Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H9NO |
| Molecular Weight | 195.2167 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1NC2=C(C=CC=C2)C3=C1C=CC=C3
InChI
InChIKey=RZFVLEJOHSLEFR-UHFFFAOYSA-N
InChI=1S/C13H9NO/c15-13-11-7-2-1-5-9(11)10-6-3-4-8-12(10)14-13/h1-8H,(H,14,15)
| Molecular Formula | C13H9NO |
| Molecular Weight | 195.2167 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
CNS Activity
Curator's Comment: An in vitro lesion model using the neonatal rat spinal cord has recently shown PARP-1 overactivity to be closely related to neuronal losses after an excitotoxic challenge by kainate: in this system, the PARP-1 inhibitor phenanthridinone appeared to be a moderate histological neuroprotector.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3105 |
7.07 null [pIC50] | ||
Target ID: CHEMBL6164 |
0.054 µM [IC50] | ||
Target ID: CHEMBL5366 |
0.088 µM [IC50] | ||
Target ID: CHEMBL6142 |
11.95 µM [Kd] | ||
Target ID: CHEMBL6154 |
6.2 µM [Kd] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| 6,(5H)-phenanthridinone protects against carbon tetrachloride-induced cytotoxicity in human HepG2 cells. | 2011-04-08 |
|
| Synthesis and evaluation of substituted benzoisoquinolinones as potent inhibitors of Chk1 kinase. | 2007-11-15 |
|
| A key role for poly(ADP-ribose) polymerase-1 activity during human dendritic cell maturation. | 2007-07-01 |
|
| Effects of proximity on the relaxation dynamics of flindersine and 6(5H)-phenanthridinone. | 2007-01-18 |
|
| Discovery of potent poly(ADP-ribose) polymerase-1 inhibitors from the modification of indeno[1,2-c]isoquinolinone. | 2005-08-11 |
|
| Fungal biotransformation of benzo[f]quinoline, benzo[h]quinoline, and phenanthridine. | 2005-05 |
|
| The monofunctional alkylating agent N-methyl-N'-nitro-N-nitrosoguanidine triggers apoptosis through p53-dependent and -independent pathways. | 2005-01-01 |
|
| Dual regulation of AP-2alpha transcriptional activation by poly(ADP-ribose) polymerase-1. | 2004-08-15 |
|
| An enzymatic assay for poly(ADP-ribose) polymerase-1 (PARP-1) via the chemical quantitation of NAD(+): application to the high-throughput screening of small molecules as potential inhibitors. | 2004-03-01 |
|
| Hepatoprotective effects of 6(5H)-phenanthridinone from chemical-induced centrilobular necrosis. | 2004 |
|
| Nicotinamide is a potent inhibitor of proinflammatory cytokines. | 2003-01 |
|
| Inhibitors of poly(ADP-ribose) polymerase-1 suppress transcriptional activation in lymphocytes and ameliorate autoimmune encephalomyelitis in rats. | 2002-11 |
|
| Poly(ADP-ribose) polymerase inhibitors attenuate necrotic but not apoptotic neuronal death in experimental models of cerebral ischemia. | 2001-09 |
|
| Novel inhibitors of poly(ADP-ribose) polymerase/PARP1 and PARP2 identified using a cell-based screen in yeast. | 2001-05-15 |
|
| Comparative metabolism of phenanthridine by carp (Cyprinus carpio) and midge larvae (Chironomus riparius). | 2001 |
|
| Excitotoxicity in the lung: N-methyl-D-aspartate-induced, nitric oxide-dependent, pulmonary edema is attenuated by vasoactive intestinal peptide and by inhibitors of poly(ADP-ribose) polymerase. | 1996-05-14 |
|
| N-acetylcysteine protects lymphocytes from nitrogen mustard-induced apoptosis. | 1996-05-03 |
Patents
Sample Use Guides
The ability of phenanthridinone, a new potent poly(ADP-ribose)polymerase (PARP) inhibitor, to potentiate the effect of ionizing radiation on tumor cells was evaluated. RDM4 murine lymphoma cells were irradiated using a 60Co panoramic source and then examined for their growth, cell cycle distribution, and apoptosis. Phenanthridinone (100 microM) was found to inhibit more than 90% of the PARP activity in control and irradiated cells. It was found to sharply increase the radiation-induced inhibition of cell proliferation. Indeed, at 2.5 Gy the relative cell number of phenanthridinone-treated cells was 60% below control levels. At the same radiation dose, the G2M arrest was also significantly reinforced by the addition of phenanthridinone. Furthermore, this PARP inhibitor was shown to significantly increase the amount of DNA fragmentation. Comparable results were obtained with 3-aminobenzamide, another PARP inhibitor, but at concentrations 200-fold higher.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:25:47 GMT 2025
by
admin
on
Mon Mar 31 22:25:47 GMT 2025
|
| Record UNII |
AVQ13AUB5J
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Systematic Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Code | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
40943
Created by
admin on Mon Mar 31 22:25:47 GMT 2025 , Edited by admin on Mon Mar 31 22:25:47 GMT 2025
|
PRIMARY | |||
|
61083
Created by
admin on Mon Mar 31 22:25:47 GMT 2025 , Edited by admin on Mon Mar 31 22:25:47 GMT 2025
|
PRIMARY | |||
|
75292
Created by
admin on Mon Mar 31 22:25:47 GMT 2025 , Edited by admin on Mon Mar 31 22:25:47 GMT 2025
|
PRIMARY | |||
|
1015-89-0
Created by
admin on Mon Mar 31 22:25:47 GMT 2025 , Edited by admin on Mon Mar 31 22:25:47 GMT 2025
|
PRIMARY | |||
|
DTXSID0074423
Created by
admin on Mon Mar 31 22:25:47 GMT 2025 , Edited by admin on Mon Mar 31 22:25:47 GMT 2025
|
PRIMARY | |||
|
AVQ13AUB5J
Created by
admin on Mon Mar 31 22:25:47 GMT 2025 , Edited by admin on Mon Mar 31 22:25:47 GMT 2025
|
PRIMARY | |||
|
11021
Created by
admin on Mon Mar 31 22:25:47 GMT 2025 , Edited by admin on Mon Mar 31 22:25:47 GMT 2025
|
PRIMARY | |||
|
213-804-3
Created by
admin on Mon Mar 31 22:25:47 GMT 2025 , Edited by admin on Mon Mar 31 22:25:47 GMT 2025
|
PRIMARY | |||
|
1853
Created by
admin on Mon Mar 31 22:25:47 GMT 2025 , Edited by admin on Mon Mar 31 22:25:47 GMT 2025
|
PRIMARY |