Home Sulfos 1H-Indene-3-acetic acid,5-fluoro-2-methyl-1-[[4-(methylsulfonyl)phenyl]methylene]-, (1Z)-

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

CAS No.:
59973-80-7
Catalog Number:
AG00EC0N
Molecular Formula:
C20H17FO4S
Molecular Weight:
372.4100
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
Product Description
Catalog Number:
AG00EC0N
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
IUPAC Name:
2-[(3Z)-6-fluoro-2-methyl-3-[(4-methylsulfonylphenyl)methylidene]inden-1-yl]acetic acid
InChI:
InChI=1S/C20H17FO4S/c1-12-17(9-13-3-6-15(7-4-13)26(2,24)25)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-
InChI Key:
MVGSNCBCUWPVDA-MFOYZWKCSA-N
SMILES:
OC(=O)CC1=C(C)/C(=C/c2ccc(cc2)S(=O)(=O)C)/c2c1cc(F)cc2
UNII:
K619IIG2R9
NSC Number:
719619
Properties
Complexity:
723  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1  
Exact Mass:
372.083g/mol
Formal Charge:
0
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
372.41g/mol
Monoisotopic Mass:
372.083g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
79.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.5  
Literature
Title Journal
Structural analysis of sulindac as an inhibitor of aldose reductase and AKR1B10. Chemico-biological interactions 20150605
Nitric oxide donor exisulind is an effective inhibitor of murine photocarcinogenesis. Photochemistry and photobiology 20120901
A prospective, controlled phase II study of neoadjuvant exisulind therapy before radical prostatectomy: effect on apoptosis. Urology 20120801
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. Medical oncology (Northwood, London, England) 20120601
The molecular basis for inhibition of sulindac and its metabolites towards human aldose reductase. FEBS letters 20120102
Regulation of 15-hydroxyprostaglandin dehydrogenase (15-PGDH) by non-steroidal anti-inflammatory drugs (NSAIDs). Prostaglandins & other lipid mediators 20111101
Sulindac and its metabolites: sulindac sulfide and sulindac sulfone enhance cytotoxic effects of arsenic trioxide on leukemic cell lines. Toxicology in vitro : an international journal published in association with BIBRA 20110801
Studies on the metabolism and biological activity of the epimers of sulindac. Drug metabolism and disposition: the biological fate of chemicals 20110601
Optimisation and validation of a fast HPLC method for the quantification of sulindac and its related impurities. Journal of pharmaceutical and biomedical analysis 20110325
[Antitumor effects of sulindac in ovarian cell cultures]. Ginekologia polska 20110301
Sulindac sulfide reverses aberrant self-renewal of progenitor cells induced by the AML-associated fusion proteins PML/RARα and PLZF/RARα. PloS one 20110101
Therapeutic potential of sulindac hydroxamic acid against human pancreatic and colonic cancer cells. European journal of medicinal chemistry 20101101
Sulindac and its metabolites inhibit multiple transport proteins in rat and human hepatocytes. The Journal of pharmacology and experimental therapeutics 20100801
Sulindac metabolites induce proteosomal and lysosomal degradation of the epidermal growth factor receptor. Cancer prevention research (Philadelphia, Pa.) 20100401
Curcumin potentiates the pro-apoptotic effects of sulindac sulfone in colorectal cancer. Expert opinion on investigational drugs 20100401
Sulindac sulfone induces a decrease of beta-catenin in HNSCC. Anticancer research 20100201
15-Hydroxyprostaglandin dehydrogenase (15-PGDH) is up-regulated by flurbiprofen and other non-steroidal anti-inflammatory drugs in human colon cancer HT29 cells. Archives of biochemistry and biophysics 20090715
Synthesis, pharmacological evaluation and docking studies of new sulindac analogues. European journal of medicinal chemistry 20090501
A phase II study of carboplatin, etoposide, and exisulind in patients with extensive small cell lung cancer: CALGB 30104. Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20090201
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 of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20080901
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. Clinical genitourinary cancer 20080901
Activation of protein kinase G Increases the expression of p21CIP1, p27KIP1, and histidine triad protein 1 through Sp1. Cancer research 20080701
Interactions of sulindac and its metabolites with phospholipid membranes: an explanation for the peroxidation protective effect of the bioactive metabolite. Free radical research 20080701
Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2). Journal of medicinal chemistry 20080612
The proapoptotic effects of sulindac, sulindac sulfone and indomethacin are mediated by nucleolar translocation of the RelA(p65) subunit of NF-kappaB. Oncogene 20080417
Sulindac and its metabolites induce carcinogen metabolizing enzymes in human colon cancer cells. International journal of cancer 20080301
A comparison of the effectiveness of selected non-steroidal anti-inflammatory drugs and their derivatives against cancer cells in vitro. Cancer chemotherapy and pharmacology 20080201
Malignant transformation of normal enterocytes following downregulation of Bak expression. Digestion 20080101
Exisulind in combination with celecoxib modulates epidermal growth factor receptor, cyclooxygenase-2, and cyclin D1 against prostate carcinogenesis: in vivo evidence. Clinical cancer research : an official journal of the American Association for Cancer Research 20071001
Docetaxel and exisulind in previously treated non-small cell lung cancer (NSCLC) patients: a multicenter, phase II clinical trial. Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20071001
Sulindac sulfone modulates beta-catenin in human cholesteatoma cell culture. Archives of medical research 20070501
Nonsteroidal anti-inflammatory drugs induce colorectal cancer cell apoptosis by suppressing 14-3-3epsilon. Cancer research 20070401
Alpha-tocopheryl succinate sensitizes human colon cancer cells to exisulind-induced apoptosis. Apoptosis : an international journal on programmed cell death 20070201
Differential activity of sulindac metabolites against squamous cell carcinoma of the head and neck is mediated by p21waf1/cip1 induction and cell cycle inhibition. Cancer biology & therapy 20070101
Effects of oral dosing paradigms (gavage versus diet) on pharmacokinetics and pharmacodynamics. Chemico-biological interactions 20061201
Gene expression profiling in R-flurbiprofen-treated prostate cancer: R-Flurbiprofen regulates prostate stem cell antigen through activation of AKT kinase. Biochemical pharmacology 20061115
Exisulind induces apoptosis in advanced myelodysplastic syndrome (MDS) and acute myeloid leukaemia/MDS. British journal of haematology 20061101
p38MAPK inhibitor SB203580 sensitizes human SNU-C4 colon cancer cells to exisulind-induced apoptosis. Oncology reports 20061101
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. Prostaglandins & other lipid mediators 20061001
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 of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20060901
Chemopreventive alteration of the cell-cell adhesion in head and neck squamous cell cancer. Oncology reports 20060801
Phase II evaluation of docetaxel plus exisulind in patients with androgen independent prostate carcinoma. American journal of clinical oncology 20060801
Capillary electrophoresis combining field-amplified sample stacking and electroosmotic flow suppressant for analysis of sulindac and its two metabolites in plasma. Journal of chromatography. A 20060630
Sulindac sulfide and exisulind inhibit expression of the estrogen and progesterone receptors in human breast cancer cells. Clinical cancer research : an official journal of the American Association for Cancer Research 20060601
Apoptosis: a relevant tool for anticancer therapy. Annals of oncology : official journal of the European Society for Medical Oncology 20060601
Exisulind and guanylyl cyclase C induce distinct antineoplastic signaling mechanisms in human colon cancer cells. Molecular cancer therapeutics 20060501
The geminal dimethyl analogue of Flurbiprofen as a novel Abeta42 inhibitor and potential Alzheimer's disease modifying agent. Bioorganic & medicinal chemistry letters 20060415
Sporadic adenomatous polyp regression with exisulind is effective but toxic: a randomised, double blind, placebo controlled, dose-response study. Gut 20060301
Phase I/II study of gemcitabine and exisulind as second-line therapy in patients with advanced non-small cell lung cancer. Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20060301
Induction of spermidine/spermine N1-acetyltransferase (SSAT) by aspirin in Caco-2 colon cancer cells. The Biochemical journal 20060215
Phase I clinical trial of weekly docetaxel and exisulind, a novel inducer of apoptosis. Investigational new drugs 20060101
The sulindac derivatives OSI-461, OSIP486823, and OSIP487703 arrest colon cancer cells in mitosis by causing microtubule depolymerization. Molecular cancer therapeutics 20060101
Exisulind in the treatment of prostate cancer. Expert review of anticancer therapy 20051201
