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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=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

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
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...
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
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...
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
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%)
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
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

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
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:
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
Evaluation of the antiviral activity of anthraquinones, anthrones and anthraquinone derivatives against human cytomegalovirus.
1992 Jan
Inhibitors of human immunodeficiency virus integrase.
1993 Mar 15
Differential inhibition of HIV-1 preintegration complexes and purified integrase protein by small molecules.
1996 Sep 3
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
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
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 Fri Dec 15 15:14:52 GMT 2023
Edited
by admin
on Fri Dec 15 15:14:52 GMT 2023
Record UNII
Z4XE6IBF3V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
INN   MART.   WHO-DD  
INN  
Official 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 Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
WHO-ATC A06AB53
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
WHO-ATC A06AG03
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
WHO-VATC QA06AB03
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
WHO-ATC A06AB03
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
WHO-VATC QA06AB53
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
WHO-VATC QA06AG03
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
Code System Code Type Description
CAS
117-10-2
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
RXCUI
22293
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB04816
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
EVMPD
SUB06904MIG
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
SMS_ID
100000092595
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
CHEBI
3682
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID9020328
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
DRUG CENTRAL
3125
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
FDA UNII
Z4XE6IBF3V
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
INN
81
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
WIKIPEDIA
DANTRON
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-173-5
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
ChEMBL
CHEMBL53418
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
PUBCHEM
2950
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
NCI_THESAURUS
C44363
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
MESH
C004315
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
HSDB
7764
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
NSC
38626
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
MERCK INDEX
m4084
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY Merck Index
NSC
646568
Created by admin on Fri Dec 15 15:14:52 GMT 2023 , Edited by admin on Fri Dec 15 15:14:52 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY