Identification

Name
Dantron
Accession Number
DB04816
Description

Withdrawn from the Canadian, US, and UK markets in 1998 due to genotoxicity.

Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
Structure
Thumb
Weight
Average: 240.2109
Monoisotopic: 240.042258744
Chemical Formula
C14H8O4
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
  • Danthron
  • Dantron
  • Dantrona
  • Dantrone
  • Dantronum

Pharmacology

Indication
Not Available
Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
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.
DrugInteraction
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Dantron.
AclidiniumThe therapeutic efficacy of Dantron can be decreased when used in combination with Aclidinium.
AlfentanilThe therapeutic efficacy of Dantron can be decreased when used in combination with Alfentanil.
AlloinThe risk or severity of adverse effects can be increased when Dantron is combined with Alloin.
AmantadineThe therapeutic efficacy of Dantron can be decreased when used in combination with Amantadine.
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Dantron.
AmiodaroneThe therapeutic efficacy of Dantron can be decreased when used in combination with Amiodarone.
AmitriptylineThe therapeutic efficacy of Dantron can be decreased when used in combination with Amitriptyline.
AmlodipineThe therapeutic efficacy of Dantron can be decreased when used in combination with Amlodipine.
AmobarbitalThe therapeutic efficacy of Dantron can be decreased when used in combination with Amobarbital.
Additional Data Available
  • Extended Description
    Extended Description
    Available for Purchase

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
    Available for Purchase

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
    Available for Purchase

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action
    Available for Purchase

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

Products

International/Other Brands
Altan / Antrapurol / Bancon / Duolax / Prugol / Roydan / Scatron D / Zwitsalax
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Doss TabDantron (50 mg) + Docusate sodium (60 mg)TabletOralSmithkline Beecham Pharma Division Of Smithkline Beecham Inc1993-12-311997-12-17Canada flag
Regulex D CapDantron (50 mg) + Docusate sodium (60 mg)CapsuleOralWhitehall Robins Inc.1993-12-311998-07-29Canada flag

Categories

ATC Codes
A06AB03 — DantronA06AB53 — Dantron, combinationsA06AG03 — Dantron, incl. combinations
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Anthracenes
Sub Class
Anthraquinones
Direct Parent
Anthraquinones
Alternative Parents
Aryl ketones / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Organic oxides / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 9,10-anthraquinone / Anthraquinone / Aromatic homopolycyclic compound / Aryl ketone / Hydrocarbon derivative / Ketone / Organic oxide / Organic oxygen compound
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
dihydroxyanthraquinone (CHEBI:3682) / Anthraquinone type (C10312)

Chemical Identifiers

UNII
Z4XE6IBF3V
CAS number
117-10-2
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

References

General References
Not Available
Human Metabolome Database
HMDB0029752
KEGG Drug
D07107
KEGG Compound
C10312
PubChem Compound
2950
PubChem Substance
46509077
ChemSpider
2845
BindingDB
11316
RxNav
22293
ChEBI
3682
ChEMBL
CHEMBL53418
ZINC
ZINC000003860369
PharmGKB
PA449206
PDBe Ligand
CHZ
Wikipedia
Danthron
PDB Entries
3nsq

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
SolutionBuccal; Oral5 g
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
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
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

Carriers

Kind
Protein
Organism
Humans
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 June 12, 2020 10:52