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Details

Stereochemistry ACHIRAL
Molecular Formula C26H30FN7O3
Molecular Weight 507.5599
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEFOSBARASERTIB

SMILES

CCN(CCO)CCCOC1=CC2=NC=NC(NC3=NNC(CC(=O)NC4=CC=CC(F)=C4)=C3)=C2C=C1

InChI

InChIKey=QYZOGCMHVIGURT-UHFFFAOYSA-N
InChI=1S/C26H30FN7O3/c1-2-34(10-11-35)9-4-12-37-21-7-8-22-23(16-21)28-17-29-26(22)31-24-14-20(32-33-24)15-25(36)30-19-6-3-5-18(27)13-19/h3,5-8,13-14,16-17,35H,2,4,9-12,15H2,1H3,(H,30,36)(H2,28,29,31,32,33)

HIDE SMILES / InChI

Molecular Formula C26H30FN7O3
Molecular Weight 507.5599
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17575233

AstraZeneca and BIND Therapeutics (formerly BIND Biosciences) are collaborating to develop AZD-1152HQPA (AZD2811) for the treatment of cancer. AZD2811, a novel, selective inhibitor of Aurora B kinase that has been shown to be active in both solid and hematological tumors in preclinical models, is the second Accurin candidate to enter clinical development. AZD1152-HQPA is a highly selective Aurora B inhibitor with IC50 of 0.37 nM in a cell-free assay. AZD1152-HQPA inhibited the proliferation of AML lines (HL-60, NB4, MOLM13), ALL line (PALL-2), biphenotypic leukemia (MV4-11), acute eosinophilic leukemia (EOL-1), and the blast crisis of chronic myeloid leukemia K562 cells with an IC50 ranging from 3 nM to 40 nM. The phase 1 trial is enrolling patients with advanced solid tumors, including patients with small cell lung cancer, and is being conducted by AstraZeneca under the companies’ 2013 collaboration agreement with BIND managing all chemistry, manufacturing and control activities.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.37 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Discovery, synthesis, and in vivo activity of a new class of pyrazoloquinazolines as selective inhibitors of aurora B kinase.
2007 May 3
Discovery and development of aurora kinase inhibitors as anticancer agents.
2009 May 14
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
Phase I study of barasertib (AZD1152), a selective inhibitor of Aurora B kinase, in patients with advanced solid tumors.
2013 Apr
Patents

Sample Use Guides

Rats: 25 mg/kg/d as a daily i.v. bolus dose for 4 consecutive days
Route of Administration: Intravenous
Exposure of U251 cells to AZD1152-HQPA from 25 nM to 10 uM for 24 h resulted in a reduction of histone H3 serine 10 phosphorylation and Aurora B autophosphorylation. All GBM cell lines showed a block in cell division with variable reduction in total cell numbers between day 2 and 8 of continuous exposure to 1 uM AZD1152-HQPA
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:41:46 UTC 2023
Edited
by admin
on Sat Dec 16 05:41:46 UTC 2023
Record UNII
29P8LWS24N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEFOSBARASERTIB
INN  
Official Name English
AZD 2811 [WHO-DD]
Common Name English
2-(5-((7-(3-(ETHYL(2- HYDROXYETHYL)AMINO)PROPOXY)QUINAZOLIN-4-YL)AMINO)- 1H-PYRAZOL-3-YL)-N-(3-FLUOROPHENYL)ACETAMIDE
Systematic Name English
2-(3-((7-(3-(ETHYL(2-HYDROXYETHYL)AMINO)PROPOXY)QUINAZOLIN-4-YL)AMINO)-1H-PYRAZOL-5-YL)-N-(3-FLUOROPHENYL)ACETAMIDE
Systematic Name English
AZD-1152HQPA
Code English
1H-PYRAZOLE-5-ACETAMIDE, 3-((7-(3-(ETHYL(2-HYDROXYETHYL)AMINO)PROPOXY)-4-QUINAZOLINYL)AMINO)-N-(3-FLUOROPHENYL)-
Systematic Name English
BARASERTIB-HQPA
Common Name English
1H-PYRAZOLE-3-ACETAMIDE, 5-((7-(3-(ETHYL(2-HYDROXYETHYL)AMINO)PROPOXY)-4-QUINAZOLINYL)AMINO)-N-(3-FLUOROPHENYL)-
Systematic Name English
defosbarasertib [INN]
Common Name English
AZD-1152 HQPA
Code English
INH-34
Code English
AZD-2811
Code English
Code System Code Type Description
CHEBI
167636
Created by admin on Sat Dec 16 05:41:46 UTC 2023 , Edited by admin on Sat Dec 16 05:41:46 UTC 2023
PRIMARY
INN
11594
Created by admin on Sat Dec 16 05:41:46 UTC 2023 , Edited by admin on Sat Dec 16 05:41:46 UTC 2023
PRIMARY INN
PUBCHEM
16007391
Created by admin on Sat Dec 16 05:41:46 UTC 2023 , Edited by admin on Sat Dec 16 05:41:46 UTC 2023
PRIMARY
CAS
1218904-24-5
Created by admin on Sat Dec 16 05:41:46 UTC 2023 , Edited by admin on Sat Dec 16 05:41:46 UTC 2023
SUPERSEDED
SMS_ID
100000181860
Created by admin on Sat Dec 16 05:41:46 UTC 2023 , Edited by admin on Sat Dec 16 05:41:46 UTC 2023
PRIMARY
EPA CompTox
DTXSID60222584
Created by admin on Sat Dec 16 05:41:46 UTC 2023 , Edited by admin on Sat Dec 16 05:41:46 UTC 2023
PRIMARY
NCI_THESAURUS
C179080
Created by admin on Sat Dec 16 05:41:46 UTC 2023 , Edited by admin on Sat Dec 16 05:41:46 UTC 2023
PRIMARY
CHEBI
91367
Created by admin on Sat Dec 16 05:41:46 UTC 2023 , Edited by admin on Sat Dec 16 05:41:46 UTC 2023
PRIMARY
CAS
722544-51-6
Created by admin on Sat Dec 16 05:41:46 UTC 2023 , Edited by admin on Sat Dec 16 05:41:46 UTC 2023
PRIMARY
FDA UNII
29P8LWS24N
Created by admin on Sat Dec 16 05:41:46 UTC 2023 , Edited by admin on Sat Dec 16 05:41:46 UTC 2023
PRIMARY
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TARGET -> INHIBITOR
SELECTIVE
Ki
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PRODRUG -> METABOLITE ACTIVE
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ACTIVE MOIETY