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Key Documents

Y0001596

Diacerein impurity B

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

Aloe-emodin, 1,8-Dihydroxy 3-hydroxymethylanthraquinone, 1,8-Dihydroxy-3-(hydroxymethyl)anthraquinone, 3-Hydroxymethylchrysazine, Rhabarberone

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About This Item

Empirical Formula (Hill Notation):
C15H10O5
CAS Number:
Molecular Weight:
270.24
Beilstein/REAXYS Number:
2059062
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24

biological source

synthetic

grade

pharmaceutical primary standard

agency

EP

API family

diacerein

form

solid

manufacturer/tradename

EDQM

technique(s)

gas chromatography (GC): suitable
liquid chromatography (LC): suitable

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

OCc1cc(O)c2C(=O)c3c(O)cccc3C(=O)c2c1

InChI

1S/C15H10O5/c16-6-7-4-9-13(11(18)5-7)15(20)12-8(14(9)19)2-1-3-10(12)17/h1-5,16-18H,6H2

InChI key

YDQWDHRMZQUTBA-UHFFFAOYSA-N

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General description

Diacerein is known to be a suitable drug to treat osteoarthritis and prevent vascular diseases. It is a semi-synthetic anthraquinone derivative which acts by inhibiting the production of interleukin-1 and secretion of metalloproteases.
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.

Application

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

Biochem/physiol Actions

Laxative/cathartic compound; increases the contraction of intestinal smooth muscle by releasing endogenous acetylcholine. Anti-tumor activity is associated with an increased production of reactive oxygen species (ROS) that, in turn, reduces the mitochondrial transmembrane electrical potential, thus inducing a permeability transition that sets in motion a series of events culminating in cellular apoptosis. Genotoxicity and mutagenicity appear to be due to the inhibition of topoisomerase II activity by aloe emodin.

Packaging

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

Other Notes

Sales restrictions may apply.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable


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A solid-liquid extraction and high performance thin layer chromatographic determination of diacerein and aceclofenac in pharmaceutical tablet dosage form
Bhalerao S, et al.
Asian Journal of Pharmaceutical and Clinical Research, 3(1), 25-30 (2010)
Chaudhari Ashok et al.
Journal of pharmaceutical and biomedical analysis, 49(2), 525-528 (2009-01-10)
Two impurities were found in the crude sample of diacerein. The level of these impurities 1.14% and 1.24% were detected by isocratic reverse-phase high performance liquid chromatography (HPLC). The molecular weights of the impurities were determined by liquid chromatography-mass spectroscopy
Naraganahalli R Thimmegowda et al.
Chemical biology & drug design, 85(5), 638-644 (2014-10-18)
In this study, we have synthesized novel water soluble derivatives of natural compound aloe emodin 4(a-j) by coupling with various amino acid esters and substituted aromatic amines, in an attempt to improve the anticancer activity and to explore the structure-activity
Khalilah Haris et al.
Asian Pacific journal of cancer prevention : APJCP, 15(11), 4499-4505 (2014-06-28)
Glioblastoma, the most aggressive and malignant form of glioma, appears to be resistant to various chemotherapeutic agents. Hence, approaches have been intensively investigated to targeti specific molecular pathways involved in glioblastoma development and progression. Aloe emodin is believed to modulate

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