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Merck
CN

Y0001595

Diacerein

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

1,8-Diacetoxy-3-carboxyanthraquinone

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About This Item

Empirical Formula (Hill Notation):
C19H12O8
CAS Number:
13739-02-1
Molecular Weight:
368.29
NACRES:
NA.24
PubChem Substance ID:
329831501
UNSPSC Code:
41116107
MDL number:
MFCD00468030

Key Documents

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Product Name

Diacerein, European Pharmacopoeia (EP) Reference Standard

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)

SMILES string

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

InChI key

TYNLGDBUJLVSMA-UHFFFAOYSA-N

grade

pharmaceutical primary standard

API family

diacerein

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

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Application

Diacerein EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Other Notes

Sales restrictions may apply.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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C M Spencer et al.
Drugs, 53(1), 98-106 (1997-01-01)
Rhein, the active metabolite of diacerein, inhibits interleukin-1 activity. Consequently, collagenase production in articular cartilage is reduced. Rhein dose-dependently inhibits superoxide anion production, chemotaxis and phagocytic activity of neutrophils, and macrophage migration and phagocytosis. Articular cartilage damage is reduced by
T S A Fidelix et al.
The Cochrane database of systematic reviews, (1)(1), CD005117-CD005117 (2006-01-27)
Osteoarthritis (OA) is one of the most prevalent musculoskeletal diseases. Diacerein acts differently from traditional non-steroidal anti-inflammatory drugs (NSAIDs) which inhibit prostaglandin synthesis, leading to adverse gastrointestinal effects. It has been proposed that diacerein acts as a slow-acting, symptom-modifying and
J P Pujol et al.
Biorheology, 37(1-2), 177-184 (2000-07-27)
The maintenance of articular cartilage integrity requires a balance between anabolic and catabolic processes which are under the control of chondrocytes. These cells are living in an anaerobic environment and normally do not divide. They are responsible for the continuous
P Nicolas et al.
Clinical pharmacokinetics, 35(5), 347-359 (1998-12-05)
Diacerein is a drug for the treatment of patients with osteoarthritis. This drug is administered orally as 50 mg twice daily. Diacerein is entirely converted into rhein before reaching the systemic circulation. Rhein itself is either eliminated by the renal
D Provvedini et al.
Presse medicale (Paris, France : 1983), 31(39 Pt 2), 4S13-4S15 (2003-01-09)
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 observed with non-steroidal anti-inflammatory drugs (NSAIDS) after four to six weeks of treatment
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