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Merck
CN

S1438

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
NACRES:
NA.77
PubChem Substance ID:
24278693
UNSPSC Code:
51111800
MDL number:
MFCD01317811

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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+

SMILES string

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

InChI key

MVGSNCBCUWPVDA-RQZCQDPDSA-N

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.

Quality Level

100

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

Metabolite of sulindac that inhibits cell growth by inducing apoptosis independently of cyclooxygenase inhibition. Inhibits the development and induces regression of premalignant adenomatous polyps.
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

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCJ8579
MKCH1764
MKCF3239
MKCD7802
MKCD7516

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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
Steven Attia et al.
Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer, 3(9), 1018-1025 (2008-09-02)
Exisulind is an apoptotic agent with preclinical activity in non-small cell lung cancer (NSCLC). Vinorelbine is safe and effective in older patients with advanced NSCLC. We assessed these agents together as palliative treatment for older patients with advanced NSCLC. Chemotherapy-naive
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
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Data Sheet - S1438

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