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UC179

(R)-(−)-Nirvanol

Name: (R)-(−)-Nirvanol
Brand: SIGMA

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

NACRES:

NA.77

PubChem Substance ID:

329827655

UNSPSC Code:

12161501

MDL number:

MFCD00754497

Form:

solid

Quality level:

200

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Properties

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

Description

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

GHS07

signalword

Warning

hcodes

H302,H315,H319,H335

pcodes

P261 - P305 + P351 + P338

Hazard Classifications

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

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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Catalytic role of cytochrome P4502B6 in the N-demethylation of S-mephenytoin.

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

Pharmacogenetics of mephenytoin: a new drug hydroxylation polymorphism in man.

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

Absence of enantioselectivity in the pharmacodynamics of P450 2B induction by 5-ethyl-5-phenylhydantoin in the male rat liver or in cultured rat hepatocytes.

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

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Global Trade Item Number

SKU	GTIN
UC179-10MG	04061832277202
UC179-5MG	04061832931838