Sulindac sulfone is most effective in modulating beta-catenin-mediated transcription in cells with mutant APC. Annals of the New York Academy of Sciences 20051101
Activation of protein kinase G up-regulates expression of 15-lipoxygenase-1 in human colon cancer cells. Cancer research 20050915
Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug metabolism and disposition: the biological fate of chemicals 20050701
The nonsteroidal anti-inflammatory drug Exisulind selectively induces apoptosis via JNK in secondary acute myeloid leukemia after myelodysplastic syndrome. Cell cycle (Georgetown, Tex.) 20050601
A phase I/II dose-escalation study of exisulind and docetaxel in patients with hormone-refractory prostate cancer. BJU international 20050501
A phase I/II study of exisulind in combination with docetaxel/carboplatin in patients with metastatic non-small-cell lung cancer. Clinical lung cancer 20050501
Sulindac enhances adenoviral vector expressing mda-7/IL-24-mediated apoptosis in human lung cancer. Molecular cancer therapeutics 20050201
Nobiletin, a citrus flavonoid, down-regulates matrix metalloproteinase-7 (matrilysin) expression in HT-29 human colorectal cancer cells. Bioscience, biotechnology, and biochemistry 20050201
Inhibition of extracellular-signal regulated kinases 1/2 is required for apoptosis of human colon cancer cells in vitro by sulindac metabolites. Cancer research 20041115
Regression of mouse prostatic intraepithelial neoplasia by nonsteroidal anti-inflammatory drugs in the transgenic adenocarcinoma mouse prostate model. Clinical cancer research : an official journal of the American Association for Cancer Research 20041115
A phase I and pharmacokinetic study of exisulind and docetaxel in patients with advanced solid tumors. Clinical cancer research : an official journal of the American Association for Cancer Research 20041101
Suppression of angiogenic activity of sera from diabetic patients with non-proliferative retinopathy by compounds of herbal origin and sulindac sulfone. International journal of molecular medicine 20041001
Glutathione-S-transferase P1-1 protects aberrant crypt foci from apoptosis induced by deoxycholic acid. Gastroenterology 20040801
Effect of nonsteroidal anti-inflammatory drugs on beta-catenin protein levels and catenin-related transcription in human colorectal cancer cells. British journal of cancer 20040705
Activation of protein kinase G is sufficient to induce apoptosis and inhibit cell migration in colon cancer cells. Cancer research 20040601
Exisulind: Aptosyn, FGN 1, Prevatac, sulindac sulfone. Drugs in R&D 20040101
Combinatorial chemoprevention: efficacy of lovostatin and exisulind on the formation and progression of aberrant crypt foci. Anticancer research 20040101
Cox-2 is needed but not sufficient for apoptosis induced by Cox-2 selective inhibitors in colon cancer cells. Apoptosis : an international journal on programmed cell death 20031201
Cyclooxygenase-independent induction of apoptosis by sulindac sulfone is mediated by polyamines in colon cancer. The Journal of biological chemistry 20031128
The metabolism of sulindac enhances its scavenging activity against reactive oxygen and nitrogen species. Free radical biology & medicine 20031101
Exisulind and related compounds inhibit expression and function of the androgen receptor in human prostate cancer cells. Clinical cancer research : an official journal of the American Association for Cancer Research 20031015
Phase I and II study of exisulind in combination with capecitabine in patients with metastatic breast cancer. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20030915
Sulindac metabolites induce caspase- and proteasome-dependent degradation of beta-catenin protein in human colon cancer cells. Molecular cancer therapeutics 20030901
Exisulind-induced apoptosis in a non-small cell lung cancer orthotopic lung tumor model augments docetaxel treatment and contributes to increased survival. Molecular cancer therapeutics 20030501
Chemoprevention of colorectal cancer: slow, steady progress. Cleveland Clinic journal of medicine 20030401
What's new in the treatment of advanced prostate cancer? European journal of cancer (Oxford, England : 1990) 20030101
Exisulind and CP248 induce growth inhibition and apoptosis in human esophageal adenocarcinoma and squamous carcinoma cells. Journal of experimental therapeutics & oncology 20030101
Pro-apoptotic actions of exisulind and CP461 in SW480 colon tumor cells involve beta-catenin and cyclin D1 down-regulation. Biochemical pharmacology 20021101
