Fenobam

Last updated
Fenobam
Fenobam.svg
Names
Preferred IUPAC name
N-(3-Chlorophenyl)-N′-(1-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)urea
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.165.052 OOjs UI icon edit-ltr-progressive.svg
MeSH Fenobam
PubChem CID
UNII
  • 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) X mark.svgN
    Key: DWPQODZAOSWNHB-UHFFFAOYSA-N X mark.svgN
  • InChI=1/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)
    Key: DWPQODZAOSWNHB-UHFFFAOYAC
  • O=C1CN(C)C(NC(NC2=CC=CC(Cl)=C2)=O)=N1
Properties
C11H11ClN4O2
Molar mass 266.684
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Fenobam is an imidazole derivative developed by McNeil Laboratories in the late 1970s as a novel anxiolytic drug with an at-the-time-unidentified molecular target in the brain. Subsequently, it was determined that fenobam acts as a potent and selective negative allosteric modulator of the metabotropic glutamate receptor subtype mGluR5, [1] [2] and it has been used as a lead compound for the development of a range of newer mGluR5 antagonists. [3] [4] [5] [6]

Contents

Fenobam has anxiolytic effects comparable to those of benzodiazepine drugs, [1] [7] [8] but was never commercially marketed for the treatment of anxiety due to dose-limiting side effects such as amnesia and psychotomimetic symptoms. [9] [10] Following the discovery of its activity as a potent negative allosteric modulator of mGluR5, fenobam has been re-investigated for many applications, with its profile of combined antidepressant, anxiolytic, analgesic and anti-addictive effects potentially useful given the common co-morbidity of these symptoms. [11] [12] It has also shown promising initial results in the treatment of fragile X syndrome. [13] It was developed by a team at McNeil Laboratories in the 1970s. [14]

Chemistry

Fenobam is known to exist in five crystalline forms, all of them exhibiting a tautomeric structure with the proton attached to the five membered ring nitrogen. [15]

See also

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References

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  14. US Patent 3983135 4-Oxo-2-imidazolidinylidene ureas
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