Fenobam

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 319679

CAS#: 57653-26-6

Description: 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.

Chemical Structure

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Fenobam
CAS# 57653-26-6
Instruction

Theoretical Analysis

MedKoo Cat#: 319679
Name: Fenobam
CAS#: 57653-26-6
Chemical Formula: C11H11ClN4O2
Exact Mass: 266.06
Molecular Weight: 266.685
Elemental Analysis: C, 49.54; H, 4.16; Cl, 13.29; N, 21.01; O, 12.00

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Synonym: Fenobam; NPL-2009; NPL2009; NPL 2009

IUPAC/Chemical Name: 1-(3-chlorophenyl)-3-(3-methyl-5-oxo-4H-imidazol-2-yl)urea

InChi Key: DWPQODZAOSWNHB-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(NC(N(C)C1)=NC1=O)NC2=CC=CC(Cl)=C2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 266.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Wang GX, Smith SJ, Mourrain P. Fmr1 KO and fenobam treatment differentially impact distinct synapse populations of mouse neocortex. Neuron. 2014 Dec 17;84(6):1273-86. doi: 10.1016/j.neuron.2014.11.016. PubMed PMID: 25521380; PubMed Central PMCID: PMC4479348.

2: Mathews WB, Kuwabara H, Stansfield K, Valentine H, Alexander M, Kumar A, Hilton J, Dannals RF, Wong DF, Gasparini F. Dose-dependent, saturable occupancy of the metabotropic glutamate subtype 5 receptor by fenobam as measured with [(11) C]ABP688 PET imaging. Synapse. 2014 Aug 6. doi: 10.1002/syn.21775. [Epub ahead of print] PubMed PMID: 25098663; PubMed Central PMCID: PMC4320023.

3: Lax NC, George DC, Ignatz C, Kolber BJ. The mGluR5 antagonist fenobam induces analgesic conditioned place preference in mice with spared nerve injury. PLoS One. 2014 Jul 25;9(7):e103524. doi: 10.1371/journal.pone.0103524. eCollection 2014. PubMed PMID: 25061818; PubMed Central PMCID: PMC4111598.

4: Ko WK, Pioli E, Li Q, McGuire S, Dufour A, Sherer TB, Bezard E, Facheris MF. 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. Mov Disord. 2014 May;29(6):772-9. doi: 10.1002/mds.25859. Epub 2014 Mar 7. PubMed PMID: 24610195.

5: 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. Fenobam promoted the neuroprotective effect of PEP-1-FK506BP following oxidative stress by increasing its transduction efficiency. BMB Rep. 2013 Nov;46(11):561-6. PubMed PMID: 24152913; PubMed Central PMCID: PMC4133844.

6: Keck TM, Yang HJ, Bi GH, Huang Y, Zhang HY, Srivastava R, Gardner EL, Newman AH, Xi ZX. Fenobam sulfate inhibits cocaine-taking and cocaine-seeking behavior in rats: implications for addiction treatment in humans. Psychopharmacology (Berl). 2013 Sep;229(2):253-65. doi: 10.1007/s00213-013-3106-9. Epub 2013 Apr 25. PubMed PMID: 23615919; PubMed Central PMCID: PMC4191672.

7: Thomas SP, Nagarajan K, Row TN. Polymorphism and tautomeric preference in fenobam and the utility of NLO response to detect polymorphic impurities. Chem Commun (Camb). 2012 Nov 4;48(85):10559-61. PubMed PMID: 23000909.

8: Watterson LR, Kufahl PR, Nemirovsky NE, Sewalia K, Hood LE, Olive MF. Attenuation of reinstatement of methamphetamine-, sucrose-, and food-seeking behavior in rats by fenobam, a metabotropic glutamate receptor 5 negative allosteric modulator. Psychopharmacology (Berl). 2013 Jan;225(1):151-9. doi: 10.1007/s00213-012-2804-z. Epub 2012 Jul 21. PubMed PMID: 22820868; PubMed Central PMCID: PMC3742304.

9: Gichinga MG, Olson JP, Butala E, Navarro HA, Gilmour BP, Mascarella SW, Carroll FI. Synthesis and Evaluation of Metabotropic Glutamate Receptor Subtype 5 Antagonists Based on Fenobam(). ACS Med Chem Lett. 2011 Dec 8;2(12):882-884. Epub 2011 Oct 5. PubMed PMID: 22523618; PubMed Central PMCID: PMC3328804.

