Phenoxodiol
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Phenoxodiol
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CAS No:
81267-65-4
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Formula:
C15H12O3
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Chemical Name:
Phenoxodiol
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Synonyms:
2H-1-Benzopyran-7-ol,3-(4-hydroxyphenyl)-;3-(4-Hydroxyphenyl)-2H-1-benzopyran-7-ol;Haginin E;Phenoxodiol;Dehydroequol;NV 06;Idronoxil;3-(4-Hydroxyphenyl)-2H-benzopyran-7-ol;D 7446
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CAS No:
Description
Phenoxodiol, a synthetic analog of Genestein, activates the mitochondrial caspase system, inhibits XIAP (an apoptosis inhibitor), and sensitizes the cancer cells to Fas-mediated apoptosis. This agent also inhibits DNA topoisomerase II by stabilizing the cleavable complex. Phenoxodiol induces cell cycle arrest in the G1/S phase of the cell cycle and upregulates p21WAF1 via a p53 independent manner[1][2].
Idronoxil is a substance that is being studied in the treatment of cancer. It belongs to the family of drugs called signal transduction inhibitors.|Idronoxil is a synthetic flavonoid derivative. Idronoxil activates the mitochondrial caspase system, inhibits X-linked inhibitor of apoptosis (XIAP), and disrupts FLICE inhibitory protein (FLIP) expression, resulting in tumor cell apoptosis. This agent also inhibits DNA topoisomerase II by stabilizing the cleavable complex, thereby preventing DNA replication and resulting in tumor cell death.
Characteristics
49.69000
4.35
1.3±0.1 g/cm3
165-166 °C
463.7±45.0 °C at 760 mmHg
234.3±28.7 °C
1.679
Safety Information
UN 3077 9 / PGIII
3
61
Xn,N
P273
H302-H400
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Intended for the treatment of various forms of cancer.
Phenoxodiol 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, phenoxodiol sensitizes drug-resistant tumour cells to anticancer drugs including paclitaxel, carboplatin and gemcitabine.
The antiproliferative effects of phenoxodiol are associated with inhibition of plasma membrane electron transport in tumour cell lines and primary immune cells. Results from one study (PMID: 17904534) indicate that plasma membrane electron transport (PMET) may be a primary target for phenoxodiol in tumour cells and in activated T cells.
7-hydroxy-3-hydroxyphenyl-1H-benzopyran
Phenoxodiol Use and Manufacturing
Antineoplastic which acts as an antiproliferative, topoisomerase II inhibitor; 5 reductase inhibitor[Note— The trivial name, phenoxodiol, has appeared in literature].
Computed Properties
Molecular Weight:240.25
XLogP3:2.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:240.078644241
Monoisotopic Mass:240.078644241
Topological Polar Surface Area:49.7
Heavy Atom Count:18
Complexity:318
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes