SC-236 - CAS 170569-86-5
Catalog number: 170569-86-5
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C16H11ClF3N3O2S
Molecular Weight:
401.8
COA:
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Targets:
Cox-2
Description:
A potent, selective COX-2 inhibitor
Brife Description:
A potent, selective COX-2 inhibitor
Appearance:
A crystalline solid
Synonyms:
SC-236; SC 236; SC236; 4-[5-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-benzenesulfonamide
Solubility:
Soluble to 100 mM in DMSO and to 100 mM in ethanol
Storage:
Store at -20°C
MSDS:
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Quality Standard:
In-house
Quantity:
Grams-Kilos
InChIKey:
NSQNZEUFHPTJME-UHFFFAOYSA-N
InChI:
1S/C16H11ClF3N3O2S/c17-11-3-1-10(2-4-11)14-9-15(16(18,19)20)22-23(14)12-5-7-13(8-6-12)26(21,24)25/h1-9H,(H2,21,24,25)
Canonical SMILES:
ClC1=CC=C(C=C1)C2=CC(C(F)(F)F)=NN2C3=CC=C(S(=O)(N)=O)C=C3
1.Enhancement of doxorubicin cytotoxicity on human esophageal squamous cell carcinoma cells by indomethacin and 4-[5-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC236) via inhibiting P-glycoprotein activity.
Yu L;Wu WK;Li ZJ;Liu QC;Li HT;Wu YC;Cho CH Mol Pharmacol. 2009 Jun;75(6):1364-73. doi: 10.1124/mol.108.053546. Epub 2009 Mar 5.
Doxorubicin is a chemotherapeutic drug widely used for the treatment of advanced esophageal squamous cell carcinoma. However, its efficacy is usually limited by the development of multidrug resistance (MDR), which has been linked to the up-regulation of P-glycoprotein (P-gp) in cancer cells. Conventional nonsteroidal anti-inflammatory drugs and cyclooxygenase 2 (COX-2)-selective inhibitors have been demonstrated to overcome MDR in some cancer cells. Here we sought to elucidate the effect of COX inhibitors on doxorubicin-induced cytotoxicity in relation to P-gp function in human esophageal squamous cell carcinoma cells. Among the five tested COX inhibitors [indomethacin, 4-[5-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-benzenesulfonamide (SC236), 5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-trifluorom-ethylpyrazole (SC560), nimesulide, and N-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide (NS398)], all of which substantially suppressed prostaglandin E(2) (PGE(2)) production to a similar extent, only the nonselective COX inhibitor indomethacin and the COX-2-selective inhibitor SC236 enhanced cytotoxic effects of doxorubicin on HKESC-1 and HKESC-2 cells. Moreover, these effects could not be reversed by the addition of PGE(2).
2.Pronounced radiosensitization of cultured human cancer cells by COX inhibitor under acidic microenvironment.
Shah T;Ryu S;Lee HJ;Brown S;Kim JH Int J Radiat Oncol Biol Phys. 2002 Aug 1;53(5):1314-8.
PURPOSE: ;To demonstrate the influence of pH on the cytotoxicity and radiosensitization by COX (cyclooxygenase) -1 and -2 inhibitors using established human cancer cells in culture.;METHODS AND MATERIALS: ;Nonselective COX inhibitor, ibuprofen (IB), and selective COX-2 inhibitor, SC-236, were used to determine the cytotoxicity and radiosensitization at varying pH of culture media. Human colon carcinoma cell line (HT-29) was exposed to the drug alone and in combination with radiation at different pH of the cell culture media. The end point was clonogenic ability of the single-plated cells after the treatment.;RESULTS: ;Cytotoxicity and radiosensitization of IB increased with higher drug concentration and longer exposure time. The most significant radiosensitization was seen with IB (1.5 mM) for 2-h treatment at pH 6.7 before irradiation. The dose-modifying factor as defined by the ratio of radiation doses required to achieve the same effect on cell survival was 1.8 at 10% survival level. In contrast, SC-236 (50 microM for 2-8 h) showed no pH-dependent cytotoxicity. There was modest increase in the cell killing at lower doses of radiation.;CONCLUSION: ;An acidic pH was an important factor affecting the increased cytotoxicity and radiosensitization by ibuprofen.
3.Cyclooxygenase-2 inhibitor SC-236 [4-[5-(4-chlorophenyl)-3-(trifluoromethyl)-1-pyrazol-1-l] benzenesulfonamide] suppresses nuclear factor-kappaB activation and phosphorylation of p38 mitogen-activated protein kinase, extracellular signal-regulated kinase, and c-Jun N-terminal kinase in human mast cell line cells.
Kim SJ;Jeong HJ;Choi IY;Lee KM;Park RK;Hong SH;Kim HM J Pharmacol Exp Ther. 2005 Jul;314(1):27-34. Epub 2005 Mar 22.
SC-236 [4-[5-(4-chlorophenyl)-3-(trifluoromethyl)-1-pyrazol-1-l] benzenesulfonamide; C16H11ClF3N3O2S] is a highly selective cyclooxygenase (COX)-2 inhibitor. However, the exact mechanism that accounts for the anti-inflammatory effect of SC-236 is not completely understood. The aim of the present study was to elucidate whether and how SC-236 modulates the inflammatory reaction in a stimulated human mast cell (HMC) line, HMC-1. SC-236 inhibited the expression of tumor necrosis factor-alpha, interleukin (IL)-6, IL-8, vascular endothelial growth factor, COX-2, inducible nitric-oxide synthase, and hypoxia-inducible factor-1alpha in phorbol 12-myristate 13-acetate plus calcium ionophore A23187 (PMACI)-stimulated HMC-1. SC-236 suppressed nuclear factor (NF)-kappaB activation induced by PMACI, leading to suppression of IkappaB-alpha phosphorylation and degradation. SC-236 also suppressed strong induction of NF-kappaB promoter-mediated luciferase activity. In addition, SC-236 suppressed PMACI-induced phosphorylation of the mitogen-activated protein kinase p38, the extracellular-regulated kinase p44, and the c-Jun N-terminal kinase and induced expression of mitogen-activated protein kinase phosphatase-1.
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CAS 170569-86-5 SC-236

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