Home Carboxys 4,5-bis(acetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

4,5-bis(acetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

CAS No.:
13739-02-1
Catalog Number:
AG00138E
Molecular Formula:
C19H12O8
Molecular Weight:
368.2938
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1g
96%
In Stock USA
United States
$117
- +
5g
96%
In Stock USA
United States
$419
- +
25g
96%
In Stock USA
United States
$1225
- +
Product Description
Catalog Number:
AG00138E
Chemical Name:
4,5-bis(acetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
CAS Number:
13739-02-1
Molecular Formula:
C19H12O8
Molecular Weight:
368.2938
MDL Number:
MFCD00468030
IUPAC Name:
4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acid
InChI:
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
SMILES:
CC(=O)Oc1cc(cc2c1C(=O)c1c(C2=O)cccc1OC(=O)C)C(=O)O
EC Number:
237-310-2
UNII:
4HU6J11EL5
NSC Number:
758147
Properties
Complexity:
683  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
368.053g/mol
Formal Charge:
0
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
368.297g/mol
Monoisotopic Mass:
368.053g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
124A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.9  
Literature
Title Journal
Diacerein decreases visceral pain through inhibition of glutamatergic neurotransmission and cytokine signaling in mice. Pharmacology, biochemistry, and behavior 20121001
Bone-targeting glycol and NSAIDS ester prodrugs of rhein: synthesis, hydroxyapatite affinity, stability, anti-inflammatory, ulcerogenicity index and pharmacokinetics studies. European journal of medicinal chemistry 20120901
Nutraceuticals in the management of osteoarthritis : a critical review. Drugs & aging 20120901
Diacerein: a potential therapeutic drug for periodontal disease. Medical hypotheses 20120801
[Clinical study of Qianggu granule and diacerein capsule in treating knee osteoarthritis]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine 20120601
[Management of osteoarthritis: oral therapies]. La Revue du praticien 20120501
Comment on: Ramos-Zavala et al. Effect of diacerein on insulin secretion and metabolic control in drug-naïve patients with type 2 diabetes: a randomized clinical trial. Diabetes Care 2011;34:1591-1594. Diabetes care 20120201
Diacerein as adjuvant to diclofenac sodium in osteoarthritis knee. International journal of rheumatic diseases 20120201
[Clinical efficacy of bushen huoxue qubi decoction on treatment of knee-osteoarthritis and its effect on hemarheology, anti-inflammation and antioxidation]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20120201
A comparison of the therapeutic efficacy of diclofenac in osteoarthritis: a systematic review of randomised controlled trials. Current medical research and opinion 20120101
Effect of the Japanese herbal medicine, Boiogito, on the osteoarthritis of the knee with joint effusion. Sports medicine, arthroscopy, rehabilitation, therapy & technology : SMARTT 20120101
Scientific evidence and rationale for the development of curcumin and resveratrol as nutraceutricals for joint health. International journal of molecular sciences 20120101
Fast-dissolving and high-drug-loaded, Fatty Acid-based self-emulsifying solid dispersions of diacerein. PDA journal of pharmaceutical science and technology 20120101
Combined effect of subchondral drilling and hyaluronic acid with/without diacerein in full-thickness articular cartilage lesion in rabbits. TheScientificWorldJournal 20120101
Rhein: a potential biological therapeutic drug for intervertebral disc degeneration. Medical hypotheses 20111201
Diacerhein improves glucose tolerance and insulin sensitivity in mice on a high-fat diet. Endocrinology 20111101
Physicochemical characterization and dissolution study of solid dispersions of diacerein with polyethylene glycol 6000. Drug development and industrial pharmacy 20111001
Effect of diacerein on insulin secretion and metabolic control in drug-naive patients with type 2 diabetes: a randomized clinical trial. Diabetes care 20110701
Chondroitin sulphate reduces both cartilage volume loss and bone marrow lesions in knee osteoarthritis patients starting as early as 6 months after initiation of therapy: a randomised, double-blind, placebo-controlled pilot study using MRI. Annals of the rheumatic diseases 20110601
Stability-indicating spectrophotometric and spectrodensitometric methods for the determination of diacerein in the presence of its degradation product. Drug testing and analysis 20110401
