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Details

Stereochemistry ACHIRAL
Molecular Formula C19H12O8
Molecular Weight 368.2945
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIACEREIN

SMILES

CC(=O)Oc1cccc2c1C(=O)c3c(cc(cc3OC(=O)C)C(=O)O)C2=O

InChI

InChIKey=TYNLGDBUJLVSMA-UHFFFAOYSA-N
InChI=1S/C19H12O8/c1-8(20)26-13-5-3-4-11-15(13)18(23)16-12(17(11)22)6-10(19(24)25)7-14(16)27-9(2)21/h3-7H,1-2H3,(H,24,25)

HIDE SMILES / InChI

Molecular Formula C19H12O8
Molecular Weight 368.2945
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://www.ncbi.nlm.nih.gov/pubmed/24699148 | https://www.ncbi.nlm.nih.gov/pubmed/14402302 | https://www.ncbi.nlm.nih.gov/pubmed/9010651 | https://www.ncbi.nlm.nih.gov/pubmed/18123056 | https://www.ncbi.nlm.nih.gov/pubmed/2512175 | https://www.ncbi.nlm.nih.gov/pubmed/25435889

Rhein, also known as cassic acid, is a substance in the anthraquinone group obtained from rhubarb species like Rheum undulatum and Rheum palmatum as well as in Cassia reticulata. Rhein, a metabolite of Diacerein and sennosides, alleviates pain and fever, inhibits inflammation, and has weak laxative. Rhein dose-dependently inhibits superoxide anion production, chemotaxis and phagocytic activity of neutrophils, and macrophage migration and phagocytosis. In addition, rhein exerts its anticancer effects via the modulation of processes of cellular proliferation, apoptosis, migration, and invasion. The pharmacokinetics of rhein have not been intensively studied in humans, but at least one study in healthy male volunteers found that rhein was better absorbed from oral administration of rhubarb than from a retention enema. Rhein (at an oral dose of 50 mg twice per day) was shown to be safe when administered for five days to elderly patients with chronic congestive heart failure.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Advances in the study on molecular mechanism of diabetic nephropathy treated with Rheum officinale].
2003 Aug
Solvent effects in permeation assessed in vivo by skin surface biopsy.
2003 Dec 18
The lead extractor's toolbox: a review of current endovascular pacemaker and ICD lead extraction techniques.
2003 Jul 1
Pulmonary tuberculosis due to Mycobacterium bovis subsp. caprae in captive Siberian tiger.
2003 Nov
Preparative separation of rhein from Chinese traditional herb by repeated high-speed counter-current chromatography.
2003 Oct 31
Articular chondrocytes cultured in hypoxia: their response to interleukin-1beta and rhein, the active metabolite of diacerhein.
2004
Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones.
2004 Apr
Identification and determination of active anthraquinones in Chinese teas by micellar electrokinetic capillary chromatography.
2004 Apr
Expedient total syntheses of rhein and diacerhein via Fries rearrangement.
2004 Dec 10
Rhein inhibits the growth and induces the apoptosis of Hep G2 cells.
2004 Jan
Determination of rhein, baicalin and berberine in traditional Chinese medicinal preparations by capillary electrophoresis with two-marker technique.
2004 Jun
Determination of active ingredients in Huangdan Yinchen Keli by CZE with amperometric detection.
2004 Jun 29
Stability control of senna leaves and senna extracts.
2004 May
[Effects of rhein on the function of human mesangial cells in high glucose environment].
2004 Nov
[Simultaneous determination of 4 anthraquinones in Kuhuang injection by RP-HPLC].
2004 Nov
[Effects of combination therapy of rehin and tetramethylpyrazine on experimental hepatic fibrosis induced by tetrachloride].
2004 Nov
Antigenotoxic properties of Cassia tea (Cassia tora L.): mechanism of action and the influence of roasting process.
2004 Nov 19
Preparative isolation and purification of hydroxyanthraquinones and cinnamic acid from the chinese medicinal herb Rheum officinale Baill. by high-speed counter-current chromatography.
2004 Oct 15
Anthraquinones isolated from Cassia tora (Leguminosae) seed show an antifungal property against phytopathogenic fungi.
2004 Oct 6
