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156897-06-2,MFCD00929900
Catalog No.:AA001OYX

156897-06-2 | Licofelone

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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA001OYX
Chemical Name:
Licofelone
CAS Number:
156897-06-2
Molecular Formula:
C23H22ClNO2
Molecular Weight:
379.8793
MDL Number:
MFCD00929900
SMILES:
OC(=O)Cc1c(c2ccc(cc2)Cl)c(c2n1CC(C2)(C)C)c1ccccc1
Properties
Properties
 
BP:
539.7°C at 760 mmHg  
Form:
Solid  
MP:
162-163°C  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
537  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
4  
XLogP3:
5.2  

Literature

Title: Identification of potent Yes1 kinase inhibitors using a library screening approach.

Journal: Bioorganic & medicinal chemistry letters 20130801

Title: Licofelone inhibits interleukin-18-induced pro-inflammatory cytokine release and cellular proliferation in human mesangial cells.

Journal: Basic & clinical pharmacology & toxicology 20120901

Title: The decrease of cell membrane fluidity by the non-steroidal anti-inflammatory drug Licofelone inhibits epidermal growth factor receptor signalling and triggers apoptosis in HCA-7 colon cancer cells.

Journal: Cancer letters 20120828

Title: Ciliary beating is depressed in nasal cilia from chronic obstructive pulmonary disease subjects.

Journal: Respiratory medicine 20120801

Title: Efficient synthesis and 5-LOX/COX-inhibitory activity of some 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives.

Journal: Bioorganic & medicinal chemistry letters 20120801

Title: Dynamic modeling of human 5-lipoxygenase-inhibitor interactions helps to discover novel inhibitors.

Journal: Journal of medicinal chemistry 20120322

Title: Targeting bone alleviates osteoarthritis in osteopenic mice and modulates cartilage catabolism.

Journal: PloS one 20120101

Title: Prostaglandins in cancer cell adhesion, migration, and invasion.

Journal: International journal of cell biology 20120101

Title: Anti-inflammatory drugs and prediction of new structures by comparative analysis.

Journal: Anti-inflammatory & anti-allergy agents in medicinal chemistry 20120101

Title: Chemoprevention of colon and small intestinal tumorigenesis in APC(Min/+) mice by licofelone, a novel dual 5-LOX/COX inhibitor: potential implications for human colon cancer prevention.

Journal: Cancer prevention research (Philadelphia, Pa.) 20111201

Title: Role of LOX/COX pathways in 3-nitropropionic acid-induced Huntington's disease-like symptoms in rats: protective effect of licofelone.

Journal: British journal of pharmacology 20110901

Title: Risk factors predictive of joint replacement in a 2-year multicentre clinical trial in knee osteoarthritis using MRI: results from over 6 years of observation.

Journal: Annals of the rheumatic diseases 20110801

Title: Chemopreventive efficacy and mechanism of licofelone in a mouse lung tumor model via aspiration.

Journal: Cancer prevention research (Philadelphia, Pa.) 20110801

Title: Licofelone-nitric oxide donors as anticancer agents.

Journal: Archiv der Pharmazie 20110801

Title: 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.

Journal: Annals of the rheumatic diseases 20110601

Title: Antibody-mediated 'universal' osteoclast targeting platform using calcitonin as a model drug.

Journal: Pharmaceutical research 20110501

Title: Synthesis and structure-activity relationship studies of urea-containing pyrazoles as dual inhibitors of cyclooxygenase-2 and soluble epoxide hydrolase.

Journal: Journal of medicinal chemistry 20110428

Title: Licofelone attenuates quinolinic acid induced Huntington like symptoms: possible behavioral, biochemical and cellular alterations.

Journal: Progress in neuro-psychopharmacology & biological psychiatry 20110330

Title: Investigations on cytotoxicity and anti-inflammatory potency of licofelone derivatives.

Journal: European journal of medicinal chemistry 20110301

Title: [Cyclooxygenases inhibitors and other compounds with antiinflammatory potential in osteoarthrosis--part I].

