Diacerein NEW

Diacerein (INN; also known as diacetylrhein) is an anti-osteoarthritic prodrug and the active metabolite of the natural compound rhein, derived from anthraquinones (e.g., in senna plants). Here's a concise chemical and pharmacological profile:

Key Chemical Details:

• IUPAC Name: 4,5-Diacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Formula:CX19HX12OX

Structure: Features a diacetylated anthraquinone core with a carboxylic acid group:

• Properties: Yellow-orange crystalline solid, poorly water-soluble.

Mechanism of Action:

• Prodrug: Metabolized to rhein (its active form) in the gut.

• Primary Target: Inhibits interleukin-1β (IL-1β), a key inflammatory cytokine in osteoarthritis (OA).

• Effects:

• Reduces cartilage degradation and synovial inflammation.

  Stimulates collagen synthesis in chondrocytes.

  Slows OA progression (disease-modifying action).

Clinical Use & Safety:

• Indication: Symptomatic slow-acting OA treatment (knee/hip).

• Advantage: Non-opioid, non-NSAID option with disease-modifying potential.

• Side Effects:

• Diarrhea (common, due to gut motility effects).

  Urine/skin discoloration (yellow-orange).

• Controversy: Withdrawn in EU (2014) over safety concerns but available in Asia/Latin America.

Origin:

Semi-synthetic derivative of rhein (from Senna plants/Cassia bark).

In short: Diacerein ($\mathrm{C}{\phantom{}}_{19}\mathrm{H}{\phantom{}}_{12}\mathrm{O}{\phantom{}}_8$C19H12O8) ) is an anthraquinone-based prodrug metabolized to rhein, acting as an IL-1β inhibitor to reduce inflammation and cartilage breakdown in osteoarthritis. Its slow efficacy (weeks) and GI side effects limit use. CAS: 13739-02-1.