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SML1166

Sigma-Aldrich

Salirasib

≥98% (HPLC)

Synonym(s):

2-(((2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrienyl)sulfanyl)benzoic acid, FTS, Farnesylthiosalicylic acid, S-Farnesylthiosalicylic acid

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About This Item

Empirical Formula (Hill Notation):
C22H30O2S
CAS Number:
162520-00-5
Molecular Weight:
358.54
MDL number:
MFCD00467723
UNSPSC Code:
12352200
PubChem Substance ID:
329825696
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C(O)C1=CC=CC=C1SC/C=C(C)/CC/C=C(C)/CCC=C(C)C

InChI

1S/C22H30O2S/c1-17(2)9-7-10-18(3)11-8-12-19(4)15-16-25-21-14-6-5-13-20(21)22(23)24/h5-6,9,11,13-15H,7-8,10,12,16H2,1-4H3,(H,23,24)/b18-11+,19-15+

InChI key

WUILNKCFCLNXOK-CFBAGHHKSA-N

Application

Salirasib has been used as a farnesyltransferase inhibitor.

Biochem/physiol Actions

Salirasib (Farnesylthiosalicylic acid) is a RAS inhibitor that acts by dislodging the farnesylated protein from the membrane, facilitating Ras degradation. Salirasib impairs downstream signaling and suppresses growth and migration of proliferating tumor cells in in vitro and in vivo models. Salirasib (Farnesylthiosalicylic acid) has recently been shown to possess significant anti-inflammatory and anti-arthritic properties.
Salirasib (S-trans,trans-Farnesylthiosalicylic Acid /FTS) is a synthetic small molecule that has an ability to block all forms of Ras, unlike farnesyltransferase inhibitors, which fail to inhibit K-Ras and N-Ras function due to alternative membrane-binding mechanisms. Salirasib along with gemcitabine, exhibits anti-tumor activity and biomarker modulation in preclinical models of metastatic pancreatic adenocarcinoma (PDA). It is also used as a potent therapeutic for lung cancer.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Orally administered FTS (salirasib) inhibits human pancreatic tumor growth in nude mice.
Haklai R, et al.
Cancer Chemotherapy and Pharmacology, 61(1), 89-96 (2008)
Suppression of lung cancer tumor growth in a nude mouse model by the Ras inhibitor salirasib (farnesylthiosalicylic acid).
Zundelevich A, et al.
Molecular Cancer Therapeutics, 6(6), 1765-1773 (2007)
Membrane localization of acetylated CNK1 mediates a positive feedback on RAF/ERK signaling.
Fischer A, et al.
Science Advances, 3(8), e1700475-e1700475 (2017)
Corina Beerli et al.
Nature microbiology, 4(2), 216-225 (2018-11-14)
Cell motility is essential for viral dissemination1. Vaccinia virus (VACV), a close relative of smallpox virus, is thought to exploit cell motility as a means to enhance the spread of infection1. A single viral protein, F11L, contributes to this by
A phase II trial of Salirasib in patients with lung adenocarcinomas with KRAS mutations.
Riely G J, et al.
Journal of Thoracic Oncology : Official Publication of the International Association for the Study of Lung Cancer, 6(8), 1435-1437 (2011)
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