Argirein alleviates diabetic nephropathy through attenuating NADPH oxidase, Cx43, and PERK in renal tissue. Naunyn-Schmiedeberg's archives of pharmacology 20110301
Changes of body weight and inflammatory markers after 12-week intervention trial: results of a double-blind, placebo-control pilot study. Yonsei medical journal 20110301
Lyprinol-is it a useful anti-inflammatory agent? Evidence-based complementary and alternative medicine : eCAM 20110101
Comparison of general practitioners and rheumatologists' prescription patterns for patients with knee osteoarthritis. BMC musculoskeletal disorders 20110101
Prescription patterns and appropriateness of NSAID therapy according to gastrointestinal risk and cardiovascular history in patients with diagnoses of osteoarthritis. BMC medicine 20110101
A highly selective, orally active inhibitor of Janus kinase 2, CEP-33779, ablates disease in two mouse models of rheumatoid arthritis. Arthritis research & therapy 20110101
T'ai chi for the treatment of osteoarthritis: a systematic review and meta-analysis. BMJ open 20110101
[Pharmacological therapies for osteoarthritis]. Therapie 20110101
Development and validation of simultaneous spectrophotometric methods for drotaverine hydrochloride and aceclofenac from tablet dosage form. Indian journal of pharmaceutical sciences 20110101
Improvement in the dissolution profile of diacerein using a surfactant-based solid dispersion technique. Drug discoveries & therapeutics 20101201
Effects of diacerein at the molecular level in the osteoarthritis disease process. Therapeutic advances in musculoskeletal disease 20100401
Diacerein decreases TNF-alpha and IL-1beta levels in peritoneal fluid and prevents Baker's yeast-induced fever in young rats. Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20100301
Symptomatic efficacy and safety of diacerein in the treatment of osteoarthritis: a meta-analysis of randomized placebo-controlled trials. Osteoarthritis and cartilage 20100301
Effects of risedronate on osteoarthritis of the knee. Yonsei medical journal 20100301
A peptidyl-glucosamine derivative affects IKKalpha kinase activity in human chondrocytes. Arthritis research & therapy 20100101
Is Phytalgic(R) a goldmine for osteoarthritis patients or is there something fishy about this nutraceutical? A summary of findings and risk-of-bias assessment. Arthritis research & therapy 20100101
Curcumin mediated suppression of nuclear factor-κB promotes chondrogenic differentiation of mesenchymal stem cells in a high-density co-culture microenvironment. Arthritis research & therapy 20100101
Small study effects in meta-analyses of osteoarthritis trials: meta-epidemiological study. BMJ (Clinical research ed.) 20100101
Visible spectrophotometric estimation of diacerein in bulk and pharmaceutical dosage forms. Journal of young pharmacists : JYP 20100101
Efficacy and safety of diacerein in early knee osteoarthritis: a randomized placebo-controlled trial. Clinical rheumatology 20091001
Anti-inflammatory and anti-peroxidative roles of diacerein are possibly mediated through an alteration in thyroid functions in animal model of inflammation. Fundamental & clinical pharmacology 20090801
Self-reported prevalence of psoriasis and evaluation of the impact on the natural history of hip osteoarthritis: results of a 10 years follow-up study of 507 patients (ECHODIAH study). Joint, bone, spine : revue du rhumatisme 20090701
Physico-chemical and structural characterization of diacerhein. Journal of pharmaceutical and biomedical analysis 20090501
PAC-1 activates procaspase-3 in vitro through relief of zinc-mediated inhibition. Journal of molecular biology 20090424
Simultaneous HPLC-UV determination of rhein and aceclofenac in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20090415
Isolation and structural elucidation of two impurities from a diacerein bulk drug. Journal of pharmaceutical and biomedical analysis 20090220
Comment on: comparison between chondroprotective effects of glucosamine, curcumin and diacerein in IL-1beta-stimulated C-28/I2 chondrocytes. Osteoarthritis and cartilage 20090101
[Non-surgical treatment of osteoarthritis of large joints - new aspects]. Wiener medizinische Wochenschrift (1946) 20090101
Rhein, the metabolite of diacerhein, reduces the proliferation of osteoarthritic chondrocytes and synoviocytes without inducing apoptosis. Scandinavian journal of rheumatology 20090101
The effects of excluding patients from the analysis in randomised controlled trials: meta-epidemiological study. BMJ (Clinical research ed.) 20090101
