S3131

Sulindac sulfide

Name: Sulindac sulfide
Brand: SIGMA

≥98% (HPLC), solid

Synonym(s):

(Z)-5-Fluoro-2-methyl-1-[p-(methylthio)benzylidene]indene-3-acetic acid

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All Photos(2)

About This Item

Empirical Formula (Hill Notation):

C₂₀H₁₇FO₂S

CAS Number:

32004-67-4

Molecular Weight:

340.41

NACRES:

NA.77

PubChem Substance ID:

24899543

UNSPSC Code:

12352200

EC Number:

250-892-2

MDL number:

MFCD00869764

Product Name

Sulindac sulfide, ≥98% (HPLC), solid

SMILES string

[H]\C(c1ccc(SC)cc1)=C2/C(C)=C(CC(O)=O)c3cc(F)ccc23

assay

≥98% (HPLC)

form

solid

color

yellow

solubility

DMSO: ≥22 mg/mL

Quality Level

200

InChI key

LFWHFZJPXXOYNR-MFOYZWKCSA-N

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-

Related Categories

Bioactive Small Molecule Inhibitors

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.

pictograms

GHS08,GHS07

signalword

Danger

hcodes

H302,H317,H334,H361

pcodes

P201 - P280 - P301 + P312 + P330 - P302 + P352 - P308 + P313

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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Certificates of Analysis (COA)

Lot/Batch Number

0000499838

0000421266

0000300188

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Par-4, a proapoptotic gene, is regulated by NSAIDs in human colon carcinoma cells.

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

Sulindac sulfide inhibits Ras signaling.

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

Sulindac derivatives inhibit growth and induce apoptosis in human prostate cancer cell lines.

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

Cyclooxygenase-1-selective inhibitors based on the (E)-2'-des-methyl-sulindac sulfide scaffold.

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

Insight into the colonic disposition of celecoxib in humans.

Glenn Lemmens et al.

European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 145, 105242-105242 (2020-02-06)

Although the effect of NSAIDs such as celecoxib on the progression of colorectal polyps has been established, it is currently unknown how sufficiently high concentrations of celecoxib are reached in colonic tissue. Indeed, the lipophilic and poorly soluble celecoxib is

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