A metabolite of sulindac
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Parent Compound(s)
10004386Sulindac
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Sulindac sulfone

Item No. 16805

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-fluoro-2-methyl-1-[[4-(methylsulfonyl)phenyl]methylene]-1H-indene-3-acetic acid
CAS Number
59864-04-9
Synonyms
  • Exisulind
Molecular Formula
C20H17FO4S
Formula Weight
372.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:5): .15 mg/mlDMSO: 30 mg/mlEthanol: 2 mg/mlPBS (pH 7.2): .05 mg/ml
λmax
231, 283, 330 nm
SMILES
FC1=CC=C(/C(C(C)=C2CC(O)=O)=C/C3=CC=C(S(C)(=O)=O)C=C3)C2=C1
InChi Code
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-RQZCQDPDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $51

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    10 mg

    $97

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    25 mg

    $191

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    Product Description

    Sulindac (Item No. 10004386) is a non-steroidal anti-inflammatory drug that has an extensive epidemiology documenting reduced human colorectal cancer. In mouse models, sulindac was found not only to inhibit the enzymatic activity of polyp-associated COX-2, but also to downregulate the expression of colonic COX-2 protein to control levels.1 Sulindac sulfone is an oxidized metabolite of sulindac that is produced in many mammals but minimally in mice and rats.2,3 It is generally considered to be inactive against COX enzymes, although it can reduce azoxymethane-induced colon cancer in rats.4,5 Sulindac sulfone inhibits aldose reductase (IC50 = 367 nM) in vitro and may contribute to the beneficial pharmacological effects of sulindac on type 2 diabetic complications.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Boolbol, S.K., Dannenberg, A.J., Chadburn, A., et al. Cyclooxygenase-2 overexpression and tumor formation are blocked by sulindac in a murine model of familial adenomatous polyposis. Cancer Res. 56(11), 2556-2560 (1996).

    2. Kitamura, S., and Tatsumi, K. In vitro metabolism of sulindac and sulindac sulfide: Enzymatic formation of sulfoxide and sulfone. Jpn. J. Pharmacol. 32(5), 833-838 (1982).

    3. Brunell, D., Sagher, D., Kesaraju, S., et al. Studies on the metabolism and biological activity of the epimers of sulindac. Drug Metab. Dispos. 39(6), 1014-1021 (2011).

    4. Babbar, N., Ignatenko, N.A., Casero, R.A., Jr., et al. Cyclooxygenase-independent induction of apoptosis by sulindac sulfone is mediated by polyamines in colon cancer. The Journal of Biological Chemisty 278(48), 47762-47775 (2003).

    5. Piazza, G.A., Alberts, D.S., Hixson, L.J., et al. Sulindac sulfone inhibits azoxymethane-induced colon carcinogenesis in rats without reducing prostaglandin levels. Cancer Res. 57(14), 2909-2915 (1997).

    6. Zheng, X., Zhang, L., Zhai, J., et al. The molecular basis for inhibition of sulindac and its metabolites towards human aldose reductase. FEBS Lett. 586(1), 55-59 (2012).