Suppressive effect of secretory phospholipase A2 inhibitory peptide on interleukin-1beta-induced matrix metalloproteinase production in rheumatoid synovial fibroblasts, and its antiarthritic activity in hTNFtg mice. Arthritis research & therapy 20090101
Safety and efficacy of undenatured type II collagen in the treatment of osteoarthritis of the knee: a clinical trial. International journal of medical sciences 20090101
A stability-indicating high performance liquid chromatographic method for the determination of diacerein in capsules. Indian journal of pharmaceutical sciences 20090101
A modified method for isolation of rhein from senna. Indian journal of pharmaceutical sciences 20090101
[Treatment of osteoarthritis with drugs and other modalities]. Der Internist 20081201
Comparison between chondroprotective effects of glucosamine, curcumin, and diacerein in IL-1beta-stimulated C-28/I2 chondrocytes. Osteoarthritis and cartilage 20081001
Immune system and inflammation. Indian journal of pharmacology 20081001
Prize sessions. Indian journal of pharmacology 20081001
The disease modifying osteoarthritis drug (DMOAD): Is it in the horizon? Pharmacological research 20080701
Diacerhein downregulate proinflammatory cytokines expression and decrease the autoimmune diabetes frequency in nonobese diabetic (NOD) mice. International immunopharmacology 20080601
Diacerein has a weak effect on the catabolic pathway of human osteoarthritis synovial fibroblast--comparison to its effects on osteoarthritic chondrocytes. Rheumatology (Oxford, England) 20080501
[Effectiveness of drugs used in degenerative joint diseases (arthroses)]. Medicina clinica 20080405
OARSI recommendations for the management of hip and knee osteoarthritis, Part II: OARSI evidence-based, expert consensus guidelines. Osteoarthritis and cartilage 20080201
Intra-articular hyaluronic acid for treatment of osteoarthritis: a nationwide study among the older population of Taiwan. BMC health services research 20080101
The effectiveness of pulsed electrical stimulation (E-PES) in the management of osteoarthritis of the knee: a protocol for a randomised controlled trial. BMC musculoskeletal disorders 20080101
In vitro effects of diacerein on NO production by chondrocytes in response to proinflammatory mediators. Bio-medical materials and engineering 20080101
Diacerein inhibits the synthesis of resorptive enzymes and reduces osteoclastic differentiation/survival in osteoarthritic subchondral bone: a possible mechanism for a protective effect against subchondral bone remodelling. Arthritis research & therapy 20080101
Clinical review of chondroitin sulfate in osteoarthritis. Osteoarthritis and cartilage 20080101
Role of fibroblast growth factor 8 (FGF8) in animal models of osteoarthritis. Arthritis research & therapy 20080101
An open prospective study on postmarketing evaluation of the efficacy and tolerability of diacerein in osteo-arthritis of the knee (DOK). Journal of the Indian Medical Association 20080101
Bioequivalence study of two capsule formulations containing diacerein 50 mg in healthy human subjects. Arzneimittel-Forschung 20080101
In vitro inhibition of IL-1beta catabolic effects on cartilage: a mechanism involved on diacerein anti-OA properties. Biorheology 20080101
P38 MAP kinase inhibitors as potential therapeutics for the treatment of joint degeneration and pain associated with osteoarthritis. Journal of inflammation (London, England) 20080101
Evaluation of symptomatic slow-acting drugs in osteoarthritis using the GRADE system. BMC musculoskeletal disorders 20080101
The efficacy and safety of diacerein in the treatment of painful osteoarthritis of the knee: a randomized, multicenter, double-blind, placebo-controlled study with primary end points at two months after the end of a three-month treatment period. Arthritis and rheumatism 20071201
[Review of the evidence about drugs used as SYSADOA]. Medicina clinica 20071103
Nutraceuticals in the management of osteoarthritis. Orthopedics 20070801
The efficacy, safety and carry-over effect of diacerein in the treatment of painful knee osteoarthritis: a randomised, double-blind, NSAID-controlled study. Osteoarthritis and cartilage 20070601
Review: diacerein is more effective than placebo and is as effective as NSAIDs for knee and hip osteoarthritis. Evidence-based medicine 20070601
Selection of reliable reference genes for qPCR studies on chondroprotective action. BMC molecular biology 20070101
DMOAD developments: present and future. Bulletin of the NYU hospital for joint diseases 20070101
