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59973-80-7,MFCD00871143
Catalog No.:AA00EBXV

59973-80-7 | 1H-Indene-3-acetic acid,5-fluoro-2-methyl-1-[[4-(methylsulfonyl)phenyl]methylene]-, (1Z)-

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  • Technical Information
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  • Downstream Synthesis Route
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00EBXV
Chemical Name:
1H-Indene-3-acetic acid,5-fluoro-2-methyl-1-[[4-(methylsulfonyl)phenyl]methylene]-, (1Z)-
CAS Number:
59973-80-7
Molecular Formula:
C20H17FO4S
Molecular Weight:
372.4100
MDL Number:
MFCD00871143
SMILES:
OC(=O)CC1=C(C)/C(=C/c2ccc(cc2)S(=O)(=O)C)/c2c1cc(F)cc2
NSC Number:
719619
Properties
Computed Properties
 
Complexity:
723  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
4  
XLogP3:
3.5  

Downstream Synthesis Route
polyethyleneglycolpolyamideresin 
  59973-80-7   
C20H17FNO3PolS 

[1]Patent:EP1690852,2006,A1.Locationinpatent:Page/Pagecolumn17

[1]Patent:WO2006/134489,2006,A1.Locationinpatent:Page/Pagecolumn15

[1]Patent:WO2006/134489,2006,A1.Locationinpatent:Page/Pagecolumn20

[1]EuropeanJournalofMedicinalChemistry,2009,vol.44,p.1959-1971

Literature

Title: Structural analysis of sulindac as an inhibitor of aldose reductase and AKR1B10.

Journal: Chemico-biological interactions 20150605

Title: Nitric oxide donor exisulind is an effective inhibitor of murine photocarcinogenesis.

Journal: Photochemistry and photobiology 20120901

Title: A prospective, controlled phase II study of neoadjuvant exisulind therapy before radical prostatectomy: effect on apoptosis.

Journal: Urology 20120801

Title: Assessment of the involvement of oxidative stress and Mitogen-Activated Protein Kinase signaling pathways in the cytotoxic effects of arsenic trioxide and its combination with sulindac or its metabolites: sulindac sulfide and sulindac sulfone on human leukemic cell lines.

Journal: Medical oncology (Northwood, London, England) 20120601

Title: The molecular basis for inhibition of sulindac and its metabolites towards human aldose reductase.

Journal: FEBS letters 20120102

Title: Regulation of 15-hydroxyprostaglandin dehydrogenase (15-PGDH) by non-steroidal anti-inflammatory drugs (NSAIDs).

Journal: Prostaglandins & other lipid mediators 20111101

Title: Sulindac and its metabolites: sulindac sulfide and sulindac sulfone enhance cytotoxic effects of arsenic trioxide on leukemic cell lines.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20110801

Title: Studies on the metabolism and biological activity of the epimers of sulindac.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20110601

Title: Optimisation and validation of a fast HPLC method for the quantification of sulindac and its related impurities.

Journal: Journal of pharmaceutical and biomedical analysis 20110325

Title: [Antitumor effects of sulindac in ovarian cell cultures].

Journal: Ginekologia polska 20110301

Title: Sulindac sulfide reverses aberrant self-renewal of progenitor cells induced by the AML-associated fusion proteins PML/RARα and PLZF/RARα.

Journal: PloS one 20110101

Title: Therapeutic potential of sulindac hydroxamic acid against human pancreatic and colonic cancer cells.

Journal: European journal of medicinal chemistry 20101101

Title: Sulindac and its metabolites inhibit multiple transport proteins in rat and human hepatocytes.

Journal: The Journal of pharmacology and experimental therapeutics 20100801

Title: Sulindac metabolites induce proteosomal and lysosomal degradation of the epidermal growth factor receptor.

Journal: Cancer prevention research (Philadelphia, Pa.) 20100401

Title: Curcumin potentiates the pro-apoptotic effects of sulindac sulfone in colorectal cancer.

Journal: Expert opinion on investigational drugs 20100401

Title: Sulindac sulfone induces a decrease of beta-catenin in HNSCC.

