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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
Pricing and availability is not currently available.

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-/m1/s1

InChI key

UDTWZFJEMMUFLC-LLVKDONJSA-N

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Pellicon® 2 Maxi Ultrafiltration Module filtration area 2.5 m2, NMWCO 300 kDa

P2C300C25

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Pellicon® 2 Maxi Ultrafiltration Module filtration area 2.5 m2, NMWCO 1000 kDa

P2C01MC25

Pellicon® 2 Maxi Ultrafiltration Module

Pellicon® 2 Maxi Ultrafiltration Module filtration area 2.5 m2, NMWCO 100 kDa

P2C100C25

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Pellicon® 2 Maxi Ultrafiltration Module filtration area 2.5 m2, NMWCO 30 kDa

P2C030C25

Pellicon® 2 Maxi Ultrafiltration Module

pore size

300 kDa NMWCO

pore size

1000 kDa NMWCO

pore size

100 kDa NMWCO

pore size

30 kDa NMWCO

material

composite regenerated cellulose (CRC) , polyurethane adhesive, polypropylene screen

material

composite regenerated cellulose (CRC) , polypropylene screen, polyurethane adhesive

material

composite regenerated cellulose (CRC) , polypropylene screen, polyurethane adhesive

material

composite regenerated cellulose (CRC) , polypropylene screen, polyurethane adhesive

parameter

0.33 bar max. transmembrane pressure (5 psig) (reverse), 5-35 L/min recirculation rate at 0.4 bar (6 psi), 3.5 bar max. transmembrane pressure (50 psig) at 30 °C (forward)

parameter

0.33 bar max. transmembrane pressure (5 psig) (reverse), 3.5 bar max. transmembrane pressure (50 psig) at 30 °C (forward), 5-35 L/min recirculation rate at 0.4 bar (6 psi)

parameter

0.33 bar max. transmembrane pressure (5 psig) (reverse), 3.5 bar max. transmembrane pressure (50 psig) at 30 °C (forward), 5-35 L/min recirculation rate at 0.4 bar (6 psi)

parameter

0.33 bar max. transmembrane pressure (5 psig) (reverse), 3.5 bar max. transmembrane pressure (50 psig) at 30 °C (forward), 5-35 L/min recirculation rate at 0.4 bar (6 psi)

technique(s)

protein purification: suitable, analytical sample preparation: suitable

technique(s)

analytical sample preparation: suitable, protein purification: suitable

technique(s)

analytical sample preparation: suitable, protein purification: suitable

technique(s)

analytical sample preparation: suitable, protein purification: suitable

manufacturer/tradename

Pellicon®

manufacturer/tradename

Pellicon®

manufacturer/tradename

Pellicon®

manufacturer/tradename

Pellicon®

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

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    Certificates of Analysis (COA)

    Lot/Batch Number
    BGBC4814V
    1407520V
    1407520
    1385692
    036K3260

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    W Kalow
    Xenobiotica; the fate of foreign compounds in biological systems, 16(5), 379-389 (1986-05-01)
    The antiepileptic drug mephenytoin is a racemate. Mephenytoin hydroxylation is a stereospecific reaction and is confined to the S-enantiomer, which is normally eliminated within hours, allowing the R-enantiomer to accumulate since it can be eliminated only within days or weeks.
    W H Theodore et al.
    Neurology, 34(8), 1100-1102 (1984-08-01)
    We investigated the conversion of mephenytoin to nirvanol in five patients with uncontrolled complex partial seizures. After a 50-mg single oral dose, mean peak mephenytoin level was 0.48 microgram/ml and nirvanol 0.37 microgram/ml. After 400 mg, peak mephenytoin level was
    S H Akrawi et al.
    European journal of drug metabolism and pharmacokinetics, 14(4), 269-278 (1989-10-01)
    The stereoselective clearances of R- and S-mephenytoin were determined in rats receiving either an intravenous or hepatic portal vein infusion of racemic mephenytoin. The mean +/- SD intravenous clearances of R- and S-mephenytoin were 1630 +/- 250 ml/hr and 630
    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
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