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Fenobam

≥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
MDL number:
MFCD00868019
UNSPSC Code:
12352200
PubChem Substance ID:
24894721
NACRES:
NA.77

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

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 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.

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Lucas R Watterson et al.
Psychopharmacology, 225(1), 151-159 (2012-07-24)
Methamphetamine (METH) is a highly potent and addictive psychostimulant with severe detrimental effects to the health of users. Currently, METH addiction is treated with a combination of cognitive and behavioral therapies, but these traditional approaches suffer from high relapse rates.
Michael J Marino et al.
Current opinion in pharmacology, 6(1), 98-102 (2005-12-22)
Metabotropic glutamate receptors (mGluRs) have been proposed as novel targets for the treatment of a variety of disorders. Recently, highly selective allosteric modulators of the mGluRs have been developed by several groups. These allosteric compounds provide an unprecedented degree of
Michael C Montana et al.
The Journal of pharmacology and experimental therapeutics, 330(3), 834-843 (2009-06-12)
Metabotropic glutamate receptor subtype 5 (mGlu5) has been demonstrated to play a role in the modulation of numerous nociceptive modalities. When administered via peripheral, intrathecal, or systemic routes, mGlu5 antagonists have analgesic properties in a variety of preclinical pain models.
Sajesh P Thomas et al.
Chemical communications (Cambridge, England), 48(85), 10559-10561 (2012-09-25)
Crystal structures of polymorphs and solvatomorphs of the potential anxiolytic drug fenobam exhibit an exclusive preference for one of the two possible tautomeric structures. A novel methodology based on nonlinear optical response has been successfully employed to detect the presence
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