13739-02-1 Usage
Immunosuppressive drugs
Diacerein is a novel interleukin (IL)-1 inhibitor , the chemical name is diacetyl rhein,it is a compound of anthraquinones, the product can induce cartilage generation, it has analgesic, antipyretic and anti-inflammatory effects, but also it can significantly improve joint function in patients with osteoarthritis, and delay duration, and reduce pain to improve the quality of life of patients, it has better security, it is mainly used in clinical treatment of osteoarthritis (OA) to exert an antibacterial effect.
Solubility: soluble in dimethyl sulfoxide, dimethyl acetamide; insoluble in water, methanol, chloroform.
Diacerein and its active metabolite rhubarb (rhein) can reduce the generation and activity of IL-1β by inhibiting IL-1 converting enzyme. Mechanisms include:
1, inhibit the IL-1 synthesis of synovial tissue.
2, inhibit the expression of IL-1 receptor in chondrocytes .
3, inhibition of IL-1 activity.
4, repress formation of metalloproteinases such as collagenase and matrix dissolved elements and peroxide.
5, promote the synthesis of collagen and glycosaminoglycan.
6, inhibit the leukocyte chemotaxis and lysosomal stability.
Diacerein does not change the cyclooxygenase activity of kidneys and platelets, and does not inhibit the synthesis of prostaglandin , so prostaglandin-dependent renal dysfunction patients can tolerate.
Oral 50mg, PPB is 99%, Tmax is 2.2 h, Cmax is 3.2 mg/L, AUC is 21.3 mg ? h/L, T1/2β is 4.3 h. Tmax and AUC values can be increased if it is administrated with food .
Adverse reactions: 50% of patients suffer diarrhea, abdominal pain and loose stools.
The above information is edited by the lookchem of Tian Ye.
Uses
Different sources of media describe the Uses of 13739-02-1 differently. You can refer to the following data:
1. It is widely used in new liquid crystal polymer, engineering plastics and high-strength fibers with high performance.
This product is an important osteoarthritis IL-1 inhibitor. It is used for osteoarthritis.
It is a natural antioxidant, it has anti-aging, enhance immunity, removing sub-health state, physical recovery, increasing energy and body immunity effects.
2. A diacetyl derivative of Rhein. Demonstrates anti-arthritic activity without inhibiting prostaglandin synthesis. Antiarthritic
3. antiinflammatory
4. A diacetyl derivative of Rhein (R318500). Demonstrates anti-arthritic activity without inhibiting prostaglandin synthesis. Antiarthritic.
5. Treatment of Osteoarthritis (Prevent cartilage destruction)
6. Diacerein is a diacetyl precursor of rhein, an anthraquinone found in plants. Rhein, at 10 μM, inhibits IL-1β signaling, suppressing signaling through NF-κB and AP-1, and reduces the expression of the matrix metalloproteases MMP-1 and MMP-13. Diacerein, presumably after conversion to rhein, down-regulates the expression of the IL-1β receptor on articular chondrocytes, enhances the expression of TGF-β, and increases collagen and aggrecan. It does not alter COX activity. It is mildly effective in ameliorating osteoarthritis.
Description
Diacerein is a disease-modifying antirheumatic drug (DMARD), reported to be
useful in the treatment of various inflammatory conditions, including
osteoarthritis. It forms water soluble chelates with calcium and copper, acting
ultimately to reduce the activity of lysosomal enzymes and decrease the formation
of rheumatoid factor.
Chemical Properties
Yellow Crystalline Solid
Originator
Proter (Italy)
Brand name
ARTRODAR
Check Digit Verification of cas no
The CAS Registry Mumber 13739-02-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,7,3 and 9 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 13739-02:
(7*1)+(6*3)+(5*7)+(4*3)+(3*9)+(2*0)+(1*2)=101
101 % 10 = 1
So 13739-02-1 is a valid CAS Registry Number.
InChI:InChI=1/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)
13739-02-1Relevant articles and documents
Murty et al.
, p. 515 (1967)
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Stoll,Becker,Kussmaul
, p. 1892,1902 (1949)
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Synthesis and biological evaluation of rhein amides as inhibitors of osteoclast differentiation and bone resorption
Xu, Xing,Qi, Xueyu,Yan, Yufei,Qi, Jin,Qian, Niandong,Guo, Lei,Li, Changwei,Wang, Fei,Huang, Ping,Zhou, Hanbing,Jiang, Min,Yang, Chunhao,Deng, Lianfu
, p. 769 - 776 (2016)
Approaches of targeting excessive activation and differentiation of osteoclasts were considered as an effective treatment option for osteoporosis or osteopenia. In the present work, a series of rhein derivatives were synthesized and employed for their cytotoxicity screening against bone marrow-derived macrophages cells (BMMs) and their inhibition effects on osteoclasts activation and differentiation in?vitro using an MTT assay and a TRAP activity assay respectively. Two rhein derivatives d6 and d11 inhibited BMMs activation and differentiation with 98% and 85% inhibitory activity respectively, without showing any cytotoxicity on BMMs. Subsequently, the most potent compound d6 was further validated for its inhibitory effects on the formation of TRAP-positive multinucleated cells and bone resorption as evaluated by TRAP staining and bone resorption assay. The regulation by d6 of osteoclast marker genes assay revealed that treatment of BMMs with M-CSF and RANKL resulted in the stimulation of mRNA expressions of NFATc1, c-fos, TRAP, MMP-9 and cathepsin K which were highly related with osteoclast activation and differentiation, while d6 decreased mRNA expressions of these genes. It was indicated that d6 might regulate osteoclasts activity through RANKL/RANK/NFATc1 pathway. Thus our current work is expected to provide a highly promising approach for the development of a new type of anti-osteoporosis agent.
Synthesis of rhein and diacerein: a chemoenzymatic approach using anthrol reductase of Talaromyces islandicus
Rajput, Anshul,Mondal, Amit,Pandey, Satyendra Kumar,Husain, Syed Masood
supporting information, p. 358 - 361 (2022/01/20)
Herein, we report two methods for the synthesis of the osteoarthritis drug rhein and its prodrug diacerein using a chemoenzymatic approach. The strategy relies on the use of an NADPH-dependent anthrol reductase of Talaromyces islandicus (ARti-2), which mediates the regioselective and reductive deoxygenation of anthraquinones. The work further implies similar biosynthesis of rhein in fungi.
Industrial production method suitable for diacerein
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, (2018/07/30)
The invention discloses an industrial production method suitable for diacerein. A compound as shown in a formula I is obtained after carrying out secondary oxidation on raw materials. The industrial production disclosed by the invention overcomes the disadvantages of excessive heavy metal, serious pollution, and inflammability and explosibility of a finished product prepared through a synthesis route reported in existing literatures; a reagent used by the industrial production method is low in cost, environment pollution is small, the operation is easy, and the industrial production method issuitable for industrial production; a product is good in quality, total impurities are less, the content of single impurity is controlled to be 0.1 percent or less, the finished product is controlledto be in a single and stable crystal form, and the requirements of medicinal-class bulk drugs can be met.
