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13739-02-1 | 2-Anthracenecarboxylic acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-
CAS No: 13739-02-1 Catalog No: AG00138E MDL No:MFCD00468030
Product Description
Catalog Number:
AG00138E
Chemical Name:
2-Anthracenecarboxylic acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-
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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| Review: diacerein is more effective than placebo and is as effective as NSAIDs for knee and hip osteoarthritis. | Evidence-based medicine 20070601 |
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| 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 |
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| IL-1beta synthesis by chondrocyte analyzed by 3D microscopy and flow cytometry: effect of Rhein. | Biorheology 20060101 |
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| 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 |
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