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D9302

Sigma-Aldrich

Diacerein

≥95% (HPLC)

Synonym(s):

1,8-Diacetoxy-3-carboxyanthraquinone

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About This Item

Empirical Formula (Hill Notation):
C19H12O8
CAS Number:
Molecular Weight:
368.29
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.25
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Quality Level

Assay

≥95% (HPLC)

form

powder

SMILES string

CC(=O)Oc1cccc2C(=O)c3cc(cc(OC(C)=O)c3C(=O)c12)C(O)=O

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)

InChI key

TYNLGDBUJLVSMA-UHFFFAOYSA-N

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Biochem/physiol Actions

Diacerin is an inhibitor of Interleukin-1B (IL-1B) production.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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E M Bartels et al.
Osteoarthritis and cartilage, 18(3), 289-296 (2009-10-28)
To estimate the efficacy and safety of diacerein as a pain-reducing agent in the treatment of osteoarthritis (OA), using meta-analysis of published randomized placebo-controlled trials (RCTs). Systematic searches of the bibliographic databases Medline, Embase, Cinahl, Chemical Abstracts, Cochrane and Web
Vinícius Maria Gadotti et al.
Pharmacology, biochemistry, and behavior, 102(4), 549-554 (2012-07-04)
The present study evaluated the antinociceptive effect of the pro-inflammatory cytokines inhibitor diacerein in mice and its possible mechanism of action. The antinociception produced by diacerein was tested at different sites of action, moreover selective antagonists or agonists were used
The pathogenetic role of IL-1β in severe epidermolysis bullosa simplex.
Verena Wally et al.
The Journal of investigative dermatology, 133(7), 1901-1903 (2013-01-25)
Pascal Richette
Therapie, 66(5), 383-390 (2011-10-28)
According to international recommendations, acetaminophen should be used as a first-line therapy in patients with osteoarthritis, because of its safety and effectiveness. NSAIDs should be considered in patients unresponsive to acetaminophen, and should be prescribed at the lowest effective dose
Maria G Ramos-Zavala et al.
Diabetes care, 34(7), 1591-1594 (2011-05-26)
To assess the effect of diacerein on insulin secretion and metabolic control in drug-naïve patients with type 2 diabetes. A randomized, double-blind, placebo-controlled clinical trial was carried out in 40 drug-naïve adult patients with type 2 diabetes. A metabolic profile

Questions

1–5 of 5 Questions  
  1. Can Product D9302, Diacerein, be dissolved in DMSO?

    1 answer
    1. Yes. Diacerein is soluble in DMSO at 1 mg/mL.  The compound is also soluble in acetic acid at a concentration of 25 mg in 8 mL, as stated on the specification sheet.

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  2. What is the melting point of Product D9302, Diacerein?

    1 answer
    1. The chemicals encyclopedia published by the Royal Society of Chemistry (11th ed., entry #2939) reports a melting point of 217-218°C.

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  3. What is the biological activity of Product D9302, Diacerein?

    1 answer
    1. Martindale, 30th ed. indicates that "Diacerein is a non-steroidal anti-inflammatory agent that has been used in musculoskeletal and joint disorders."  Diacerein acts by inhibiting interleukin-1. The chemicals encyclopedia published by the Royal Society of Chemistry, 11th ed., indicates that Diacerein "demonstrates anti-arthritic activity without inhibiting prostaglandin synthesis".

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  4. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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  5. What is the mechanism of action of Product D9302, Diacerein?

    1 answer
    1. "Diacerein is a slow acting symptomatic treatment of osteoarthritis which has demonstrated efficacy on functional manifestations of osteoarthritis and on the structural component. Two mechanisms of action have been validated: in vitro inhibition of interleukin-1 (IL-1) synthesis, the main cytokine involved in cartilage destruction, and activity on the synthesis of proteoglycans, and hyaluronic acid, the principal component of cartilage. Other studies presented here have provided further details concerning other mechanisms of action of diacerein", according to Presse Med., 33(9 Pt 2), S10-S12 (2004).

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