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Details

Stereochemistry ACHIRAL
Molecular Formula C20H20N4O
Molecular Weight 332.3998
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of KW-2449

SMILES

c1ccc2c(c1)c(/C(/[H])=C(\[H])/c3ccc(cc3)C(=O)N4CCNCC4)n[nH]2

InChI

InChIKey=YYLKKYCXAOBSRM-JXMROGBWSA-N
InChI=1S/C20H20N4O/c25-20(24-13-11-21-12-14-24)16-8-5-15(6-9-16)7-10-19-17-3-1-2-4-18(17)22-23-19/h1-10,21H,11-14H2,(H,22,23)/b10-7+

HIDE SMILES / InChI

Molecular Formula C20H20N4O
Molecular Weight 332.3998
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19541823

KW-2449, a multikinase inhibitor of FLT3, ABL, ABL-T315I, and Aurora kinase, is under investigation to treat leukemia patients. KW-2449 is a multikinase inhibitor of FLT3, ABL, ABL-T315I, and Aurora kinase with IC50 values of 6.6nM, 14nM, 4nM and 48nM, respectively. KW-2449 has potent growth inhibitory activity against various types of leukemia by several mechanisms of action. Kyowa Hakko Kirin Pharma Inc. (a US subsidiary of Kyowa Hakko Kirin Co) was developing KW-2449 for the treatment of acute lymphoblastic leukaemia; acute myeloid leukaemia; chronic myeloid leukaemia; myelodysplastic syndromes, but later these studies were discontinued.

Approval Year

TargetsConditions
PubMed

PubMed

TitleDatePubMed
KW-2449, a novel multikinase inhibitor, suppresses the growth of leukemia cells with FLT3 mutations or T315I-mutated BCR/ABL translocation.
2009 Aug 20
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.
2010 Nov 24
Comprehensive analysis of kinase inhibitor selectivity.
2011 Oct 30
Patents

Sample Use Guides

KW-2449 50 mg capsules administered 3 or 4 times per day for 21-day cycles up to 6 cycles
Route of Administration: Oral
KW-2449 showed growth inhibitory activities against FLT3/ITD-, FLT3/D835Y-, and wt-FLT3/FL-expressing 32D cells, MOLM-13 and MV4;11 with half-maximal growth inhibitory concentration (GI50) values of 0.024, 0.046, 0.014, 0.024, and 0.011 uM, respectively. KW-2449 (0.60 uM) induced G2/M arrest and apparent increase of sub-G1 apoptotic RS4;11 cells after 24 hours and 48 hours of exposure, respectively.
Substance Class Chemical
Created
by admin
on Fri Jun 25 23:05:53 UTC 2021
Edited
by admin
on Fri Jun 25 23:05:53 UTC 2021
Record UNII
2D9N67F58G
Record Status Validated (UNII)
Record Version
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Name Type Language
KW-2449
Common Name English
(4-((1E)-2-(1H-INDAZOL-3-YL)ETHENYL)PHENYL)-1-PIPERAZINYLMETHANONE
Systematic Name English
KW 2449 [WHO-DD]
Common Name English
PIPERAZINE, 1-(4-((1E)-2-(1H-INDAZOL-3-YL)ETHENYL)BENZOYL)-
Systematic Name English
Code System Code Type Description
CAS
841258-76-2
Created by admin on Fri Jun 25 23:05:53 UTC 2021 , Edited by admin on Fri Jun 25 23:05:53 UTC 2021
PRIMARY
FDA UNII
2D9N67F58G
Created by admin on Fri Jun 25 23:05:53 UTC 2021 , Edited by admin on Fri Jun 25 23:05:53 UTC 2021
PRIMARY
ChEMBL
CHEMBL1908397
Created by admin on Fri Jun 25 23:05:53 UTC 2021 , Edited by admin on Fri Jun 25 23:05:53 UTC 2021
PRIMARY
PUBCHEM
11427553
Created by admin on Fri Jun 25 23:05:53 UTC 2021 , Edited by admin on Fri Jun 25 23:05:53 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
IC50
TARGET -> INHIBITOR
IC50
TARGET -> INHIBITOR
TARGET -> INHIBITOR
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ACTIVE MOIETY