Journal: Anticancer research 20100201

Title: 15-Hydroxyprostaglandin dehydrogenase (15-PGDH) is up-regulated by flurbiprofen and other non-steroidal anti-inflammatory drugs in human colon cancer HT29 cells.

Journal: Archives of biochemistry and biophysics 20090715

Title: Synthesis, pharmacological evaluation and docking studies of new sulindac analogues.

Journal: European journal of medicinal chemistry 20090501

Title: A phase II study of carboplatin, etoposide, and exisulind in patients with extensive small cell lung cancer: CALGB 30104.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20090201

Title: Phase I/II study of vinorelbine and exisulind as first-line treatment of advanced non-small cell lung cancer in patients at least 70 years old: a wisconsin oncology network study.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20080901

Title: A phase II study of estramustine, docetaxel, and exisulind in patients with hormone- refractory prostate cancer: results of cancer and leukemia group B trial 90004.

Journal: Clinical genitourinary cancer 20080901

Title: Activation of protein kinase G Increases the expression of p21CIP1, p27KIP1, and histidine triad protein 1 through Sp1.

Journal: Cancer research 20080701

Title: Interactions of sulindac and its metabolites with phospholipid membranes: an explanation for the peroxidation protective effect of the bioactive metabolite.

Journal: Free radical research 20080701

Title: Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).

Journal: Journal of medicinal chemistry 20080612

Title: The proapoptotic effects of sulindac, sulindac sulfone and indomethacin are mediated by nucleolar translocation of the RelA(p65) subunit of NF-kappaB.

Journal: Oncogene 20080417

Title: Sulindac and its metabolites induce carcinogen metabolizing enzymes in human colon cancer cells.

Journal: International journal of cancer 20080301

Title: A comparison of the effectiveness of selected non-steroidal anti-inflammatory drugs and their derivatives against cancer cells in vitro.

Journal: Cancer chemotherapy and pharmacology 20080201

Title: Malignant transformation of normal enterocytes following downregulation of Bak expression.

Journal: Digestion 20080101

Title: Exisulind in combination with celecoxib modulates epidermal growth factor receptor, cyclooxygenase-2, and cyclin D1 against prostate carcinogenesis: in vivo evidence.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20071001

Title: Docetaxel and exisulind in previously treated non-small cell lung cancer (NSCLC) patients: a multicenter, phase II clinical trial.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20071001

Title: Sulindac sulfone modulates beta-catenin in human cholesteatoma cell culture.

Journal: Archives of medical research 20070501

Title: Nonsteroidal anti-inflammatory drugs induce colorectal cancer cell apoptosis by suppressing 14-3-3epsilon.

Journal: Cancer research 20070401

Title: Alpha-tocopheryl succinate sensitizes human colon cancer cells to exisulind-induced apoptosis.

Journal: Apoptosis : an international journal on programmed cell death 20070201

Title: Differential activity of sulindac metabolites against squamous cell carcinoma of the head and neck is mediated by p21waf1/cip1 induction and cell cycle inhibition.

Journal: Cancer biology & therapy 20070101

Title: Effects of oral dosing paradigms (gavage versus diet) on pharmacokinetics and pharmacodynamics.

Journal: Chemico-biological interactions 20061201

Title: Gene expression profiling in R-flurbiprofen-treated prostate cancer: R-Flurbiprofen regulates prostate stem cell antigen through activation of AKT kinase.

Journal: Biochemical pharmacology 20061115

Title: Exisulind induces apoptosis in advanced myelodysplastic syndrome (MDS) and acute myeloid leukaemia/MDS.

Journal: British journal of haematology 20061101

Title: p38MAPK inhibitor SB203580 sensitizes human SNU-C4 colon cancer cells to exisulind-induced apoptosis.

Journal: Oncology reports 20061101

Title: 15-Hydroxyprostaglandin-dehydrogenase is involved in anti-proliferative effect of non-steroidal anti-inflammatory drugs COX-1 inhibitors on a human medullary thyroid carcinoma cell line.

