A negative allosteric modulator of α5 subunit-containing GABAA receptors
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ONO-8590580

Item No. 35297

Technical Information
Formal Name
1-(cyclopropylmethyl)-5-fluoro-4-methyl-N-[5-(1-methyl-1H-imidazol-4-yl)-2-pyridinyl]-1H-benzimidazol-6-amine
CAS Number
1802661-73-9
Molecular Formula
C21H21FN6
Formula Weight
Purity
≥98%
Formulation
A crystalline solid
λmax
266, 290, 320 nm
SMILES
FC1=C(NC2=CC=C(C3=CN(C)C=N3)C=N2)C=C4C(N=CN4CC5CC5)=C1C
InChi Code
InChI=1S/C21H21FN6/c1-13-20(22)16(7-18-21(13)25-12-28(18)9-14-3-4-14)26-19-6-5-15(8-23-19)17-10-27(2)11-24-17/h5-8,10-12,14H,3-4,9H2,1-2H3,(H,23,26)
InChi Key
INGJMHPGMVUEKY-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    ONO-8590580 is a negative allosteric modulator of α5 subunit-containing GABAA receptors that binds at the benzodiazepine binding site.1 It binds to α1, α2, α3, and α5 subunit-containing GABAA receptors (Kis = 140, 32, 24, and 7.9 nM, respectively). It is selective for inhibiting GABA-induced currents in HEK293 cells expressing human recombinant α5β3γ2 subunits (EC50 = 1.1 nM) over those expressing human recombinant α1β3γ2, α2β3γ2, or α3β3γ2 subunits for which it has little to no activity. ONO-8590580 (300 nM) enhances long-term potentiation in rat hippocampal brain slices. It decreases MK-801-induced memory deficits in the rat passive avoidance test when administered at doses ranging from 3 to 20 mg/kg. ONO-8590580 (20 mg/kg, p.o.) decreases MK-801- and scopolamine-induced increases in the latency to complete, and the number of errors made in, the eight-arm radial maze test in rats. It does not induce anxiety-like or proconvulsant behavior in rats in the elevated zero maze or pentylenetetrazole-induced seizure test when administered at a dose of 20 mg/kg.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kawaharada, S., Nakanishi, M., Nakanishi, N., et alONO-8590580, a novel GABAA α5 negative allosteric modulator enhances long-term potentiation and improves cognitive deficits in preclinical models. J. Pharmacol. Exp. Ther. 366(1), 58-65 (2018).