Identification
- Generic Name
- Idronoxil
- DrugBank Accession Number
- DB04915
- Background
Idronoxil is a substance that is being studied in the treatment of cancer. It belongs to the family of drugs called signal transduction inhibitors.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Idronoxil (DB04915)
- Weight
- Average: 240.254
Monoisotopic: 240.07864425 - Chemical Formula
- C15H12O3
- Synonyms
- (+/-)-cis-3-(4-hydroxyphenyl)-4-(4-methoxyphenyl)-3,4-dihydro-2H-cromen-7-ol
- 3-(4-hydroxyphenyl)-2H-chromen-7-ol
- Dehydroequol
- Haginin E
- Idronoxil
- Phenoxodiol
- External IDs
- NV-06
- NV06
Pharmacology
- Indication
Intended for the treatment of various forms of cancer.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
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.
- Mechanism of action
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.
Target Actions Organism UEcto-NOX disulfide-thiol exchanger 2 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Isoflavonoids
- Sub Class
- Hydroxyisoflavonoids
- Direct Parent
- Hydroxyisoflavonoids
- Alternative Parents
- Isoflav-3-enes / 1-benzopyrans / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Oxacyclic compounds / Hydrocarbon derivatives
- Substituents
- 1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / Ether / Hydrocarbon derivative / Hydroxyisoflavonoid / Isoflav-3-ene skeleton
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 995FT1W541
- CAS number
- 81267-65-4
- InChI Key
- ZZUBHVMHNVYXRR-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- 3-(4-hydroxyphenyl)-2H-chromen-7-ol
- SMILES
- OC1=CC=C(C=C1)C1=CC2=C(OC1)C=C(O)C=C2
References
- General References
- Herst PM, Petersen T, Jerram P, Baty J, Berridge MV: The antiproliferative effects of phenoxodiol are associated with inhibition of plasma membrane electron transport in tumour cell lines and primary immune cells. Biochem Pharmacol. 2007 Dec 3;74(11):1587-95. Epub 2007 Aug 19. [Article]
- Choueiri TK, Wesolowski R, Mekhail TM: Phenoxodiol: isoflavone analog with antineoplastic activity. Curr Oncol Rep. 2006 Mar;8(2):104-7. [Article]
- Mor G, Fu HH, Alvero AB: Phenoxodiol, a novel approach for the treatment of ovarian cancer. Curr Opin Investig Drugs. 2006 Jun;7(6):542-8. [Article]
- Klein R, Brown D, Turnley AM: Phenoxodiol protects against Cisplatin induced neurite toxicity in a PC-12 cell model. BMC Neurosci. 2007 Aug 1;8:61. [Article]
- External Links
- Human Metabolome Database
- HMDB0256416
- PubChem Compound
- 219100
- PubChem Substance
- 175426901
- ChemSpider
- 189918
- BindingDB
- 50419932
- ChEMBL
- CHEMBL1957038
- ZINC
- ZINC000001491943
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Abdominal wall neoplasm / Fallopian Tube Cancer / Ovarian Cancer 1 2 Completed Treatment Prostate Cancer 1 1 Completed Treatment Unspecified Adult Solid Tumor, Protocol Specific 1 1 Terminated Treatment Fallopian Tube Cancer / Ovarian Cancer / Primary Peritoneal Cancer 1 1 Terminated Treatment Metastatic Castration-Resistant Prostate Cancer (mCRPC) 1 1 Withdrawn Treatment Healthy Subjects (HS) 1 1, 2 Completed Treatment Cancer 1 1, 2 Completed Treatment Fallopian Tube Cancer / Ovarian Cancer / Primary Peritoneal Cancer 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0693 mg/mL ALOGPS logP 2.82 ALOGPS logP 3.09 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 8.63 Chemaxon pKa (Strongest Basic) -4.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 49.69 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 69.73 m3·mol-1 Chemaxon Polarizability 25.76 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier - 0.5249 Caco-2 permeable + 0.7327 P-glycoprotein substrate Substrate 0.5689 P-glycoprotein inhibitor I Non-inhibitor 0.7986 P-glycoprotein inhibitor II Non-inhibitor 0.8194 Renal organic cation transporter Non-inhibitor 0.8197 CYP450 2C9 substrate Non-substrate 0.8351 CYP450 2D6 substrate Non-substrate 0.8967 CYP450 3A4 substrate Non-substrate 0.6399 CYP450 1A2 substrate Inhibitor 0.9043 CYP450 2C9 inhibitor Inhibitor 0.8452 CYP450 2D6 inhibitor Non-inhibitor 0.7896 CYP450 2C19 inhibitor Inhibitor 0.9193 CYP450 3A4 inhibitor Non-inhibitor 0.5889 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9489 Ames test Non AMES toxic 0.5133 Carcinogenicity Non-carcinogens 0.9184 Biodegradation Not ready biodegradable 0.7429 Rat acute toxicity 2.9655 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9073 hERG inhibition (predictor II) Non-inhibitor 0.8249
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein disulfide oxidoreductase activity
- Specific Function
- May be involved in cell growth. Probably acts as a terminal oxidase of plasma electron transport from cytosolic NAD(P)H via hydroquinones to acceptors at the cell surface. Hydroquinone oxidase acti...
- Gene Name
- ENOX2
- Uniprot ID
- Q16206
- Uniprot Name
- Ecto-NOX disulfide-thiol exchanger 2
- Molecular Weight
- 70081.515 Da
References
- Morre DJ, Chueh PJ, Yagiz K, Balicki A, Kim C, Morre DM: ECTO-NOX target for the anticancer isoflavene phenoxodiol. Oncol Res. 2007;16(7):299-312. [Article]
Drug created at October 21, 2007 22:23 / Updated at November 16, 2022 21:59