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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
Structure of AS-601245

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)

HIDE SMILES / InChI

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 ( + / - )

Description
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

Curator's Comment: Known to be CNS active in Gerbils. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.15 µM [IC50]
0.22 µM [IC50]
0.07 µM [IC50]
Target ID: P53779
Gene ID: 5602.0
Gene Symbol: MAPK10
Target Organism: Homo sapiens (Human)
70.0 nM [IC50]
Target ID: P45983|||Q308M2
Gene ID: 5599.0
Gene Symbol: MAPK8
Target Organism: Homo sapiens (Human)
150.0 nM [IC50]
Target ID: P80192
Gene ID: 4293.0
Gene Symbol: MAP3K9
Target Organism: Homo sapiens (Human)
220.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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

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
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 Sat Dec 16 10:04:47 GMT 2023
Edited
by admin
on Sat Dec 16 10:04:47 GMT 2023
Record UNII
Y9A2N9O85G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AS-601245
Common Name English
2-BENZOTHIAZOLEACETONITRILE, .ALPHA.-(2-((2-(3-PYRIDINYL)ETHYL)AMINO)-4-PYRIMIDINYL)-
Systematic Name English
AS601245
Code English
SAPK INHIBITOR V
Common Name English
JNK INHIBITOR V
Common Name English
Code System Code Type Description
CAS
861411-83-8
Created by admin on Sat Dec 16 10:04:47 GMT 2023 , Edited by admin on Sat Dec 16 10:04:47 GMT 2023
ALTERNATIVE
EPA CompTox
DTXSID401026023
Created by admin on Sat Dec 16 10:04:47 GMT 2023 , Edited by admin on Sat Dec 16 10:04:47 GMT 2023
PRIMARY
FDA UNII
Y9A2N9O85G
Created by admin on Sat Dec 16 10:04:47 GMT 2023 , Edited by admin on Sat Dec 16 10:04:47 GMT 2023
PRIMARY
CAS
345987-15-7
Created by admin on Sat Dec 16 10:04:47 GMT 2023 , Edited by admin on Sat Dec 16 10:04:47 GMT 2023
PRIMARY
PUBCHEM
10109823
Created by admin on Sat Dec 16 10:04:47 GMT 2023 , Edited by admin on Sat Dec 16 10:04:47 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY