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Merck
CN

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

Key Documents

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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

SMILES string

CC[C@]1(NC(=O)NC1=O)c2ccccc2

InChI key

UDTWZFJEMMUFLC-NSHDSACASA-N

form

solid

color

off-white

solubility

DMF: soluble

storage temp.

2-8°C

Quality Level

200

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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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
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
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
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
R W Nims et al.
Chemical research in toxicology, 6(2), 188-196 (1993-03-01)
The pharmacodynamics of rat hepatic cytochrome P450 2B (P450 2B) induction by phenobarbital (PB) and two structural congeners, dl-5-ethyl-5-phenylhydantoin (EPH) and dl-5-ethyl-5-phenyloxazolidinedione (EPO), were investigated. The in vivo induction of P450 2B was probed in F344/NCr rats by measuring immunoreactive
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