| Identification | Back Directory | [Name]
Salirasib | [CAS]
162520-00-5 | [Synonyms]
FTS
irasib
CS-1744
Salirasib
Unii-mzh0om550m
Salirasib USP/EP/BP
Farnesylthiosalicylate
FARNESYLTHIOSALICYLIC ACID
S-Farnesylthiosalicylic acid
Salirasib(S-Farnesylthiosalicylic aci)
Salirasib (Farnesyl Thiosalicylic Acid)
S-trans,trans-Farnesylthiosalicylic acid
(3,7,11-TRIMETHYLDODECA-2,6,10-TRIENYL)-2-THIOBENZOIC ACID
2-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)benzoic acid
(E,E)-2-[(3,7,11-TriMethyl-2,6,10-dodecatrienyl)thio]benzoic Acid
2-(((2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-yl)thio)benzoicacid
2-[[(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl]thio]benzoic acid
Benzoic acid, 2-[[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]thio]- | [Molecular Formula]
C22H30O2S | [MDL Number]
MFCD00467723 | [MOL File]
162520-00-5.mol | [Molecular Weight]
358.54 |
| Chemical Properties | Back Directory | [Melting point ]
64-66°C | [Boiling point ]
486.0±45.0 °C(Predicted) | [density ]
1.05 | [storage temp. ]
-20°C Freezer | [solubility ]
DMSO: soluble20mg/mL, clear | [form ]
powder | [pka]
3.50±0.36(Predicted) | [color ]
white to beige | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. | [InChI]
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+ | [InChIKey]
WUILNKCFCLNXOK-CFBAGHHKSA-N | [SMILES]
C(O)(=O)C1=CC=CC=C1SC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/C |
| Hazard Information | Back Directory | [Description]
Association of Ras protein with the inner surface of the plasma membrane is required for Ras signaling activity. Farnesyl thiosalicylic acid (FTS) is an inhibitor of Ras-mediated signaling that functions by dislodging Ras from the cell membrane thereby rendering it susceptible to proteolytic degradation.1 FTS inhibits the growth of human Ha-ras-transformed Rat1 fibroblasts with an IC50 value of 7.5 μM.2 It does not inhibit Ras farnesylation in vitro and although FTS does inhibit prenylated protein methyltransferase (PPMTase) in cell-free systems with a Ki value of 2.6 μM, it is relatively ineffective at inhibiting methylation in whole cells.3 Treatment of chow-fed ApoE-deficient mice with 5 mg/kg FTS three times per week for six weeks reduces early atherosclerotic lesion development by 52% compared to controls.4 | [Chemical Properties]
Pale Yellow Solid | [Uses]
Salirasib is a new specific nontoxic drug with a mild hydrophobic nature, which acts as a Ras antagonist and can therefore be used for stent applications as well as for local cancer treatment.
| [Definition]
ChEBI: Salirasib is a sesquiterpenoid. | [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. | [References]
1) Marciano?et al. (1995),?Farnesyl Derivatives of Rigid Carboxylic Acids – Inhibitors of ras-Dependent Cell Growth; J. Med. Chem.,?38?1267
2) Marom?et al. (1995),?Selective inhibition of Ras-dependent cell growth by farnesylthiosalicylic acid (salirasib) in patients with solid tumors; J. Biol. Chem.,?270?22263
3) Haklai?et al. (1998),?Dislodgement and Accelerated Degradation of Ras; Biochemistry,?37?1306
4) Laheru?et al. (2012),?Integrated preclinical and clinical development of S-trans,trans-Farnesylthiosalicylic acid (FTS, Salirasib) in pancreatic cancer; Invest .New Drugs,?30?2391
5) Tsimberidou?et al. (2010),?Phase 1 first-in-human clinical study of S-trans,trans-farnesylthiosalicylic acid (salirasib) in patients with solid tumors; Cancer Chemother. Pharmacol.,?65?235
6) Charette?et al. (2013),?Salirasib sensitizes hepatocarcinoma cells to TRAIL-induced apoptosis through DR5 and survivin-dependent mechanisms; Cell Death and Disease.?4?e471
7) Maher?et al. (2008),?Activation of TRPA1 by farnesyl thiosalicylic acid; Mol. Pharmacol.,?73?1225 |
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J & K SCIENTIFIC LTD.
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LETOPHARM LIMITED
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Sigma-Aldrich
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SPIRO PHARMA
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