SALIRASIB

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H30O2S
Molecular Weight	358.537
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CSC1=CC=CC=C1C(O)=O

InChI

InChIKey=WUILNKCFCLNXOK-CFBAGHHKSA-N

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+

HIDE SMILES / InChI

Molecular Formula	C22H30O2S
Molecular Weight	358.537
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	2
Optical Activity	NONE

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug/def/salirasib | https://www.ncbi.nlm.nih.gov/pubmed/7673206 | https://www.ncbi.nlm.nih.gov/pubmed/18374183 | http://adisinsight.springer.com/drugs/800026972

Salirasib or S-trans,trans-Farnesylthiosalicylic acid (FTS) is a salicylic acid derivative with potential antineoplastic activity. It acts as a potent competitive inhibitor of the enzyme prenylated protein methyltransferase (PPMTase), which methylates the carboxyl-terminal S-prenylcysteine in a large number of prenylated proteins including Ras. In such systems, Salirasib inhibits Ras methylation but not Ras farnesylation. Salirasib selectively disrupts the association of chronically active Ras proteins with the plasma membrane. Salirasib competes with Ras for binding to Ras-escort proteins, which possess putative farnesyl-binding domains and interact only with the activated form of Ras proteins, thereby promoting Ras nanoclusterization in the plasma membrane and robust signals. Salirasib was studied in the clinical trials in patients with solid tumors, however its development was discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Isoprenylcysteine carboxyl methyltransferase 2 Target ID: CHEMBL4699 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7673206	Inhibitor 8504		2.6 µM [Ki]
Ras protein signal transduction 1 Target ID: GO:0007265 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7731012 \| https://www.ncbi.nlm.nih.gov/pubmed/7673206	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Non-small cell lung cancer 211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18374183 https://www.ncbi.nlm.nih.gov/pubmed/21847063 https://www.ncbi.nlm.nih.gov/pubmed/17541036	Primary		Phase II 1147	Unknown Approved Use Unknown
Pancreatic cancer 98 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22547163 https://www.ncbi.nlm.nih.gov/pubmed/18374183	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
1340 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
2830 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3630 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
4790 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
4990 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
1180 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
2610 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3250 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
3840 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	800 mg 2 times / day multiple, oral dose: 800 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
2630 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	1000 mg 2 times / day multiple, oral dose: 1000 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Analyte	Population
4970 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
11400 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
20300 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
26600 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
26900 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
4610 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
10500 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
14800 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
16300 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	800 mg 2 times / day multiple, oral dose: 800 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
15700 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	1000 mg 2 times / day multiple, oral dose: 1000 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
3.81 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
4.16 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
3.67 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
9.11 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/29992354	1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered:	SALIRASIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P001TON	https://www.1pchem.com/search?query=1P001TON
AChemBlock	Q65695	http://www.achemblock.com/catalogsearch/result/?q=Q65695
AK Scientific	2030AH	https://aksci.com/item_detail.php?cat=2030AH
Ambeed	A100859	http://www.ambeed.com/search/Search.html?keyword=A100859
Angene	AGN-PC-0O4NAI	http://www.angenechemical.com/productshow/AGN-PC-0O4NAI.html
ApexBio Technology	A3787	https://www.apexbt.com/catalogsearch/result/?q=A3787
AstaTech	42154	http://astatechinc.com/CPSResult.php?CRNO=42154
BLD Pharm	BD316909	http://www.bldpharm.com/search/Search.html?keyword=BD316909
Cayman Chemical	10010501	http://www.caymanchem.com/app/template/Product.vm/catalog/10010501
Chem Scene	CS-0681	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0681
ChemShuttle	104283	https://www.chemshuttle.com/catalogsearch/result/?q=104283
Combi-Blocks	QJ-1858	http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-1858
eMolecules	206919416	https://orderbb.emolecules.com/search/#?query=206919416
eMolecules	22697584	https://orderbb.emolecules.com/search/#?query=22697584
eMolecules	300125297	https://orderbb.emolecules.com/search/#?query=300125297
eNovation Chemicals	D408759	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D408759&searchbtn.x=0&searchbtn.y=0
Excenen	EX-A1170	http://www.excenen.com/searchresultlist.php?id=EX-A1170
Fluorochem	468408	http://www.fluorochem.co.uk/Products/Product?code=468408
KeyOrganics	AS-73028	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-73028
Lab Network	LN01298611	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01298611
Matrix Scientific	145002	http://www.matrixscientific.com/145002.html
mcule	MCULE-2155058647	https://mcule.com/MCULE-2155058647/
mcule	MCULE-5926123267	https://mcule.com/MCULE-5926123267/
MedChem Express	HY-14754	https://www.medchemexpress.com/search.html?q=HY-14754&ft=&fa=&fp=
Molnova	M18095	https://www.molnova.com/en/serch-list.html?keywords=M18095
MolPort	MolPort-003-847-356	https://www.molport.com/shop/molecule-link/MolPort-003-847-356
MuseChem	I002092	https://www.musechem.com/product/I002092.html
Selleck Chemicals	S7684	http://www.selleckchem.com/search.html?searchDTO.searchParam=S7684
ShangHai Biochempartner	BCP27978	http://www.biochempartner.com/search_BCP27978
TargetMol	T6163	https://www.targetmol.com/search?keyword=T6163
Tocris	4989	https://www.tocris.com/search.php?Type=QuickSearch&Value=4989
Toronto Research Chemicals	F102500	https://www.trc-canada.com/product-detail/?CatNum=F102500
Toronto Research Chemicals	I786502	https://www.trc-canada.com/product-detail/?CatNum=I786502

