Symadex free base

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MedKoo CAT#: 201510

CAS#: 138154-39-9 (free base)

Description: Symadex, also known as imidazoacridone; XLS-002 and C-1311, is a member of the novel imidazoacridinone family of anticancer agents. Imidazoacridone has shown activity in experimental tumour models both in vitro and in nude mice. C-1311 at the EC(99) dose delayed progression of cells through the S phase which was followed by G2 arrest. C-1311 does not induce rapid apoptosis in HT-29 cells, instead drug exposure leads to prolonged G2 arrest followed by G2 to M transit and cell death during mitosis in the process of mitotic catastrophe.

Chemical Structure

Symadex free base
CAS# 138154-39-9 (free base)

Theoretical Analysis

MedKoo Cat#: 201510
Name: Symadex free base
CAS#: 138154-39-9 (free base)
Chemical Formula: C20H22N4O2
Exact Mass: 350.17428
Molecular Weight: 350.422
Elemental Analysis: C, 68.55; H, 6.33; N, 15.99; O, 9.13

Price and Availability

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5.0mg USD 295.0 2 Weeks
25.0mg USD 850.0 2 Weeks
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Related CAS #: 138154-55-9 (HCl)   138154-39-9 (free base)  

Synonym: C-1311, C1311; C 1311; XLS-002; XLS 002; XLS002; Imidacrine; SYMADEX.

IUPAC/Chemical Name: 5-((2-(diethylamino)ethyl)amino)-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one


InChi Code: InChI=1S/C20H22N4O2/c1-3-23(4-2)10-9-21-15-6-7-16-19-18(15)20(26)14-11-13(25)5-8-17(14)24(19)12-22-16/h5-8,11-12,21,25H,3-4,9-10H2,1-2H3


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 (5mg/mL)

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

Certificate of Analysis:

Safety Data Sheet (SDS):

Preparing Stock Solutions

The following data is based on the product molecular weight 350.422 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

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1: Skwarska A, Augustin E, Beffinger M, Wojtczyk A, Konicz S, Laskowska K, Polewska J. Targeting of FLT3-ITD kinase contributes to high selectivity of imidazoacridinone C-1311 against FLT3-activated leukemia cells. Biochem Pharmacol. 2015 Jun 15;95(4):238-52. doi: 10.1016/j.bcp.2015.04.006. Epub 2015 Apr 17. PubMed PMID: 25896848.

2: Pawłowska M, Augustin E, Mazerska Z. CYP3A4 overexpression enhances apoptosis induced by anticancer agent imidazoacridinone C-1311, but does not change the metabolism of C-1311 in CHO cells. Acta Pharmacol Sin. 2014 Jan;35(1):98-112. doi: 10.1038/aps.2013.132. Epub 2013 Dec 2. PubMed PMID: 24292379; PubMed Central PMCID: PMC4075741.

3: Polewska J, Skwarska A, Augustin E, Konopa J. DNA-damaging imidazoacridinone C-1311 induces autophagy followed by irreversible growth arrest and senescence in human lung cancer cells. J Pharmacol Exp Ther. 2013 Sep;346(3):393-405. doi: 10.1124/jpet.113.203851. Epub 2013 Jul 3. PubMed PMID: 23823138.

4: Augustin E, Pawłowska M, Polewska J, Potega A, Mazerska Z. Modulation of CYP3A4 activity and induction of apoptosis, necrosis and senescence by the anti-tumour imidazoacridinone C-1311 in human hepatoma cells. Cell Biol Int. 2013 Feb;37(2):109-20. doi: 10.1002/cbin.10018. Epub 2013 Jan 14. PubMed PMID: 23319370.

5: Pawlowska M, Chu R, Fedejko-Kap B, Augustin E, Mazerska Z, Radominska-Pandya A, Chambers TC. Metabolic transformation of antitumor acridinone C-1305 but not C-1311 via selective cellular expression of UGT1A10 increases cytotoxic response: implications for clinical use. Drug Metab Dispos. 2013 Feb;41(2):414-21. doi: 10.1124/dmd.112.047811. Epub 2012 Nov 16. PubMed PMID: 23160818; PubMed Central PMCID: PMC3558869.

6: Fedejko-Kap B, Bratton SM, Finel M, Radominska-Pandya A, Mazerska Z. Role of human UDP-glucuronosyltransferases in the biotransformation of the triazoloacridinone and imidazoacridinone antitumor agents C-1305 and C-1311: highly selective substrates for UGT1A10. Drug Metab Dispos. 2012 Sep;40(9):1736-43. doi: 10.1124/dmd.112.045401. Epub 2012 Jun 1. PubMed PMID: 22659092; PubMed Central PMCID: PMC3422538.

7: Sirdah M, Reading NS, Perkins SL, Shubair M, Aboud L, Prchal JT. Hemolysis and Mediterranean G6PD mutation (c.563 C>T) and c.1311 C>T polymorphism among Palestinians at Gaza Strip. Blood Cells Mol Dis. 2012 Apr 15;48(4):203-8. doi: 10.1016/j.bcmd.2012.01.007. Epub 2012 Feb 22. PubMed PMID: 22364808.

8: Paradziej-Łukowicz J, Skwarska A, Peszyńska-Sularz G, Brillowska-Dąbrowska A, Konopa J. Anticancer imidazoacridinone C-1311 inhibits hypoxia-inducible factor-1α (HIF-1α), vascular endothelial growth factor (VEGF) and angiogenesis. Cancer Biol Ther. 2011 Oct 1;12(7):586-97. Epub 2011 Oct 1. PubMed PMID: 21775820.

9: Potega A, Dabrowska E, Niemira M, Kot-Wasik A, Ronseaux S, Henderson CJ, Wolf CR, Mazerska Z. The imidazoacridinone antitumor drug, C-1311, is metabolized by flavin monooxygenases but not by cytochrome P450s. Drug Metab Dispos. 2011 Aug;39(8):1423-32. doi: 10.1124/dmd.111.038984. Epub 2011 May 9. PubMed PMID: 21555506.

10: Isambert N, Campone M, Bourbouloux E, Drouin M, Major A, Yin W, Loadman P, Capizzi R, Grieshaber C, Fumoleau P. Evaluation of the safety of C-1311 (SYMADEX) administered in a phase 1 dose escalation trial as a weekly infusion for 3 consecutive weeks in patients with advanced solid tumours. Eur J Cancer. 2010 Mar;46(4):729-34. doi: 10.1016/j.ejca.2009.12.005. Epub 2009 Dec 22. PubMed PMID: 20031390.

11: Wiśniewska A, Chrapkowska A, Kot-Wasik A, Konopa J, Mazerska Z. Metabolic transformations of antitumor imidazoacridinone, C-1311, with microsomal fractions of rat and human liver. Acta Biochim Pol. 2007;54(4):831-8. Epub 2007 Dec 17. PubMed PMID: 18084652.

12: Alami N, Paterson J, Belanger S, Juste S, Grieshaber CK, Leyland-Jones B. Comparative cytotoxicity of C-1311 in colon cancer in vitro and in vivo using the hollow fiber assay. J Chemother. 2007 Oct;19(5):546-53. PubMed PMID: 18073154.

13: Skwarska A, Augustin E, Konopa J. Sequential induction of mitotic catastrophe followed by apoptosis in human leukemia MOLT4 cells by imidazoacridinone C-1311. Apoptosis. 2007 Dec;12(12):2245-57. PubMed PMID: 17924195.

14: Hyzy M, Bozko P, Konopa J, Skladanowski A. Antitumour imidazoacridone C-1311 induces cell death by mitotic catastrophe in human colon carcinoma cells. Biochem Pharmacol. 2005 Mar 1;69(5):801-9. Epub 2005 Jan 18. PubMed PMID: 15710357.

15: Mazerska Z, Sowiński P, Konopa J. Molecular mechanism of the enzymatic oxidation investigated for imidazoacridinone antitumor drug, C-1311. Biochem Pharmacol. 2003 Nov 1;66(9):1727-36. PubMed PMID: 14563483.

16: Mazerska Z, Dziegielewski J, Konopa J. Enzymatic activation of a new antitumour drug, 5-diethylaminoethylamino-8-hydroxyimidazoacridinone, C-1311, observed after its intercalation into DNA. Biochem Pharmacol. 2001 Mar 15;61(6):685-94. PubMed PMID: 11266653.

17: Lamb J, Wheatley DN. Cell killing by the novel imidazoacridinone antineoplastic agent, C-1311, is inhibited at high concentrations coincident with dose-differentiated cell cycle perturbation. Br J Cancer. 1996 Nov;74(9):1359-68. PubMed PMID: 8912530; PubMed Central PMCID: PMC2074775.

Additional Information

Related CAS#
138154-55-9 (Imidazoacridone hydrochloride)
138154-39-9 (Imidazoacridone free base)