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UC179

Sigma-Aldrich

(R)-(−)-Nirvanol

Synonym(s):

(R)-(−)-5-Ethyl-5-phenyl-2,4-imidazolidinedione, (R)-(−)-5-Ethyl-5-phenylhydantoin

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About This Item

Empirical Formula (Hill Notation):
C11H12N2O2
CAS Number:
65567-32-0
Molecular Weight:
204.23
MDL number:
MFCD00754497
UNSPSC Code:
12161501
PubChem Substance ID:
329827655
NACRES:
NA.77

form

solid

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-/m1/s1

InChI key

UDTWZFJEMMUFLC-LLVKDONJSA-N

Biochem/physiol Actions

CYP2B6 metabolite of (S)-(+)-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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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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
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
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.
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
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
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