PubMed

Title	Date	PubMed
Integrated Transcriptional and Proteomic Analysis of Growth Hormone Suppression Mediated by Trichothecene T-2 Toxin in Rat GH3 Cells.	2015-10	26141394
Rosiglitazone suppresses lipopolysaccharide-induced matrix metalloproteinase-2 activity in rat aortic endothelial cells via Ras-MEK1/2 signaling.	2012-06-28	21247645
A phase II trial of Salirasib in patients with lung adenocarcinomas with KRAS mutations.	2011-08	21847063
Novel nitric oxide-releasing derivatives of farnesylthiosalicylic acid: synthesis and evaluation of antihepatocellular carcinoma activity.	2011-05-12	21504204
Salirasib inhibits the growth of hepatocarcinoma cell lines in vitro and tumor growth in vivo through ras and mTOR inhibition.	2010-09-22	20860815
Simvastatin suppresses LPS-induced MMP-1 expression in U937 mononuclear cells by inhibiting protein isoprenylation-mediated ERK activation.	2008-10	18625914
Activation of TRPA1 by farnesyl thiosalicylic acid.	2008-04	18171730
The Ras inhibitor farnesylthiosalicylic acid (Salirasib) disrupts the spatiotemporal localization of active Ras: a potential treatment for cancer.	2008	18374183
Ras inhibition results in growth arrest and death of androgen-dependent and androgen-independent prostate cancer cells.	2006-08-14	16780807
Ras inhibition in glioblastoma down-regulates hypoxia-inducible factor-1alpha, causing glycolysis shutdown and cell death.	2005-02-01	15705901
Hydrogen peroxide-induced extracellular signal-regulated kinase activation in cultured feline ileal smooth muscle cells.	2005-01	15328380
Treatment of thioacetamide-induced liver cirrhosis by the Ras antagonist, farnesylthiosalicylic acid.	2004-08	15288472
Farnesyl thiosalicylic acid chemosensitizes human melanoma in vivo.	2003-01	12535206
Farnesyl-L-cysteine analogs block SAM-induced Parkinson's disease-like symptoms in rats.	2000-08	10973524
Dislodgment and accelerated degradation of Ras.	1998-02-03	9477957

Patents

Sample Use Guides

In Vivo Use Guide

A phase II trial of Salirasib in patients with lung adenocarcinomas with KRAS mutations. Patients were treated with salirasib 800 mg twice daily on days 1 to 28 of a 35-day cycle. The schedule of days 1 to 28 of a 35-day cycle was chosen to allow initial imaging after 4 weeks of continuous treatment. After 10 patients were enrolled, because of toxicity (described in Results), the initial dose was changed to 600 mg twice daily.

Route of Administration: Oral

In Vitro Use Guide

Salirasib or S-trans,trans-Farnesylthiosalicylic acid (FTS) inhibits the growth of human Ha-ras-transformed cells (EJ cells) and reverses their transformed morphology in a dose-dependent manner (0.1-10 microM). The drug does not interfere with the growth of cells transformed by v-Raf or T-antigen but inhibits the growth of ErbB2-transformed cells and blocks the mitogenic effects of epidermal and basic fibroblast growth factors, thus implying its selectivity toward Ras growth signaling, possibly via modulation of Ras-Raf communication.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:28:12 GMT 2025` Edited by `admin` on `Mon Mar 31 18:28:12 GMT 2025`
Record UNII	MZH0OM550M
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SALIRASIB

Official Name

English

FARNESYLTHIOSALICYLATE

Preferred Name

English

SALIRASIB [USAN]

Common Name

English

Salirasib [WHO-DD]

Common Name

English

S-Farnesylthiosalicylic acid

Systematic Name

English

salirasib [INN]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

231306