Fenobam
Encyclopedia
Fenobam is an imidazole
Imidazole
Imidazole is an organic compound with the formula C3H4N2. This aromatic heterocyclic is a diazole and is classified as an alkaloid. Imidazole refers to the parent compound, whereas imidazoles are a class of heterocycles with similar ring structure, but varying substituents...

 derivative developed by McNeil Laboratories
McNeil Laboratories
McNeil Consumer Healthcare is a medicals products company belonging to the Johnson & Johnson healthcare products group.-History:The company was founded on March 16, 1879 by 23-year-old Robert McNeil, who paid $167 for a drugstore complete with fixtures, inventory and soda fountain, as a retail...

 in the late 1970s as a novel anxiolytic
Anxiolytic
An anxiolytic is a drug used for the treatment of anxiety, and its related psychological and physical symptoms...

 drug with an at-the-time-unidentified molecular target in the brain. Subsequently, it was determined that fenobam acts as a potent
Potency (pharmacology)
In the field of pharmacology, potency is a measure of drug activity expressed in terms of the amount required to produce an effect of given intensity. A highly potent drug evokes a larger response at low concentrations, while a drug of lower potency evokes a small response at low concentrations...

 and selective negative allosteric modulator
Negative allosteric modulator
A negative allosteric modulator is a drug which decreases the activity of a receptor indirectly via disactivation of an allosteric site on the protein. NAMs are similar to inverse agonists in that they conteract overall receptor activation, but they are different because they do so in a...

 of the metabotropic glutamate receptor
Metabotropic glutamate receptor
The metabotropic glutamate receptors, or mGluRs, are a type of glutamate receptor that are active through an indirect metabotropic process. They are members of the group C family of G-protein-coupled receptors, or GPCRs...

 subtype mGluR5
Metabotropic glutamate receptor 5
Metabotropic glutamate receptor 5 is a protein that in humans is encoded by the GRM5 gene.- Function :The amino acid L-glutamate is the major excitatory neurotransmitter in the central nervous system and activates both ionotropic and metabotropic glutamate receptors...

, and it has been used as a lead compound
Lead compound
A lead compound in drug discovery is a chemical compound that has pharmacological or biological activity and whose chemical structure is used as a starting point for chemical modifications in order to improve potency, selectivity, or pharmacokinetic parameters.Lead compounds are often found in...

 for the development of a range of newer mGluR5 antagonists.

Fenobam has anxiolytic effects comparable to those of benzodiazepine
Benzodiazepine
A benzodiazepine is a psychoactive drug whose core chemical structure is the fusion of a benzene ring and a diazepine ring...

 drugs, but was never commercially marketed for the treatment of anxiety due to dose-limiting side effects such as amnesia and psychotomimetic symptoms. 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. It has also shown promising initial results in the treatment of Fragile X syndrome
Fragile X syndrome
Fragile X syndrome , Martin–Bell syndrome, or Escalante's syndrome , is a genetic syndrome that is the most commonly known single-gene cause of autism and the most common inherited cause of intellectual disability...

.

Chemistry

Fenobam can be prepared in a two-step sequence from creatine
Creatine
Creatine is a nitrogenous organic acid that occurs naturally in vertebrates and helps to supply energy to all cells in the body, primarily muscle. This is achieved by increasing the formation of Adenosine triphosphate...

.
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