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F0430

Sigma-Aldrich

Fenobam

≥98% (HPLC), solid

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C11H11ClN4O2
CAS-Nummer:
57653-26-6
Molekulargewicht:
266.68
MDL-Nummer:
MFCD00868019
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24894721
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

solid

Farbe

white

Löslichkeit

DMSO: >20 mg/mL

Ersteller

Johnson & Johnson

Lagertemp.

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)

InChIKey

DWPQODZAOSWNHB-UHFFFAOYSA-N

Biochem./physiol. Wirkung

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 Kd 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.

Leistungsmerkmale und Vorteile

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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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
1H- and 13C-NMR spectra of fenobam.
G Pellizer et al.
Journal of pharmaceutical sciences, 72(2), 189-190 (1983-02-01)
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
Laura F Cavallone et al.
Pain, 161(1), 135-146 (2019-10-01)
Metabotropic glutamate receptor 5 (mGlu5) has been shown to modulate nociception in animals, but no mGlu5 antagonists have been developed commercially as analgesics. The mGlu5 antagonist fenobam [N-(3-chlorophenyl)-N'-(4,5-dihydro-1-methyl-4-oxo-1H-imidazole-2-yl)urea] was originally evaluated for development as a nonbenzodiazepine anxiolytic. Fenobam is analgesic
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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