Journal: Polski merkuriusz lekarski : organ Polskiego Towarzystwa Lekarskiego 20110101

Title: Tiludronate treatment improves structural changes and symptoms of osteoarthritis in the canine anterior cruciate ligament model.

Journal: Arthritis research & therapy 20110101

Title: The implications of relationships between human diseases and metabolic subpathways.

Journal: PloS one 20110101

Title: Molecular changes in articular cartilage and subchondral bone in the rat anterior cruciate ligament transection and meniscectomized models of osteoarthritis.

Journal: BMC musculoskeletal disorders 20110101

Title: Sequential alterations in catabolic and anabolic gene expression parallel pathological changes during progression of monoiodoacetate-induced arthritis.

Journal: PloS one 20110101

Title: Quantitative cartilage imaging in knee osteoarthritis.

Journal: Arthritis 20110101

Title: Decrease in serum level of matrix metalloproteinases is predictive of the disease-modifying effect of osteoarthritis drugs assessed by quantitative MRI in patients with knee osteoarthritis.

Journal: Annals of the rheumatic diseases 20101201

Title: Relationship between bone marrow lesions, cartilage loss and pain in knee osteoarthritis: results from a randomised controlled clinical trial using MRI.

Journal: Annals of the rheumatic diseases 20101201

Title: Licofelone attenuates MPTP-induced neuronal toxicity: behavioral, biochemical and cellular evidence.

Journal: Inflammopharmacology 20101001

Title: Anti-atherogenic effect of BHB-TZD having inhibitory activities on cyclooxygenase and 5-lipoxygenase in hyperlipidemic mice.

Journal: Atherosclerosis 20100901

Title: Identification and characterisation of new inhibitors for the human hematopoietic prostaglandin D2 synthase.

Journal: European journal of medicinal chemistry 20100201

Title: Pharmacophore modeling and virtual screening for designing potential 5-lipoxygenase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20100201

Title: Regulation of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase-activating protein/5-lipoxygenase by 4-hydroxynonenal in human osteoarthritic chondrocytes.

Journal: Arthritis research & therapy 20100101

Title: High mobility group box 1 potentiates the pro-inflammatory effects of interleukin-1β in osteoarthritic synoviocytes.

Journal: Arthritis research & therapy 20100101

Title: Oestrogen is important for maintenance of cartilage and subchondral bone in a murine model of knee osteoarthritis.

Journal: Arthritis research & therapy 20100101

Title: Upregulation of MMP-13 and TIMP-1 expression in response to mechanical strain in MC3T3-E1 osteoblastic cells.

Journal: BMC research notes 20100101

Title: Investigational pharmacology for low back pain.

Journal: Journal of pain research 20100101

Title: 5-lipoxygenase: underappreciated role of a pro-inflammatory enzyme in tumorigenesis.

Journal: Frontiers in pharmacology 20100101

Title: Protective effects of licofelone, a 5-lipoxygenase and cyclo-oxygenase inhibitor, versus naproxen on cartilage loss in knee osteoarthritis: a first multicentre clinical trial using quantitative MRI.

Journal: Annals of the rheumatic diseases 20090601

Title: Systematic review of the management of canine osteoarthritis.

Journal: The Veterinary record 20090404

Title: Protective effects of total fraction of avocado/soybean unsaponifiables on the structural changes in experimental dog osteoarthritis: inhibition of nitric oxide synthase and matrix metalloproteinase-13.

Journal: Arthritis research & therapy 20090101

Title: An exploration of the ability of tepoxalin to ameliorate the degradation of articular cartilage in a canine in vitro model.

Journal: BMC veterinary research 20090101

Title: Treatment with ephrin B2 positively impacts the abnormal metabolism of human osteoarthritic chondrocytes.

Journal: Arthritis research & therapy 20090101

Title: The target of arachidonic acid pathway is a new anticancer strategy for human prostate cancer.

Journal: Biologics : targets & therapy 20081201

Title: Licofelone suppresses prostaglandin E2 formation by interference with the inducible microsomal prostaglandin E2 synthase-1.

