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F0430

Sigma-Aldrich

Fenobam

≥98% (HPLC), solid

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C11H11ClN4O2
Numéro CAS:
57653-26-6
Poids moléculaire :
266.68
Numéro MDL:
MFCD00868019
Code UNSPSC :
12352200
ID de substance PubChem :
24894721
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

solid

Couleur

white

Solubilité

DMSO: >20 mg/mL

Auteur

Johnson & Johnson

Température de stockage

2-8°C

Chaîne SMILES 

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)

Clé InChI

DWPQODZAOSWNHB-UHFFFAOYSA-N

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

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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
Michael C Montana et al.
Anesthesiology, 115(6), 1239-1250 (2011-11-01)
The metabotropic glutamate receptor 5 noncompetitive antagonist fenobam is analgesic in rodents. Future development of fenobam as an analgesic in humans will require a favorable long-term treatment profile and a lack of significant deleterious side effects. This study aimed to
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.
Lara W Crock et al.
Molecular pain, 8, 20-20 (2012-03-28)
Interstitial cystitis/painful bladder syndrome (IC/PBS), is a severely debilitating chronic condition that is frequently unresponsive to conventional pain medications. The etiology is unknown, however evidence suggests that nervous system sensitization contributes to enhanced pain in IC/PBS. In particular, central nervous
W N Wu et al.
Journal of pharmaceutical sciences, 84(2), 185-189 (1995-02-01)
Fenobam [(Fn); N-(3-chlorophenyl)-N-(4,5-dihydro-1-methyl-4-oxo-1H-imidazole-2-yl)urea] sulfate is a novel agent with potent anxiolytic activity in rats. [14C]Fn sulfate was administered as an oral solution (250 mg/kg) to male Wistar rats, and 52% of the administered dose was excreted in urine (0-5 days).
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