S3131
Sulindac sulfide
≥98% (HPLC), solid
Synonym(s):
(Z)-5-Fluoro-2-methyl-1-[p-(methylthio)benzylidene]indene-3-acetic acid
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About This Item
Empirical Formula (Hill Notation):
C20H17FO2S
CAS Number:
Molecular Weight:
340.41
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
250-892-2
MDL number:
Quality Level
assay
≥98% (HPLC)
form
solid
color
yellow
solubility
DMSO: ≥22 mg/mL
SMILES string
[H]\C(c1ccc(SC)cc1)=C2/C(C)=C(CC(O)=O)c3cc(F)ccc23
InChI
1S/C20H17FO2S/c1-12-17(9-13-3-6-15(24-2)7-4-13)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
LFWHFZJPXXOYNR-MFOYZWKCSA-N
Application
Human endothelial cells, HMEC-1 were treated with Sulindac sulfide and the effect on cell survival was studies by MTT assay.
Biochem/physiol Actions
Sulindac sulfide is a non-steroidal anti-inflammatory compound with a preference for COX-1; it is an inhibitor of Ras activation of Raf-1. It impairs nucleotide exchange on Ras by CDC25 and accelerates Ras hydrolysis of GTP by p120GAP. It is an active metabolite of sulindac. It is also shown to inhibit growth and induce apoptosis in human prostate cancer cells through a COX-1 and COX-2 independent mechanism. Sulindac sulfide is an analgesic that has antiproliferative and apoptotic effects. It inhibits the expression and activity of cyclooxygenase-2 in human colon cancer cells and reduces tumor burden in adenomatous polyposis patients.
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signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Repr. 2 - Resp. Sens. 1 - Skin Sens. 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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Related Content
Z Zhang et al.
Gastroenterology, 118(6), 1012-1017 (2000-06-02)
Many reports indicate that nonsteroidal anti-inflammatory drugs (NSAIDs) have antineoplastic effects, but the precise molecular mechanism(s) responsible are unclear. We evaluated the effect of cyclooxygenase (COX) inhibitors (NSAIDs) on human colon carcinoma cells (HCA-7) and identified several genes that are
J T Lim et al.
Biochemical pharmacology, 58(7), 1097-1107 (1999-09-14)
We examined the activity of two metabolites of sulindac (a nonsteroidal anti-inflammatory drug), sulindac sulfide and sulindac sulfone (exisulind, Prevatec), and a novel highly potent analog of exisulind (CP248) on a series of human prostate epithelial cell lines. Marked growth
Andy J Liedtke et al.
Journal of medicinal chemistry, 55(5), 2287-2300 (2012-01-24)
Prostaglandins (PGs) are powerful lipid mediators in many physiological and pathophysiological responses. They are produced by oxidation of arachidonic acid (AA) by cyclooxygenases (COX-1 and COX-2) followed by metabolism of endoperoxide intermediates by terminal PG synthases. PG biosynthesis is inhibited