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MedKoo Cat#: 564301 | Name: ONO-8590580
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

ONO-8590580 is a GABAAα5 negative allosteric modulator which enhances long-term potentiation and improves cognitive deficits in preclinical models.

Chemical Structure

ONO-8590580
ONO-8590580
CAS#1802661-73-9

Theoretical Analysis

MedKoo Cat#: 564301

Name: ONO-8590580

CAS#: 1802661-73-9

Chemical Formula: C21H21FN6

Exact Mass: 376.1812

Molecular Weight: 376.44

Elemental Analysis: C, 67.00; H, 5.62; F, 5.05; N, 22.33

Price and Availability

Size Price Availability Quantity
100mg USD 950.00 2 Weeks
200mg USD 1,650.00 2 Weeks
500mg USD 3,650.00 2 Weeks
1g USD 4,950.00 2 Weeks
2g USD 7,850.00 2 Weeks
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Related CAS #
No Data
Synonym
ONO8590580; ONO 8590580; ONO-8590580
IUPAC/Chemical Name
1-(Cyclopropylmethyl)-5-fluoro-4-methyl-N-(5-(1-methyl-1H-imidazol-4-yl)pyridin-2-yl)-1H-benzo[d]imidazol-6-amine
InChi Key
INGJMHPGMVUEKY-UHFFFAOYSA-N
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)
SMILES Code
CN1C=C(C2=CN=C(NC3=C(F)C(C)=C4C(N(CC5CC5)C=N4)=C3)C=C2)N=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
ONO-8590580 is a GABAA α5 negative allosteric modulator.
In vitro activity:
ONO-8590580 [1-(cyclopropylmethyl)-5-fluoro-4-methyl-N-[5-(1-methyl-1H-imidazol-4-yl)-2-pyridinyl]-1H-benzimidazol-6-amine] binds to the benzodiazepine binding sites on recombinant human α5-containing GABAA receptors with a Ki of 7.9 nM, and showed functionally selective GABAAα5 NAM activity for GABA-induced Cl- channel activity with a maximum 44.4% inhibition and an EC50 of 1.1 nM. In rat hippocampal slices, tetanus-induced long-term potentiation of CA1 synapse response was significantly augmented in the presence of 300 nM ONO-8590580. Reference: J Pharmacol Exp Ther. 2018 Jul;366(1):58-65. https://pubmed.ncbi.nlm.nih.gov/29674331/
In vivo activity:
Orally administered ONO-8590580 (1-20 mg/kg) dose-dependently occupied hippocampal GABAAα5 in a range of 40%-90% at 1 hour after intake. In the rat passive avoidance test, ONO-8590580 (3-20 mg/kg, by mouth) significantly prevented (+)-MK-801 hydrogen maleate (MK-801)-induced memory deficit. In addition, ONO-8590580 (20 mg/kg, p.o.) was also effective in improving the cognitive deficit induced by scopolamine and MK-801 in the rat eight-arm radial maze test with equal or greater activity than 0.5 mg/kg donepezil. Reference: J Pharmacol Exp Ther. 2018 Jul;366(1):58-65. https://pubmed.ncbi.nlm.nih.gov/29674331/
Solvent mg/mL mM
Solubility
DMSO 62.5 166.03
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 376.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
Kawaharada S, Nakanishi M, Nakanishi N, Hazama K, Higashino M, Yasuhiro T, Lewis A, Clark GS, Chambers MS, Maidment SA, Katsumata S, Kaneko S. ONO-8590580, a Novel GABAAα5 Negative Allosteric Modulator Enhances Long-Term Potentiation and Improves Cognitive Deficits in Preclinical Models. J Pharmacol Exp Ther. 2018 Jul;366(1):58-65. doi: 10.1124/jpet.117.247627. Epub 2018 Apr 19. PMID: 29674331.
In vitro protocol:
Kawaharada S, Nakanishi M, Nakanishi N, Hazama K, Higashino M, Yasuhiro T, Lewis A, Clark GS, Chambers MS, Maidment SA, Katsumata S, Kaneko S. ONO-8590580, a Novel GABAAα5 Negative Allosteric Modulator Enhances Long-Term Potentiation and Improves Cognitive Deficits in Preclinical Models. J Pharmacol Exp Ther. 2018 Jul;366(1):58-65. doi: 10.1124/jpet.117.247627. Epub 2018 Apr 19. PMID: 29674331.
In vivo protocol:
Kawaharada S, Nakanishi M, Nakanishi N, Hazama K, Higashino M, Yasuhiro T, Lewis A, Clark GS, Chambers MS, Maidment SA, Katsumata S, Kaneko S. ONO-8590580, a Novel GABAAα5 Negative Allosteric Modulator Enhances Long-Term Potentiation and Improves Cognitive Deficits in Preclinical Models. J Pharmacol Exp Ther. 2018 Jul;366(1):58-65. doi: 10.1124/jpet.117.247627. Epub 2018 Apr 19. PMID: 29674331.
1: Kawaharada S, Nakanishi M, Nakanishi N, Hazama K, Higashino M, Yasuhiro T, Lewis A, Clark GS, Chambers MS, Maidment SA, Katsumata S, Kaneko S. ONO-8590580, a Novel GABA(A)α5 Negative Allosteric Modulator Enhances Long-Term Potentiation and Improves Cognitive Deficits in Preclinical Models. J Pharmacol Exp Ther. 2018 Jul;366(1):58-65. doi: 10.1124/jpet.117.247627. Epub 2018 Apr 19. PubMed PMID: 29674331.