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Diacerein

Diacerein structure

CAS No:
13739-02-1
Formula:
C19H12O8
Chemical Name:
Diacerein
Synonyms:
2-Anthracenecarboxylic acid,4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-;2-Anthroic acid,9,10-dihydro-4,5-dihydroxy-9,10-dioxo-,diacetate;Rhein,diacetate;4,5-Bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid;1,8-Diacetoxy-3-carboxyanthraquinone;Diacetylrhein;4,5-Diacetylrhein;Diacerhein;Diacerein;4,5-Diacetoxyanthraquinone-2-carboxylic acid;DAR;SF 277;Fisiodar;Artrodar;4,5-Diacetoxy-9,10-dioxoanthracene-2-carboxylic acid;Osteocerein;AC 201;Inflabion
Categories:
Active Pharmaceutical Ingredients > Drugs Influencing Immune Function

Description

Yellow Crystalline SolidDiacerein 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.Diacerein is a novel interleukin (IL)-1 inhibitor , the chemical name is diacetyl rhein,it is a compound of anthraquinones, the product can i

4,5-diacetyloxy-9,10-dioxo-2-anthracenecarboxylic acid is an anthraquinone.|Diacerein is a prodrug which is metabolized to rhein. It is currently approved in France for the treatment of osteoarthritis although the use of diacerein is restricted due to the side effects including sevre diarrhea. Diacerein is under investigation for the treatment of Insulin Resistance, Diabetes Mellitus (Type 2), and Diabetes-Related Complications.

Diacerein Basic Attributes

Molecular Weight：

368.29400

Exact Mass：

368.29

EC Number：

237-310-2

UNII：

4HU6J11EL5

NSC Number：

758147

DSSTox ID：

DTXSID4045636

ATC Code：

M - Musculo-skeletal system

HScode：

2918990090

Characteristics

PSA：

124.04000

XLogP3：

1.9

Density：

1.491±0.06 g/cm3(Predicted)

Melting Point：

217.5 °C

Boiling Point：

631.5±55.0 °C(Predicted)

Flash Point：

231.8±25.0 °C

Refractive Index：

1.634

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36

RTECS Number：

CB8781000

Marks：

Precautionary statement(s)：

P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 59 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Rhein [DB13174] has an oral LD50 of >5000mg/kg in mice. This is equivalent to a diacerein dose of >6476mg/kg.

Protein Binding：

99% of rhein is bound to plasma proteins.

Drug Information

Drug Indication：

For the treatment of osteoarthritis affecting the hip or knee.

Pharmacology：

Decreases inflammation and cartilage destruction and also corrects altered osteoblast acitivity.

MeSH：

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

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.

Metabolism/Metabolites：

Entirely converted to rhien [DB13174] through double deacetylation before reaching systemic circulation. Rhein [DB13174] is further metabolized to rhein glucuronide and rhein sulfate.

Biological Half-Life：

4-10h.

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.

MeSH Entry Terms：

diacerein

Diacerein Use and Manufacturing

Uses

It is widely used in new liquid crystal polymers, high-strength fibers and engineering plastics with excellent performance; this product is an important inhibitor of osteoarthritis IL-1. Natural antioxidants, have the effects of delaying aging, enhancing immunity, clearing sub-health conditions, restoring physical fitness, improving energy and body immunity; an interleukin-1β inhibitor, a slow-acting anthraquinone compound.

Use Classification：

Human drugs -> Rare disease (orphan)|Pharmaceuticals

Computed Properties

Molecular Weight:368.3
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:368.05321734
Monoisotopic Mass:368.05321734
Topological Polar Surface Area:124
Heavy Atom Count:27
Complexity:683
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Acetic acid

Drug Function and Efficacy

No specific pharmacological effects mentioned

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Diacerein Capsules
Ingredients	The main ingredient of this product is diacerein.
Indication	Diacerein capsules should not be taken while taking drugs that improve intestinal transit and/or intestinal content properties. To improve the bioavailability of diacerein, avoid taking drugs containing aluminum hydroxide and/or magnesium hydroxide at the same time. Taking diacerein increases the likelihood of enterocolitis in patients using antibiotics and/or chemotherapy because antibiotics and chemotherapy affect the intestinal flora.
Specifications	50mg*10 tablets/box

Diacerein Capsules
Specifications	50mg

Diacerein Capsules
Ingredients	Diacerein. Chemical name: 4,5-diacetyl-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid. Molecular weight: C19H12O8
Indication	This drug should not be taken while taking drugs that improve intestinal transit and/or the properties of intestinal contents. To improve the bioavailability of diacerein, avoid taking drugs containing aluminum hydroxide and/or magnesium hydroxide at the same time. Taking diacerein increases the likelihood of enterocolitis in patients using antibiotics and/or chemotherapy because antibiotics and chemotherapy affect the intestinal flora.
Specifications	50mg

See More Related Drugs

Registered Holders

Hangzhou Whiteoak MEDICAL Consult Co., Ltd.

China
Active
Harmony PharmaTech (Nanjing) Co., Ltd.

China
Active
Cang Zhou Wisdom Pharma Co., Ltd.

China
Active

See More Registered Holders

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