Diacerein

Names

[ Name ]:
Diacerein

[Synonym ]:
4,5-Diacetoxy-9,10-dioxo-9,10-dihydro-2-anthracenecarboxylic acid
DIACERHEIN
MFCD00468030
DIACETYL RHEIN
2-Anthracenecarboxylic acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-
Fisiodar
4,5-diacetylrhein
Rhein Diacetate
4,5-diacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
SF 277
rhein,diacetate
Diacerein
4,5-Bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic Acid
artrodar
Diacereine
EINECS 237-310-2
DAR
4,5-Diacetoxyanthraquinone-2-carboxylic Acid
diacetylrhein

Biological Activity

[Description]:

Diacerein, a interleukin-1 beta inhibitor, is a slow-acting medicine of the class anthraquinone used to treat joint diseases.Target: IL-1 betaDiacerein, a interleukin-1 beta inhibitor, is a slow-acting medicine of the class anthraquinone used to treat joint diseases. Diacerein works by blocking the actions of interleukin-1 beta, a protein involved in the inflammation and destruction of cartilage that play a role in the development of symptoms of degenerative joint diseases such as osteoarthritis. Due to its specific mode of action, which does not involve the inhibition of prostaglandin synthesis, diacerein has been shown to have anti-osteoarthritis and cartilage stimulating properties in vitro and animal models, together with analgesic and anti-inflammatory properties. Due to its excellent gastro-intestinal tolerance, a combination therapy with an analgesic or a NSAID may be recommended during the first 2-4 weeks of treatment. From Wikipedia.

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Interleukin Related

Research Areas >> Inflammation/Immunology

Natural Products >> Quinones

[References]

[1]. http://en.wikipedia.org/wiki/Diacerein

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
631.5±55.0 °C at 760 mmHg

[ Melting Point ]:
217-2180C

[ Molecular Formula ]:
C₁₉H₁₂O₈

[ Molecular Weight ]:
368.294

[ Flash Point ]:
231.8±25.0 °C

[ Exact Mass ]:
368.053223

[ PSA ]:
124.04000

[ LogP ]:
1.99

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.634

[ Storage condition ]:
Refrigerator

Toxicological Information

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

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P305 + P351 + P338

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
CB8781000

[ HS Code ]:
2918990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918990090

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

[Diacerein].

Ann. Ital. Med. Int. 1(2) , 172-4, (1986)

[Efficacy of diacerein on the symptoms and radiographic progression of osteoarthritis].

Presse Med. 31(39 Pt 2) , 4S13-5, (2002)

SYMPTOMATIC EFFECTS OF DIACEREIN: Data obtained from several clinical trials have demonstrated that relief of joint pain obtained with the interleukin-1 inhibitor diacerein is comparable with that obs...

Diacerein as a disease-modulating agent in osteoarthritis.

Curr. Rheumatol. Rep. 3(6) , 479-83, (2001)

This paper reviews the most recent clinical and experimental studies on diacerein, both of which are under investigation. Diacerein could be a disease-modulating agent in osteoarthritis because struct...