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Details

Stereochemistry ACHIRAL
Molecular Formula C33H25F6N3O3
Molecular Weight 625.5603
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APOPTOZOLE

SMILES

COC1=CC=C(C=C1)C2=C(N(CC3=CC=C(C=C3)C(N)=O)C(=N2)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)C5=CC=C(OC)C=C5

InChI

InChIKey=ZIMMTPFXOMAJTQ-UHFFFAOYSA-N
InChI=1S/C33H25F6N3O3/c1-44-26-11-7-20(8-12-26)28-29(21-9-13-27(45-2)14-10-21)42(18-19-3-5-22(6-4-19)30(40)43)31(41-28)23-15-24(32(34,35)36)17-25(16-23)33(37,38)39/h3-17H,18H2,1-2H3,(H2,40,43)

HIDE SMILES / InChI

Molecular Formula C33H25F6N3O3
Molecular Weight 625.5603
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Apoptozole is an imidazole-based molecule, which induces apoptosis in cancer cells and can be investigated for cancer therapy. It was found, that apoptozole inhibits Heat shock proteins: Hsp70 and Hsc70. Further investigations have not found any experimental evidence that apoptozole interacts with HSP70 proteins in a specific and developable manner. Instead, was found, that apoptozole might form aggregates under aqueous conditions which could interact with HSP70 proteins in a non-specific manner, potentially leading to false positives and inconsistent data.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A small molecule that binds to an ATPase domain of Hsc70 promotes membrane trafficking of mutant cystic fibrosis transmembrane conductance regulator.
2011 Dec 21
Investigating Apoptozole as a Chemical Probe for HSP70 Inhibition.
2015
A small molecule inhibitor for ATPase activity of Hsp70 and Hsc70 enhances the immune response to protein antigens.
2015 Dec 3
Patents

Patents

Sample Use Guides

mice: Apoptozole (Az) enhances antibody production in mice administered with protein antigens. In an initial study aimed at evaluating the effect of Az on the immune response to antigens, C57BL/6 mice which lack an immunoglobulin G2a (IgG2a) gene were intraperitoneally (i.p.) immunized with each of the two immunogenic protein antigens, keyhole limpet hemocyanin (KLH) and ovalbumin (OVA). Various amounts (0–7.55 mg/kg mouse) of Az were then i.p. injected daily five times from 0 to 4 days after antigen immunization.
Route of Administration: Intraperitoneal
In order to determine if apoptozole (Az) stimulates production of infammatory cytokines in antigen presenting cells (APCs), RAW264.7 cells, a mouse macrophage cell line, were incubated with 3 μM of Az for 3, 6 and 12 h. The released cytokines were determined by using a multiplex cytokine assay. The results reveal that Az treatment enhances the secretion of tumor necrosis factor-α (TNF-α) and IL-18. Notably, Az treatment induces more secretion of TNF-α from RAW264.7 cells. In addition, the level of TNF-α production was found to be Az dose-dependent. The results suggested, that Az stimulated APCs to produce TNF-α, which subsequently mediated IFN-γ and IL-6 production from other types of immune cells.
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:44:12 GMT 2023
Edited
by admin
on Sat Dec 16 15:44:12 GMT 2023
Record UNII
WD0EH16QCD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APOPTOZOLE
Common Name English
4-((2-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-4,5-BIS(4-METHOXYPHENYL)-1H-IMIDAZOL-1-YL)METHYL)BENZAMIDE
Common Name English
BENZAMIDE, 4-((2-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-4,5-BIS(4-METHOXYPHENYL)-1H-IMIDAZOL-1-YL)METHYL)-
Common Name English
Code System Code Type Description
WIKIPEDIA
Apoptozole
Created by admin on Sat Dec 16 15:44:12 GMT 2023 , Edited by admin on Sat Dec 16 15:44:12 GMT 2023
PRIMARY
CAS
1054543-47-3
Created by admin on Sat Dec 16 15:44:12 GMT 2023 , Edited by admin on Sat Dec 16 15:44:12 GMT 2023
PRIMARY
PUBCHEM
24894064
Created by admin on Sat Dec 16 15:44:12 GMT 2023 , Edited by admin on Sat Dec 16 15:44:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID201027756
Created by admin on Sat Dec 16 15:44:12 GMT 2023 , Edited by admin on Sat Dec 16 15:44:12 GMT 2023
PRIMARY
FDA UNII
WD0EH16QCD
Created by admin on Sat Dec 16 15:44:12 GMT 2023 , Edited by admin on Sat Dec 16 15:44:12 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY