Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H8O4 |
Molecular Weight | 240.2109 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=CC2=C1C(=O)C3=C(O)C=CC=C3C2=O
InChI
InChIKey=QBPFLULOKWLNNW-UHFFFAOYSA-N
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
Molecular Formula | C14H8O4 |
Molecular Weight | 240.2109 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including https://ntp.niehs.nih.gov/ntp/roc/content/profiles/danthron.pdf
Curator's Comment: Description was created based on several sources, including https://ntp.niehs.nih.gov/ntp/roc/content/profiles/danthron.pdf
Danthron, a natural product, was originally extracted from the roots and rhizome of Polygonaceae plant. Danthron is an anthraquinone. Danthron has been widely administrated as a laxative since the 1900s. In the United States, danthron has been forbidden to continual use as laxative because it is considered to be a carcinogen. In the UK, it is not marketed alone but in combination with poloxamer 188 as co-danthramer and with docusate as co-danthrusate; in the UK, its use is strictly restricted to the elderly and to the terminally ill of all ages because of concerns about carcinogenicity and hepatotoxicity. It has only a limited role in the treatment of constipation.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2096907 |
|||
Target ID: CHEMBL3586 Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=9630566 |
14.0 µM [IC50] | ||
Target ID: CHEMBL2061 Sources: http://www.jbc.org/content/286/3/1868.full.pdf+html |
7.5 µM [Kd] | ||
Target ID: map04210 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19784869 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Normax Approved UseNormax 50mg/60mg Capsules should only be used to relieve constipation in patients who are seriously ill. Normax 50mg/60mg Capsules work by encouraging normal bowel movements. |
Doses
Dose | Population | Adverse events |
---|---|---|
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Co-administed with:: poloxalkol(200 mg; oral; 1/day) Sources: |
unhealthy, 18 years n = 1 Health Status: unhealthy Condition: constipation Age Group: 18 years Sex: F Population Size: 1 Sources: |
Other AEs: Leiomyosarcoma... |
25 mg 1 times / day single, oral Studied dose Dose: 25 mg, 1 times / day Route: oral Route: single Dose: 25 mg, 1 times / day Co-administed with:: poloxalkol(200 mg; oral; 1/day) Sources: |
unhealthy, 51 years n = 1 Health Status: unhealthy Condition: psychiatric ailments Age Group: 51 years Sex: F Population Size: 1 Sources: |
Other AEs: Skin discoloration... |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Co-administed with:: poloxalkol(200 mg; oral; 1/day) Sources: |
unhealthy, 65 to 88 years n = 20 Health Status: unhealthy Condition: constipation Age Group: 65 to 88 years Sex: M+F Population Size: 20 Sources: |
Other AEs: Diarrhoea, Faecal incontinence... Other AEs: Diarrhoea (35%) Sources: Faecal incontinence (55%) Rash (15%) |
50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Co-administed with:: docusate sodium(60 mg; oral; 1/day) Sources: |
unhealthy, 80 and 69 years n = 2 Health Status: unhealthy Condition: constipation Age Group: 80 and 69 years Sex: F Population Size: 2 Sources: |
Disc. AE: Contact dermatitis... AEs leading to discontinuation/dose reduction: Contact dermatitis Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Leiomyosarcoma | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Co-administed with:: poloxalkol(200 mg; oral; 1/day) Sources: |
unhealthy, 18 years n = 1 Health Status: unhealthy Condition: constipation Age Group: 18 years Sex: F Population Size: 1 Sources: |
|
Skin discoloration | 25 mg 1 times / day single, oral Studied dose Dose: 25 mg, 1 times / day Route: oral Route: single Dose: 25 mg, 1 times / day Co-administed with:: poloxalkol(200 mg; oral; 1/day) Sources: |
unhealthy, 51 years n = 1 Health Status: unhealthy Condition: psychiatric ailments Age Group: 51 years Sex: F Population Size: 1 Sources: |
|
Rash | 15% | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Co-administed with:: poloxalkol(200 mg; oral; 1/day) Sources: |
unhealthy, 65 to 88 years n = 20 Health Status: unhealthy Condition: constipation Age Group: 65 to 88 years Sex: M+F Population Size: 20 Sources: |
Diarrhoea | 35% | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Co-administed with:: poloxalkol(200 mg; oral; 1/day) Sources: |
unhealthy, 65 to 88 years n = 20 Health Status: unhealthy Condition: constipation Age Group: 65 to 88 years Sex: M+F Population Size: 20 Sources: |
Faecal incontinence | 55% | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Co-administed with:: poloxalkol(200 mg; oral; 1/day) Sources: |
unhealthy, 65 to 88 years n = 20 Health Status: unhealthy Condition: constipation Age Group: 65 to 88 years Sex: M+F Population Size: 20 Sources: |
Contact dermatitis | Disc. AE | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Co-administed with:: docusate sodium(60 mg; oral; 1/day) Sources: |
unhealthy, 80 and 69 years n = 2 Health Status: unhealthy Condition: constipation Age Group: 80 and 69 years Sex: F Population Size: 2 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Screening for new compounds with antiherpes activity. | 1984 Oct |
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Evaluation of the antiviral activity of anthraquinones, anthrones and anthraquinone derivatives against human cytomegalovirus. | 1992 Jan |
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Inhibitors of human immunodeficiency virus integrase. | 1993 Mar 15 |
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Hydroxyquinones are competitive non-peptide inhibitors of HIV-1 proteinase. | 1995 Nov 15 |
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Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): structure-requirement of hydroxyanthraquinones for estrogenic activity. | 2001 Jul 23 |
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Antimutagenic effects of black tea (World Blend) and its two active polyphenols theaflavins and thearubigins in Salmonella assays. | 2002 Nov |
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Enrichment of iron(III), cobalt(II), nickel(II), and copper(II) by solid-phase extraction with 1,8-dihydroxyanthraquinone anchored to silica gel before their determination by flame atomic absorption spectrometry. | 2002 Oct |
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Cytotoxicity of natural hydroxyanthraquinones: role of oxidative stress. | 2002 Sep-Oct |
|
Dithranol reaction with nitroxide radicals in DMSO, a HPLC study. | 2003 Jul |
|
Factors influencing constipation in advanced cancer patients: a prospective study of opioid dose, dantron dose and physical functioning. | 2003 Jul |
|
Danthron (1,8-dihydroxyanthraquinone). | 2004 |
|
Methotrexate for ankylosing spondylitis. | 2004 |
|
[Toxic effects of 1,8-dihydroxyanthraquinone on Daphnia magna]. | 2005 Jun |
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Interaction of anthracene and its oxidative derivatives with human serum albumin. | 2006 |
|
Electrocoagulation of quinone pigments. | 2006 Jul 14 |
|
Laxatives for the management of constipation in palliative care patients. | 2006 Oct 18 |
|
Defensive components in insect eggs: are anthraquinones produced during egg development? | 2006 Sep |
|
The right dose for every sex. | 2007 Apr |
|
Anthranoid laxatives influence the absorption of poorly permeable drugs in human intestinal cell culture model (Caco-2). | 2007 Apr |
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Initial in vitro screening approach to investigate the potential health and environmental hazards of Enviroxtrade mark - a nanoparticulate cerium oxide diesel fuel additive. | 2007 Dec 5 |
|
Antiprotozoal activity of Senna racemosa. | 2007 Jun 13 |
|
Potential benefits of non-pharmacological therapies in fibromyalgia. | 2008 |
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On the interaction of the anthraquinone barbaloin with negatively charged DMPG bilayers. | 2008 Apr 15 |
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Dissociative photoionization mechanism of 1,8-dihydroxyanthraquinone: an experimental and theoretical study. | 2008 Oct 30 |
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1,8-Bis(tos-yloxy)-9,10-anthraquinone. | 2009 Dec 4 |
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Structure-activity relationships of anthraquinones on the suppression of DNA-binding activity of the aryl hydrocarbon receptor induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. | 2009 Mar |
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Differential inhibition of matrix metalloproteinases-2, -9, and -13 activities by selected anthraquinones. | 2009 Mar |
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The coverage problem in video-based wireless sensor networks: a survey. | 2010 |
|
1,8-Dihydr-oxy-2,4,5,7-tetra-nitro-9,10-anthraquinone. | 2010 Apr 24 |
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Anthraquinones danthron and quinizarin exert antiproliferative and antimetastatic activity on murine B16-F10 melanoma cells. | 2010 Feb |
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Synchrotron radiation linear dichroism (SRLD) investigation of the electronic transitions of quinizarin, chrysazin, and anthrarufin. | 2010 Sep 15 |
|
Danthron, an anthraquinone derivative, induces DNA damage and caspase cascades-mediated apoptosis in SNU-1 human gastric cancer cells through mitochondrial permeability transition pores and Bax-triggered pathways. | 2011 Jan 14 |
|
Comparative developmental toxicity of environmentally relevant oxygenated PAHs. | 2013 Sep 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.drugs.com/uk/pdf/leaflet/676118.pdf
Curator's Comment: Normax 50mg/60mg Capsules (also known as Co-danthrusate) contain dantron and a faecal softener (docusate sodium).
The usual dose for adults is one to three capsules at bedtime. The usual dose for children aged 6-12 years is one capsule at bedtime. Normax 50mg/60mg Capsules are not recommended for use by children under 6 years of age.
This product should be taken orally (by mouth). You must swallow the capsules
whole with a drink of water. The capsules must not be crushed or chewed. Normax 50mg/60mg Capsules normally begin to work 8 hours after the dose is taken.
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/20332452
Curator's Comment: Treatments of B16-F10 melanoma cells with 10 μM DA and QZ affected cell proliferation; in fact the treatments reduced cell growth, with respect to the control, by 41.9% and 46.4%, respectively, after 24 h, by 75.9% and 60.6% after 48 h, and by 83% and 75.6% after 72 h.
10 uM danthron reduces growth of B16-F10 melanoma by 83%
Substance Class |
Chemical
Created
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Edited
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Record UNII |
Z4XE6IBF3V
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C45177
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A06AB53
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QA06AB03
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A06AB03
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QA06AB53
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QA06AG03
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22293
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DB04816
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DANTRON
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m4084
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646568
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