Rapid development of colitis in NSAID-treated IL-10-deficient mice. Gastroenterology 20021101
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. Cancer research 20021015
Vasodilator-stimulated phosphoprotein (VASP) phosphorylation provides a biomarker for the action of exisulind and related agents that activate protein kinase G. Molecular cancer therapeutics 20020801
Sulindac derivative-induced apoptosis in a human umbilical vein endothelial cell line ECV304. Chinese medical journal 20020701
Novel clinical trials in androgen-independent prostate cancer. Clinical prostate cancer 20020601
PPARgamma-mediated antineoplastic effect of NSAID sulindac on human oral squamous carcinoma cells. International journal of cancer 20020420
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. The Journal of biological chemistry 20020419
CP248, a derivative of exisulind, causes growth inhibition, mitotic arrest, and abnormalities in microtubule polymerization in glioma cells. Molecular cancer therapeutics 20020401
Exisulind in combination with docetaxel inhibits growth and metastasis of human lung cancer and prolongs survival in athymic nude rats with orthotopic lung tumors. Clinical cancer research : an official journal of the American Association for Cancer Research 20020301
GATA-6 transcriptional regulation of 15-lipoxygenase-1 during NSAID-induced apoptosis in colorectal cancer cells. Cancer research 20020215
Preclinical and clinical studies of docetaxel and exisulind in the treatment of human lung cancer. Seminars in oncology 20020201
Sulindac induces apoptosis, inhibits proliferation and activates caspase-3 in Hep G2 cells. Anticancer research 20020101
beta-Catenin signaling: therapeutic strategies in oncology. Cancer biology & therapy 20020101
Progression and NSAID-induced apoptosis in malignant melanomas are independent of cyclooxygenase II. Melanoma research 20011201
Cyclic GMP-dependent protein kinase activation and induction by exisulind and CP461 in colon tumor cells. The Journal of pharmacology and experimental therapeutics 20011101
Exisulind, a selective apoptotic antineoplastic drug. Expert opinion on investigational drugs 20011001
Sulindac sulfide-induced apoptosis involves death receptor 5 and the caspase 8-dependent pathway in human colon and prostate cancer cells. Cancer research 20010915
Safety and efficacy of exisulind for treatment of recurrent prostate cancer after radical prostatectomy. The Journal of urology 20010901
Docetaxel and exisulind in hormone-refractory prostate cancer. Seminars in oncology 20010801
Sulindac-associated choledocholithiasis. The American journal of gastroenterology 20010701
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. Carcinogenesis 20010601
Exisulind, a novel proapoptotic drug, inhibits rat urinary bladder tumorigenesis. Cancer research 20010515
Protein kinase G activates the JNK1 pathway via phosphorylation of MEKK1. The Journal of biological chemistry 20010511
Sulindac and its derivatives: a novel class of anticancer agents. Current opinion in investigational drugs (London, England : 2000) 20010501
Proapoptotic anti-inflammatory drugs. Urology 20010401
Inhibition of extracellular signal-regulated kinase 1/2 phosphorylation and induction of apoptosis by sulindac metabolites. Cancer research 20010215
Chemoprevention of intestinal polyposis in the Apcdelta716 mouse by rofecoxib, a specific cyclooxygenase-2 inhibitor. Cancer research 20010215
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. International journal of cancer 20001215
Sulindac sulfone inhibits K-ras-dependent cyclooxygenase-2 expression in human colon cancer cells. Cancer research 20001201
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 of gastroenterology and hepatology 20001201
Cyclic GMP mediates apoptosis induced by sulindac derivatives via activation of c-Jun NH2-terminal kinase 1. Clinical cancer research : an official journal of the American Association for Cancer Research 20001001
Exisulind induction of apoptosis involves guanosine 3',5'-cyclic monophosphate phosphodiesterase inhibition, protein kinase G activation, and attenuated beta-catenin. Cancer research 20000701
Inhibition of rat colon tumors by sulindac and sulindac sulfone is independent of K-ras (codon 12) mutation. American journal of physiology. Gastrointestinal and liver physiology 20000201
Chemopreventive efficacy of sulindac sulfone against colon cancer depends on time of administration during carcinogenic process. Cancer research 19990715
Properties