Journal: The Journal of pharmacology and experimental therapeutics 20080901

Title: In vitro metabolism of 2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl] acetic acid (licofelone, ML3000), an inhibitor of cyclooxygenase-1 and -2 and 5-lipoxygenase.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20080501

Title: The dual inhibitor of lipoxygenase and cyclooxygenase ML3000 decreases the expression of CXCR3 ligands.

Journal: Annals of the rheumatic diseases 20080401

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20080301

Title: Licofelone, a dual COX/5-LOX inhibitor, induces apoptosis in HCA-7 colon cancer cells through the mitochondrial pathway independently from its ability to affect the arachidonic acid cascade.

Journal: Carcinogenesis 20080201

Title: Cyclooxygenase (COX) and 5-lipoxygenase (5-LOX) selectivity of COX inhibitors.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20080201

Title: A role for subchondral bone changes in the process of osteoarthritis; a micro-CT study of two canine models.

Journal: BMC musculoskeletal disorders 20080101

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20080101

Title: Licofelone: the answer to unmet needs in osteoarthritis therapy?

Journal: Current rheumatology reports 20080101

Title: Is collagenase-3 (MMP-13) expression in chondrosarcoma of the jaws a true marker for tumor aggressiveness?

Journal: Diagnostic pathology 20080101

Title: 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.

Journal: Arthritis research & therapy 20080101

Title: Finding multiple target optimal intervention in disease-related molecular network.

Journal: Molecular systems biology 20080101

Title: Analysis of the precision and sensitivity to change of different approaches to assess cartilage loss by quantitative MRI in a longitudinal multicentre clinical trial in patients with knee osteoarthritis.

Journal: Arthritis research & therapy 20080101

Title: Combination Therapy of PPARgamma Ligands and Inhibitors of Arachidonic Acid in Lung Cancer.

Journal: PPAR research 20080101

Title: Comparative protection against liver inflammation and fibrosis by a selective cyclooxygenase-2 inhibitor and a nonredox-type 5-lipoxygenase inhibitor.

Journal: The Journal of pharmacology and experimental therapeutics 20071201

Title: The molecular mechanism of the inhibition by licofelone of the biosynthesis of 5-lipoxygenase products.

Journal: British journal of pharmacology 20071001

Title: Gastrointestinal safety of novel nonsteroidal antiinflammatory drugs: selective COX-2 inhibitors and beyond.

Journal: Acta bio-medica : Atenei Parmensis 20070801

Title: Efficacy of licofelone in dogs with clinical osteoarthritis.

Journal: The Veterinary record 20070428

Title: Dynamic simulations on the arachidonic acid metabolic network.

Journal: PLoS computational biology 20070301

Title: Activity and potential role of licofelone in the management of osteoarthritis.

Journal: Clinical interventions in aging 20070301

Title: Arthritis clinical trial results revealed.

Journal: JAMA 20070103

Title: Licofelone, a balanced inhibitor of cyclooxygenase and 5-lipoxygenase, reduces inflammation in a rabbit model of atherosclerosis.

Journal: The Journal of pharmacology and experimental therapeutics 20070101

Title: Licofelone--a novel analgesic and anti-inflammatory agent.

Journal: Current topics in medicinal chemistry 20070101

Title: Selection of reliable reference genes for qPCR studies on chondroprotective action.

Journal: BMC molecular biology 20070101

Title: Extracellular localization of galectin-3 has a deleterious role in joint tissues.

Journal: Arthritis research & therapy 20070101

Title: Anticancer effects of licofelone (ML-3000) in prostate cancer cells.

Journal: Anticancer research 20070101

Title: DMOAD developments: present and future.

Journal: Bulletin of the NYU hospital for joint diseases 20070101

Title: Activation of proteinase-activated receptor 2 in human osteoarthritic cartilage upregulates catabolic and proinflammatory pathways capable of inducing cartilage degradation: a basic science study.

Journal: Arthritis research & therapy 20070101

Title: Effects on primary haemostasis of an anti-inflammatory agent with 5-lipoxygenase and cyclooxygenase inhibitory activity.

Journal: Journal of cardiovascular medicine (Hagerstown, Md.) 20061201

Title: The lipoxygenase-cyclooxygenase inhibitor licofelone prevents thromboxane A2-mediated cardiovascular derangement triggered by the inflammatory peptide fMLP in the rabbit.

