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
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)
| Molecular Formula | C19H12O8 |
| Molecular Weight | 368.2938 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator'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
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Advances in the study on molecular mechanism of diabetic nephropathy treated with Rheum officinale]. | 2003 Aug |
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| The lead extractor's toolbox: a review of current endovascular pacemaker and ICD lead extraction techniques. | 2003 Jul 1 |
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| Pulmonary tuberculosis due to Mycobacterium bovis subsp. caprae in captive Siberian tiger. | 2003 Nov |
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| [Precipitation reaction between berberine and rheinic acid by capillary electrophoresis]. | 2003 Oct |
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| Articular chondrocytes cultured in hypoxia: their response to interleukin-1beta and rhein, the active metabolite of diacerhein. | 2004 |
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| Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones. | 2004 Apr |
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| Identification and determination of active anthraquinones in Chinese teas by micellar electrokinetic capillary chromatography. | 2004 Apr |
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| Expedient total syntheses of rhein and diacerhein via Fries rearrangement. | 2004 Dec 10 |
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| Inhibition of human tumor cell proliferation by novel anthraquinones from daylilies. | 2004 Feb 20 |
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| Rhein inhibits the growth and induces the apoptosis of Hep G2 cells. | 2004 Jan |
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| Determination of rhein, baicalin and berberine in traditional Chinese medicinal preparations by capillary electrophoresis with two-marker technique. | 2004 Jun |
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| Determination of active ingredients in Huangdan Yinchen Keli by CZE with amperometric detection. | 2004 Jun 29 |
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| Stability control of senna leaves and senna extracts. | 2004 May |
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| [Effects of rhein on the function of human mesangial cells in high glucose environment]. | 2004 Nov |
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| [Simultaneous determination of 4 anthraquinones in Kuhuang injection by RP-HPLC]. | 2004 Nov |
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| [Effects of combination therapy of rehin and tetramethylpyrazine on experimental hepatic fibrosis induced by tetrachloride]. | 2004 Nov |
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| Antigenotoxic properties of Cassia tea (Cassia tora L.): mechanism of action and the influence of roasting process. | 2004 Nov 19 |
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| 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 |
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| 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 |
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| Separation and determination of anthraquinones in Cassia obtusifolia (Leguminosae) by micellar electrokinetic capillary electrophoresis. | 2005 Nov |
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| 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 |
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| 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 |
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| 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 |
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| 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
Sample Use Guides
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
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admin
on
Edited
Thu Jul 06 21:55:17 UTC 2023
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Thu Jul 06 21:55:17 UTC 2023
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| Record UNII |
4HU6J11EL5
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
660318
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EU-Orphan Drug |
EMA/OD/0000001223
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WHO-VATC |
QM01AX21
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WHO-ATC |
M01AX21
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FDA ORPHAN DRUG |
448614
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5371
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DB11994
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13739-02-1
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FG-184
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C166759
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4HU6J11EL5
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CHEMBL41286
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M4233
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22759
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M9569
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758147
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237-310-2
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849
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26248
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100000090475
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SUB07060MIG
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DTXSID4045636
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DIACEREIN
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C025292
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| Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
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