Journal: Prostaglandins & other lipid mediators 20061001

Title: A phase II trial of carboplatin and gemcitabine with exisulind (IND #65,056) in patients with advanced non-small cell lung cancer: an Eastern Cooperative Oncology Group study (E1501).

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20060901

Title: Chemopreventive alteration of the cell-cell adhesion in head and neck squamous cell cancer.

Journal: Oncology reports 20060801

Title: Phase II evaluation of docetaxel plus exisulind in patients with androgen independent prostate carcinoma.

Journal: American journal of clinical oncology 20060801

Title: Capillary electrophoresis combining field-amplified sample stacking and electroosmotic flow suppressant for analysis of sulindac and its two metabolites in plasma.

Journal: Journal of chromatography. A 20060630

Title: Sulindac sulfide and exisulind inhibit expression of the estrogen and progesterone receptors in human breast cancer cells.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20060601

Title: Apoptosis: a relevant tool for anticancer therapy.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20060601

Title: Exisulind and guanylyl cyclase C induce distinct antineoplastic signaling mechanisms in human colon cancer cells.

Journal: Molecular cancer therapeutics 20060501

Title: The geminal dimethyl analogue of Flurbiprofen as a novel Abeta42 inhibitor and potential Alzheimer's disease modifying agent.

Journal: Bioorganic & medicinal chemistry letters 20060415

Title: Sporadic adenomatous polyp regression with exisulind is effective but toxic: a randomised, double blind, placebo controlled, dose-response study.

Journal: Gut 20060301

Title: Phase I/II study of gemcitabine and exisulind as second-line therapy in patients with advanced non-small cell lung cancer.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20060301

Title: Induction of spermidine/spermine N1-acetyltransferase (SSAT) by aspirin in Caco-2 colon cancer cells.

Journal: The Biochemical journal 20060215

Title: Phase I clinical trial of weekly docetaxel and exisulind, a novel inducer of apoptosis.

Journal: Investigational new drugs 20060101

Title: The sulindac derivatives OSI-461, OSIP486823, and OSIP487703 arrest colon cancer cells in mitosis by causing microtubule depolymerization.

Journal: Molecular cancer therapeutics 20060101

Title: Exisulind in the treatment of prostate cancer.

Journal: Expert review of anticancer therapy 20051201

Title: Sulindac sulfone is most effective in modulating beta-catenin-mediated transcription in cells with mutant APC.

Journal: Annals of the New York Academy of Sciences 20051101

Title: Activation of protein kinase G up-regulates expression of 15-lipoxygenase-1 in human colon cancer cells.

Journal: Cancer research 20050915

Title: Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20050701

Title: The nonsteroidal anti-inflammatory drug Exisulind selectively induces apoptosis via JNK in secondary acute myeloid leukemia after myelodysplastic syndrome.

Journal: Cell cycle (Georgetown, Tex.) 20050601

Title: A phase I/II dose-escalation study of exisulind and docetaxel in patients with hormone-refractory prostate cancer.

Journal: BJU international 20050501

Title: A phase I/II study of exisulind in combination with docetaxel/carboplatin in patients with metastatic non-small-cell lung cancer.

Journal: Clinical lung cancer 20050501

Title: Sulindac enhances adenoviral vector expressing mda-7/IL-24-mediated apoptosis in human lung cancer.

Journal: Molecular cancer therapeutics 20050201

Title: Nobiletin, a citrus flavonoid, down-regulates matrix metalloproteinase-7 (matrilysin) expression in HT-29 human colorectal cancer cells.

Journal: Bioscience, biotechnology, and biochemistry 20050201

Title: Inhibition of extracellular-signal regulated kinases 1/2 is required for apoptosis of human colon cancer cells in vitro by sulindac metabolites.

Journal: Cancer research 20041115

Title: Regression of mouse prostatic intraepithelial neoplasia by nonsteroidal anti-inflammatory drugs in the transgenic adenocarcinoma mouse prostate model.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20041115

Title: A phase I and pharmacokinetic study of exisulind and docetaxel in patients with advanced solid tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20041101

Title: Suppression of angiogenic activity of sera from diabetic patients with non-proliferative retinopathy by compounds of herbal origin and sulindac sulfone.

