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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
Structure of DANTHRON

SMILES

OC1=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=CC=C1

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

HIDE SMILES / InChI

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

Description
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Normax

Approved Use

Normax 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

Doses

DosePopulationAdverse 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
Sources:
unhealthy, 18 years
Health Status: unhealthy
Age Group: 18 years
Sex: F
Sources:
Other AEs: Leiomyosarcoma...
Other AEs:
Leiomyosarcoma
Sources:
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
Sources:
unhealthy, 51 years
Health Status: unhealthy
Age Group: 51 years
Sex: F
Sources:
Other AEs: Skin discoloration...
Other AEs:
Skin discoloration
Sources:
25 mg 1 times / day multiple, oral
Recommended
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
unhealthy, 65 to 88 years
Health Status: unhealthy
Age Group: 65 to 88 years
Sex: M+F
Sources:
Other AEs: Diarrhoea, Faecal incontinence...
Other AEs:
Diarrhoea (35%)
Faecal incontinence (55%)
Rash (15%)
Sources:
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Sources:
unhealthy, 80 and 69 years
Health Status: unhealthy
Age Group: 80 and 69 years
Sex: F
Sources:
Disc. AE: Contact dermatitis...
AEs leading to
discontinuation/dose reduction:
Contact dermatitis
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Sources:
unhealthy, 18 years
Health Status: unhealthy
Age Group: 18 years
Sex: F
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
Sources:
unhealthy, 51 years
Health Status: unhealthy
Age Group: 51 years
Sex: F
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
Sources:
unhealthy, 65 to 88 years
Health Status: unhealthy
Age Group: 65 to 88 years
Sex: M+F
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
Sources:
unhealthy, 65 to 88 years
Health Status: unhealthy
Age Group: 65 to 88 years
Sex: M+F
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
Sources:
unhealthy, 65 to 88 years
Health Status: unhealthy
Age Group: 65 to 88 years
Sex: M+F
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
Sources:
unhealthy, 80 and 69 years
Health Status: unhealthy
Age Group: 80 and 69 years
Sex: F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
yes
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Comparative developmental toxicity of environmentally relevant oxygenated PAHs.
2013-09-01
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.
2011-01-14
Synchrotron radiation linear dichroism (SRLD) investigation of the electronic transitions of quinizarin, chrysazin, and anthrarufin.
2010-09-15
Danthron induces DNA damage and inhibits DNA repair gene expressions in GBM 8401 human brain glioblastoma multiforms cells.
2010-07
1,8-Dihydr-oxy-2,4,5,7-tetra-nitro-9,10-anthraquinone.
2010-04-24
Danthron induced apoptosis through mitochondria- and caspase-3-dependent pathways in human brain glioblastoma multiforms GBM 8401 cells.
2010-03
Anthraquinones danthron and quinizarin exert antiproliferative and antimetastatic activity on murine B16-F10 melanoma cells.
2010-02
Enzymatic reduction of complex redox dyes using NADH-dependent reductase from Bacillus subtilis coupled with cofactor regeneration.
2010-01
The coverage problem in video-based wireless sensor networks: a survey.
2010
1,8-Bis(tos-yloxy)-9,10-anthraquinone.
2009-12-04
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.
2009-11
A high-throughput approach for identification of novel general anesthetics.
2009-09-24
Aloe-emodin-induced DNA fragmentation in the mouse in vivo comet assay.
2009-08
A 73-year-old man with long-term immobility presenting with abdominal pain.
2009-07-14
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.
2009-03
Differential inhibition of matrix metalloproteinases-2, -9, and -13 activities by selected anthraquinones.
2009-03
Is senna laxative use associated to cathartic colon, genotoxicity, or carcinogenicity?
2009
Dissociative photoionization mechanism of 1,8-dihydroxyanthraquinone: an experimental and theoretical study.
2008-10-30
Study of interactions of anthraquinones with DNA using ethidium bromide as a fluorescence probe.
2008-06
On the interaction of the anthraquinone barbaloin with negatively charged DMPG bilayers.
2008-04-15
Solvent effect on the physical quenching of singlet molecular oxygen by p-quinones.
2008-04
Voltammetric Behavior of o-Nitrophenol and Damage to DNA.
2008-03
Towards reconciling structure and function in the nuclear pore complex.
2008-02
Potential benefits of non-pharmacological therapies in fibromyalgia.
2008
Initial in vitro screening approach to investigate the potential health and environmental hazards of Enviroxtrade mark - a nanoparticulate cerium oxide diesel fuel additive.
2007-12-05
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.
2007-07
Antiprotozoal activity of Senna racemosa.
2007-06-13
Simultaneous quantification of five anthraquinones in rat plasma by high-performance liquid chromatography with fluorescence detection.
2007-05
The right dose for every sex.
2007-04
Anthranoid laxatives influence the absorption of poorly permeable drugs in human intestinal cell culture model (Caco-2).
2007-04
Reactivity of aromatic amines with triplet 1,8-dihydroxyanthraquinone: a laser flash photolysis study.
2007-01
Laxatives for the management of constipation in palliative care patients.
2006-10-18
Intramolecular hydrogen bonding in 1,8-dihydroxyanthraquinone, 1-aminoanthraquinone, and 9-hydroxyphenalenone studied by picosecond time-resolved fluorescence spectroscopy in a supersonic jet.
2006-10-12
Microbial transformation of amino- and hydroxyanthraquinones by Beauveria bassiana ATCC 7159.
2006-10
Defensive components in insect eggs: are anthraquinones produced during egg development?
2006-09
Electrocoagulation of quinone pigments.
2006-07-14
Interaction of anthracene and its oxidative derivatives with human serum albumin.
2006
Oxoazabenzo[de]anthracenes conjugated to amino acids: synthesis and evaluation as DNA-binding antitumor agents.
2005-07-21
[Toxic effects of 1,8-dihydroxyanthraquinone on Daphnia magna].
2005-06
Electrochemical studies of danthron and the DNA-danthron interaction.
2005-04-01
Serially balanced designs for two sets of treatments.
2005
Growth responses of Cassia obtusifolia toward human intestinal bacteria.
2004-07
Danthron (1,8-dihydroxyanthraquinone).
2004
Methotrexate for ankylosing spondylitis.
2004
1,8-Dihydroxyanthraquinone anchored on silica gel: synthesis and application as solid phase extractant for lead(II), zinc(II) and cadmium(II) prior to their determination by flame atomic absorption spectrometry.
2002-10-16
Danthron (1,8-dihydroxyanthraquinone).
2002
Differential inhibition of HIV-1 preintegration complexes and purified integrase protein by small molecules.
1996-09-03
Hydroxyquinones are competitive non-peptide inhibitors of HIV-1 proteinase.
1995-11-15
Inhibitors of human immunodeficiency virus integrase.
1993-03-15
Screening for new compounds with antiherpes activity.
1984-10
Patents

Sample Use Guides

In Vivo Use Guide
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
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
by admin
on Mon Mar 31 17:51:33 GMT 2025
Edited
by admin
on Mon Mar 31 17:51:33 GMT 2025
Record UNII
Z4XE6IBF3V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DANTRON
INN   MART.   WHO-DD  
INN  
Preferred Name English
DANTHRON
HSDB   MI   VANDF  
Common Name English
1,8-DIHYDROXYANTHRACENE-9,10-DIONE
Systematic Name English
CHRYSAZIN
Common Name English
DITHRANOL IMPURITY B [EP IMPURITY]
Common Name English
NSC-38626
Code English
DANTHRON [MI]
Common Name English
Dantron [WHO-DD]
Common Name English
DANTRON [MART.]
Common Name English
NSC-646568
Code English
DORBANE
Brand Name English
dantron [INN]
Common Name English
DANTHRON [HSDB]
Common Name English
1,8-Dihydroxyanthraquinone
Systematic Name English
DANTRON [IARC]
Common Name English
ISTIZIN
Brand Name English
PILULES VINCHY N.F.
Brand Name English
DANTHRON [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C45177
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
WHO-ATC A06AB53
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
WHO-ATC A06AG03
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
WHO-VATC QA06AB03
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
WHO-ATC A06AB03
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
WHO-VATC QA06AB53
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
WHO-VATC QA06AG03
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
Code System Code Type Description
CAS
117-10-2
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY
RXCUI
22293
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY RxNorm
DRUG BANK
DB04816
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PRIMARY
EVMPD
SUB06904MIG
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PRIMARY
SMS_ID
100000092595
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY
CHEBI
3682
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID9020328
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PRIMARY
DRUG CENTRAL
3125
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PRIMARY
FDA UNII
Z4XE6IBF3V
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY
INN
81
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY
WIKIPEDIA
DANTRON
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-173-5
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY
ChEMBL
CHEMBL53418
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY
PUBCHEM
2950
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY
NCI_THESAURUS
C44363
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY
MESH
C004315
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY
HSDB
7764
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY
NSC
38626
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY
MERCK INDEX
m4084
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY Merck Index
NSC
646568
Created by admin on Mon Mar 31 17:51:33 GMT 2025 , Edited by admin on Mon Mar 31 17:51:33 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY