Cysmethynil
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MedKoo CAT#: 406303

CAS#: 851636-83-4

Description: Cysmethynil is a potent inhibitor of isoprenylcysteine carboxyl methyltransferase (ICMT) with antitumor activity in cancer cells. Cysmethynil treatment results in inhibition of cell growth in an Icmt-dependent fashion, demonstrating mechanism-based activity of the compound. Treatment of cancer cells with cysmethynil results in mislocalization of Ras and impaired epidermal growth factor signaling. In a human colon cancer cell line, cysmethynil treatment blocks anchorage-independent growth, and this effect is reversed by overexpression of Icmt.


Chemical Structure

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Cysmethynil
CAS# 851636-83-4

Theoretical Analysis

MedKoo Cat#: 406303
Name: Cysmethynil
CAS#: 851636-83-4
Chemical Formula: C25H32N2O
Exact Mass: 376.25
Molecular Weight: 376.534
Elemental Analysis: C, 79.75; H, 8.57; N, 7.44; O, 4.25

Price and Availability

Size Price Availability Quantity
10mg USD 400 2 Weeks
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Synonym: Cysmethynil

IUPAC/Chemical Name: 2-(1-octyl-5-(m-tolyl)-1H-indol-3-yl)acetamide

InChi Key: QIXBOOVPFRZHQQ-UHFFFAOYSA-N

InChi Code: InChI=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)

SMILES Code: O=C(N)CC1=CN(CCCCCCCC)C2=C1C=C(C3=CC=CC(C)=C3)C=C2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:         

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 376.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: 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. Epub 2017 Jun 19. PMID: 28631011; PMCID: PMC5561173.


2: Wang M, Khoo YM, Zhou J, Casey P, Lee HS. A high-performance liquid chromatography method for the quantification of cysmethynil, an inhibitor of isoprenylcysteine carboxylmethyl transferase, in mouse plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Feb 15;877(5-6):553-7. doi: 10.1016/j.jchromb.2008.12.067. Epub 2009 Jan 6. PMID: 19157999.


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9: Wang M, Tan W, Zhou J, Leow J, Go M, Lee HS, Casey PJ. A small molecule inhibitor of isoprenylcysteine carboxymethyltransferase induces autophagic cell death in PC3 prostate cancer cells. J Biol Chem. 2008 Jul 4;283(27):18678-84. doi: 10.1074/jbc.M801855200. Epub 2008 Apr 23. PMID: 18434300.


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12: Ramanujulu PM, Yang T, Yap SQ, Wong FC, Casey PJ, Wang M, Go ML. Functionalized indoleamines as potent, drug-like inhibitors of isoprenylcysteine carboxyl methyltransferase (Icmt). Eur J Med Chem. 2013 May;63:378-86. doi: 10.1016/j.ejmech.2013.02.007. Epub 2013 Feb 21. PMID: 23514631.


13: Pan Q, Liu R, Banu H, Ma L, Li H. Inhibition of isoprenylcysteine carboxylmethyltransferase sensitizes common chemotherapies in cervical cancer via Ras-dependent pathway. Biomed Pharmacother. 2018 Mar;99:169-175. doi: 10.1016/j.biopha.2018.01.048. Epub 2018 Jan 11. PMID: 29331763.


14: Yang WS, Kim HG, Lee Y, Yoon K, Kim S, Kim JH, Cho JY. Isoprenylcysteine carboxyl methyltransferase inhibitors exerts anti-inflammatory activity. Biochem Pharmacol. 2020 Dec;182:114219. doi: 10.1016/j.bcp.2020.114219. Epub 2020 Sep 12. PMID: 32931773.


15: Baron RA, Peterson YK, Otto JC, Rudolph J, Casey PJ. Time-dependent inhibition of isoprenylcysteine carboxyl methyltransferase by indole-based small molecules. Biochemistry. 2007 Jan 16;46(2):554-60. doi: 10.1021/bi060344n. PMID: 17209565.


16: Liu Q, Chen J, Fu B, Dai J, Zhao Y, Lai L. Isoprenylcysteine carboxylmethyltransferase regulates ovarian cancer cell response to chemotherapy and Ras activation. Biochem Biophys Res Commun. 2018 Jun 22;501(2):556-562. doi: 10.1016/j.bbrc.2018.05.038. Epub 2018 May 11. PMID: 29746868.


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20: Svensson AW, Casey PJ, Young SG, Bergo MO. Genetic and pharmacologic analyses of the role of Icmt in Ras membrane association and function. Methods Enzymol. 2006;407:144-59. doi: 10.1016/S0076-6879(05)07013-8. PMID: 16757321.