunoreactive hepatic cytochrome P450 2B (CYP2B) protein and associated catalytic activity (benzyloxyresorufin O-dealkylation) in the male B6C3F1 mouse were examined. Interspecies differences in inducing ability were examined through comparison of the
R W Nims et al.
Journal of biochemical toxicology, 9(6), 279-288 (1994-12-01)
To explore the enantioselectivity of ligand interaction with the putative phenobarbital receptor, the pharmacodynamics of cytochrome P450 2B (CYP2B) induction by racemic 5-ethyl-5-phenylhydantoin and its two enantiomers were investigated in the male F344/NCr rat and in cultured adult male rat
H Heyn et al.
Drug metabolism and disposition: the biological fate of chemicals, 24(9), 948-954 (1996-09-01)
In vitro methods were used to identify the cytochrome P450 (CYP) enzyme(s) involved in S-mephenytoin N-demethylation. S-Mephenytoin (200 microM) was incubated with human liver microsomes, and nirvanol formation was quantitated by reversed-phase HPLC. S-Mephenytoin N-demethylase activity in a panel of
A Küpfer et al.
European journal of clinical pharmacology, 26(6), 753-759 (1984-01-01)
Inherited deficiency in mephenytoin hydroxylation was observed in a family study. It is important that the propositus was of the extensive metabolizer phenotype for the genetically controlled hydroxylation of debrisoquine. Thus, a genetic polymorphism of drug hydroxylation was suspected for
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