[Determination of active anthraquinones in Rheum and its tea preparations by micellar electrokinetic capillary electrophoresis].
2004 Sep
Exposure to malaria affects the regression of hepatosplenomegaly after treatment for Schistosoma mansoni infection in Kenyan children.
2004 Sep 27
Pharmacokinetic of rhein in healthy male volunteers following oral and retention enema administration of rhubarb extract: a single dose study.
2005
Screening procedure for detection of stimulant laxatives and/or their metabolites in human urine using gas chromatography-mass spectrometry after enzymatic cleavage of conjugates and extractive methylation.
2005 Apr
[A new isoflavone from Huoxue Yiqi Tang].
2005 Aug
Habitat characterization and spatial distribution of Anopheles sp. mosquito larvae in Dar es Salaam (Tanzania) during an extended dry period.
2005 Jan 14
[Effects of rhein on activity of caspase-3 in kidney and cell apoptosis on the progression of renal injury in glomerulosclerosis].
2005 Jul 13
Peptide-based approaches to treat asthma, arthritis, other autoimmune diseases and pathologies of the central nervous system.
2005 Jul-Aug
[Influence of processing rhubarb on it's anthraquinone contents].
2005 Jun
[Progress in study on mechanisms of rhubarb in treating chronic renal failure].
2005 May
Simultaneous determination of anthraquinones, their 8-beta-D-glucosides, and sennosides of Rhei Rhizoma by capillary electrophoresis.
2005 May
Simultaneous determination of anthraquinones in Rhubarb by pressurized liquid extraction and capillary zone electrophoresis.
2005 May
Effects and wavelet spectral entropy analysis of rhubarb extracts rhein on synaptic transmission in rat hippocampal ca1 area in vitro.
2005 May 20
Separation and determination of anthraquinones in Cassia obtusifolia (Leguminosae) by micellar electrokinetic capillary electrophoresis.
2005 Nov
Spectroscopic characterization of effective components anthraquinones in Chinese medicinal herbs binding with serum albumins.
2005 Nov
The influence of the sennosides on absorption of glycyrrhetic acid in rats.
2005 Oct
[The pharmacokinetics of rhein in 12 healthy volunteers after oral administration of rhubarb extract].
2005 Sep
IL-1beta synthesis by chondrocyte analyzed by 3D microscopy and flow cytometry: effect of Rhein.
2006
Inhibition of interleukin-1beta-induced activation of MEK/ERK pathway and DNA binding of NF-kappaB and AP-1: potential mechanism for Diacerein effects in osteoarthritis.
2006
Most recent developments in strategies to reduce the progression of structural changes in osteoarthritis: today and tomorrow.
2006
[Study on the selection of crude drugs of rhubarb dispensing granule].
2006 Apr
High-performance liquid chromatographic method for simultaneous quantification of eight major biologically active ingredients in 'Da-Chai-Hu-Tang' preparation.
2006 Apr
Determination of five anthraquinones in medicinal plants by capillary zone electrophoresis with beta-cyclodextrin addition.
2006 Aug 4
Safety and efficacy of NT, an herbal supplement, in treating human obesity.
2006 Dec
Insulin sensitizing and alpha-glucoamylase inhibitory action of sennosides, rheins and rhaponticin in Rhei Rhizoma.
2006 Jan 25
Simultaneous determination of baicalin, rhein and berberine in rat plasma by column-switching high-performance liquid chromatography.
2006 Jun 21
[The content condition of effective composition in Sanhuang Xiexin decoction].
2006 Mar
[The effects of tetramethylpyrazine in combination with rhein on proliferation and apoptosis in human liver cell L-02 induced by TGFb1 and TG].
2006 Mar
Rapid separation and determination of structurally related anthraquinones in Rhubarb by pressurized capillary electrochromatography.
2007 Jan 4
Simultaneous determination of eight active components in Chinese medicine 'YIQING' capsule using high-performance liquid chromatography.
2007 Jan 4
Study on the electrochemical behavior and differential pulse voltammetric determination of rhein using a nanoparticle composite film-modified electrode.
2007 May
Patents

