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MedKoo Cat#: 329996 | Name: Diacerein
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Diacerein, also known as diacetylrhein, is a slow-acting medicine of the class anthraquinone used to treat joint diseases such as osteoarthritis (swelling and pain in the joints). It works by inhibiting interleukin-1 beta. An updated 2014 Cochrane review found diacerein had a small beneficial effect on pain. Diacerein-containing medications are registered in some European Union and Asian countries and included as a treatment option on several international therapeutic guidelines.

Chemical Structure

Diacerein
CAS#13739-02-1

Theoretical Analysis

MedKoo Cat#: 329996

Name: Diacerein

CAS#: 13739-02-1

Chemical Formula: C19H12O8

Exact Mass: 368.0532

Molecular Weight: 368.30

Elemental Analysis: C, 61.96; H, 3.28; O, 34.75

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 weeks
5g USD 550.00 2 weeks
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Related CAS #
No Data
Synonym
Diacerein; DAR; 4,5-Diacetylrhein; Artrodar; Diacetylrhein; Diacerhein; Fisiodar; NSC-758147; NSC 758147; NSC758147;
IUPAC/Chemical Name
4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid
InChi Key
TYNLGDBUJLVSMA-UHFFFAOYSA-N
InChi Code
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 Code
O=C(C(C=C1C2=O)=CC(OC(C)=O)=C1C(C3=C2C=CC=C3OC(C)=O)=O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 368.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Aziz DE, Abdelbary AA, Elassasy AI. Investigating superiority of novel bilosomes over niosomes in the transdermal delivery of diacerein: In vitro characterization, ex vivo permeation and in vivo skin deposition study. J Liposome Res. 2018 Jan 21:1-40. doi: 10.1080/08982104.2018.1430831. [Epub ahead of print] PubMed PMID: 29355060. 2: Zhang Q, Zhou J, Wang Y, Chen D. The effect and safety of diacerein in patients with type 2 diabetes mellitus : a systematic review and meta-analysis. Am J Clin Exp Immunol. 2017 Dec 20;6(6):97-106. eCollection 2017. PubMed PMID: 29348985; PubMed Central PMCID: PMC5768895. 3: Chueakula N, Jaikumkao K, Arjinajarn P, Pongchaidecha A, Chatsudthipong V, Chattipakorn N, Lungkaphin A. Diacerein alleviates kidney injury through attenuating inflammation and oxidative stress in obese insulin-resistant rats. Free Radic Biol Med. 2018 Feb 1;115:146-155. doi: 10.1016/j.freeradbiomed.2017.11.021. Epub 2017 Nov 28. PubMed PMID: 29195834. 4: Piovesan F, Tres GS, Moreira LB, Andrades ME, Lisboa HK, Fuchs SC. Effect of diacerein on renal function and inflammatory cytokines in participants with type 2 diabetes mellitus and chronic kidney disease: A randomized controlled trial. PLoS One. 2017 Oct 19;12(10):e0186554. doi: 10.1371/journal.pone.0186554. eCollection 2017. PubMed PMID: 29049415; PubMed Central PMCID: PMC5648185. 5: Alegría A, Irarrázaval S. Is diacerein an alternative for the treatment of osteoarthritis? Medwave. 2017 Oct 12;17(8):e7041. doi: 10.5867/medwave.2017.08.7041. Spanish, English. PubMed PMID: 29028791. 6: Liu X, Machado GC, Eyles JP, Ravi V, Hunter DJ. Dietary supplements for treating osteoarthritis: a systematic review and meta-analysis. Br J Sports Med. 2018 Feb;52(3):167-175. doi: 10.1136/bjsports-2016-097333. Epub 2017 Oct 10. Review. PubMed PMID: 29018060. 7: Steinecker-Frohnwieser B, Kaltenegger H, Weigl L, Mann A, Kullich W, Leithner A, Lohberger B. Pharmacological treatment with diacerein combined with mechanical stimulation affects the expression of growth factors in human chondrocytes. Biochem Biophys Rep. 2017 Jul 1;11:154-160. doi: 10.1016/j.bbrep.2017.06.006. eCollection 2017 Sep. PubMed PMID: 28955780; PubMed Central PMCID: PMC5614688. 8: Yuan Y, Yang H, Kong L, Li Y, Li P, Zhang H, Ruan J. Interaction between rhein acyl glucuronide and methotrexate based on human organic anion transporters. Chem Biol Interact. 