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 |
---|---|---|
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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Differential inhibition of HIV-1 preintegration complexes and purified integrase protein by small molecules. | 1996 Sep 3 |
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In vitro antiviral activity of the anthraquinone chrysophanic acid against poliovirus. | 2001 Mar |
|
Antimutagenic effects of black tea (World Blend) and its two active polyphenols theaflavins and thearubigins in Salmonella assays. | 2002 Nov |
|
Bryoanthrathiophene, a new antiangiogenic constituent from the bryozoan Watersipora subtorquata (d'Orbigny, 1852). | 2002 Sep |
|
Emodin isolated from Cassia obtusifolia (Leguminosae) seed shows larvicidal activity against three mosquito species. | 2003 Dec 17 |
|
Circular dichroism imaging microscopy: application to enantiomorphous twinning in biaxial crystals of 1,8-dihydroxyanthraquinone. | 2003 Dec 3 |
|
Methotrexate for ankylosing spondylitis. | 2004 |
|
Oxoazabenzo[de]anthracenes conjugated to amino acids: synthesis and evaluation as DNA-binding antitumor agents. | 2005 Jul-Aug |
|
Interaction of anthracene and its oxidative derivatives with human serum albumin. | 2006 |
|
Defensive components in insect eggs: are anthraquinones produced during egg development? | 2006 Sep |
|
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 |
|
Reactivity of aromatic amines with triplet 1,8-dihydroxyanthraquinone: a laser flash photolysis study. | 2007 Jan |
|
Simultaneous determination and pharmacokinetic studies of aloe emodin and chrysophanol in rats after oral administration of Da-Cheng-Qi decoction by high-performance liquid chromatography. | 2007 Jul |
|
Antiprotozoal activity of Senna racemosa. | 2007 Jun 13 |
|
Potential benefits of non-pharmacological therapies in fibromyalgia. | 2008 |
|
Solvent effect on the physical quenching of singlet molecular oxygen by p-quinones. | 2008 Apr |
|
Towards reconciling structure and function in the nuclear pore complex. | 2008 Feb |
|
Is senna laxative use associated to cathartic colon, genotoxicity, or carcinogenicity? | 2009 |
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Aloe-emodin-induced DNA fragmentation in the mouse in vivo comet assay. | 2009 Aug |
|
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 |
|
Danthron inhibits the migration and invasion of human brain glioblastoma multiforme cells through the inhibition of mRNA expression of focal adhesion kinase, Rho kinases-1 and metalloproteinase-9. | 2009 Nov |
|
A high-throughput approach for identification of novel general anesthetics. | 2009 Sep 24 |
|
The coverage problem in video-based wireless sensor networks: a survey. | 2010 |
|
Enzymatic reduction of complex redox dyes using NADH-dependent reductase from Bacillus subtilis coupled with cofactor regeneration. | 2010 Jan |
|
Danthron induces DNA damage and inhibits DNA repair gene expressions in GBM 8401 human brain glioblastoma multiforms cells. | 2010 Jul |
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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admin
on
Edited
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Record UNII |
Z4XE6IBF3V
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C45177
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A06AB53
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QA06AB03
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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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C44363
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m4084
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646568
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