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574102

Sigma-Aldrich

Sulindac Sulfide

A cell-permeable, active metabolite of Sulindac.

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Synonym(s):
Sulindac Sulfide, (Z)-5-Fluoro-2-methyl-1-[ p-(methylthio)benzylidene]indene-3-acetic Acid
Empirical Formula (Hill Notation):
C20H17FO2S
CAS Number:
Molecular Weight:
340.41
MDL number:

Quality Level

assay

≥98% (TLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

yellow-orange

solubility

DMSO: 25 mg/mL
ethanol: 5 mg/mL

shipped in

ambient

storage temp.

10-30°C

InChI

1S/C20H17FO2S/c1-12-17(9-13-3-6-15(24-2)7-4-13)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

LFWHFZJPXXOYNR-RQZCQDPDSA-N

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This Item
S8139S3131S1438
vibrant-m

574102

Sulindac Sulfide

vibrant-m

S8139

Sulindac

vibrant-m

S3131

Sulindac sulfide

vibrant-m

S1438

Sulindac sulfone

assay

≥98% (TLC)

assay

≥98.0%

assay

≥98% (HPLC)

assay

≥94% (HPLC)

manufacturer/tradename

Calbiochem®

manufacturer/tradename

-

manufacturer/tradename

-

manufacturer/tradename

-

Quality Level

100

Quality Level

200

Quality Level

-

Quality Level

100

storage temp.

10-30°C

storage temp.

-

storage temp.

-

storage temp.

-

storage condition

OK to freeze

storage condition

-

storage condition

-

storage condition

-

General description

A cell-permeable, active metabolite of Sulindac (Cat. No. 574100). Strongly inhibits Ras-induced malignant transformation and Ras/Raf-dependent transactivation. Also decreases the Ras-induced activation of c-Raf-1 kinase. Inhibits growth and induces apoptosis in prostate cancer cell lines. Selectively inhibits COX-1 (ID50 = 500 nM) compared to prostaglandin H synthase-2 (PGHS-2; COX-2; ID50 = 14 µM). Preferentially inhibits the secretion of Aβ42 in CHO cells stably transfected with both APP75, and the PS1 mutant M146L.
An active metabolite of the non-steroidal anti-inflammatory drug Sulindac (Cat. No. 574100). Inhibits Ras signaling. Strongly inhibits Ras-induced malignant transformation and Ras/Raf-dependent transactivation. Also decreases the Ras-induced activation of c-Raf-1 kinase. Inhibits cell growth and induces apoptosis in a time-and dose-dependent manner. Selectively inhibits prostaglandin H synthase-1 (PGHS-1; COX-1; ID50 = 0.5 µM) relative to prostaglandin H synthase-2 (PGHS-2; COX-2; ID50 = 14 µM). Reduces Aβ42 production independently of COX inhibition.

Biochem/physiol Actions

Cell permeable: yes
ID50 = 500 nM against COX-1
Product does not compete with ATP.
Reversible: no

Warning

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Other Notes

Weggen, S., et al. 2001. Nature414, 212.
Lim, J.T., et al. 1999. Biochem. Pharmacol. 58, 1097.
Herrmann, C., et al. 1998. Oncogene 17, 1769.
Picariello, L., et al. 1998. Eur. J. Pharmacol. 360, 105.
Arber, N., et al. 1997. Gastroenterology 113, 1892.
Meade, E.A., et al. 1993. J. Biol. Chem. 268, 6610.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Exclamation markHealth hazard

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2 - Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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