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Merck

S3131

Sulindac sulfide

≥98% (HPLC), solid

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :
C20H17FO2S
Numéro CAS:
32004-67-4
Poids moléculaire :
340.41
NACRES:
NA.77
PubChem Substance ID:
24899543
UNSPSC Code:
12352200
EC Number:
250-892-2
MDL number:
MFCD00869764

Principaux documents

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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-

Catégories apparentées

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

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

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

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number
0000499838
0000499838
0000421266
0000421266
0000300188

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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
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
Luise Richter et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(33), 14597-14602 (2010-08-04)
Following ectodomain shedding by beta-secretase, successive proteolytic cleavages within the transmembrane sequence (TMS) of the amyloid precursor protein (APP) catalyzed by gamma-secretase result in the release of amyloid-beta (Abeta) peptides of variable length. Abeta peptides with 42 amino acids appear
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
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