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S1438

Sigma-Aldrich

Sulindac sulfone

≥94% (HPLC), (solid or powder)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H17FO4S
CAS Number:
59864-04-9
Molecular Weight:
372.41
MDL number:
MFCD01317811
UNSPSC Code:
51111800
PubChem Substance ID:
24278693
NACRES:
NA.77

Quality Level

100

Assay

≥94% (HPLC)

form

(solid or powder)

color

, Light Yellow to Dark Yellow

solubility

DMSO: >25 mg/mL
ethanol: 3 mg/mL (warm)
acetone: 5 mg (plus 0.1 ml)

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

SMILES string

CC1=C(CC(O)=O)c2cc(F)ccc2\C1=C\c3ccc(cc3)S(C)(=O)=O

InChI

1S/C20H17FO4S/c1-12-17(9-13-3-6-15(7-4-13)26(2,24)25)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

MVGSNCBCUWPVDA-RQZCQDPDSA-N

Application

Human endothelial cells, HMEC-1 were treated with Sulindac sulfone and the effect on cell survival was studied by MTT assay.

Biochem/physiol Actions

Sulindac sulfone is non-steroidal anti-inflammatory drug and an analgesic that has antiproliferative and apoptotic effects. It inhibits the expression and activity of cyclooxygenase-2 in human colon cancer cells1,2 and reduces tumor burden in adenomatous polyposis patients.3
Metabolite of sulindac that inhibits cell growth by inducing apoptosis independently of cyclooxygenase inhibition. Inhibits the development and induces regression of premalignant adenomatous polyps.

Features and Benefits

This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Sulindac sulfone yields clear, light yellow to dark yellow solution in acetone at 50 mg/ml.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jin Kyung Lee et al.
The Journal of pharmacology and experimental therapeutics, 334(2), 410-418 (2010-05-01)
Sulindac is a commonly used nonsteroidal anti-inflammatory drug. This study tested the hypothesis that sulindac-mediated drug-drug interactions and/or hepatotoxicity may be caused, in part, by inhibition of proteins responsible for the hepatic transport of drugs and/or bile acids by sulindac
Tien Hoang et al.
Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer, 1(3), 218-225 (2007-04-06)
The study was designed to evaluate the safety and efficacy of exisulind, a selective apoptotic antineoplastic drug, in combination with gemcitabine as second-line therapy in patients with progressing advanced non-small cell lung cancer. Patients whose disease progressed more than 3
Jun-Yang Liou et al.
Cancer research, 67(7), 3185-3191 (2007-04-06)
To determine the role of 14-3-3 in colorectal cancer apoptosis induced by nonsteroidal anti-inflammatory drugs (NSAIDs), we evaluated the effects of sulindac on 14-3-3epsilon protein expression in colorectal cancer cells. Sulindac sulfide inhibited 14-3-3epsilon proteins in HT-29 and DLD-1 cells
Gregory A Masters et al.
Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer, 1(7), 673-678 (2007-04-06)
Carboplatin and gemcitabine are one standard regimen for patients with advanced non-small cell lung cancer (NSCLC). The oral proapoptotic agent exisulind is a cyclic guanosine monophosphate phosphodiesterase that increases apoptosis in vitro. We performed a phase II trial of carboplatin
Nis Giladi et al.
Expert opinion on investigational drugs, 19 Suppl 1, S117-S124 (2010-04-14)
The use of sulindac sulfone (SFN) for colorectal cancer (CRC) therapy is limited due to its toxicity. The present study was carried out to examine whether curcumin, a novel chemopreventive agent, can potentiate the effects of low dosages of SFN
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