XK469

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 206014

CAS#: 157435-10-4 (free)

Description: XK489 is a synthetic quinoxaline phenoxypropionic acid derivative with proapoptotic and antiproliferative activities. R(+)XK469 selectively inhibits topoisomerase II-beta, blocks activation of MEK/MAPK signaling kinases, stimulates caspases, and upregulates p53-dependent proteins, including cyclins A and B1, thereby arresting cancer cells in the G2/M phase of the cell cycle. Both R(+) and S(-) isomers of this agent are cytotoxic, although the R-isomer is more potent.


Chemical Structure

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XK469
CAS# 157435-10-4 (free)

Theoretical Analysis

MedKoo Cat#: 206014
Name: XK469
CAS#: 157435-10-4 (free)
Chemical Formula: C17H13ClN2O4
Exact Mass: 344.05638
Molecular Weight: 344.74912
Elemental Analysis: C, 59.23; H, 3.80; Cl, 10.28; N, 8.13; O, 18.56

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Related CAS #: 157435-10-4 (free)   157434-99-6 (sodium)    

Synonym: XK469; XK 469; XK-469; NSC697887; NSC-697887; NSC 697887.

IUPAC/Chemical Name: 2-(4-((7-chloroquinoxalin-2-yl)oxy)phenoxy)propanoic acid

InChi Key: NUQZXROIVGBRGR-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H13ClN2O4/c1-10(17(21)22)23-12-3-5-13(6-4-12)24-16-9-19-14-7-2-11(18)8-15(14)20-16/h2-10H,1H3,(H,21,22)

SMILES Code: CC(OC1=CC=C(OC2=NC3=CC(Cl)=CC=C3N=C2)C=C1)C(O)=O

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

Preparing Stock Solutions

The following data is based on the product molecular weight 344.74912 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: Kakodkar NC, Peddinti R, Kletzel M, Tian Y, Guerrero LJ, Undevia SD, Geary D, Chlenski A, Yang Q, Salwen HR, Cohn SL. The quinoxaline anti-tumor agent (R+)XK469 inhibits neuroblastoma tumor growth. Pediatr Blood Cancer. 2011 Jan;56(1):164-7. doi: 10.1002/pbc.22639. PubMed PMID: 20860039.

2: Yong WP, Kim TW, Undevia SD, Innocenti F, Ratain MJ. R(+)XK469 inhibits hydroxylation of S-warfarin by CYP2C9. Eur J Cancer. 2009 Jul;45(11):1904-8. doi: 10.1016/j.ejca.2009.04.032. Epub 2009 May 21. PubMed PMID: 19464879; PubMed Central PMCID: PMC2758059.

3: Reiners JJ Jr, Kleinman M, Joiakim A, Mathieu PA. The chemotherapeutic agents XK469 (2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy}propionic acid) and SH80 (2-{4-[(7-bromo-2-quinolinyl)oxy]phenoxy}propionic acid) inhibit cytokinesis and promote polyploidy and induce senescence. J Pharmacol Exp Ther. 2009 Mar;328(3):796-806. doi: 10.1124/jpet.108.144808. Epub 2008 Dec 9. PubMed PMID: 19066341; PubMed Central PMCID: PMC2682258.

4: Undevia SD, Innocenti F, Ramirez J, House L, Desai AA, Skoog LA, Singh DA, Karrison T, Kindler HL, Ratain MJ. A phase I and pharmacokinetic study of the quinoxaline antitumour Agent R(+)XK469 in patients with advanced solid tumours. Eur J Cancer. 2008 Aug;44(12):1684-92. doi: 10.1016/j.ejca.2008.05.018. Epub 2008 Jul 21. PubMed PMID: 18650079; PubMed Central PMCID: PMC2731567.

5: Kessel D, Reiners JJ Jr, Hazeldine ST, Polin L, Horwitz JP. The role of autophagy in the death of L1210 leukemia cells initiated by the new antitumor agents, XK469 and SH80. Mol Cancer Ther. 2007 Jan;6(1):370-9. PubMed PMID: 17237296; PubMed Central PMCID: PMC2877038.

6: Alousi AM, Boinpally R, Wiegand R, Parchment R, Gadgeel S, Heilbrun LK, Wozniak AJ, DeLuca P, LoRusso PM. A phase 1 trial of XK469: toxicity profile of a selective topoisomerase IIbeta inhibitor. Invest New Drugs. 2007 Apr;25(2):147-54. Epub 2006 Nov 11. PubMed PMID: 17103044.

7: Hazeldine ST, Polin L, Kushner J, White K, Corbett TH, Horwitz JP. Synthesis and biological evaluation of conformationally constrained analogs of the antitumor agents XK469 and SH80. Part 5. Bioorg Med Chem. 2006 Apr 1;14(7):2462-7. Epub 2005 Dec 5. PubMed PMID: 16337128.

8: Hazeldine ST, Polin L, Kushner J, White K, Corbett TH, Horwitz JP. Synthetic modification of the 2-oxypropionic acid moiety in 2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy}propionic acid (XK469), and consequent antitumor effects. Part 4. Bioorg Med Chem. 2005 Jun 2;13(12):3910-20. PubMed PMID: 15911307.

9: Anderson LW, Collins JM, Klecker RW, Katki AG, Parchment RE, Boinpally RR, LoRusso PM, Ivy SP. Metabolic profile of XK469 (2(R)-[4-(7-chloro-2-quinoxalinyl)oxyphenoxy]-propionic acid; NSC698215) in patients and in vitro: low potential for active or toxic metabolites or for drug-drug interactions. Cancer Chemother Pharmacol. 2005 Oct;56(4):351-7. Epub 2005 May 13. PubMed PMID: 15895233.

10: Boinpally RR, Zhou SL, LoRusso PM, Parchment RE. Bioavailability and pharmacokinetics of the investigational anticancer agent XK469 (NSC 698215) in rats following oral and intravenous administration. Cancer Chemother Pharmacol. 2005 Apr;55(4):404-7. Epub 2004 Dec 9. PubMed PMID: 15592839.

XK469

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