Idronoxil

Identification

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Name
Idronoxil
Accession Number
DB04915
Type
Small Molecule
Groups
Investigational
Description

Idronoxil is a substance that is being studied in the treatment of cancer. It belongs to the family of drugs called signal transduction inhibitors.

Structure
Thumb
Synonyms
  • 3-(4-hydroxyphenyl)-2H-chromen-7-ol
  • Dehydroequol
  • Haginin E
  • Phenoxodiol
External IDs
NV-06 / NV06
Categories
UNII
995FT1W541
CAS number
81267-65-4
Weight
Average: 240.254
Monoisotopic: 240.07864425
Chemical Formula
C15H12O3
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

Pharmacology

Indication

Intended for the treatment of various forms of cancer.

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.

TargetActionsOrganism
UEcto-NOX disulfide-thiol exchanger 2Not AvailableHumans
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:17904534]
  2. Choueiri TK, Wesolowski R, Mekhail TM: Phenoxodiol: isoflavone analog with antineoplastic activity. Curr Oncol Rep. 2006 Mar;8(2):104-7. [PubMed:16507219]
  3. 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. [PubMed:16784025]
  4. 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. [PubMed:17672914]
External Links
PubChem Compound
219100
PubChem Substance
175426901
ChemSpider
189918
BindingDB
50419932
ChEMBL
CHEMBL1957038

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1TerminatedTreatmentCancer of the Ovary / Fallopian Tube Cancer / Peritoneal Cavity Cancer / Primary Peritoneal Cavity Cancer1
1WithdrawnTreatmentHealthy Volunteers1
1, 2Active Not RecruitingTreatmentMalignancies1
1, 2CompletedTreatmentCancer of the Ovary / Fallopian Tube Cancer / Primary Peritoneal Cavity Cancer1
2CompletedTreatmentProstate Cancer1
3CompletedTreatmentAbdominal wall neoplasm / Cancer of the Ovary / Fallopian Tube Cancer1

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
PropertyValueSource
Water Solubility0.0693 mg/mLALOGPS
logP2.82ALOGPS
logP3.09ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.13ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.73 m3·mol-1ChemAxon
Polarizability25.76 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier-0.5249
Caco-2 permeable+0.7327
P-glycoprotein substrateSubstrate0.5689
P-glycoprotein inhibitor INon-inhibitor0.7986
P-glycoprotein inhibitor IINon-inhibitor0.8194
Renal organic cation transporterNon-inhibitor0.8197
CYP450 2C9 substrateNon-substrate0.8351
CYP450 2D6 substrateNon-substrate0.8967
CYP450 3A4 substrateNon-substrate0.6399
CYP450 1A2 substrateInhibitor0.9043
CYP450 2C9 inhibitorInhibitor0.8452
CYP450 2D6 inhibitorNon-inhibitor0.7896
CYP450 2C19 inhibitorInhibitor0.9193
CYP450 3A4 inhibitorNon-inhibitor0.5889
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9489
Ames testNon AMES toxic0.5133
CarcinogenicityNon-carcinogens0.9184
BiodegradationNot ready biodegradable0.7429
Rat acute toxicity2.9655 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9073
hERG inhibition (predictor II)Non-inhibitor0.8249
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Hydroxyisoflavonoid / Isoflav-3-ene skeleton / Benzopyran / 1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Phenol / Monocyclic benzene moiety / Benzenoid / Oxacycle
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

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
  1. 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. [PubMed:17518268]

Drug created on October 21, 2007 16:23 / Updated on June 04, 2019 06:13