2017 Nov 1;277:79-84. doi: 10.1016/j.cbi.2017.09.001. Epub 2017 Sep 7. PubMed PMID: 28890383. 9: Hermann W, Lambova S, Müller-Ladner U. Current Treatment Options for Osteoarthritis. Curr Rheumatol Rev. 2017 Aug 29. doi: 10.2174/1573397113666170829155149. [Epub ahead of print] PubMed PMID: 28875826. 10: Refaie MMM, El-Hussieny M. Diacerein inhibits Estradiol-benzoate induced cervical hyperkeratosis in female rats. Biomed Pharmacother. 2017 Nov;95:223-229. doi: 10.1016/j.biopha.2017.08.053. Epub 2017 Sep 12. PubMed PMID: 28843910. 11: Cardoso CRL, Leite NC, Carlos FO, Loureiro AA, Viegas BB, Salles GF. Efficacy and Safety of Diacerein in Patients With Inadequately Controlled Type 2 Diabetes: A Randomized Controlled Trial. Diabetes Care. 2017 Oct;40(10):1356-1363. doi: 10.2337/dc17-0374. Epub 2017 Aug 17. PubMed PMID: 28818994. 12: Mâncio RD, Hermes TA, Macedo AB, Mizobuti DS, Rupcic IF, Minatel E. Dystrophic phenotype improvement in the diaphragm muscle of mdx mice by diacerhein. PLoS One. 2017 Aug 7;12(8):e0182449. doi: 10.1371/journal.pone.0182449. eCollection 2017. PubMed PMID: 28787441; PubMed Central PMCID: PMC5546703. 13: Allam AN, Hamdallah SI, Abdallah OY. Chitosan-coated diacerein nanosuspensions as a platform for enhancing bioavailability and lowering side effects: preparation, characterization, and ex vivo/in vivo evaluation. Int J Nanomedicine. 2017 Jul 4;12:4733-4745. doi: 10.2147/IJN.S139706. eCollection 2017. PubMed PMID: 28740381; PubMed Central PMCID: PMC5503500. 14: Hassib ST, Hassan GS, El-Zaher AA, Fouad MA, Taha EA. Quantitative analysis of anti-inflammatory drugs using FTIR-ATR spectrometry. Spectrochim Acta A Mol Biomol Spectrosc. 2017 Nov 5;186:59-65. doi: 10.1016/j.saa.2017.06.002. Epub 2017 Jun 13. PubMed PMID: 28622543. 15: Pavelka K, Bruyère O, Cooper C, Kanis JA, Leeb BF, Maheu E, Martel-Pelletier J, Monfort J, Pelletier JP, Rizzoli R, Reginster JY. Erratum to: Diacerein: Benefits, Risks and Place in the Management of Osteoarthritis. An Opinion-Based Report from the ESCEO. Drugs Aging. 2017 May;34(5):413. doi: 10.1007/s40266-017-0457-7. PubMed PMID: 28349413. 16: Mohan GC, Zhang H, Bao L, Many B, Chan LS. Diacerein inhibits the pro-atherogenic & pro-inflammatory effects of IL-1 on human keratinocytes & endothelial cells. PLoS One. 2017 Mar 21;12(3):e0173981. doi: 10.1371/journal.pone.0173981. eCollection 2017. PubMed PMID: 28323859; PubMed Central PMCID: PMC5360272. 17: Refaie MMM, El-Hussieny M. The role of interleukin-1b and its antagonist (diacerein) in estradiol benzoate-induced endometrial hyperplasia and atypia in female rats. Fundam Clin Pharmacol. 2017 Aug;31(4):438-446. doi: 10.1111/fcp.12285. Epub 2017 Apr 26. PubMed PMID: 28299811. 18: Villar MM, Martínez-Abundis E, Preciado-Márquez RO, González-Ortiz M. Effect of diacerein as an add-on to metformin in patients with type 2 diabetes mellitus and inadequate glycemic control. Arch Endocrinol Metab. 2017 Mar-Apr;61(2):188-192. doi: 10.1590/2359-3997000000242. Epub 2017 Feb 13. PubMed PMID: 28225996. 19: Bharti R, Dey G, Banerjee I, Dey KK, Parida S, Kumar BN, Das CK, Pal I, Mukherjee M, Misra M, Pradhan AK, Emdad L, Das SK, Fisher PB, Mandal M. Somatostatin receptor targeted liposomes with Diacerein inhibit IL-6 for breast cancer therapy. Cancer Lett. 2017 Mar 1;388:292-302. doi: 10.1016/j.canlet.2016.12.021. Epub 2016 Dec 24. PubMed PMID: 28025102. 20: Haseeb MT, Hussain MA, Bashir S, Ashraf MU, Ahmad N. Evaluation of superabsorbent linseed-polysaccharides as a novel stimuli-responsive oral sustained release drug delivery system. Drug Dev Ind Pharm. 2017 Mar;43(3):409-420. doi: 10.1080/03639045.2016.1257017. Epub 2016 Nov 28. PubMed PMID: 27808567.

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PF-03654746

PF-03654746