A critical appraisal of guidelines for the management of knee osteoarthritis using Appraisal of Guidelines Research and Evaluation criteria. Arthritis research & therapy 20070101
Diacerhein versus glucosamine in a rat model of osteoarthritis. Clinics (Sao Paulo, Brazil) 20061001
A meta-analysis of controlled clinical studies with diacerein in the treatment of osteoarthritis. Archives of internal medicine 20060925
Effect of oral diacerein (DAR) in an experimental hip chondrolysis model. Journal of orthopaedic research : official publication of the Orthopaedic Research Society 20060601
Evaluation of efficacy and safety of diacerein in knee osteoarthritis in Chinese patients. Chinese medical sciences journal = Chung-kuo i hsueh k'o hsueh tsa chih 20060601
[Inhibitory effect of diacerein on osteoclastic bone destruction and its possible mechanism of action]. Yao xue xue bao = Acta pharmaceutica Sinica 20060601
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Molecular markers of cartilage breakdown and synovitis at baseline as predictors of structural progression of hip osteoarthritis. The ECHODIAH Cohort. Annals of the rheumatic diseases 20060301
Diacerein for osteoarthritis. The Cochrane database of systematic reviews 20060125
Most recent developments in strategies to reduce the progression of structural changes in osteoarthritis: today and tomorrow. Arthritis research & therapy 20060101
Inhibition of interleukin-1beta-induced activation of MEK/ERK pathway and DNA binding of NF-kappaB and AP-1: potential mechanism for Diacerein effects in osteoarthritis. Biorheology 20060101
IL-1beta synthesis by chondrocyte analyzed by 3D microscopy and flow cytometry: effect of Rhein. Biorheology 20060101
The effects of diacerhein on mechanical allodynia in inflammatory and neuropathic models of nociception in mice. Anesthesia and analgesia 20051201
Osteoarthritis: an overview of the disease and its treatment strategies. Seminars in arthritis and rheumatism 20050801
[Pharmacological treatment of osteoarthritis. Expectations and reality]. Revista clinica espanola 20050401
Future treatment of osteoarthritis. Orthopedics 20050201
Subjective impact of osteoarthritis flare-ups on patients' quality of life. Health and quality of life outcomes 20050101
Regional assessment of articular cartilage gene expression and small proteoglycan metabolism in an animal model of osteoarthritis. Arthritis research & therapy 20050101
Expedient total syntheses of rhein and diacerhein via Fries rearrangement. The Journal of organic chemistry 20041210
Evaluation of the symptomatic and structural efficacy of a new hyaluronic acid compound, NRD101, in comparison with diacerein and placebo in a 1 year randomised controlled study in symptomatic knee osteoarthritis. Annals of the rheumatic diseases 20041201
[Total hip arthroplasty indication, evaluation criteria for structure modifying trials. Lessons from the ECHODIAH and PHARE studies]. Presse medicale (Paris, France : 1983) 20040522
[Mechanisms of action of diacerein, the first inhibitor of interleukin-1 in osteoarthritis]. Presse medicale (Paris, France : 1983) 20040522
Recommendations for the use of new methods to assess the efficacy of disease-modifying drugs in the treatment of osteoarthritis. Osteoarthritis and cartilage 20040401
[Chondromodulation in 2003: dream or reality?]. Revue medicale de la Suisse romande 20040201
Measurement of structure (disease) modification in osteoarthritis. Osteoarthritis and cartilage 20040101
Effect of phospholipase A2 inhibitory peptide on inflammatory arthritis in a TNF transgenic mouse model: a time-course ultrastructural study. Arthritis research & therapy 20040101
Similar group mean scores, but large individual variations, in patient-relevant outcomes over 2 years in meniscectomized subjects with and without radiographic knee osteoarthritis. Health and quality of life outcomes 20040101
Diacerein has a structure/disease-modifying effect on hip osteoarthritis. Clinical and experimental rheumatology 20040101
New perspectives in the management of osteoarthritis. structure modification: facts or fantasy? The Journal of rheumatology. Supplement 20030801
The true results of the ECHODIAH study with diacerein. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20030501
Diacerein reduces the level of cartilage chondrocyte DNA fragmentation and death in experimental dog osteoarthritic cartilage at the same time that it inhibits caspase-3 and inducible nitric oxide synthase. Clinical and experimental rheumatology 20030101