Journal: European journal of pharmacology 20060928

Title: Licofelone reduces progression of structural changes in a canine model of osteoarthritis under curative conditions: effect on protease expression and activity.

Journal: The Journal of rheumatology 20060601

Title: Anti-inflammatory effect of licofelone against various inflammatory challenges.

Journal: Fundamental & clinical pharmacology 20060201

Title: Most recent developments in strategies to reduce the progression of structural changes in osteoarthritis: today and tomorrow.

Journal: Arthritis research & therapy 20060101

Title: Licofelone, a novel 5-LOX/COX-inhibitor, attenuates leukocyte rolling and adhesion on endothelium under flow.

Journal: Biochemical pharmacology 20050701

Title: The regulation of human MMP-13 by licofelone, an inhibitor of cyclo-oxygenases and 5-lipoxygenase, in human osteoarthritic chondrocytes is mediated by the inhibition of the p38 MAP kinase signalling pathway.

Journal: Annals of the rheumatic diseases 20050601

Title: Eicosanoids, osteoarthritis, and crystal deposition diseases.

Journal: Current opinion in rheumatology 20050501

Title: Dual inhibition of cyclo-oxygenases and 5-lipoxygenase: a novel therapeutic approach to inflammation?

Journal: Joint, bone, spine : revue du rhumatisme 20050501

Title: Leukotriene and prostaglandin synthesis pathways in osteoarthritic synovial membranes: regulating factors for interleukin 1beta synthesis.

Journal: The Journal of rheumatology 20050401

Title: Effect of licofelone against NSAIDs-induced gastrointestinal ulceration and inflammation.

Journal: Indian journal of experimental biology 20050301

Title: Superiority of the gastroduodenal safety profile of licofelone over rofecoxib, a COX-2 selective inhibitor, in dogs.

Journal: Journal of veterinary pharmacology and therapeutics 20050201

Title: Combined lipoxygenase/cyclo-oxygenase inhibition in the elderly: the example of licofelone.

Journal: Drugs & aging 20050101

Title: Effect of licofelone against mechanical hyperalgesia and cold allodynia in the rat model of incisional pain.

Journal: Pharmacological reports : PR 20050101

Title: The protective effect of licofelone on experimental osteoarthritis is correlated with the downregulation of gene expression and protein synthesis of several major cartilage catabolic factors: MMP-13, cathepsin K and aggrecanases.

Journal: Arthritis research & therapy 20050101

Title: Regulation of the expression of 5-lipoxygenase-activating protein/5-lipoxygenase and the synthesis of leukotriene B(4) in osteoarthritic chondrocytes: role of transforming growth factor beta and eicosanoids.

Journal: Arthritis and rheumatism 20041201

Title: Pain and osteoarthritis: new drugs and mechanisms.

Journal: Current opinion in rheumatology 20040901

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20040901

Title: The gastrointestinal tolerability of the LOX/COX inhibitor, licofelone, is similar to placebo and superior to naproxen therapy in healthy volunteers: results from a randomized, controlled trial.

Journal: The American journal of gastroenterology 20040401

Title: Licofelone, an inhibitor of cyclooxygenase and 5-lipoxygenase, specifically inhibits cyclooxygenase-1-dependent platelet activation.

Journal: European journal of pharmacology 20040319

Title: The inhibition of subchondral bone resorption in the early phase of experimental dog osteoarthritis by licofelone is associated with a reduction in the synthesis of MMP-13 and cathepsin K.

Journal: Bone 20040301

Title: Is licofelone, a dual inhibitor of cyclo-oxygenase and 5-lipoxygenase, a promising alternative in anti-inflammatory therapy?

Journal: Fundamental & clinical pharmacology 20040201

Title: Osteoarthritis therapy--are there still unmet needs?

Journal: Rheumatology (Oxford, England) 20040201

Title: Safety of anti-inflammatory treatment--new ways of thinking.

Journal: Rheumatology (Oxford, England) 20040201

Title: Licofelone--clinical update on a novel LOX/COX inhibitor for the treatment of osteoarthritis.

