Fenobam hydrate | CAS# 63540-28-3 | mGluR5 noncompetitive antagonist

MedKoo Cat#: 574318 | Name: Fenobam hydrate

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Description:

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

Fenobam hydrate is a noncompetitive antagonist and inverse agonist of metabotropic glutamate receptor 5 (mGluR5). It inhibits intracellular calcium mobilization induced by the glutamate analog quisqualate and inhibits basal activity of mGluR5. Fenobam reduces stress-induced hyperthermia, exhibits anxiolytic-like activity, and may induce analgesia.

Chemical Structure

Fenobam hydrate

CAS#63540-28-3 (hydrate)

Theoretical Analysis

MedKoo Cat#: 574318

Name: Fenobam hydrate

CAS#: 63540-28-3 (hydrate)

Chemical Formula: C11H13ClN4O3

Exact Mass: 284.0676

Molecular Weight: 284.70

Elemental Analysis: C, 46.41; H, 4.60; Cl, 12.45; N, 19.68; O, 16.86

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 600.00	2 Weeks

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Related CAS #

57653-26-6 (free base) 63540-28-3 (hydrate) Fenobam HCl

Synonym

Fenobam hydrate; Fenobam monohydrate

IUPAC/Chemical Name

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

InChi Key

UNFQKKSADLVQJE-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H11ClN4O2.H2O/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);1H2

SMILES Code

ClC1=CC=CC(NC(NC(N(C)C2)=NC2=O)=O)=C1.O

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

Shelf Life

>3 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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

A noncompetitive antagonist and inverse agonist of mGluR5.

In vitro activity:

By contrast, single treatment with fenobam rarely produced significant protection against DNA damage. From these results, it is suggested that fenobam promotes the protective effect of PEP-1-FK506BP against H2O2-inducedoxidative stress in C6 cells. Reference: BMB Rep. 2013 Nov; 46(11): 561–566. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4133844/

In vivo activity:

Both fenobam and MPEP induced preference in the SNI mice, such that SNI mice spent significantly more time in the mGluR5 antagonist-paired chamber compared to a vehicle-paired chamber. Reference: PLoS One. 2014 Jul 25;9(7):e103524. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4111598/

	Solvent	mg/mL	mM
Solubility
	DMSO	28.5	100.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 284.70 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.

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:

1. 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. PMID: 25061818; PMCID: PMC4111598. 2. 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. doi: 10.5483/bmbrep.2013.46.11.080. PMID: 24152913; PMCID: PMC4133844.

In vitro protocol:

1. 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. doi: 10.5483/bmbrep.2013.46.11.080. PMID: 24152913; PMCID: PMC4133844.

In vivo protocol:

1: 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. doi: 10.5483/bmbrep.2013.46.11.080. PMID: 24152913; PMCID: PMC4133844. 2: Sha X, Chen S, Zheng X, Ye X, Zhang H, Huang S. Determination of tautomeric preference of fenobam in solution by high-resolution NMR spectroscopy. Magn Reson Chem. 2021 Jun;59(6):641-647. doi: 10.1002/mrc.5127. Epub 2021 Jan 14. PMID: 33368586. 3: 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. PMID: 23615919; PMCID: PMC4191672. 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. PMID: 24610195. 5: 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. doi: 10.1124/jpet.105.089839. Epub 2005 Jul 22. PMID: 16040814. 6: Cavallone LF, Montana MC, Frey K, Kallogjeri D, Wages JM, Rodebaugh TL, Doshi T, Kharasch ED, Gereau RW 4th. The metabotropic glutamate receptor 5 negative allosteric modulator fenobam: pharmacokinetics, side effects, and analgesic effects in healthy human subjects. Pain. 2020 Jan;161(1):135-146. doi: 10.1097/j.pain.0000000000001695. PMID: 31568235; PMCID: PMC6923598. 7: Varnäs K, Cselényi Z, Arakawa R, Nag S, Stepanov V, Moein MM, Johnström P, Kingston L, Elmore CS, Halldin C, Farde L. The pro-psychotic metabotropic glutamate receptor compounds fenobam and AZD9272 share binding sites with monoamine oxidase-B inhibitors in humans. Neuropharmacology. 2020 Jan 1;162:107809. doi: 10.1016/j.neuropharm.2019.107809. Epub 2019 Oct 4. PMID: 31589885. 8: 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. PMID: 22037639; PMCID: PMC3226928. 9: Javidan A, Taghizadeh MJ, Hosseini SA, Iman M, Jafari R. Docking, Molecular Dynamics Simulation and Synthesis of New Fenobam Analogues as mGlu5 Receptor Antagonists. Comb Chem High Throughput Screen. 2016;19(9):764-770. doi: 10.2174/1386207319666160831150500. PMID: 27585831. 10: 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. PMID: 25061818; PMCID: PMC4111598. 11: Goldberg ME, Salama AI, Patel JB, Malick JB. Novel non-benzodiazepine anxiolytics. Neuropharmacology. 1983 Dec;22(12B):1499-504. doi: 10.1016/0028-3908(83)90118-1. PMID: 6142427. 12: 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. PMID: 19126569; PMCID: PMC2658751. 13: 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. PMID: 19426746. 14: 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. PMID: 25521380; PMCID: PMC4479348. 15: 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. PMID: 19515968; PMCID: PMC2729799. 16: 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. PMID: 22820868; PMCID: PMC3742304. 17: 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 Dec;68(12):565-573. doi: 10.1002/syn.21775. Epub 2014 Aug 19. PMID: 25098663; PMCID: PMC4320023. 18: 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. doi: 10.1016/j.bmcl.2005.11.092. Epub 2005 Dec 27. PMID: 16380255. 19: 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. doi: 10.1002/jps.2600840212. PMID: 7738798. 20: 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. doi: 10.1016/j.bmcl.2006.12.033. Epub 2006 Dec 15. PMID: 17196387.