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UC178

Sigma-Aldrich

(±)-Nirvanol

Synonym(s):

(±)-5-Ethyl-5-phenyl-2,4-imidazolidinedione, (±)-5-Ethyl-5-phenylhydantoin

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About This Item

Empirical Formula (Hill Notation):
C11H12N2O2
CAS Number:
631-07-2
Molecular Weight:
204.23
MDL number:
MFCD00022401
UNSPSC Code:
12161501
PubChem Substance ID:
329827654

form

solid

Quality Level

200

color

off-white

solubility

acetone: soluble
ethanol: soluble
methanol: soluble

storage temp.

2-8°C

SMILES string

CCC1(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)

InChI key

UDTWZFJEMMUFLC-UHFFFAOYSA-N

Biochem/physiol Actions

CYP2B6 N-demethyl metabolite of (±)-mephenytoin; anticonvulsive; hypnotic

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

(±)-Nirvanol is soluble in methanol, acetone and ethanol.

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

Certificates of Analysis (COA)

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B F Bourgeois et al.
Epilepsia, 27(4), 412-418 (1986-07-01)
Stereoselective metabolism has been demonstrated for mephenytoin (MHT), R-MHT being demethylated to the pharmacologically active metabolite 5-phenyl-5-ethylhydantoin (PEH; nirvanol), and S-MHT undergoing aromatic hydroxylation to 4-OH-MHT, with formation of an intermediate arene oxide metabolite. PEH is responsible for the therapeutic
A Pezeshk et al.
Journal of inorganic biochemistry, 42(4), 267-272 (1991-06-01)
The preparation and spectral properties of copper(II) complexes of two hydantoins are reported. Complexes of the general formula Cu(hyd)2(py)2, where hyd = phenytoin or nirvanol; and py = pyridine were prepared and characterized by infrared and ESR. Spectral data show
H Fujioka et al.
Journal of pharmacobio-dynamics, 9(3), 303-314 (1986-03-01)
Disposition of 1-benzenesulfonyl-5,5-diphenylhydantoin (II) having a potent anti-inflammatory activity was compared with that of 5,5-diphenylhydantoin (I), an antiepileptic drug, in order to elucidate whether the pharmacodynamic difference between them can be explained by their physicochemical and pharmacokinetic properties. After oral
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
T Inaba et al.
American journal of human genetics, 38(5), 768-772 (1986-05-01)
A genetic polymorphism characterized by deficient drug oxidation exists for the hydroxylation of mephenytoin. This deficiency was first recognized in a family study that suggested an autosomal recessive pattern of inheritance. To confirm the observation, we investigated 28 relatives of
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