1-(3-chlorophenyl)-3-(1-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)urea

• ChemBase ID: 127404
• Molecular Formular: C11H11ClN4O2
• Molecular Mass: 266.68364
• Monoisotopic Mass: 266.05705329
• SMILES: O=C1CN(C)C(=N1)NC(=O)Nc1cccc(Cl)c1
• Canonical SMILES: O=C(NC1=NC(=O)CN1C)Nc1cccc(c1)Cl
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(3-chlorophenyl)-3-(1-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)urea
• IUPAC Traditional name: fenobam
• Synonyms: N-(3-Chlorophenyl)-N′-(4,5-dihydro-1-methyl-4-oxo-1H-imidazole-2-yl)urea; Fenobam; Fenobam

Database IDs

• CAS Number: 57653-26-6
• MDL Number: MFCD00868019
• PubChem SID: 162221725; 24894721
• PubChem CID: 162834
• CHEMBL: 239800
• IUPHAR ligand ID: 1434
• MeSH Name: fenobam
• Wikipedia Title: Fenobam

CALCULATED PROPERTIES

• Acid pKa: 6.9630623
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.96908426
• LogD (pH = 7.4): 0.4131045
• Log P: 0.9837657
• Molar Refractivity: 67.7004 cm^3
• Polarizability: 25.048826 Å^3
• Polar Surface Area: 73.8 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C11H11ClN4O2

DETAILS

Sigma Aldrich - F0430

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.