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S8139

Sigma-Aldrich

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
EC Number:
253-819-2
MDL number:
MFCD00599589
UNSPSC Code:
12161501
PubChem Substance ID:
57654635
NACRES:
NA.77

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.

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

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

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
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H317,H334,H361

Hazard Classifications

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

Storage Class Code

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

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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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
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
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
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