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Basimglurant

Names

[ CAS No. ]:
802906-73-6

[ Name ]:
Basimglurant

[Synonym ]:
2-chloro-4-{2-[1-(4-fluorophenyl)-2,5-dimethyl-1H-imidazol-4-yl]ethynyl}pyridine
RO4917523
RG-7090
2-Chloro-4-{[1-(4-fluorophenyl)-2,5-dimethyl-1H-imidazol-4-yl]ethynyl}pyridine
UNII-3110E3AO8S
Basimglurant
Pyridine, 2-chloro-4-[2-[1-(4-fluorophenyl)-2,5-dimethyl-1H-imidazol-4-yl]ethynyl]-
RG7090

Biological Activity

[Description]:

Basimglurant (RG7090) is a potent, selective and orally available mGlu5 negative allosteric modulator with a Kd of 1.1 nM.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> mGluR
Research Areas >> Neurological Disease

[Target]

Kd: 1.1 nM (mGlu5)[1]


[In Vitro]

[3H]-basimglurant saturation analysis on recombinant human mGlu5 reveals monophasic saturation isotherms with Kd of 1.1 nM. In competition binding experiments on human recombinant mGlu5, Basimglurant (RG7090) fully displaces [3H]-MPEP with a Ki of 35.6 nM and [3H]-ABP688 with a Ki of 1.4 nM. In HEK293 cells stably expressing human mGlu5, Basimglurant (RG7090) inhibits quisqualate induced Ca2+ mobilization with an IC50 of 7.0 nM and [3H]-inositolphosphate accumulation with an IC50 of 5.9 nM. Basimglurant (RG7090) shows similar potencies in radioligand binding and functional assay on human and rodent mGlu5 receptor orthologues[1].

[In Vivo]

Basimglurant (RG7090) is a potent, selective, and safe mGlu5 inhibitor with good oral bioavailability and long half-life supportive of once-daily administration, good brain penetration, and high in vivo potency. It has antidepressant properties which are corroborated by its functional magnetic imaging (fMRI) profile, as well as anxiolytic-like and antinociceptive features[1]. It is currently in phase II clinical studies for the treatment of depression and fragile X syndrome. In the Vogel conflict drinking test, Basimglurant dose dependently increases the drinking time. The total plasma exposure of efficacious doses of Basimglurant (RG7090) ranges from 5 ng/mL (0.03 mg/kg) to 37 ng/mL (0.3 mg/kg)[2].

[Animal admin]

Rats: For intravenous PK, Basimglurant (RG7090) is formulated in N-methyl-pyrollidone (NMP)/saline (30%/70%) as vehicle and administered at a volume of 2 mL/kg. For oral gavage (p.o.) the compound is administered as suspension using gelatine/saline (7.5%/0.62% in water) at an administration volume of 4 mL/kg[1]. Monkey: For intravenous PK, Basimglurant (RG7090) is formulated in cyclodextrin solution as vehicle and administered at a volume of 2 mL/kg. For oral gavage (p.o.), the compound is administered in capsule (2 mg in size-2 capsules, i.e. ~0.3 mg/kg) to fasted or fed monkeys in a cross-over design[1].

[References]

[1]. Lindemann L, et al. Pharmacology of basimglurant (RO4917523, RG7090), a unique metabotropic glutamate receptor 5 negative allosteric modulator in clinical development for depression. J Pharmacol Exp Ther. 2015 Apr;353(1):213-33.

[2]. Jaeschke G, et al. Metabotropic glutamate receptor 5 negative allosteric modulators: discovery of 2-chloro-4-[1-(4-fluorophenyl)-2,5-dimethyl-1H-imidazol-4-ylethynyl]pyridine (basimglurant, RO4917523), a promising novel medicine for psychiatric diseases.


[Related Small Molecules]

mavoglurant | L-Glutamine | CTEP (RO4956371) | LY 354740 | L-(+)Sodium glutamate | ADX-88178 | MPEP (Hydrochloride) | FITM | (S)-MCPG | LY341495 | Dipraglurant | JNJ-40411813 | LY404039 | JNJ 16259685 | ADX-47273

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
526.6±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C18H13ClFN3

[ Molecular Weight ]:
325.767

[ Flash Point ]:
272.3±32.9 °C

[ Exact Mass ]:
325.078217

[ PSA ]:
30.71000

[ LogP ]:
4.49

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.604

[ Storage condition ]:
2-8℃

Related Compounds