Journal: International journal of molecular medicine 20041001

Title: Glutathione-S-transferase P1-1 protects aberrant crypt foci from apoptosis induced by deoxycholic acid.

Journal: Gastroenterology 20040801

Title: Effect of nonsteroidal anti-inflammatory drugs on beta-catenin protein levels and catenin-related transcription in human colorectal cancer cells.

Journal: British journal of cancer 20040705

Title: Activation of protein kinase G is sufficient to induce apoptosis and inhibit cell migration in colon cancer cells.

Journal: Cancer research 20040601

Title: Exisulind: Aptosyn, FGN 1, Prevatac, sulindac sulfone.

Journal: Drugs in R&D 20040101

Title: Combinatorial chemoprevention: efficacy of lovostatin and exisulind on the formation and progression of aberrant crypt foci.

Journal: Anticancer research 20040101

Title: Cox-2 is needed but not sufficient for apoptosis induced by Cox-2 selective inhibitors in colon cancer cells.

Journal: Apoptosis : an international journal on programmed cell death 20031201

Title: Cyclooxygenase-independent induction of apoptosis by sulindac sulfone is mediated by polyamines in colon cancer.

Journal: The Journal of biological chemistry 20031128

Title: The metabolism of sulindac enhances its scavenging activity against reactive oxygen and nitrogen species.

Journal: Free radical biology & medicine 20031101

Title: Exisulind and related compounds inhibit expression and function of the androgen receptor in human prostate cancer cells.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20031015

Title: Phase I and II study of exisulind in combination with capecitabine in patients with metastatic breast cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20030915

Title: Sulindac metabolites induce caspase- and proteasome-dependent degradation of beta-catenin protein in human colon cancer cells.

Journal: Molecular cancer therapeutics 20030901

Title: Exisulind-induced apoptosis in a non-small cell lung cancer orthotopic lung tumor model augments docetaxel treatment and contributes to increased survival.

Journal: Molecular cancer therapeutics 20030501

Title: Chemoprevention of colorectal cancer: slow, steady progress.

Journal: Cleveland Clinic journal of medicine 20030401

Title: What's new in the treatment of advanced prostate cancer?

Journal: European journal of cancer (Oxford, England : 1990) 20030101

Title: Exisulind and CP248 induce growth inhibition and apoptosis in human esophageal adenocarcinoma and squamous carcinoma cells.

Journal: Journal of experimental therapeutics & oncology 20030101

Title: Pro-apoptotic actions of exisulind and CP461 in SW480 colon tumor cells involve beta-catenin and cyclin D1 down-regulation.

Journal: Biochemical pharmacology 20021101

Title: Rapid development of colitis in NSAID-treated IL-10-deficient mice.

Journal: Gastroenterology 20021101

Title: Benzylamide sulindac analogues induce changes in cell shape, loss of microtubules and G(2)-M arrest in a chronic lymphocytic leukemia (CLL) cell line and apoptosis in primary CLL cells.

Journal: Cancer research 20021015

Title: Vasodilator-stimulated phosphoprotein (VASP) phosphorylation provides a biomarker for the action of exisulind and related agents that activate protein kinase G.

Journal: Molecular cancer therapeutics 20020801

Title: Sulindac derivative-induced apoptosis in a human umbilical vein endothelial cell line ECV304.

Journal: Chinese medical journal 20020701

Title: Novel clinical trials in androgen-independent prostate cancer.

Journal: Clinical prostate cancer 20020601

Title: PPARgamma-mediated antineoplastic effect of NSAID sulindac on human oral squamous carcinoma cells.

Journal: International journal of cancer 20020420

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: CP248, a derivative of exisulind, causes growth inhibition, mitotic arrest, and abnormalities in microtubule polymerization in glioma cells.

Journal: Molecular cancer therapeutics 20020401

Title: Exisulind in combination with docetaxel inhibits growth and metastasis of human lung cancer and prolongs survival in athymic nude rats with orthotopic lung tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20020301

Title: GATA-6 transcriptional regulation of 15-lipoxygenase-1 during NSAID-induced apoptosis in colorectal cancer cells.

