Fenobam

• CAT Number: I006260
• CAS Number: 57653-26-6
• Molecular Formula: C11H11ClN4O2
• Molecular Weight: 266.685
• Purity: ≥95%
• Target: GluR
• Solubility: Soluble in DMSO, not in water
• Storage: Store at RT
• IUPAC Name: 1-(3-chlorophenyl)-3-(3-methyl-5-oxo-4H-imidazol-2-yl)urea
• 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
• SMILES: CN1CC(=O)N=C1NC(=O)NC2=CC(=CC=C2)Cl

Fenobam is a a potent and selective negative allosteric modulator of the metabotropic glutamate receptor subtype mGluR5. Fenobam displays inverse agonist properties; blocks mGluR5 constitutive activity in vitro (IC50 = 87 nM, slightly weaker than MPEP). Fenobam has been used as a lead compound for the development of a range of newer mGluR5 antagonists.

Reference

1:Docking, Molecular Dynamics Simulation and Synthesis of New Fenobam Analogues as mGlu5 Receptor Antagonists. Javidan A, Taghizadeh MJ, Hosseini SA, Iman M, Jafari R.Comb Chem High Throughput Screen. 2016;19(9):764-770. PMID: 27585831 2:Fmr1 KO and fenobam treatment differentially impact distinct synapse populations of mouse neocortex. Wang GX, Smith SJ, Mourrain P.Neuron. 2014 Dec 17;84(6):1273-86. doi: 10.1016/j.neuron.2014.11.016. PMID: 25521380 Free PMC Article3:Dose-dependent, saturable occupancy of the metabotropic glutamate subtype 5 receptor by fenobam as measured with [11 C]ABP688 PET imaging. Mathews WB, Kuwabara H, Stansfield K, Valentine H, Alexander M, Kumar A, Hilton J, Dannals RF, Wong DF, Gasparini F.Synapse. 2014 Aug 6. doi: 10.1002/syn.21775. [Epub ahead of print] PMID: 25098663 Free PMC Article4:The mGluR5 antagonist fenobam induces analgesic conditioned place preference in mice with spared nerve injury. Lax NC, George DC, Ignatz C, Kolber BJ.PLoS One. 2014 Jul 25;9(7):e103524. doi: 10.1371/journal.pone.0103524. eCollection 2014. PMID: 25061818 Free PMC Article5:Combined fenobam and amantadine treatment promotes robust antidyskinetic effects in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-lesioned primate model of Parkinson/’s disease. Ko WK, Pioli E, Li Q, McGuire S, Dufour A, Sherer TB, Bezard E, Facheris MF.Mov Disord. 2014 May;29(6):772-9. doi: 10.1002/mds.25859. Epub 2014 Mar 7. PMID: 24610195 6:Fenobam promoted the neuroprotective effect of PEP-1-FK506BP following oxidative stress by increasing its transduction efficiency. Ahn EH, Kim DW, Shin MJ, Jo HS, Eom SA, Kim DS, Park EY, Park JH, Cho SW, Park J, Eum WS, Son O, Hwang HS, Choi SY.BMB Rep. 2013 Nov;46(11):561-6. PMID: 24152913 Free PMC Article7:Fenobam sulfate inhibits cocaine-taking and cocaine-seeking behavior in rats: implications for addiction treatment in humans. Keck TM, Yang HJ, Bi GH, Huang Y, Zhang HY, Srivastava R, Gardner EL, Newman AH, Xi ZX.Psychopharmacology (Berl). 2013 Sep;229(2):253-65. doi: 10.1007/s00213-013-3106-9. Epub 2013 Apr 25. PMID: 23615919 Free PMC Article8:Polymorphism and tautomeric preference in fenobam and the utility of NLO response to detect polymorphic impurities. Thomas SP, Nagarajan K, Row TN.Chem Commun (Camb). 2012 Nov 4;48(85):10559-61. PMID: 23000909 9:Attenuation of reinstatement of methamphetamine-, sucrose-, and food-seeking behavior in rats by fenobam, a metabotropic glutamate receptor 5 negative allosteric modulator. Watterson LR, Kufahl PR, Nemirovsky NE, Sewalia K, Hood LE, Olive MF.Psychopharmacology (Berl). 2013 Jan;225(1):151-9. doi: 10.1007/s00213-012-2804-z. Epub 2012 Jul 21. PMID: 22820868 Free PMC Article10:Synthesis and Evaluation of Metabotropic Glutamate Receptor Subtype 5 Antagonists Based on Fenobam(). Gichinga MG, Olson JP, Butala E, Navarro HA, Gilmour BP, Mascarella SW, Carroll FI.ACS Med Chem Lett. 2011 Dec 8;2(12):882-884. Epub 2011 Oct 5. PMID: 22523618 Free PMC Article