10: Montana MC, Conrardy BA, Cavallone LF, Kolber BJ, Rao LK, Greco SC, Gereau RW 4th. Metabotropic glutamate receptor 5 antagonism with fenobam: examination of analgesic tolerance and side effect profile in mice. Anesthesiology. 2011 Dec;115(6):1239-50. doi: 10.1097/ALN.0b013e318238c051. PubMed PMID: 22037639; PubMed Central PMCID: PMC3226928.

11: Montana MC, Cavallone LF, Stubbert KK, Stefanescu AD, Kharasch ED, Gereau RW 4th. The metabotropic glutamate receptor subtype 5 antagonist fenobam is analgesic and has improved in vivo selectivity compared with the prototypical antagonist 2-methyl-6-(phenylethynyl)-pyridine. J Pharmacol Exp Ther. 2009 Sep;330(3):834-43. doi: 10.1124/jpet.109.154138. Epub 2009 Jun 10. PubMed PMID: 19515968; PubMed Central PMCID: PMC2729799.

12: Jacob W, Gravius A, Pietraszek M, Nagel J, Belozertseva I, Shekunova E, Malyshkin A, Greco S, Barberi C, Danysz W. The anxiolytic and analgesic properties of fenobam, a potent mGlu5 receptor antagonist, in relation to the impairment of learning. Neuropharmacology. 2009 Aug;57(2):97-108. doi: 10.1016/j.neuropharm.2009.04.011. Epub 2009 May 6. PubMed PMID: 19426746.

13: Berry-Kravis E, Hessl D, Coffey S, Hervey C, Schneider A, Yuhas J, Hutchison J, Snape M, Tranfaglia M, Nguyen DV, Hagerman R. A pilot open label, single dose trial of fenobam in adults with fragile X syndrome. J Med Genet. 2009 Apr;46(4):266-71. doi: 10.1136/jmg.2008.063701. Epub 2009 Jan 6. PubMed PMID: 19126569; PubMed Central PMCID: PMC2658751.

14: Jaeschke G, Porter R, Büttelmann B, Ceccarelli SM, Guba W, Kuhn B, Kolczewski S, Huwyler J, Mutel V, Peters JU, Ballard T, Prinssen E, Vieira E, Wichmann J, Spooren W. Synthesis and biological evaluation of fenobam analogs as mGlu5 receptor antagonists. Bioorg Med Chem Lett. 2007 Mar 1;17(5):1307-11. Epub 2006 Dec 15. PubMed PMID: 17196387.

15: Ceccarelli SM, Jaeschke G, Buettelmann B, Huwyler J, Kolczewski S, Peters JU, Prinssen E, Porter R, Spooren W, Vieira E. Rational design, synthesis, and structure-activity relationship of benzoxazolones: new potent mglu5 receptor antagonists based on the fenobam structure. Bioorg Med Chem Lett. 2007 Mar 1;17(5):1302-6. Epub 2006 Dec 15. PubMed PMID: 17189691.

16: Wållberg A, Nilsson K, Osterlund K, Peterson A, Elg S, Raboisson P, Bauer U, Hammerland LG, Mattsson JP. Phenyl ureas of creatinine as mGluR5 antagonists. A structure-activity relationship study of fenobam analogues. Bioorg Med Chem Lett. 2006 Mar 1;16(5):1142-5. Epub 2005 Dec 27. PubMed PMID: 16380255.

17: Porter RH, Jaeschke G, Spooren W, Ballard TM, Büttelmann B, Kolczewski S, Peters JU, Prinssen E, Wichmann J, Vieira E, Mühlemann A, Gatti S, Mutel V, Malherbe P. Fenobam: a clinically validated nonbenzodiazepine anxiolytic is a potent, selective, and noncompetitive mGlu5 receptor antagonist with inverse agonist activity. J Pharmacol Exp Ther. 2005 Nov;315(2):711-21. Epub 2005 Jul 22. PubMed PMID: 16040814.

18: Wu WN, McKown LA, O'Neill PJ. In vitro and in vivo metabolism of the antianxiolytic agent fenobam in the rat. J Pharm Sci. 1995 Feb;84(2):185-9. PubMed PMID: 7738798.

19: Pellizer G, Rubessa F. 1H- and 13C-NMR spectra of fenobam. J Pharm Sci. 1983 Feb;72(2):189-90. PubMed PMID: 6300369.

20: Pecknold JC, McClure DJ, Appeltauer L, Wrzesinski L, Allan T. Treatment of anxiety using fenobam (a nonbenzodiazepine) in a double-blind standard (diazepam) placebo-controlled study. J Clin Psychopharmacol. 1982 Apr;2(2):129-33. PubMed PMID: 7042771.