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Merck

S8139

Sigma-Aldrich

Sulindac

≥98.0%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C20H17FO3S
Número de CAS:
Peso molecular:
356.41
EC Number:
MDL number:
UNSPSC Code:
12161501
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

assay

≥98.0%

form

powder

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

solubility

methanol: 50 mg/mL

application(s)

forensics and toxicology
veterinary

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

InChI

1S/C20H17FO3S/c1-12-17(9-13-3-6-15(7-4-13)25(2)24)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

MLKXDPUZXIRXEP-MFOYZWKCSA-N

Gene Information

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Application

Treatment of human colorectal cancer cell lines induces MRP1 and MRP3 but not other members of the MRP family. Reported to significantly increase the cytotoxicity of the anthracyclines (doxorubicin, daunorubicin and epirubicin), as well as teniposide, VP-16 and vincristine. Sulindac was tested for its effect on heat-induced denaturation of albumin in vitro28 and its ability to bind to human plasma protein.29

Biochem/physiol Actions

Sulindac 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 cells25,26 and reduces tumor burden in adenomatous polyposis patients.27
Nonsteroidal anti-inflammatory; preferential inhibitor of COX-1.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
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.

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Repr. 2 - Resp. Sens. 1 - Skin Sens. 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


Certificados de análisis (COA)

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Stephen X Skapek et al.
Pediatric blood & cancer, 60(7), 1108-1112 (2013-01-03)
Desmoid fibromatosis (desmoid tumor, DT) is a soft tissue neoplasm prone to recurrence despite complete surgical resection. Numerous small retrospective reports suggest that non-cytotoxic chemotherapy using tamoxifen and sulindac may be effective for DT. We evaluated the safety and efficacy
N M Davies et al.
Clinical pharmacokinetics, 32(6), 437-459 (1997-06-01)
Sulindac is a nonsteroidal anti-inflammatory drug (NSAID) of the indene acetic acid class. The absorption of sulindac is rapid when given orally. Sulindac is reversibly metabolised to sulindac sulphide which has anti-inflammatory and analgesic properties and is irreversibly metabolised to
Nicole A Kratochwil et al.
Biochemical pharmacology, 64(9), 1355-1374 (2002-10-24)
In spite of the large amount of plasma protein binding data for drugs, it is not obvious and there is no clear consensus among different disciplines how to deal with this parameter in multidimensional lead optimization strategies. In this work
D E Duggan
Drug metabolism reviews, 12(2), 325-337 (1981-01-01)
Sulindac is a prodrug which, following absorption, rapidly attains a metabolic equilibrium with its active pharmacophore, the sulfide metabolite. At the level of the whole body, the reversible interconversion sulindac in equilibrium sulfide, and the differing distributional and excretory properties
Johanna Wanngren et al.
The Journal of biological chemistry, 287(39), 32640-32650 (2012-08-02)
The γ-secretase complex is an appealing drug target when the therapeutic strategy is to alter amyloid-β peptide (Aβ) aggregation in Alzheimer disease. γ-Secretase is directly involved in Aβ formation and determines the pathogenic potential of Aβ by generating the aggregation-prone

Artículos

Protein-based drug transporters are expressed in Sf9 cells. Understanding the specific mechanisms of tumor cell transporters is an essential aspect of chemotherapeutic drug design.

Protein-based drug transporters are expressed in Sf9 cells. Understanding the specific mechanisms of tumor cell transporters is an essential aspect of chemotherapeutic drug design.

Protein-based drug transporters are expressed in Sf9 cells. Understanding the specific mechanisms of tumor cell transporters is an essential aspect of chemotherapeutic drug design.

Protein-based drug transporters are expressed in Sf9 cells. Understanding the specific mechanisms of tumor cell transporters is an essential aspect of chemotherapeutic drug design.

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