Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H16N6S |
Molecular Weight | 372.446 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N#CC(C1=NC2=CC=CC=C2S1)C3=NC(NCCC4=CC=CN=C4)=NC=C3
InChI
InChIKey=RCYPVQCPYKNSTG-UHFFFAOYSA-N
InChI=1S/C20H16N6S/c21-12-15(19-25-17-5-1-2-6-18(17)27-19)16-8-11-24-20(26-16)23-10-7-14-4-3-9-22-13-14/h1-6,8-9,11,13,15H,7,10H2,(H,23,24,26)
Molecular Formula | C20H16N6S |
Molecular Weight | 372.446 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/14988419 | https://www.ncbi.nlm.nih.gov/pubmed/15999997https://www.ncbi.nlm.nih.gov/pubmed/14988419Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15210584 | https://www.ncbi.nlm.nih.gov/pubmed/15715656 | https://www.ncbi.nlm.nih.gov/pubmed/19947601 | https://www.ncbi.nlm.nih.gov/pubmed/16972261
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419 | https://www.ncbi.nlm.nih.gov/pubmed/15999997https://www.ncbi.nlm.nih.gov/pubmed/14988419
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15210584 | https://www.ncbi.nlm.nih.gov/pubmed/15715656 | https://www.ncbi.nlm.nih.gov/pubmed/19947601 | https://www.ncbi.nlm.nih.gov/pubmed/16972261
AS601245 (1,3-benzothiazol-2-yl (2-{[2-(3-pyridinyl) ethyl] amino}-4 pyrimidinyl) acetonitrile) is a potent and selective JNK inhibitor developed by Applied Research Systems ARS Holding as promising neuroprotective agent. In vitro AS601245 is a potent and cell permeable ATP competitive JNK inhibitor, which has been shown to inhibit the JNK signaling pathway, promotes cell survival after cerebral ischemia. AS601245 and clofibrate have a synergistic effect in inducing cell responses and in affecting the gene expression profile in CaCo-2 colon cancer cells. AS601245 is a new potent adenosine triphosphate-competitive JNK inhibitor, provides significant protection against the delayed loss of hippocampal CA1 neurons in a gerbil model of transient global ischemia and is also neuroprotective in rats after focal cerebral ischemia. The ischemia-induced phospho-c-Jun expression is attenuated by AS601245, providing a mechanism through which AS601245 blocks the loss of neuronal cells.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19947601
Curator's Comment: Known to be CNS active in Gerbils. Human data not available.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2276 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419 |
0.15 µM [IC50] | ||
Target ID: CHEMBL4179 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419 |
0.22 µM [IC50] | ||
Target ID: CHEMBL2637 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419 |
0.07 µM [IC50] | ||
Target ID: P53779 Gene ID: 5602.0 Gene Symbol: MAPK10 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419 |
70.0 nM [IC50] | ||
Target ID: P45983|||Q308M2 Gene ID: 5599.0 Gene Symbol: MAPK8 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419 |
150.0 nM [IC50] | ||
Target ID: P80192 Gene ID: 4293.0 Gene Symbol: MAP3K9 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419 |
220.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
AS601245 (1,3-benzothiazol-2-yl (2-[[2-(3-pyridinyl) ethyl] amino]-4 pyrimidinyl) acetonitrile): a c-Jun NH2-terminal protein kinase inhibitor with neuroprotective properties. | 2004 Jul |
|
Inhibition of c-Jun N-terminal kinase decreases cardiomyocyte apoptosis and infarct size after myocardial ischemia and reperfusion in anaesthetized rats. | 2004 Jul |
|
AS601245, a c-Jun NH2-terminal kinase (JNK) inhibitor, reduces axon/dendrite damage and cognitive deficits after global cerebral ischaemia in gerbils. | 2008 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14988419
AS601245 was injected as an i.v. bolus dose (1 mg/kg) at the initiation of reperfusion followed by an i.v. infusion (0.6 mg/kg/h) during 22h.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17581813
PC12 cells were incubated with 1uM rotenone for 24, 36 and 48 h. AS601245 at 2 uM was added to the medium 2 h prior to 1 uM rotenone exposure. AS601245 almost completely prevented the apoptosis inducing factor release.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:04:47 GMT 2023
by
admin
on
Sat Dec 16 10:04:47 GMT 2023
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Record UNII |
Y9A2N9O85G
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Record Status |
Validated (UNII)
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Record Version |
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ACTIVE MOIETY |