Structure via PubChem · Public domain (PubChem)
fenobam
Sign in to saveAlso known as MCN-3377-98, fenobam anhydrous, Fenobam anhydrous
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, and it has been used as a lead compound for the development of a range of newer mGluR5 antagonists.
Chemical data
- Formula
- C11H11ClN4O2
- Molecular weight
- 266.68 g/mol
- IUPAC name
- (3Z)-1-(3-chlorophenyl)-3-(1-methyl-4-oxoimidazolidin-2-ylidene)urea
- SMILES
- CN\1CC(=O)N/C1=N/C(=O)NC2=CC(=CC=C2)Cl
- InChIKey
- DWPQODZAOSWNHB-UHFFFAOYSA-N
- XLogP
- 1.2
- Polar surface area
- 73.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 266.057053
Show 4 more facts
- chemical formula
- C₁₁H₁₁ClN₄O₂
- canonical SMILES
- CN1CC(=O)N=C1NC(=O)NC2=CC(=CC=C2)Cl
- physically interacts with
- Glutamate metabotropic receptor 5
- Commons category
- Fenobam
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Chemistry
- See also
- 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, and it has been used as a lead compound for the development of a range of newer mGluR5 antagonists.
Fenobam has anxiolytic effects comparable to those of benzodiazepine 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. It was developed by a team at McNeil Laboratories in the 1970s.
Excerpted from Wikipedia’s “fenobam” article, available under the CC BY-SA 4.0 licence.