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Details

Stereochemistry RACEMIC
Molecular Formula C23H18Cl3FN4O3S
Molecular Weight 555.836
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPHENYL ACETAMIDOTRICHLOROETHYL FLUORONITROPHENYL THIOUREA

SMILES

[O-][N+](=O)C1=C(F)C=CC(NC(=S)NC(NC(=O)C(C2=CC=CC=C2)C3=CC=CC=C3)C(Cl)(Cl)Cl)=C1

InChI

InChIKey=HLCDNLNLQNYZTK-UHFFFAOYSA-N
InChI=1S/C23H18Cl3FN4O3S/c24-23(25,26)21(30-22(35)28-16-11-12-17(27)18(13-16)31(33)34)29-20(32)19(14-7-3-1-4-8-14)15-9-5-2-6-10-15/h1-13,19,21H,(H,29,32)(H2,28,30,35)

HIDE SMILES / InChI

Molecular Formula C23H18Cl3FN4O3S
Molecular Weight 555.836
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18347191 | https://www.ncbi.nlm.nih.gov/pubmed/19903334 | http://www.selleckchem.com/products/cgk-733.html | https://www.ncbi.nlm.nih.gov/pubmed/24795863 | https://www.ncbi.nlm.nih.gov/pubmed/21865098

Diphenyl acetamidotrichloroethyl fluoronitrophenyl thiourea, CGK733, was claimed to be selective inhibitor of the ataxia telangiectasia-mutated (ATM) protein and ATM- and Rad3-related (ATR) protein, however after investigation of the contents of the original paper by Korean Advanced Institute of Science and Technology (KAIST) several irregularities has been revealed and the paper was retracted in full. Further studies were completed showing that CGK-733 has no specific inhibitory effect on ATM or ATR. Unfortunately, the compound is still being marketed as an ATM/ATR inhibitor. CGK733 inhibits the proliferation of human cancer and non-transformed mouse fibroblast cell lines and induced senescent breast, lung, and colon carcinoma cells to undergo cell death.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
Small molecule-based reversible reprogramming of cellular lifespan.
2006 Jul
The ATM and ATR inhibitors CGK733 and caffeine suppress cyclin D1 levels and inhibit cell proliferation.
2009 Nov 10
Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity.
2011 Oct 30
CGK733 enhances multinucleated cell formation and cytotoxicity induced by taxol in Chk1-deficient HBV-positive hepatocellular carcinoma cells.
2012 May 25
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.
2013 Apr 15
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
10 uM CGK733 inhibits cell proliferation in MCF-7, T47D and MDA-MB436 breast cancer cells, LNCaP prostate cancer cells, HCT116 colon cancer cells and BALB/c 3T3 fibroblasts
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:22:16 UTC 2023
Edited
by admin
on Sat Dec 16 10:22:16 UTC 2023
Record UNII
L3DGZ99QYM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIPHENYL ACETAMIDOTRICHLOROETHYL FLUORONITROPHENYL THIOUREA
INCI  
INCI  
Official Name English
DIPHENYL ACETAMIDOTRICHLOROETHYL FLUORONITROPHENYL THIOUREA [INCI]
Common Name English
ATM/ATR KINASE INHIBITOR
Common Name English
CGK 733
Code English
CGK733
Brand Name English
CGK-733
Code English
BENZENEACETAMIDE, .ALPHA.-PHENYL-N-(2,2,2-TRICHLORO-1-((((4-FLUORO-3-NITROPHENYL)AMINO)THIOXOMETHYL)AMINO)ETHYL)-
Systematic Name English
Code System Code Type Description
CAS
905973-89-9
Created by admin on Sat Dec 16 10:22:16 UTC 2023 , Edited by admin on Sat Dec 16 10:22:16 UTC 2023
PRIMARY
FDA UNII
L3DGZ99QYM
Created by admin on Sat Dec 16 10:22:16 UTC 2023 , Edited by admin on Sat Dec 16 10:22:16 UTC 2023
PRIMARY
EPA CompTox
DTXSID30424997
Created by admin on Sat Dec 16 10:22:16 UTC 2023 , Edited by admin on Sat Dec 16 10:22:16 UTC 2023
PRIMARY
PUBCHEM
6605258
Created by admin on Sat Dec 16 10:22:16 UTC 2023 , Edited by admin on Sat Dec 16 10:22:16 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR