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Substance Name: Diacerein [INN]
RN: 13739-02-1
UNII: 4HU6J11EL5
InChIKey: TYNLGDBUJLVSMA-UHFFFAOYSA-N

Note

  • Chelates with bivalent metals; a quinone which possesses redox properties; metabolized to active rhein; proposed mechanisms include inhibiting IL1 and metalloproteinases; called a slow acting symptomatic drug in osteoarthritis; no effect of cyclooxygenase.

Molecular Formula

  • C19-H12-O8

Molecular Weight

  • 368.296
 

Classification Codes

  • Anti-Inflammatory Agents
  • Drug / Therapeutic Agent
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Names and Synonyms

Name of Substance

  • Diacerein
  • Diacerein [INN]
  • Diacetylrhein

Synonyms

  • 1,8-Diacetoxyanthraquinone-3-carboxylic acid
  • 3-10-00-04790 (Beilstein Handbook Reference)
  • 4,5-Diacetoxy-9,10-dihydro-9,10-dioxo-2-anthrylcarbonsaeure
  • 4,5-Diacetylrhein
  • 9,10-Dihydro-4,5-diacetoxy-9,10-2-anthracenecarboxylic acid
  • 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid diacetate
  • ART 50
  • Artrodar
  • BRN 2184909
  • Diacerein
  • Diacereina
  • Diacereina [Spanish]
  • Diacereine
  • Diacereine [French]
  • Diacereinum
  • Diacereinum [Latin]
  • Diacerhein
  • Diacetylrhein
  • EINECS 237-310-2
  • Fisiodar
  • Rhein, diacetate (6CI)
  • SF-277
  • UNII-4HU6J11EL5

Systematic Names

  • 2-Anthracenecarboxylic acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo- (9CI)
  • 2-Anthroic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, diacetate
  • 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid, diacetate
  • Diacerein

Registry Numbers

CAS Registry Number

  • 13739-02-1

FDA UNII

  • 4HU6J11EL5

System Generated Number

  • 0013739021

Structure Descriptors

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)

InChIKey

TYNLGDBUJLVSMA-UHFFFAOYSA-N

Smiles

c12c(C(c3cccc(c3C2=O)OC(C)=O)=O)cc(C(O)=O)cc1OC(C)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 unreported 7500mg/kg (7500mg/kg)   Drugs of the Future. Vol. 4, Pg. 445, 1979.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 217.5 deg C   EXP
log P (octanol-water) 2.420 (none)   EST
Atmospheric OH Rate Constant 1.59E-12 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.