Long-term treatment with diacerein has a structure/disease modifying effect on hip osteoarthritis. Clinical and experimental rheumatology 20030101
[Efficacy of diacerein on the symptoms and radiographic progression of osteoarthritis]. Presse medicale (Paris, France : 1983) 20021207
[Comparison of the pharmacologic effect of diacerein and a selective COX-2 inhibitor in the mouse induced-granuloma model]. Presse medicale (Paris, France : 1983) 20021207
[Clinical and radiographic status of patients in the ECHODIAH study who underwent THA Pertinence of the pain-function index for operative decision making]. Presse medicale (Paris, France : 1983) 20021207
Oral and intra-articular remedies: Review of papers published from March 2001 to February 2002. Current opinion in rheumatology 20020901
Response of young, aged and osteoarthritic human articular chondrocytes to inflammatory cytokines: molecular and cellular aspects. Matrix biology : journal of the International Society for Matrix Biology 20020801
Pharmacological studies of diacerein in animal models of inflammation, arthritis and bone resorption. European journal of pharmacology 20020712
Diacerhein and rhein prevent interleukin-1beta-induced nuclear factor-kappaB activation by inhibiting the degradation of inhibitor kappaB-alpha. Pharmacology & toxicology 20020701
[Current therapeutic possibilities in the treatment of arthrosis]. La Revue du praticien 20020301
[Current medical possibilities in the treatment of arthrosis]. Presse medicale (Paris, France : 1983) 20020112
[Results of the ECHODIAH clinical trial on hip arthrosis]. Presse medicale (Paris, France : 1983) 20020112
In vitro study of intracellular IL-1beta production and beta1 integrins expression in stimulated chondrocytes--effect of rhein. Biorheology 20020101
Diacerein as a disease-modulating agent in osteoarthritis. Current rheumatology reports 20011201
Evaluation of the structure-modifying effects of diacerein in hip osteoarthritis: ECHODIAH, a three-year, placebo-controlled trial. Evaluation of the Chondromodulating Effect of Diacerein in OA of the Hip. Arthritis and rheumatism 20011101
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. Immunopharmacology and immunotoxicology 20011101
Pharmacological therapy of osteoarthritis. Best practice & research. Clinical rheumatology 20011001
Diacerein suppresses the increase in plasma nitric oxide in rat adjuvant-induced arthritis. European journal of pharmacology 20010511
A novel microassay for the quantitation of the sulfated glycosaminoglycan content of histological sections: its application to determine the effects of Diacerhein on cartilage in an ovine model of osteoarthritis. Osteoarthritis and cartilage 20010401
Rhein, an active metabolite of diacerein, down-regulates the production of pro-matrix metalloproteinases-1, -3, -9 and -13 and up-regulates the production of tissue inhibitor of metalloproteinase-1 in cultured rabbit articular chondrocytes. Osteoarthritis and cartilage 20010401
Diacerein reduces the excess synthesis of bone remodeling factors by human osteoblast cells from osteoarthritic subchondral bone. The Journal of rheumatology 20010401
The effects of orally administered diacerein on cartilage and subchondral bone in an ovine model of osteoarthritis. The Journal of rheumatology 20010401
Pharmacologic pain treatment of musculoskeletal disorders: current perspectives and future prospects. The Clinical journal of pain 20010301
Reports of equivalence trials should not mask negative or mediocre results. Joint, bone, spine : revue du rhumatisme 20010301
[Pharmacy clinics. How I treat...Osteoarthritis. 2nd part: new therapeutic perspectives]. Revue medicale de Liege 20010301
Rhein, an active metabolite of diacerein, suppresses the interleukin-1alpha-induced proteoglycan degradation in cultured rabbit articular chondrocytes. Japanese journal of pharmacology 20010101
[Case report of fatal hepatitis from diacerein]. Therapie 20010101
Effects of diacerein on indomethacin-induced gastric ulceration. Pharmacology 20010101
Diacerhein and rhein reduce the ICE-induced IL-1beta and IL-18 activation in human osteoarthritic cartilage. Osteoarthritis and cartilage 20000501
Sleep attacks and Parkinson's disease treatment. Lancet (London, England) 20000415
Clinical pharmacokinetics of diacerein. Clinical pharmacokinetics 19981101
Excretion and distribution of [14C]rhein and [14C]rhein anthrone in rat. The Journal of pharmacy and pharmacology 19880901
Properties