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F0430

Fenobam

Name: Fenobam
Brand: SIGMA

≥98% (HPLC), solid

Synonym(s):

N-(3-Chlorophenyl)-N′-(4,5-dihydro-1-methyl-4-oxo-1H-imidazole-2-yl)urea

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About This Item

Empirical Formula (Hill Notation):

C₁₁H₁₁ClN₄O₂

CAS Number:

57653-26-6

Molecular Weight:

266.68

NACRES:

NA.77

PubChem Substance ID:

24894721

UNSPSC Code:

12352200

MDL number:

MFCD00868019

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

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Quality Level

100

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >20 mg/mL

originator

Johnson & Johnson

storage temp.

2-8°C

SMILES string

CN1CC(=O)N=C1NC(=O)Nc2cccc(Cl)c2

InChI

1S/C11H11ClN4O2/c1-16-6-9(17)14-10(16)15-11(18)13-8-4-2-3-7(12)5-8/h2-5H,6H2,1H3,(H2,13,14,15,17,18)

InChI key

DWPQODZAOSWNHB-UHFFFAOYSA-N

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Biochem/physiol Actions

Fenobam is a potent, selective, noncompetitive glutamate mGluR5 receptor antagonist. Fenobam displays inverse agonist properties; blocks mGluR₅ constitutive activity in vitro (IC₅₀ = 87 nM, slightly weaker than MPEP). Fenobam acts at an allosteric modulatory site shared with MPEP and binds the mGlu₅ receptor with K_d values of 54 and 31 nM for rat and human receptors, respectively. Fenobam belongs to a structurally different class than MPEP; devoid of GABAergic activity and thus typical benzodiazepine-like side effects; displays anxiolytic activity.

Potent, selective, noncompetitive metabotropic glutamate receptor antagonist (mGluR5). Displays anxiolytic activity.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Glutamate Receptors (G Protein Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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The anxiolytic and analgesic properties of fenobam, a potent mGlu5 receptor antagonist, in relation to the impairment of learning.

Wolfgang Jacob et al.

Neuropharmacology, 57(2), 97-108 (2009-05-12)

Fenobam [N-(3-chlorophenyl)-N'-(4,5-dihydro-1-methyl-4-oxo-1H-imidazole-2-yl)urea] was suggested to possess anxiolytic actions 30 years ago. Hoffmann-La Roche researchers recently reported that it is a selective and potent mGlu5 receptor antagonist, acting as a negative allosteric modulator. In the present study, we show that fenobam

Comparison of the binding pockets of two chemically unrelated allosteric antagonists of the mGlu5 receptor and identification of crucial residues involved in the inverse agonism of MPEP.

Pari Malherbe et al.

Journal of neurochemistry, 98(2), 601-615 (2006-06-30)

Fenobam [N-(3-chlorophenyl)-N'-(4,5-dihydro-1-methyl-4-oxo-1H-imidazole-2-yl)urea], a clinically validated non-benzodiazepine anxiolytic, has been shown to be a potent and non-competitive metabotropic glutamate (mGlu)-5 receptor antagonist. In the present study, we have used the site-directed mutagenesis coupled with three-dimensional receptor-based pharmacophore modelling to elucidate the

1H- and 13C-NMR spectra of fenobam.

G Pellizer et al.

Journal of pharmaceutical sciences, 72(2), 189-190 (1983-02-01)

Treatment of anxiety using fenobam (a nonbenzodiazepine) in a double-blind standard (diazepam) placebo-controlled study.

J C Pecknold et al.

Journal of clinical psychopharmacology, 2(2), 129-133 (1982-04-01)

A pilot open label, single dose trial of fenobam in adults with fragile X syndrome.

E Berry-Kravis et al.

Journal of medical genetics, 46(4), 266-271 (2009-01-08)

A pilot open label, single dose trial of fenobam, an mGluR5 antagonist, was conducted to provide an initial evaluation of safety and pharmacokinetics in adult males and females with fragile X syndrome (FXS). Twelve subjects, recruited from two fragile X

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Global Trade Item Number

SKU	GTIN
F0430-25MG	04061832072012
F0430-5MG	04061832072029

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