Diacerein
- Iupac Name：4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acid
- CAS No.: 13739-02-1
- Molecular Weight：368.29378
- Modify Date.: 2022-11-25 02:22
- Introduction: Diacerein is a disease-modifying antirheumatic drug (DMARD), reported to beuseful in the treatment of various inflammatory conditions, includingosteoarthritis. It forms water soluble chelates with calcium and copper, actingultimately to reduce the activity of lysosomal enzymes and decrease the formationof rheumatoid factor.
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1. Names and Identifiers
- 1.1 Name
- Diacerein
- 1.2 Synonyms
1,8-DIACETOXY-3-CARBOXYANTHRAQUINONE 2-Anthracenecarboxylic acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo- 4,5-Bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic Acid 4,5-Diacetoxy-9,10-dioxo-9,10-dihydro-2-anthracenecarboxylic acid 4,5-diacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid 4,5-Diacetoxyanthraquinone-2-carboxylic Acid 4,5-diacetylrhein 9,10-dihydro-4,5-diacetoxy-9,10-2-anthracenecarboxylicacid 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroicaciddiacetate 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroicacidiacetate artrodar DAR Diacereine DIACERHEIN DIACETYL RHEIN diacetylrhein EINECS 237-310-2 Fisiodar MFCD00468030 Rhein Diacetate rhein,diacetate SF 277
- 1.3 CAS No.
- 13739-02-1
- 1.4 CID
- 26248
- 1.5 EINECS(EC#)
- 237-310-2
- 1.6 Molecular Formula
- C19H12O8 (isomer)
- 1.7 Inchi
- 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)
- 1.8 InChkey
- TYNLGDBUJLVSMA-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CC(=O)OC1=CC=CC2=C1C(=O)C3=C(C2=O)C=C(C=C3OC(=O)C)C(=O)O
- 1.10 Isomers Smiles
- CC(=O)OC1=CC=CC2=C1C(=O)C3=C(C2=O)C=C(C=C3OC(=O)C)C(=O)O
2. Properties
- 2.1 Density
- 1.491
- 2.1 Melting point
- 217-218 °C
- 2.1 Boiling point
- 631.5 °C at 760 mmHg
- 2.1 Refractive index
- 1.634
- 2.1 Flash Point
- 231.8 °C
- 2.1 Precise Quality
- 368.05300
- 2.1 PSA
- 124.04000
- 2.1 logP
- 2.01080
- 2.1 Appearance
- yellow crystalline solid
- 2.2 Storage
- Refrigerator
- 2.3 Chemical Properties
- Yellow Crystalline Solid
- 2.4 Color/Form
- Powder
- 2.5 pKa
- 3.01±0.20(Predicted)
- 2.6 Water Solubility
- Very soluble
- 2.7 Stability
- Stable at normal temperatures and pressures.
- 2.8 StorageTemp
- Sealed in dry,Room Temperature
3. Use and Manufacturing
- 3.1 Usage
- 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.
4. Safety and Handling
- 4.1 Symbol
- GHS07
- 4.1 Hazard Codes
- Xi
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R36/37/38
- 4.1 Safety Statements
- S26;S36
- 4.1 Hazard Declaration
- H315-H319-H335
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 Caution Statement
- P305 + P351 + P338
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- CB8781000
- 4.1 Safety
-
Hazard Codes:?
Xi
Risk Statements: 36/37/38
?R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.
WGK Germany?: 3
RTECS: CB8781000
- 4.2 Specification
-
?Diacerein , its cas register number is 13739-02-1. It also can be called 2-Anthracenecarboxylic acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo- (9CI) ; 2-Anthroic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, diacetate ; 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid, diacetate ; Diacerein [INN] ; Diacetylrhein ; 1,8-Diacetoxyanthraquinone-3-carboxylic acid ; 4,5-Diacetoxy-9,10-dihydro-9,10-dioxo-2-anthrylcarbonsaeure . It is a?yellow crystalline solid.
- 4.3 Toxicity
-
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- CB8781000
- CHEMICAL NAME :
- 2-Anthroic acid,
9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, diacetate
- CAS REGISTRY NUMBER :
- 13739-02-1
- BEILSTEIN REFERENCE NO. :
- 2184909
- LAST UPDATED :
- 199612
- DATA ITEMS CITED :
- 1
- MOLECULAR FORMULA :
- C19-H12-O8
- MOLECULAR WEIGHT :
- 368.31
- WISWESSER LINE NOTATION :
- L C666 BV IVJ DOV1 FVQ NOV1
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 7500 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540,
08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year:
4,445,1979
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin irritation, Category 2
Eye irritation, Category 2
Specific target organ toxicity \u2013 single exposure, Category 3
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. |
| Storage | P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
13739-02-1Total: 13 Synthesis Route
9. Other Information
- 9.0 Usage
- Interleukin-1 inhibitor
- 9.1 Mesh
- Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)
- 9.2 Absorption
- Bioavailability of 50-60%. Entirely converted to the active metabolite rhein [DB13174] before reaching systemic circulation.|37% excreted in urine and 53% in feces as estimated in rats.|15-60L.|Total CL is 1.5L/h and renal CL is 0.1L/h.
- 9.3 Metabolism
- Entirely converted to rhien [DB13174] through double deacetylation before reaching systemic circulation. Rhein [DB13174] is further metabolized to rhein glucuronide and rhein sulfate.
- 9.4 Biological Half Life
- 4-10h.
- 9.5 Mesh Entry Terms
- diacerein
- 9.6 Use Classification
- Human drugs -> Rare disease (orphan)|Pharmaceuticals
- 9.7 Merck
- 14,2960
- 9.8 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.
- 9.9 Uses
- 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.
- 9.10 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.
- 9.11 Chemical Properties
- Yellow Crystalline Solid
- 9.12 Originator
- Proter (Italy)
- 9.13 Uses
- A diacetyl derivative of Rhein. Demonstrates anti-arthritic activity without inhibiting prostaglandin synthesis. Antiarthritic
- 9.14 Uses
- antiinflammatory
- 9.15 Uses
- A diacetyl derivative of Rhein (R318500). Demonstrates anti-arthritic activity without inhibiting prostaglandin synthesis. Antiarthritic.
- 9.16 Uses
- Treatment of Osteoarthritis (Prevent cartilage destruction)
- 9.17 Uses
- 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.
- 9.18 Brand name
- ARTRODAR
10. Computational chemical data
- Molecular Weight: 368.29378g/mol
- Molecular Formula: C19H12O8
- Compound Is Canonicalized: True
- XLogP3-AA: 1.9
- Exact Mass: 368.05321734
- Monoisotopic Mass: 368.05321734
- Complexity: 683
- Rotatable Bond Count: 5
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 8
- Topological Polar Surface Area: 124
- Heavy Atom Count: 27
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccB4PAAAAAAAAAAAAAAAAAAAAAAAAAAwYMAAAAAAAADBQAAAGgAACAAADASAmAAyDoAABgCIAqDSCAACCAAkIAAIiAEGCMgMJjaENRqCe2Ck4BEIuYfL7vyuwAADAAAYAACAAAYAADAAAAAAAAAAAA==
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DIACERHEIN
- Purity:99%Packing: 200kg/bag FOB
- Price: 695 USD/kg
- Time: 2023/05/22
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Diacerein
- Purity:99%Packing: 200kg/bag FOB
- Price: 100 USD/kilogram
- Time: 2023/03/14
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12. Realated Product Infomation
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