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(S)-(+)-Nirvanol

Name: (S)-(+)-Nirvanol
Brand: SIGMA

Synonym(s):

(S)-(+)-5-Ethyl-5-phenyl-2,4-imidazolidinedione, (S)-(+)-5-Ethyl-5-phenylhydantoin

About This Item

Empirical Formula (Hill Notation):

C₁₁H₁₂N₂O₂

CAS Number:

65567-34-2

Molecular Weight:

204.23

NACRES:

NA.77

PubChem Substance ID:

329827656

UNSPSC Code:

12161501

MDL number:

MFCD00272652

Form:

solid

Quality level:

200

This product is discontinued. Contact Technical Servicefor assistance.

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-/m0/s1

InChI key

UDTWZFJEMMUFLC-NSHDSACASA-N

Description

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.[1]

CYP2B6 metabolite of (R)-(-)-mephenytoin; anticonvulsant; hypnotic.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

Nirvanol is soluble in DMF.

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1 of 1

This Item	UC179	B8686	UC175
Sigma-Aldrich UC180 (S)-(+)-Nirvanol	Sigma-Aldrich UC179 (R)-(−)-Nirvanol	Sigma-Aldrich B8686 (+)-N-3-Benzylnirvanol	Sigma-Aldrich UC175 (S)-(+)-Mephenytoin
form solid	form solid	form powder	form solid
Quality Level 200	Quality Level 200	Quality Level 100	Quality Level 200
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C
solubility DMF: soluble	solubility DMF: soluble	solubility DMSO: >20 mg/mL, H₂O: insoluble	solubility DMSO: soluble
color off-white	color off-white	color -	color off-white

pictograms

GHS07

signalword

Warning

hcodes

H302,H315,H319,H335

pcodes

P261 - P264 - P270 - P301 + P312 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

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

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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

Pharmacodynamics of cytochrome P450 2B induction by phenobarbital, 5-ethyl-5-phenylhydantoin, and 5-ethyl-5-phenyloxazolidinedione in the male rat liver or in cultured rat hepatocytes.

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

Hepatic cytochrome P450 2B induction by ethyl/phenyl-substituted congeners of phenobarbital in the B6C3F1 mouse.

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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Global Trade Item Number

SKU	GTIN
UC180-10MG	04061832277219
UC180-5MG	04061832931869

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