Fenobam - Moligand™, ≥98% , Allosteric modulator of mGlu 5 receptor, CAS No.57653-26-6, Allosteric modulator of mGlu 5 receptor

CAS: 57653-26-6 Cat. No.: F274825 Molecular Weight: 266.68 EC Number: 637-337-3

GRADE & PURITY Moligand™, ≥98%

Synonyms

MLS006011708 | [3H]fenobam | LP00842 | GTPL1433 | DWPQODZAOSWNHB-UHFFFAOYSA-N | Fenobam | NCGC00092384-04 | FT-0630701 | 1-m-chlorophenyl-3-(1-methyl-4-oxo-2-imidazolidinylidene)urea | Q5443558 | 1-(3-chlorophenyl)-3-[(2Z)-1-methyl-4-oxoimidazolidin-2-yli

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Fenobam is a selective, orally active, and brain-penetrant mGluR5 antagonist acting at an allosteric modulatory site (Kds of 54 and 31 nM for rat and human recombinant mGlu5 receptors, respectively). Fenobam displays inverse agonist activity which blocks the mGlu5 receptor basal activity with an IC50 of 84 nM. Fenobam exerts anxiolytic activity。

Specifications

Synonyms

MLS006011708 | [3H]fenobam | LP00842 | GTPL1433 | DWPQODZAOSWNHB-UHFFFAOYSA-N | Fenobam | NCGC00092384-04 | FT-0630701 | 1-m-chlorophenyl-3-(1-methyl-4-oxo-2-imidazolidinylidene)urea | Q5443558 | 1-(3-chlorophenyl)-3-[(2Z)-1-methyl-4-oxoimidazolidin-2-yli

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Selective and effective mGlu 5 receptor antagonists acting on allosteric regulatory sites (with Kd values of 54 and 31 nM for rat and human recombinant mGlu 5 receptors, respectively). Display reverse agonist properties and block the basal activity of mGl

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ALLOSTERIC MODULATOR

Mechanism of action

Allosteric modulator of mGlu 5 receptor

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CN1CC(=O)NC1=NC(=O)NC2=CC(=CC=C2)Cl
• IUPAC Name: 1-(3-chlorophenyl)-3-(1-methyl-4-oxoimidazolidin-2-ylidene)urea
• InChIKey: DWPQODZAOSWNHB-UHFFFAOYSA-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)
• Isomeric SMILES: CN1CC(=O)NC1=NC(=O)NC2=CC(=CC=C2)Cl
• Alternate CAS: 57653-26-6
• MeSH Entry Terms: fenobam;fenobam anhydrous;fenobam monohydrate
• Molecular Weight: 266.68
• Reaxy-Rn: 671831
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=671831&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass N-phenylureas

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: N-phenylureas
• Intermediate Tree Nodes: Not available
• Direct Parent: N-phenylureas
• Alternative Parents: Alpha amino acids and derivatives Chlorobenzenes Imidazolinones Aryl chlorides Ureas N-acylimines Guanidines Propargyl-type 1,3-dipolar organic compounds Carboximidamides Azacyclic compounds Organopnictogen compounds Organochlorides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Alpha-amino acid or derivatives - N-phenylurea - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Imidazolinone - 2-imidazoline - Guanidine - Carbonic acid derivative - N-acylimine - Urea - Carboxylic acid derivative - Azacycle - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Organopnictogen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organic nitrogen compound - Organohalogen compound - Organochloride - Organonitrogen compound - Organooxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as n-phenylureas. These are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

GRM1 Tchem Metabotropic glutamate receptor 1 (0 Activities)

Discover Target: GRM1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GRM5 Tchem Metabotropic glutamate receptor 5 (2 Activities)

Discover Target: GRM5

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Solubility: Soluble in DMSO to 100 mM
• Molecular Weight: 266.680 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 266.057 Da
• Monoisotopic Mass: 266.057 Da
• Topological Polar Surface Area: 73.800 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 385.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 1
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Pengfei Wang, Weina Dai, Hongbin Liu, Han Liu, Yuming Xu.  (2024)  Fenobam modulates distinct electrophysiological mechanisms for regulating excessive gamma oscillations in the striatum of dyskinetic rats.  EXPERIMENTAL NEUROLOGY,      [PMID:38782350] [10.1016/j.expneurol.2024.114833]