Fenobam

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Fenobam
Fenobam.svg
Names
IUPAC name
1-(3-chlorophenyl)-3-(3-methyl-5-oxo-4H-imidazol-2-yl)urea
Identifiers
57653-26-6 YesY
ChEMBL ChEMBL239800 N
ChemSpider 142953 N
1434
Jmol 3D model Interactive image
MeSH fenobam
PubChem 162834
UNII 078RCY7I27 N
  • 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) N
    Key: DWPQODZAOSWNHB-UHFFFAOYSA-N N
  • 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
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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]

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]

References

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