Patents

Sample Use Guides

oral dose of 50 mg twice per day
Route of Administration: Oral
SKOV3-PM4 cells were allowed to grow in 96-well plates at 5,000 cells/well for 24 h and then treated with different concentrations of rhein, respectively. Forty-eight hours later, 20 μl of 5 mg/ml MTT solution was added to each well. The plates were incubated at 37˚C in 5% CO2 for 4 h, then the supernatant was discarded and 150 μl DMSO was added to dissolve the formazan. The absorbance at a wavelength of 490 nm was measured using a microplate reader
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:07:46 UTC 2021
Edited
by admin
on Fri Jun 25 21:07:46 UTC 2021
Record UNII
4HU6J11EL5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIACEREIN
INN   MART.   MI   WHO-DD  
INN   USAN  
Official Name English
4,5-DIACETOXYANTHRAQUINONE-2-CARBOXYLIC ACID
Systematic Name English
DIACERHEIN
Common Name English
DIACEREIN [INN]
Common Name English
DIORA
Brand Name English
VERBORIL
Brand Name English
M-01AX21
Code English
DIACETYLRHEIN
Common Name English
DIACEREIN [EP MONOGRAPH]
Common Name English
NSC-758147
Code English
DIACEREIN [MART.]
Common Name English
2-ANTHRACENECARBOXYLIC ACID, 4,5-BIS(ACETYLOXY)-9,10-DIHYDRO-9,10-DIOXO-
Systematic Name English
ARTRODAR
Brand Name English
DIACEREIN [MI]
Common Name English
9,10-DIHYDRO-4,5-DIHYDROXY-9,10-DIOXO-2-ANTHROIC ACID, DIACETATE
Common Name English
DAR
Common Name English
FISIODAR
Brand Name English
AC-201
Code English
RHEIN DIACETATE [MI]
Common Name English
M01AX21
Code English
DIACEREIN [WHO-DD]
Common Name English
SF-277
Code English
ZONDAR
Brand Name English
1,8-DIACETOXY-3-CARBOXYANTHRAQUINONE
Systematic Name English
4,5-BIS(ACETYLOXY)-9,10-DIHYDRO-9,10-DIOXO-2-ANTHRACENECARBOXYLIC ACID
Systematic Name English
DIACEREIN [USAN]
USAN  
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 660318
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
EU-Orphan Drug EMA/OD/0000001223
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
WHO-VATC QM01AX21
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
WHO-ATC M01AX21
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
FDA ORPHAN DRUG 448614
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
Code System Code Type Description
INN
5371
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY
DRUG BANK
DB11994
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY
CAS
13739-02-1
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY
NCI_THESAURUS
C166759
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY
FDA UNII
4HU6J11EL5
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY
ChEMBL
CHEMBL41286
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY
MERCK INDEX
M4233
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY Merck Index
RXCUI
22759
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M9569
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY
ECHA (EC/EINECS)
237-310-2
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY
DRUG CENTRAL
849
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY
PUBCHEM
26248
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY
EVMPD
SUB07060MIG
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY
EPA CompTox
13739-02-1
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY
WIKIPEDIA
DIACEREIN
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY
MESH
C025292
Created by admin on Fri Jun 25 21:07:46 UTC 2021 , Edited by admin on Fri Jun 25 21:07:46 UTC 2021
PRIMARY
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ACTIVE MOIETY