Danthron

Identification

Name
Danthron
Accession Number
DB04816
Type
Small Molecule
Groups
Investigational, Withdrawn
Description

Withdrawn from the Canadian, US, and UK markets in 1998 due to genotoxicity.

Structure
Thumb
Synonyms
  • 1,8-dihydroxy-9,10-anthracenedione
  • 1,8-dihydroxy-9,10-anthraquinone
  • 1,8-dihydroxyanthra-9,10-quinone
  • 1,8-Dihydroxyanthrachinon
  • 1,8-Dihydroxyanthraquinone
  • Chrysazin
  • Dantron
External IDs
Not Available
Product Ingredients
Not Available
Approved Prescription Products
Not Available
Approved Generic Prescription Products
Not Available
Approved Over the Counter Products
Not Available
Unapproved/Other Products
Not Available
International/Other Brands
Altan / Antrapurol / Bancon / Chrysazin / Chrysazine / Criasazin / Danivac / Dantron / Diaquone / Dionone / Dorbane / Dorbanex / Dorbantyl / Duolax / Istan / Istin / Istizin / Laxanorm / Laxanthreen / Laxipur / Laxipurin / LTAN / Neokutin s / Pastomin / Prugol / Roydan / Scatron d / Zwitsalax
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Doss TabTabletOralSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1993-12-311997-12-17Canada
Regulex D CapCapsuleOralWhitehall Robins Inc.1993-12-311998-07-29Canada
Categories
UNII
Z4XE6IBF3V
CAS number
117-10-2
Weight
Average: 240.2109
Monoisotopic: 240.042258744
Chemical Formula
C14H8O4
InChI Key
QBPFLULOKWLNNW-UHFFFAOYSA-N
InChI
InChI=1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16H
IUPAC Name
1,8-dihydroxy-9,10-dihydroanthracene-9,10-dione
SMILES
OC1=CC=CC2=C1C(=O)C1=C(C=CC=C1O)C2=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
Not Available
External Links
Human Metabolome Database
HMDB29752
KEGG Drug
D07107
KEGG Compound
C10312
PubChem Compound
2950
PubChem Substance
46509077
ChemSpider
2845
BindingDB
11316
ChEBI
3682
ChEMBL
CHEMBL53418
PharmGKB
PA449206
HET
CHZ
Wikipedia
Danthron
ATC Codes
A06AB53 — Dantron, combinationsA06AG03 — Dantron, incl. combinationsA06AB03 — Dantron
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral
CapsuleOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)193 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.305 mg/mLALOGPS
logP2.98ALOGPS
logP3.61ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.09ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.11 m3·mol-1ChemAxon
Polarizability23.19 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9899
Blood Brain Barrier+0.7514
Caco-2 permeable+0.6963
P-glycoprotein substrateNon-substrate0.5556
P-glycoprotein inhibitor INon-inhibitor0.9605
P-glycoprotein inhibitor IINon-inhibitor0.9419
Renal organic cation transporterNon-inhibitor0.8913
CYP450 2C9 substrateNon-substrate0.7982
CYP450 2D6 substrateNon-substrate0.9168
CYP450 3A4 substrateNon-substrate0.7151
CYP450 1A2 substrateInhibitor0.8918
CYP450 2C9 inhibitorInhibitor0.775
CYP450 2D6 inhibitorNon-inhibitor0.7456
CYP450 2C19 inhibitorNon-inhibitor0.6159
CYP450 3A4 inhibitorNon-inhibitor0.8357
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7605
Ames testAMES toxic0.9261
CarcinogenicityNon-carcinogens0.893
BiodegradationNot ready biodegradable0.7278
Rat acute toxicity2.8601 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9505
hERG inhibition (predictor II)Non-inhibitor0.9192
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)
Download (8.11 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-000i-0090000000-f33bba4b2a76f616e555
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-000i-0090000000-debf61aa41c5f09488eb
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-000i-0090000000-0b90944c9e69d24702c5
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-03dr-0290000000-b75bbfaef6b643f8b203
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-03e9-0960000000-51a32afa2b48f66fdc1f
Predicted LC-MS/MS Spectrum - 10V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 10V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, NegativePredicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of chemical entities known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Benzenoids
Sub Class
Anthracenes
Direct Parent
Anthraquinones
Alternative Parents
Aryl ketones / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Organic oxides / Hydrocarbon derivatives
Substituents
Anthraquinone / 9,10-anthraquinone / Aryl ketone / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Vinylogous acid / Ketone / Organic oxygen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
dihydroxyanthraquinone (CHEBI:3682 ) / Anthraquinone type (C10312 )

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Mikhailova ON, Filipenko ML, Timofeeva OA, Kaledin VI, Guliaeva LF, Liakhovich VV: [mRNA level and cytochrome P450 1A activity in the liver of C57BL mice induced by various xenobiotics]. Biomed Khim. 2003 Jul-Aug;49(4):388-93. [PubMed:14562683 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Skupinska K, Zylm M, Misiewicz I, Kasprzycka-Guttman T: Interaction of anthracene and its oxidative derivatives with human serum albumin. Acta Biochim Pol. 2006;53(1):101-12. Epub 2006 Jan 9. [PubMed:16404478 ]
Drug created on September 11, 2007 14:07 / Updated on September 01, 2017 11:21