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UC179

Sigma-Aldrich

(R)-(−)-Nirvanol

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C11H12N2O2
Número CAS:
65567-32-0
Peso molecular:
204.23
Número MDL:
MFCD00754497
Código UNSPSC:
12161501
ID de substância PubChem:
329827655
NACRES:
NA.77

forma

solid

cor

off-white

solubilidade

DMF: soluble

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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

chave InChI

UDTWZFJEMMUFLC-LLVKDONJSA-N

Ações bioquímicas/fisiológicas

CYP2B6 metabolite of (S)-(+)-mephenytoin; anticonvulsant; hypnotic.

Embalagem

Bottomless glass bottle. Contents are inside inserted fused cone.

Nota de preparo

Nirvanol is soluble in DMF.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H302,H315,H319,H335

Declarações de precaução

P261 - P305 + P351 + P338

Classificações de perigo

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

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análise (COA)

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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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