Merck
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S3131

Sigma-Aldrich

Sulindac sulfide

≥98% (HPLC), solid

Synonym(s):
(Z)-5-Fluoro-2-methyl-1-[p-(methylthio)benzylidene]indene-3-acetic acid
Empirical Formula (Hill Notation):
C20H17FO2S
CAS Number:
Molecular Weight:
340.41
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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.

Packaging

5, 25 mg in glass bottle

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. S3131.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2 - Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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
C Herrmann et al.
Oncogene, 17(14), 1769-1776 (1998-10-20)
The non-steroidal anti-inflammatory drug sulindac is used in cancer prevention and therapy, but the molecular aspects of its anti-tumor effect remain unresolved. In vivo the prodrug sulindac, is converted into the metabolite sulindac sulfide. We found that sulindac sulfide strongly
Eugene Futai et al.
The Journal of biological chemistry, 291(1), 435-446 (2015-11-13)
γ-Secretase is a multisubunit membrane protein complex containing presenilin (PS1) as a catalytic subunit. Familial Alzheimer disease (FAD) mutations within PS1 were analyzed in yeast cells artificially expressing membrane-bound substrate, amyloid precursor protein, or Notch fused to Gal4 transcriptional activator.
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

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