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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
Pricing and availability is not currently available.

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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P Härle et al.
Der Internist, 49(12), 1458-1462 (2008-11-18)
There is an increasing incidence in osteoarthritis, particularly following the 5th life-decade. However, also young people may suffer from severe osteoarthritis, which is estimated to be the most common cause of disability in adults resulting in substantial economic burden. To
Amit Kumar Aggarwal et al.
Drug development and industrial pharmacy, 37(10), 1181-1191 (2011-04-01)
Diacerein (DCN) is a new anti-inflammatory analgesic and antipyretic drug developed specially for the treatment of osteoarthritis. DCN is a poorly water-soluble drug with relatively low bioavailability. Therefore, the purpose of this study was to enhance the solubility and dissolution
Achint Jain et al.
Journal of biomedical nanotechnology, 9(5), 891-900 (2013-06-28)
Osteoarthritis is the most common, multi component joint disease mainly characterized by destruction of articular cartilage which leads up to subchondral bone. Current treatment by NSAID's gives only symptomatic relief but semi-synthetic anthraquinone diacerein is novel chondroprotective agent intended for
Rameshwar Jatwa et al.
Fundamental & clinical pharmacology, 23(4), 465-471 (2009-06-09)
This study was designed to reveal the possible involvement of thyroid hormones, if any, in diacerein induced alterations in glucose metabolism and tissue lipid peroxidation (LPO) in the animal model of carrageenan-induced inflammation. We studied the influence of diacerein administration
Umut Kalyoncu et al.
Joint, bone, spine : revue du rhumatisme, 76(4), 389-393 (2009-02-17)
The objective of the present study was to assess the frequency of self-reported psoriasis in a hip osteoarthritis (OA) cohort, and a secondary objective was to assess the course of hip OA with psoriasis. ECHODIAH was a 3-year, randomised double-blind

Questions

1–5 of 5 Questions  
  1. 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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  2. 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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  3. 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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  4. 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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  5. 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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