A selective inhibitor of COX-1
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SC-560

Item No. 70340

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole
CAS Number
188817-13-2
Molecular Formula
C17H12ClF3N2O
Formula Weight
352.7
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 150 mg/mlDMF:PBS (1:1): 1.2 mg/mlDMSO: 24 mg/mlEthanol: 22 mg/ml
λmax
232, 251 nm
SMILES
COc1ccc(cc1)n1nc(cc1c1ccc(Cl)cc1)C(F)(F)F
InChi Code
InChI=1S/C17H12ClF3N2O/c1-24-14-8-6-13(7-9-14)23-15(10-16(22-23)17(19,20)21)11-2-4-12(18)5-3-11/h2-10H,1H3
InChi Key
PQUGCKBLVKJMNT-UHFFFAOYSA-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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    1 mg

    $21

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    5 mg

    $86

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    10 mg

    $152

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    25 mg

    $329

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    Product Description

    SC-560 is a member of the diaryl heterocycle class of cyclooxygenase (COX) inhibitors which includes celecoxib (Celebrex™) and rofecoxib (Vioxx™). However, unlike these selective COX-2 inhibitors, SC-560 is a selective inhibitor of COX-1. Using human recombinant enzymes, the IC50 value for SC-560 with respect to COX-1 is 9 nM, while the corresponding IC50 value for COX-2 is 6.3 µM.1 Thus, SC-560 shows 700-fold selectivity for the COX-1 enzyme. SC-560 is orally active in the rat, where 10 mg/kg completely abolishes the ionophore-induced production of thromboxane B2 in whole blood. However, SC-560 is ineffective in the treatment of inflammation in models such as the LPS-induced rat air-pouch model, in which the COX-2 generated prostaglandins play a significant role in the inflammatory process.2 In whole cells, however, SC-560 appears to act as a non-selective COX inhibitor.3 The mechanism of the selective versus non-selective effects of SC-560 in a cell-free environment compared whole cells has not been elucidated.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Smith, C.J., Zhang, Y., Koboldt, C.M., et al. Pharmacological analysis of cyclooxygenase-1 in inflammation. Proc. Natl. Acad. Sci. USA 95(22), 13313-13318 (1998).

    2. Masferrer, J.L., Zweifel, B.S., Manning, P.T., et al. Selective inhibition of inducible cyclooxygenase 2 in vivo is antiinflammatory and nonulcerogenic. Proc. Natl. Acad. Sci. USA 91, 3228-3232 (1994).

    3. Brenneis, C., Maier, T.J., Schmidt, R., et al. Inhibition of prostaglandin E2 synthesis by SC-560 is independent of cyclooxygenase 1 inhibition. FASEB J. 20, 1352-1360 (2006).

    Product Citations

    Inazumi, T., Yamada, K., Shirata, N., et al. Prostaglandin E2-EP4 axis promotes lipolysis and fibrosis in adipose tissue leading to ectopic fat deposition and insulin resistance. Cell Rep. 33(2), 108265 (2020).

    Tamayose, C.I., Romoff, P., Toyama, D.O., et al. Non-clinical studies for evaluation of 8-C-rhamnosyl apigenin purified from Peperomia obtusifolia against acute edema. Int. J. Mol. Sci. 18(9), E1972 (2017).

    Hinz, C., Aldrovandi, M., Uhlson, C., et al. Human platelets utilize cycloxygenase-1 to generate dioxolane A3, a neutrophil-activating eicosanoid. The Journal of Biological Chemisty 291(26), 13448-13464 (2016).

    Roh, Y.J., Park, Y.G., Kang, S., et al. Effects of AFP-172 on COX-2-induced angiogenic activities on human umbilical vein endothelial cells. Graefes Arch. Clin. Exp. Ophthalmol. 250(12), 1765-1775 (2012).

    Dai, L., Perera, D.S., King, D.W., et al. Hemokinin-1 stimulates prostaglandin E2 production in human colon through activation of cyclooxygenase-2 and inhibition of 15-hydroxyprostaglandin dehydrogenase. J. Pharmacol. Exp. Ther. 340(1), 27-36 (2012).

    Reese, J., O'Mara, P.W., Poole, S.D., et al. Regulation of the fetal mouse ductus arteriosus is dependent on interaction of nitric oxide and COX enzymes in the ductal wall. Prostaglandins Other Lipid Mediat. 88(3-4), 89-96 (2009).

    Petzold, G.C., Albeanu, D.F., Sato, T.F., et al. Coupling of neural activity to blood flow in olfactory glomeruli is mediated by astrocytic pathways. Neuron. 58(6), 897-910 (2008).