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Safety Information

UC180

Sigma-Aldrich

(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:
65567-34-2
Molecular Weight:
204.23
MDL number:
MFCD00272652
UNSPSC Code:
12161501
PubChem Substance ID:
329827656
NACRES:
NA.77

form

solid

Quality Level

200

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

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

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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Certificates of Analysis (COA)

Lot/Batch Number
0000099143
0000075463
BGBC5174V
561-011-3V
561-011-3

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P J Wedlund et al.
Journal of chromatography, 307(1), 121-127 (1984-04-13)
A gas chromatographic method was developed for the determination of the R- and S- enantiomers of the anticonvulsant, mephenytoin, and its N-demethylated metabolite, 5-phenyl-5- ethylhydantoin ( PEH ), in plasma and blood. Direct enantiomeric separation of mephenytoin and its internal
I H Hall et al.
Biomedica biochimica acta, 46(7), 623-634 (1987-01-01)
An investigation of the effects of the S-(+) and R-(-) enantiomers of 5-ethyl-5-phenylhydantoin as hypolipidemic agents was undertaken. The serum cholesterol and triglyceride levels were reduced approximately 40% by either oral or i.p. administration at 20 mg/kg.day of either enantiomer.
Genetic polymorphism of mephenytoin metabolism.
T Inaba
Progress in clinical and biological research, 214, 139-156 (1986-01-01)
B A Diwan et al.
Cancer research, 48(9), 2492-2497 (1988-05-01)
Male F344/NCr rats, 6 wk old, were fed 500 ppm of phenobarbital (PB) or equimolar doses of either 5-ethyl-5-phenylhydantoin (EPH) or 5,5-diethylhydantoin (EEH) in diet for 2 wk and hepatic cytochrome P-450-mediated alkoxyresorufin O-dealkylase and aminopyrine N-demethylase activities were determined.
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.
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