Fenobam
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |
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| Preferred IUPAC name
N-(3-Chlorophenyl)-N′-(1-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)urea | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.165.052 |
| MeSH | Fenobam |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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).
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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]