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Merck

S8139

Sulindac

≥98.0%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H17FO3S
CAS Number:
38194-50-2
Molecular Weight:
356.41
NACRES:
NA.77
PubChem Substance ID:
57654635
UNSPSC Code:
12161501
EC Number:
253-819-2
MDL number:
MFCD00599589
Assay:
≥98.0%
Form:
powder
Quality level:
200

Key Documents

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InChI key

MLKXDPUZXIRXEP-MFOYZWKCSA-N

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-

SMILES string

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

biological source

synthetic (organic)

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.

Quality Level

200

Gene Information

human ... ALB(213), PTGS1(5742), PTGS2(5743)

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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

Nonsteroidal anti-inflammatory; preferential inhibitor of COX-1.
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

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
GHS06,GHS08

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

S8139-5G: + S8139-BULK: + S8139-25G: + S8139-VAR:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK5833
MKCH7987
MKCD9343
MKBZ4918V
MKBV4618V

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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
Caihua Zhu et al.
Stem cells (Dayton, Ohio), 30(10), 2065-2075 (2012-06-02)
Pharmacological targeting of breast cancer stem cells (CSCs) is highly promising for the treatment of breast cancer, as the small population of CSCs appears responsible for tumor initiation and progression and also for resistance to conventional treatment. Here we report
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
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
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