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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

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
[Inhibition of glucose transporter 1 overexpression in mesangial cells by rhein].
2001 Aug
Inhibition of the nitrosothiol production of cultured osteoarthritic chondrocytes by rhein, cortisol and diclofenac.
2001 Jan
[Treatment errors of metacarpal fractures. An analysis of expert testimony of the "Committee for Medical Malpractice" of the North Rhine Physician's Council].
2001 Jun
Rhein inhibits renal tubular epithelial cell hypertrophy and extracellular matrix accumulation induced by transforming growth factor beta1.
2001 Oct
Analgesic effect of meloxicam in canine acute dermatitis--a pilot study.
2002
Diacerhein and rhein prevent interleukin-1beta-induced nuclear factor-kappaB activation by inhibiting the degradation of inhibitor kappaB-alpha.
2002 Jul
Reactive nitrogen species modulate the effects of rhein, an active component of senna laxatives, on human epithelium in vitro.
2002 May
Cytotoxicity of rhein, the active metabolite of sennoside laxatives, is reduced by multidrug resistance-associated protein 1.
2002 May 6
[Determination of rhein in plasma of rat by HPLC/MS].
2002 Sep
Rhein inhibits interleukin-1 beta-induced activation of MEK/ERK pathway and DNA binding of NF-kappa B and AP-1 in chondrocytes cultured in hypoxia: a potential mechanism for its disease-modifying effect in osteoarthritis.
2003 Aug
Solvent effects in permeation assessed in vivo by skin surface biopsy.
2003 Dec 18
Relapsing fever-like spirochetes infecting European vector tick of Lyme disease agent.
2003 Jun
Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones.
2004 Apr
Inhibition of human tumor cell proliferation by novel anthraquinones from daylilies.
2004 Feb 20
Determination of active ingredients in Huangdan Yinchen Keli by CZE with amperometric detection.
2004 Jun 29
[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
Anthraquinones isolated from Cassia tora (Leguminosae) seed show an antifungal property against phytopathogenic fungi.
2004 Oct 6
Exposure to malaria affects the regression of hepatosplenomegaly after treatment for Schistosoma mansoni infection in Kenyan children.
2004 Sep 27
[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
[Progress in study on mechanisms of rhubarb in treating chronic renal failure].
2005 May
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
[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
[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
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
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