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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
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
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
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