Journal: Cancer research 20020215

Title: Preclinical and clinical studies of docetaxel and exisulind in the treatment of human lung cancer.

Journal: Seminars in oncology 20020201

Title: Sulindac induces apoptosis, inhibits proliferation and activates caspase-3 in Hep G2 cells.

Journal: Anticancer research 20020101

Title: beta-Catenin signaling: therapeutic strategies in oncology.

Journal: Cancer biology & therapy 20020101

Title: Progression and NSAID-induced apoptosis in malignant melanomas are independent of cyclooxygenase II.

Journal: Melanoma research 20011201

Title: Cyclic GMP-dependent protein kinase activation and induction by exisulind and CP461 in colon tumor cells.

Journal: The Journal of pharmacology and experimental therapeutics 20011101

Title: Exisulind, a selective apoptotic antineoplastic drug.

Journal: Expert opinion on investigational drugs 20011001

Title: Sulindac sulfide-induced apoptosis involves death receptor 5 and the caspase 8-dependent pathway in human colon and prostate cancer cells.

Journal: Cancer research 20010915

Title: Safety and efficacy of exisulind for treatment of recurrent prostate cancer after radical prostatectomy.

Journal: The Journal of urology 20010901

Title: Docetaxel and exisulind in hormone-refractory prostate cancer.

Journal: Seminars in oncology 20010801

Title: Sulindac-associated choledocholithiasis.

Journal: The American journal of gastroenterology 20010701

Title: Rat colorectal tumours treated with a range of non-steroidal anti-inflammatory drugs show altered cyclooxygenase-2 and cyclooxygenase-1 splice variant mRNA expression levels.

Journal: Carcinogenesis 20010601

Title: Exisulind, a novel proapoptotic drug, inhibits rat urinary bladder tumorigenesis.

Journal: Cancer research 20010515

Title: Protein kinase G activates the JNK1 pathway via phosphorylation of MEKK1.

Journal: The Journal of biological chemistry 20010511

Title: Sulindac and its derivatives: a novel class of anticancer agents.

Journal: Current opinion in investigational drugs (London, England : 2000) 20010501

Title: Proapoptotic anti-inflammatory drugs.

Journal: Urology 20010401

Title: Inhibition of extracellular signal-regulated kinase 1/2 phosphorylation and induction of apoptosis by sulindac metabolites.

Journal: Cancer research 20010215

Title: Chemoprevention of intestinal polyposis in the Apcdelta716 mouse by rofecoxib, a specific cyclooxygenase-2 inhibitor.

Journal: Cancer research 20010215

Title: Growth-suppressive effect of non-steroidal anti-inflammatory drugs on 11 colon-cancer cell lines and fluorescence differential display of genes whose expression is influenced by sulindac.

Journal: International journal of cancer 20001215

Title: Sulindac sulfone inhibits K-ras-dependent cyclooxygenase-2 expression in human colon cancer cells.

Journal: Cancer research 20001201

Title: Non-steroidal anti-inflammatory drugs with different cyclooxygenase inhibitory profiles that prevent aberrant crypt foci formation but vary in acute gastrotoxicity in a rat model.

Journal: Journal of gastroenterology and hepatology 20001201

Title: Cyclic GMP mediates apoptosis induced by sulindac derivatives via activation of c-Jun NH2-terminal kinase 1.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20001001

Title: Exisulind induction of apoptosis involves guanosine 3',5'-cyclic monophosphate phosphodiesterase inhibition, protein kinase G activation, and attenuated beta-catenin.

Journal: Cancer research 20000701

Title: Inhibition of rat colon tumors by sulindac and sulindac sulfone is independent of K-ras (codon 12) mutation.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20000201

Title: Chemopreventive efficacy of sulindac sulfone against colon cancer depends on time of administration during carcinogenic process.

Journal: Cancer research 19990715

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Tags:59973-80-7 Molecular Formula|59973-80-7 MDL|59973-80-7 SMILES|59973-80-7 1H-Indene-3-acetic acid,5-fluoro-2-methyl-1-[[4-(methylsulfonyl)phenyl]methylene]-, (1Z)-