DIACEREIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H12O8
Molecular Weight	368.2938
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)OC1=CC=CC2=C1C(=O)C3=C(C=C(C=C3OC(C)=O)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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28098862
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

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23049539	Antagonist 2778
NF-kB pathway 4 Target ID: WP3617 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24721152	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Diabetic nephropathy 35 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25435889	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Advances in the study on molecular mechanism of diabetic nephropathy treated with Rheum officinale].	2003 Aug	15224660
The lead extractor's toolbox: a review of current endovascular pacemaker and ICD lead extraction techniques.	2003 Jul 1	16943908
Pulmonary tuberculosis due to Mycobacterium bovis subsp. caprae in captive Siberian tiger.	2003 Nov	14718093
[Precipitation reaction between berberine and rheinic acid by capillary electrophoresis].	2003 Oct	14730904
Articular chondrocytes cultured in hypoxia: their response to interleukin-1beta and rhein, the active metabolite of diacerhein.	2004	15299286
Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones.	2004 Apr	15120460
Identification and determination of active anthraquinones in Chinese teas by micellar electrokinetic capillary chromatography.	2004 Apr	15103702
Expedient total syntheses of rhein and diacerhein via Fries rearrangement.	2004 Dec 10	15575790
Inhibition of human tumor cell proliferation by novel anthraquinones from daylilies.	2004 Feb 20	14741736
Rhein inhibits the growth and induces the apoptosis of Hep G2 cells.	2004 Jan	14765286
Determination of rhein, baicalin and berberine in traditional Chinese medicinal preparations by capillary electrophoresis with two-marker technique.	2004 Jun	15236436
Determination of active ingredients in Huangdan Yinchen Keli by CZE with amperometric detection.	2004 Jun 29	15193742
Stability control of senna leaves and senna extracts.	2004 May	15124088
[Effects of rhein on the function of human mesangial cells in high glucose environment].	2004 Nov	15696926
[Simultaneous determination of 4 anthraquinones in Kuhuang injection by RP-HPLC].	2004 Nov	15656132
[Effects of combination therapy of rehin and tetramethylpyrazine on experimental hepatic fibrosis induced by tetrachloride].	2004 Nov	15623384
Antigenotoxic properties of Cassia tea (Cassia tora L.): mechanism of action and the influence of roasting process.	2004 Nov 19	15501482
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	15527141
Anthraquinones isolated from Cassia tora (Leguminosae) seed show an antifungal property against phytopathogenic fungi.	2004 Oct 6	15453672
[Determination of active anthraquinones in Rheum and its tea preparations by micellar electrokinetic capillary electrophoresis].	2004 Sep	15575207
Exposure to malaria affects the regression of hepatosplenomegaly after treatment for Schistosoma mansoni infection in Kenyan children.	2004 Sep 27	15450118
Pharmacokinetic of rhein in healthy male volunteers following oral and retention enema administration of rhubarb extract: a single dose study.	2005	16355440
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	15795644
[A new isoflavone from Huoxue Yiqi Tang].	2005 Aug	16201689
Habitat characterization and spatial distribution of Anopheles sp. mosquito larvae in Dar es Salaam (Tanzania) during an extended dry period.	2005 Jan 14	15649333
[Effects of rhein on activity of caspase-3 in kidney and cell apoptosis on the progression of renal injury in glomerulosclerosis].	2005 Jul 13	16253190
Peptide-based approaches to treat asthma, arthritis, other autoimmune diseases and pathologies of the central nervous system.	2005 Jul-Aug	16088315
[Influence of processing rhubarb on it's anthraquinone contents].	2005 Jun	16124606
[Progress in study on mechanisms of rhubarb in treating chronic renal failure].	2005 May	15959940
Simultaneous determination of anthraquinones, their 8-beta-D-glucosides, and sennosides of Rhei Rhizoma by capillary electrophoresis.	2005 May	15863933
Simultaneous determination of anthraquinones in Rhubarb by pressurized liquid extraction and capillary zone electrophoresis.	2005 May	15800969
Effects and wavelet spectral entropy analysis of rhubarb extracts rhein on synaptic transmission in rat hippocampal ca1 area in vitro.	2005 May 20	15989761
Separation and determination of anthraquinones in Cassia obtusifolia (Leguminosae) by micellar electrokinetic capillary electrophoresis.	2005 Nov	16318221
Spectroscopic characterization of effective components anthraquinones in Chinese medicinal herbs binding with serum albumins.	2005 Nov	16257715
The influence of the sennosides on absorption of glycyrrhetic acid in rats.	2005 Oct	16204942
[The pharmacokinetics of rhein in 12 healthy volunteers after oral administration of rhubarb extract].	2005 Sep	16381472
IL-1beta synthesis by chondrocyte analyzed by 3D microscopy and flow cytometry: effect of Rhein.	2006	16912431
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	16912429
Most recent developments in strategies to reduce the progression of structural changes in osteoarthritis: today and tomorrow.	2006	16569256
[Study on the selection of crude drugs of rhubarb dispensing granule].	2006 Apr	16913494
High-performance liquid chromatographic method for simultaneous quantification of eight major biologically active ingredients in 'Da-Chai-Hu-Tang' preparation.	2006 Apr	16161181
Determination of five anthraquinones in medicinal plants by capillary zone electrophoresis with beta-cyclodextrin addition.	2006 Aug 4	16806252
Safety and efficacy of NT, an herbal supplement, in treating human obesity.	2006 Dec	16652135
Insulin sensitizing and alpha-glucoamylase inhibitory action of sennosides, rheins and rhaponticin in Rhei Rhizoma.	2006 Jan 25	16182318
Simultaneous determination of baicalin, rhein and berberine in rat plasma by column-switching high-performance liquid chromatography.	2006 Jun 21	16730245
[The content condition of effective composition in Sanhuang Xiexin decoction].	2006 Mar	16711420
[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	16556423
Rapid separation and determination of structurally related anthraquinones in Rhubarb by pressurized capillary electrochromatography.	2007 Jan 4	16875795
Simultaneous determination of eight active components in Chinese medicine 'YIQING' capsule using high-performance liquid chromatography.	2007 Jan 4	16846714
Study on the electrochemical behavior and differential pulse voltammetric determination of rhein using a nanoparticle composite film-modified electrode.	2007 May	16820331

Patents

Sample Use Guides

In Vivo Use Guide

oral dose of 50 mg twice per day

Route of Administration: Oral

In Vitro Use Guide

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

Name

Type

Language

DIACEREIN

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

AC-203

Code

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

SF-277

Code

English

ZONDAR

Brand Name

English

Diacerein [WHO-DD]

Common 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]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

660318