Journal: Rheumatology (Oxford, England) 20040201

Title: Treatment with licofelone prevents abnormal subchondral bone cell metabolism in experimental dog osteoarthritis.

Journal: Annals of the rheumatic diseases 20040101

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20040101

Title: Inhibition of gastric H,K-ATPase activity and gastric epithelial cell IL-8 secretion by the pyrrolizine derivative ML 3000.

Journal: BMC gastroenterology 20040101

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20031201

Title: Evidence that 5-lipoxygenase and acetylated cyclooxygenase 2-derived eicosanoids regulate leukocyte-endothelial adherence in response to aspirin.

Journal: British journal of pharmacology 20030801

Title: Licofelone (Merckle).

Journal: IDrugs : the investigational drugs journal 20030801

Title: International Conference on Inflammopharmacology -- VIII Side-Effects of Anti-inflammatory Drugs Symposium.

Journal: Expert opinion on investigational drugs 20030701

Title: The metabolic effects of inhibitors of 5-lipoxygenase and of cyclooxygenase 1 and 2 are an advancement in the efficacy and safety of anti-inflammatory therapy.

Journal: Prostaglandins & other lipid mediators 20030701

Title: Relative contribution of acetylated cyclo-oxygenase (COX)-2 and 5-lipooxygenase (LOX) in regulating gastric mucosal integrity and adaptation to aspirin.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20030601

Title: Anti arthritic drugs--SMi conference: dual inhibitors. 28-29 April 2003, London, UK.

Journal: IDrugs : the investigational drugs journal 20030601

Title: COX-LOX inhibition: current evidence for an emerging new therapy.

Journal: International journal of clinical practice 20030501

Title: Licofelone, a dual lipoxygenase-cyclooxygenase inhibitor, downregulates polymorphonuclear leukocyte and platelet function.

Journal: European journal of pharmacology 20021018

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20021001

Title: Study of the role of leukotriene B()4 in abnormal function of human subchondral osteoarthritis osteoblasts: effects of cyclooxygenase and/or 5-lipoxygenase inhibition.

Journal: Arthritis and rheumatism 20020701

Title: Licofelone (ML-3000), a dual inhibitor of 5-lipoxygenase and cyclooxygenase, reduces the level of cartilage chondrocyte death in vivo in experimental dog osteoarthritis: inhibition of pro-apoptotic factors.

Journal: The Journal of rheumatology 20020701

Title: Antithrombotic and platelet function inhibiting effects of ML3000, a new antiinflammatory drug with Cox/5-LOX inhibitory activity.

Journal: Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20020301

Title: The mechanism of action of the new antiinflammatory compound ML3000: inhibition of 5-LOX and COX-1/2.

Journal: Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20020301

Title: In vivo dual inhibition of cyclooxygenase and lipoxygenase by ML-3000 reduces the progression of experimental osteoarthritis: suppression of collagenase 1 and interleukin-1beta synthesis.

Journal: Arthritis and rheumatism 20011001

Title: [Double blockade should protect the stomach. New approach to rheumatism].

Journal: MMW Fortschritte der Medizin 20010920

Title: Dual inhibition of 5-lipoxygenase and cyclooxygenases 1 and 2 by ML3000 reduces joint destruction in adjuvant arthritis.

Journal: The Journal of rheumatology 20010901

Title: Tavolari S, et al. Licofelone, a dual COX/5-LOX inhibitor, induces apoptosis in HCA-7 colon cancer cells through the mitochondrial pathway independently from its ability to affect the arachidonic acid cascade. Carcinogenesis. 2008 Feb;29(2):371-80.

Title: Alvaro-Gracia JM, et al. Licofelone--clinical update on a novel LOX/COX inhibitor for the treatment of osteoarthritis. Rheumatology (Oxford). 2004 Feb;43 Suppl 1:i21-5.

Title: Laufer SA, et al. (6,7-Diaryldihydropyrrolizin-5-yl)acetic acids, a novel class of potent dual inhibitors of both cyclooxygenase and 5-lipoxygenase. J Med Chem. 1994 Jun 10;37(12):1894-7.

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