Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H12O3 |
Molecular Weight | 240.254 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(C=C1)C2=CC3=CC=C(O)C=C3OC2
InChI
InChIKey=ZZUBHVMHNVYXRR-UHFFFAOYSA-N
InChI=1S/C15H12O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-8,16-17H,9H2
Molecular Formula | C15H12O3 |
Molecular Weight | 240.254 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT00382811 | https://www.ncbi.nlm.nih.gov/pubmed/17904534 | https://clinicaltrials.gov/ct2/show/NCT03041285 | https://www.ncbi.nlm.nih.gov/pubmed/22377671 | https://clinicaltrials.gov/ct2/show/NCT00091377 | https://clinicaltrials.gov/ct2/show/NCT00303888
Curator's Comment: The description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT00382811 | https://www.ncbi.nlm.nih.gov/pubmed/17904534 | https://clinicaltrials.gov/ct2/show/NCT03041285 | https://www.ncbi.nlm.nih.gov/pubmed/22377671 | https://clinicaltrials.gov/ct2/show/NCT00091377 | https://clinicaltrials.gov/ct2/show/NCT00303888
Idronoxil (Phenoxodiol) is a synthetic flavonoid derivative developed by MEI Pharma for cancer treatment. Idronoxil inhibits proliferation of many cancer cell lines and induces apoptosis by disrupting FLICE-inhibitory protein, FLIP, expression and by caspase-dependent and -independent degradation of the X-linked inhibitor of apoptosis, XIAP. In addition, Idronoxil sensitizes drug-resistant tumour cells to anticancer drugs including paclitaxel, carboplatin, and gemcitabine. The antiproliferative effects of Idronoxil are associated with inhibition of plasma membrane electron transport in tumour cell lines and primary immune cells. Idronoxil displays anti-cancer activity against all forms of cancer tested in vitro and in vivo to date, using cells representative of all major forms of cancer. While having a modest ability to kill cancer cells(IC50 range between about 1-5 uM), preclinical studies point to its optimal use being to sensitize cancer cells to the toxic effects of standard therapies (chemotherapy and radiotherapy). The rationale is that a sub-lethal inhibitory effect on sphingosine kinase activity reduces the ability of the cancer cell to operate drug-resistance mechanisms and to effect repair of drug- or radiation-induced damage to DNA. In the case of cytotoxic drugs such as cisplatin, carboplatin, paclitaxel, Doxorubicin, and gemcitabine, Idronoxil is an exquisite sensitizer, increasing the cytotoxic potential of those agents by between 103 -105 times, in the process restoring sensitivity to cancer cells highly refractory to those agents.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2724 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22377671 |
660.69 nM [IC50] | ||
Target ID: GO:0030965 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17904534 |
32.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Phenoxodiol, a novel approach for the treatment of ovarian cancer. | 2006 Jun |
|
The antiproliferative effects of phenoxodiol are associated with inhibition of plasma membrane electron transport in tumour cell lines and primary immune cells. | 2007 Dec 3 |
|
Reciprocal relationship between cytosolic NADH and ENOX2 inhibition triggers sphingolipid-induced apoptosis in HeLa cells. | 2010 Aug 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00382811
400mg phenoxodiol three times daily in 28 day cycles.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17904534
HL60 and HL60ro cells were grown to mid-exponential phase in RPMI-1640, centrifuged at 130 x g at room temperature for 5 min and resuspended in 10 mL of fresh medium in the absence and presence of phenoxodiol and/or doxorubicin to a density of 2 x 10^5 cells/mL. Viable cells, as determined by Trypan blue exclusion, were counted in a Neubauer haemocytometer every 24 h for several days.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:28:47 GMT 2023
by
admin
on
Fri Dec 15 15:28:47 GMT 2023
|
Record UNII |
995FT1W541
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C1968
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
||
|
FDA ORPHAN DRUG |
868622
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
||
|
FDA ORPHAN DRUG |
252307
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
||
|
FDA ORPHAN DRUG |
254407
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
||
|
FDA ORPHAN DRUG |
251707
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
NN-61
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
PRIMARY | |||
|
995FT1W541
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
PRIMARY | |||
|
CHEMBL1957038
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
PRIMARY | |||
|
DB04915
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
PRIMARY | |||
|
81267-65-4
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
PRIMARY | |||
|
DTXSID50231029
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
PRIMARY | |||
|
8354
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
PRIMARY | |||
|
219100
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
PRIMARY | |||
|
m4146
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
PRIMARY | Merck Index | ||
|
SUB27079
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
PRIMARY | |||
|
100000090499
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
PRIMARY | |||
|
C471183
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
PRIMARY | |||
|
C2642
Created by
admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
TARGET -> INHIBITOR |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|