Basic information
- CAS
112118-18-0- Standard SMILES
CC(=O)Oc1cccc2c1C(=O)c1c(OC(C)=O)cc(C(=O)O)cc1C2=O- InChIKey
TYNLGDBUJLVSMA-UHFFFAOYSA-N- Molecular formula
- C19H12O8
- Average molar mass
- 368.3 g/mol
- Monoisotopic mass
- 368.05321734
Names & identifiers
- Preferred name
- Diacerein
- IUPAC
- 4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acid
- English name
- Diacerein
- Molecular formula
- C19H12O8
- Molecular weight
- 368.29
Names & synonyms
Diacerein13739-02-1DiacetylrheinArtrodarDiacerheinFisiodar1,8-DIACETOXY-3-CARBOXYANTHRAQUINONEDiacereineSF-277DiacereinaVerborilZondar
Show more names
DARDiacerein impurity mixture CRSDiacetineSF 277ICN17261ICN 17261
Diora4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acidDiacereinumRhein diacetate2-Anthracenecarboxylic acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-M01AX214,5-Bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic AcidAC-201
Database identifiers
- CAS
112118-18-0、13739-02-1- PubChem CID
- 26248
- DTXSID
DTXSID4045636- ChEMBL
CHEMBL41286- ChEBI
CHEBI:94708- UNII
- 4HU6J11EL5
- EC Number
- 237-310-2、839-256-0
- Nikkaji
- J14.479G
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 124 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 5
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 683
Experimental & physicochemical properties
Collision Cross Section
171.33 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；170.4 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；168.12 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；169.49 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 217 · 217-2180C
- Boiling point
- 631.5 · 631.5±55.0 °C(Predicted)
- Density
- 1.491 · 1.491±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- DMSO (Sparingly), Methanol (Slightly)
- form
- Solid
- pka
- 3.01 · 3.01±0.20(Predicted)
- color
- Light Yellow to Yellow
- Water Solubility
- 240 μg/L · 240μg/L at 25℃
- Merck
- 14 · 14,2960
- 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)
- InChIKey
- TYNLGDBUJLVSMA-UHFFFAOYSA-N
- SMILES
- C1=C2C(C(=O)C3=C(C2=O)C=CC=C3OC(C)=O)=C(OC(C)=O)C=C1C(O)=O
- LogP
- 3.126 · 3.126 (est)
- CAS DataBase Reference
- 13739 · 13739-02-1(CAS DataBase Reference)
- NCI Dictionary of Cancer Terms
- DAR
- FDA UNII
- 4 HU6J11EL5 · 4HU6J11EL5
- ATC code
- 1 AX21 · M01AX21
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 25 · NA.25
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 305 · P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- RTECS
- 8781000 · CB8781000
- HS Code
- 29146990 · 29146990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Toxicity
- 50 · rat,LD50,unreported,7500mg/kg (7500mg/kg),Drugs of the Future. Vol. 4, Pg. 445, 1979.
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 3.3% (2 of 60) of reports.
Warning
H315 (96.7%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (96.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (95%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 60 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 2 of 60 reports by companies.；There are 6 notifications provided by 58 of 60 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Status: Active Update: 27-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23352
Status: Active Update: 30-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/31372
Hazard Classes and Categories
Skin Irrit. 2 (96.7%)；Eye Irrit. 2 (96.7%)；STOT SE 3 (95%)
Not Classified
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Diacerein
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Regulatory information
Regulatory Information
Status: Active Update: 27-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23352
Status: Active Update: 30-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/31372
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- CB8781000
- hs_code
- 29146990
- Toxicity
- rat,LD50,unreported,7500mg/kg (7500mg/kg),Drugs of the Future. Vol. 4, Pg. 445, 1979.
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
M - Musculo-skeletal system；M01 - Antiinflammatory and antirheumatic products；M01A - Antiinflammatory and antirheumatic products, non-steroids；M01AX - Other antiinflammatory and antirheumatic agents, non-steroids；M01AX21 - Diacerein
QM - Musculo-skeletal system；QM01 - Antiinflammatory and antirheumatic products；QM01A - Antiinflammatory and antirheumatic products, non-steroids；QM01AX - Other antiinflammatory and antirheumatic agents, non-steroids；QM01AX21 - Diacerein
Protein Binding99% of rhein is bound to plasma proteins.
PharmacodynamicsDecreases inflammation and cartilage destruction and also corrects altered osteoblast acitivity.
Mechanism of Action
Diacerein's active metabolite rhein [DB13174] reduces cartilage destruction by decreasing expression of matrix metalloproteinase (MMP)-1 and -3 as well as upregulating tissue inhibitor of matrix metalloproteinases which serve to reduce the activity of several MMPs. The anti-inflammatory action of rhein reduces the level of interleukin-1beta activity which plays a large role in reduction of extracellular matrix production, MMP activity, and continued inflammation. Rhein reduces abnormal osteoblast synthetic activity through an unknown mechanism.
Biological Half-Life4-10h.
Metabolism/MetabolitesEntirely converted to rhien [DB13174] through double deacetylation before reaching systemic circulation. Rhein [DB13174] is further metabolized to rhein glucuronide and rhein sulfate.
MeSH Pharmacological ClassificationSubstances that reduce or suppress INFLAMMATION.
Absorption, Distribution and Excretion
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.
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
UsesIt 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.
DescriptionDiacerein 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.
UsesA diacetyl derivative of Rhein. Demonstrates anti-arthritic activity without inhibiting prostaglandin synthesis. Antiarthritic
Usesantiinflammatory
UsesA diacetyl derivative of Rhein (R318500). Demonstrates anti-arthritic activity without inhibiting prostaglandin synthesis. Antiarthritic.
UsesTreatment of Osteoarthritis (Prevent cartilage destruction)
UsesDiacerein 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.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
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上海泰坦科技股份有限公司400-6009262 15618770481 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
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HBCChem, Inc.+1-510-219-6317 · [email protected]
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湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
Additional notes
DefinitionChEBI: 4,5-diacetyloxy-9,10-dioxo-2-anthracenecarboxylic acid is an anthraquinone.
Related reactions
4 records
Compound notes
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