:Cysmethynil
{{Chembox
| ImageFile = Cysmethynil skeletal.png
| ImageSize =
| ImageAlt = 3D model of cysmethynil; blue bonds are resonant, grey are single. Grey atoms are carbon, blue are nitrogen, red is oxygen, & white is hydrogen.
| PIN = 2-[5-(3-Methylphenyl)-1-octyl-1H-indol-3-yl]acetamide
| OtherNames = Cysmethynil, 2-(1-octyl-5-m-tolyl-1H-indol-3-yl)acetamide, 9J20
|Section1={{Chembox Identifiers
| CASNo = 851636-83-4
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = R5MT8HFQ9E
| ChemSpiderID = 5294022
| PubChem = 6918831
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C25H32N2O/c1-3-4-5-6-7-8-14-27-18-22(17-25(26)28)23-16-21(12-13-24(23)27)20-11-9-10-19(2)15-20/h9-13,15-16,18H,3-8,14,17H2,1-2H3,(H2,26,28)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QIXBOOVPFRZHQQ-UHFFFAOYSA-N
| SMILES = O=C(N)Cc2c1cc(ccc1n(c2)CCCCCCCC)c3cccc(c3)C }}
|Section2={{Chembox Properties
| C=25 | H=32 | N=2 | O=1
| Appearance =
| Density = 1.068 g/cm3
| MeltingPtC = 247.08
| BoilingPtC = 594.156
| BoilingPt_notes = at 760 mmHg
| VaporPressure = 1.37×10−12 mmHg at 25 °C
| Solubility = 0.005429 mg/L}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPtC = 313.134
| AutoignitionPtC =
}}
}}
Cysmethynil is a chemical compound that is reported to inhibit Icmt, a protein that methylates a Ras protein, which then triggers uncontrolled cell growth. If Icmt no longer activates Ras, cell growth and proliferatation remains under normal control. As such, this small molecule has been investigated as a treatment for cancer. In animal models containing multiple human tumor growths, treatment with cysmethynil causes autophagy in the cell and results in cell death and reduced tumor burden. In prostate cancer cells, cysmethynil inhibits Icmt such that the cell is stuck in the G1 phase, and this leads to the autophagic cell death.[http://www.rxpgnews.com/cancer-therapy/Cysmethynil_A_New_Anti-Cancer_Compound_that_Blocks_782_782.shtml Cysmethynil : A New Anti-Cancer Compound That Blocks the Icmt Protein Activation. Proceedings of the National Academy of Sciences, 28 Mar. 2005. Web. 19 Oct. 2012][http://www.jbc.org/content/283/27/e99932 Arresting Prostate Cancer." The Journal of Biological Chemistry. American Society for Biochemistry and Molecular Biology, n.d. Web. 19 Oct. 2012][http://inside.duke.edu/article_print.php?id=9726 New Compound Blocks Growth of Cancer Cells." Inside- Duke University Medical Center and Health System. N.p., 04 Apr. 2005. Web. 20 Oct. 2012]Yang WS, Yeo SG, Yang S, Kim KH, Yoo BC, Cho JY. Isoprenyl carboxyl methyltransferase inhibitors: a brief review including recent patents. Amino Acids. 2017 Sep;49(9):1469-1485. {{doi|10.1007/s00726-017-2454-x}} {{pmid|28631011}}Arendt KAM, Ntaliarda G, Armenis V, Kati D, Henning C, Giotopoulou GA, Pepe MAA, Klotz LV, Lamort AS, Hatz RA, Kobold S, Schamberger AC, Stathopoulos GT. An In Vivo Inflammatory Loop Potentiates KRAS Blockade. Biomedicines. 2022 Mar 3;10(3):592. {{doi|10.3390/biomedicines10030592}} {{pmid|35327394}}